2-Benzyl-5-hydroxy-4-oxopentanoic acid 1 and its enantiomers were designed,synthesized and assayed for inhibitory activity against carboxypeptidase A(CPA,EC 3.4.17.1).To verify the role of the terminal hydroxyl group ...2-Benzyl-5-hydroxy-4-oxopentanoic acid 1 and its enantiomers were designed,synthesized and assayed for inhibitory activity against carboxypeptidase A(CPA,EC 3.4.17.1).To verify the role of the terminal hydroxyl group in 1 binding to CPA,2-benzyl-5- benzyloxy-4-oxopentanoic acid 2 was also synthesized and evaluated.The inhibition constants show that both L-1 and D-1 were shown to have strong binding affinity with L-1 being more potent than its enantiomer by 165-fold.On the other hand,the inhibition constant ...展开更多
Trans-4-hydroxy-2-hexenal(4-HHE) and trans-4-hydroxy-2-nonenal(4-HNE) are secondary lipid peroxidation products in edible oils, which are cytotoxic and genotoxic. They could covalently bind with protein, phospholipids...Trans-4-hydroxy-2-hexenal(4-HHE) and trans-4-hydroxy-2-nonenal(4-HNE) are secondary lipid peroxidation products in edible oils, which are cytotoxic and genotoxic. They could covalently bind with protein, phospholipids and DNA, further disrupting the normal function of liver, lung and brain.Derivation process was generally conducted during pretreatment before detection and quantification of 4-HHE and 4-HNE. However, the derivation procedures were time consuming and chemical degradation may occur during the process. Hence, this paper aims to establish a simple solid phase extractionhigh performance liquid chromatography(SPE-HPLC) method to determine the 4-HHE and 4-HNE contents in thermally treated soybean oil. C18 solid phase extraction was applied in the pretreatment process. Firstly, the reliability of the method was evaluated. Good linearity was observed in the range of 0.1–0.5 μg/m L and 0.5–10 μg/m L for 4-HHE and 4-HNE. The limit of detection(LOD) of 4-HHE and 4-HNE were 0.0486 and 0.0129 μg/m L, respectively. And the limit of quantitation(LOQ) of4-HHE and 4-HNE were 0.1458 and 0.0431 μg/m L, respectively. Recovery rate were in the range of89.11%–91.58% and 71.83%–79.40% for 4-HHE and 4-HNE, respectively. The method achieved the extraction, purification and detection of 4-HHE and 4-HNE simultaneously and had the advantages of simple operation, effectiveness, high precision, good repeatability. Then, the method was applied to monitor the concentrations of 4-HHE and 4-HNE in soybean oil heated at 180 °C for 40 h. The contents of 4-HHE and 4-HNE were 0–0.32 μg/g and 0–6.97 μg/g, respectively, which provided guidance for evaluating health risks of thermally treated soybean oil during heating.展开更多
Novel hexadecyl 3- { 4-[2-hydroxy-3(isopropylamino)propoxy]phenyl }propionate (HPP)was synthesized and its effect on delivery of liposomes into cultured cardiomyocytes was examined. The structure of HPP was charac...Novel hexadecyl 3- { 4-[2-hydroxy-3(isopropylamino)propoxy]phenyl }propionate (HPP)was synthesized and its effect on delivery of liposomes into cultured cardiomyocytes was examined. The structure of HPP was characterized by IH NMR, 1R and MS. The amount of cardiomyocytes uptake of HPP-liposome was 3.9-fold higher than plain-liposome, and the increase was 6.2-fold when hypoxia happens. It indicated that HPP was a potential ligand for liposome targeting to ischemic myocardium.展开更多
The title compound, 4-(tert-butyl)-5-(1 H- 1,2,4-triazol- 1 -yl)-N-(2-hydroxy-3,5-diio- dinebenzyl)thiazol-2-amine, was synthesized via the reduction of 4-(tert-butyl)-5-(1H-l,2,4- triazol-l-yl)-N-benzyliden...The title compound, 4-(tert-butyl)-5-(1 H- 1,2,4-triazol- 1 -yl)-N-(2-hydroxy-3,5-diio- dinebenzyl)thiazol-2-amine, was synthesized via the reduction of 4-(tert-butyl)-5-(1H-l,2,4- triazol-l-yl)-N-benzylidene-thiazol-2-amine with NaBH4, and its crystal structure was determined by single-crystal X-ray diffraction. The compound crystallizes in monoclinic system, space group P21/c with a = 7.91944(19), b = 10.5250(3), c = 24.4985(6) A, Z = 4, V = 2041.66(9) A3, Mr = 599.22, Dc = 1,949 Mg/m3, S = 1.120, p = 3.203 mm-1, F(000) = 1152, the final R = 0.0283 and wR = 0.0592 for 3490 observed reflections (I 〉 2σ(I)). X-ray analysis displays that the crystal water takes part in three intermolecular hydrogen bonds of O(2)-H(2A)…O(1), O(2)-H(2B)…N(I) and N(5)-H(5)…O(2), and an octatomic ring R^(8) is formed via intramolecular hydrogen bond of O(I)-H(IA)…N(4). Furthermore, the I…I contacts are involved in stabilizing the overall three-dimensional network structure. The preliminary biological test shows the title compound has good antitumor activity with the IC50 value of 26 μM against the Hela cell line.展开更多
(+)-(4S,5R)-and (-)-(4R,5S)-osmundalactones as well as (+)-(4R,5S)- and (-)-(4S,5R)- 5-hydroxy-2-hexen-4-olides were synthesized by a concise and efficient synthesis method starting from 4-benzyloxy-...(+)-(4S,5R)-and (-)-(4R,5S)-osmundalactones as well as (+)-(4R,5S)- and (-)-(4S,5R)- 5-hydroxy-2-hexen-4-olides were synthesized by a concise and efficient synthesis method starting from 4-benzyloxy-5-hydroxy-2(E)-hexenoate in good yield with over 99% e.e..展开更多
Glandular trichomes of plants produce a wide variety of secondary metabolites which are considered as major defensive chemicals. The capitate glandular trichomes of Oenothera glazioviana(Onagraceae) were collected wit...Glandular trichomes of plants produce a wide variety of secondary metabolites which are considered as major defensive chemicals. The capitate glandular trichomes of Oenothera glazioviana(Onagraceae) were collected with laser microdissection and analyzed by gas chromatography-mass spectrometry. The volatile compound 4-hydroxy-4-methylpentan-2-one(1) was identified. We found that compound 1 displays antimicrobial, insecticidal, and phytotoxic activities. These results suggest that compound 1 might function as a defensive compound in the capitate glandular trichomes of O. glazioviana against pathogens, insect herbivores, and presumably competitive plants as well.展开更多
A synthesis of methyl 2-hydroxy-4-oxo-4-(substituted phenyl)butanoates has been accomplished using Friedel-Crafts acylation of substituted benzenes with 2-acetoxybutanoyl chloride. The key feature of this strategy i...A synthesis of methyl 2-hydroxy-4-oxo-4-(substituted phenyl)butanoates has been accomplished using Friedel-Crafts acylation of substituted benzenes with 2-acetoxybutanoyl chloride. The key feature of this strategy is that various 4-arylbutanoates can be obtained conveniently, which are important intermediates for the synthesis of biologically active compounds including ACE inhibitors.?2009 Yong Sup Lee. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.展开更多
(R)-1,3-butanediol is an important pharmaceutical intermediate, and the synthesis of(R)-1,3-butanediol using green biological methods has recently been of interest for industrial application. Here, a novel strain QC-1...(R)-1,3-butanediol is an important pharmaceutical intermediate, and the synthesis of(R)-1,3-butanediol using green biological methods has recently been of interest for industrial application. Here, a novel strain QC-1 that efficiently transforms 4-hydroxy-2-butanone to(R)-1,3-butanediol was isolated from soil samples. Based on morphological, physiological, and biochemical tests and 5.8 S-internal transcribed spacer sequencing, the strain was identified as Pichia kudriavzevii QC-1. The reaction conditions were optimized to 35 ℃, pH 8.0, rotation speed 200 rpm, and 6:5 mass ratio of glucose to 4-hydroxy-2-butanone. Evaluation of the effects of 4-hydroxy-2-butanone concentrations on yield and cell survival rate showed that 85.60 g·L^-1 product accumulated, with an enantiomeric excess of more than 99%, when 30 g·L^-14-hydroxy-2-butanone was added at 0, 10, and 30 h in a 3-L bioreactor. Thus, strain QC-1 showed excellent catalytic activity and stereoselectivity for the synthesis of(R)-1,3-butanediol from 4-hydroxy-2-butanone.展开更多
Liver diseases with the central pathogenetic mechanism of oxidative stress are one of the main causes of mortality worldwide.Therefore,dihydroquinoline derivatives,which are precursors of hepatoprotectors and have ant...Liver diseases with the central pathogenetic mechanism of oxidative stress are one of the main causes of mortality worldwide.Therefore,dihydroquinoline derivatives,which are precursors of hepatoprotectors and have antioxidant activity,are of interest.We have previously found that some compounds in this class have the ability to normalize redox homeostasis under experimental conditions.Here,we initially analyzed the hepatoprotective potential of the dihydroquinoline derivative 1-benzoyl-6-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline(BHDQ)for carbon tetrachloride(CCl4)-induced liver injury in rats.Results suggested that BHDQ normalized the alanine aminotransferase,aspartate aminotransferase,and gamma-glutamyl transpeptidase in serum.We also observed an improvement in liver tissue morphology related to BHDQ.Animals with CCl4-induced liver injuries treated with BHDQ had less oxidative stress compared to animals with CCl4-induced liver injury.BHDQ promoted activation changes in superoxide dismutase,catalase,glutathione peroxidase,glutathione reductase,and glutathione transferase on control values in animals with CCl4-induced liver injury.BHDQ also activated gene transcription in Sod1 and Gpx1 via nuclear factor erythroid 2-related factor 2 and forkhead box protein O1 factors.Therefore,the compound of concern has a hepatoprotective effect by inhibiting the development of necrotic processes in the liver tissue,through antioxidation.展开更多
The title compound [2-hydroxy-5-(4-hydroxy-3-phenyliminomethyl-benzyl)-benzylidene]-phenyl-amine (C27H22N2O2, Mr = 406.47) was synthesized by 5,5′-methylene-bissalicylal- dehyde with aminobenezene, and its crysta...The title compound [2-hydroxy-5-(4-hydroxy-3-phenyliminomethyl-benzyl)-benzylidene]-phenyl-amine (C27H22N2O2, Mr = 406.47) was synthesized by 5,5′-methylene-bissalicylal- dehyde with aminobenezene, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group C2/c with a = 4.4026(6), b = 1.501(13), c = 0.95818(12) nm, β = 90.868(2)°, V= 4.2813(9) nm^3, Z= 8, Dc= 1.292 g/cm^3,μ = 0.010, F(000) = 1744, R = 0.0576 and wR = 0.1450 for 3766 observed reflections with I 〉 2σ(I). X-ray analysis reveals that the molecule has a pair of intramolecular OH…N hydrogen bonds.展开更多
It is demonstrated that (3Z)-nonenal (NON) and (3Z)-hexenal (HEX) are oxidized in a cascade by lipoxygenase (LOX) and hydroperoxide peroxygenase (HP peroxygenase) into (2E)-4-hydroxy-2- nonenal (HNE) and (2E)-4-hydrox...It is demonstrated that (3Z)-nonenal (NON) and (3Z)-hexenal (HEX) are oxidized in a cascade by lipoxygenase (LOX) and hydroperoxide peroxygenase (HP peroxygenase) into (2E)-4-hydroxy-2- nonenal (HNE) and (2E)-4-hydroxy-2-hexenal (HHE), respectively. In turn, HNE inactivates LOX terminating the cascade. The hydroxy-alkenals produced serve to inhibit plant pathogens, which initiated the cascade. In addition to LOX, other unknown oxygenases may be involved in the cascade.展开更多
Degradation of oxidized or oxidatively modified proteins is an essential part of the cellular antioxidant defense system. 4-Hydroxy-2-nonenal (HNE), a major reactive aldehyde formed by lipid peroxidation, causes many ...Degradation of oxidized or oxidatively modified proteins is an essential part of the cellular antioxidant defense system. 4-Hydroxy-2-nonenal (HNE), a major reactive aldehyde formed by lipid peroxidation, causes many types of cellular damage. HNE-modified proteins are degraded by the ubiquitin-proteasome pathway or the lysosomal pathway. However, our previous studies using U937 cells showed that HNE-modified glyceraldehyde-3-phosphate dehydrogenase (GAPDH) is degraded by cathepsin G. In the present study, we examined whether GAPDH in U937 cells treated with HNE in culture is degraded similarly to that incubated with HNE and U937 cell extract. Treatment with HNE for 10 min in culture decreased GAPDH activity in a concentration dependent manner, but did not affect GAPDH degradation. The proteasome activities were not affected by HNE, but culturing with HNE decreased cathepsin G activity and protein level in a concentration dependent manner. These results suggest that HNE-induced oxidative stress leads to decreased cathepsin G activity and results in the loss of GAPDH degradation. Taken together, our findings indicate that cathepsin G has an important role in the degradation of oxidatively modified GAPDH in U937 cells.展开更多
<span style="font-family:Verdana;">Coordination compounds of 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="fo...<span style="font-family:Verdana;">Coordination compounds of 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one with </span><span style="font-family:Verdana;">iron(III), cobat(III) and chromium(III) were synthesized with M:L (1:2)</span><span style="font-family:Verdana;">. Mixed ligand coordination compounds of 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one and 1,2-diaminocyclohexane using the same metal ions were also synthesized </span><b><span style="font-family:Verdana;">M:L1</span></b><span style="font-family:Verdana;">:</span><b><span style="font-family:Verdana;">L2</span></b><span style="font-family:Verdana;"> (1:1:1) where </span><b><span style="font-family:Verdana;">L1</span></b><span style="font-family:Verdana;"> is 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one and </span><b><span style="font-family:Verdana;">L2</span></b><span style="font-family:Verdana;"> is 1,2-diaminocyclohexane. The coordination compounds obtained were characterized using electronic and infrared spectral analyses, magnetic susceptibility and percentage metal analysis. They were also evaluated for their cytotoxic and antioxidant activities. The result obtained suggested that octahedral geometry was obtained for all the compounds, as a result of additional two molecules of the solvent coordinated to the metal ions. Both the primary and secondary ligands coordinated in a bidentate fashion. The synthesized compounds exhibited moderate cytotoxicity, although none was as active as the standard. The cobalt(III) mixed ligand complex elicited the highest activity. The synthesized compounds all exhibited good to moderate antioxidant activity.</span>展开更多
The 2-hydroxy-4-methoxybenzyl(Hmb)backbone modification can prevent amide bond-mediated sidereactions(e.g.,aspartimide formation,peptide aggregation)by installing the removable Hmb group into a peptide bond,thus impro...The 2-hydroxy-4-methoxybenzyl(Hmb)backbone modification can prevent amide bond-mediated sidereactions(e.g.,aspartimide formation,peptide aggregation)by installing the removable Hmb group into a peptide bond,thus improving the synthesis of long and challenging peptides and proteins.However,its use is largely precluded by the limited Hmb’s installation sites.In this report,an improved installation of Hmb(iHmb)method was developed to achieve the flexible installation and the convenient removal of Hmb.The iHmb method involves two critical steps:(1)oxidative diazotization of the readily installed 2-hydroxy-4-methoxy-5-amino-benzyl(Hmab)to give 2-hydroxy-4-methoxy-5-diazonium-benzyl(Hmdab)by combining soamyl nitrite(IAN)/HBF_(4),and(2)reductive elimination of Hmdab to give the desired Hmb by 1,2-ethanedithiol(EDT).The iHmb method enables the installation of Hmb at any primary amino acid including the highly sterically hindered amino acids(e.g.,valine and isoleucine).The practicality and utility of the iHmb method was demonstrated by one-shot solid-phase synthesis of a challenging aspartimide-prone peptide,the mirror-image version of a hydrophobic peptide and a long-chain peptide up to 76-residue.Furthermore,the iHmb method can be utilized to facilitate chemical protein ligation,as exemplified by the synthesis of the single-spanning membrane protein sarcolipin.The iHmb method expands the toolkit for peptide synthesis and ligation and facilitates the preparation of peptides/proteins.展开更多
The title complex [Cu3L3(H2O)]DMFH2O (H2L = 4-(3-hydroxy-2-ethyl-4- pyridinone-1-yl)-aniline condensation salicylaldehyde) was obtained. The single-crystal X-ray study shows that it is a trinuclear compound [Cu3(C20H1...The title complex [Cu3L3(H2O)]DMFH2O (H2L = 4-(3-hydroxy-2-ethyl-4- pyridinone-1-yl)-aniline condensation salicylaldehyde) was obtained. The single-crystal X-ray study shows that it is a trinuclear compound [Cu3(C20H15N2O3)3(H2O)]DMFH2O. The coordi- nation sphere about each copper ion in the complex consists of two oxygen atoms from hydroxylpyridinone moiety of one ligand and one oxygen and one nitrogen atoms from salicyladehyde Schiff-base moiety of another ligand arranged in a slightly distorted square planar geometry. Among the three copper ions, one (Cu(2)) is coordinated by the other oxygen atom of water molecule on the fifth coordinate position to form a distorted square pyramid geometry. The crystal is of monoclinic, space group P21/c with a = 12.9202(5), b = 27.197(1), c = 17.0116(7) ? b = 100.588(1), V = 5875.9(4) 3, Z = 4, C63H57N7O12Cu3, Mr = 1294.78, Dc = 1.464 g/cm3, m = 1.146 mm-1, F(000) = 2668, R = 0.0784 and wR = 0.1546 for 6926 observed reflections with I > 2s(I). The differences of coordinate bond lengths are observed between anhydrous and hydrous units: in the former unit, the average bond lengths are 1.978 ?for CuN (azomethine), 1.883 ?for CuO (phenolic) in Schiff-base moiety, 1.959 ?for CuO (keto), and 1.919 ?for CuO (hydroxy) in hydroxypyridinone moiety; while those in the latter are longer with the following corresponding values: 1.985(5), 1.908(5), 1.993(5) and 1.919(4) ? respectively. The Cu(2)O (water) bond length is 2.375(6) ?展开更多
Nine 3,3’-(arylmethylene)bis(2-hydroxynaphthalene-1,4-dione) derivatives were synthesized through the reaction between 2-hydroxy-1,4-naphthalen-1,4-dione and different aromatic alde-hydes in water applying ultrasonic...Nine 3,3’-(arylmethylene)bis(2-hydroxynaphthalene-1,4-dione) derivatives were synthesized through the reaction between 2-hydroxy-1,4-naphthalen-1,4-dione and different aromatic alde-hydes in water applying ultrasonic irradiation for 5 min at room temperature and microwave irradiation for 15 min at 70°;C. Two of the nine derivatives, compounds 3-e and 3-i, obtained from 3-bromo-hydroxybenzaldehyde and 5-methylfuran-2-carbaldehyde, respectively, are previously unpublished. The structures of all compounds were established on the basis of their spectral data and mass analysis. The attractive features of this synthesis protocol include mild conditions, high atom-economy and excellent yields with the elimination of water as the only by-product.展开更多
The title compound 4 methyl 4 hydroxy 2 pentone is obtained by the condensed reaction of acetone, and co crystallized with octamolybdate anion and tetra butyl ammonium cation. The crystal structure belongs to ...The title compound 4 methyl 4 hydroxy 2 pentone is obtained by the condensed reaction of acetone, and co crystallized with octamolybdate anion and tetra butyl ammonium cation. The crystal structure belongs to triclinic system, space group P1 , Mo 8C 44 H 98 O 30 N 2 M r=1902.77, a=11.512(6), b=12.790(3), c=13.395(4), α=65.22(2), β=78.26(4), γ=71.12(3), V=1689(1) 3, Z=1, D x =1\^869g/cm 3, F(000)=950, μ =14.79 cm -1 , final R =0.053 and R w =0.067. The orbital hybridization of C(53) and C(55) are sp 3 and sp 2 separately in (CH 3) 2COHCH 2COCH 3 and the catalysis of β octamolybdate anion might be present for the condensed reaction of acetone.展开更多
The complex MoO2(C7H7O3)2 has been prepared by the reaction of 3-hydroxy- 2-ethyl-4-pyranone with (NH4)6Mo7O244H2O. The single-crystal X-ray study shows that the coordination sphere about the molybdenum atom in the co...The complex MoO2(C7H7O3)2 has been prepared by the reaction of 3-hydroxy- 2-ethyl-4-pyranone with (NH4)6Mo7O244H2O. The single-crystal X-ray study shows that the coordination sphere about the molybdenum atom in the complex consists of six oxygen atoms arranged in a distorted octahedral geometry with the dioxo ligands in cis positions. The crystal is of monoclinic, space group P21/c with a = 8.3968(2), b = 12.7534(4), c = 14.5443(4) ? b = 96.277(1), V = 1548.18(7) ?, Z = 4, C14H14O8Mo, Mr = 406.19, Dc = 1.743g/cm3, m = 0.886mm-1, F(000) = 816, R = 0.0444 and wR = 0.1091 for 2336 observed reflections with I>2s(I). The average Mo=O bond length is 1.695(4) ? The two ketonic oxygen atoms of the pyranone moieties are trans to the oxo ligands and the hydroxy oxygen atoms are trans to each other. The average MoO bond lengths are 2.248(4) ?for the ketone oxygens and 2.005(3) ?for the hydroxy oxygens. The average ligand bite angle of OMoO is 75.2(2) and the bond angle between two Mo=O is 105.1(2). The dihedral angle is 79.16(2)?between two chelate ring planes.展开更多
文摘2-Benzyl-5-hydroxy-4-oxopentanoic acid 1 and its enantiomers were designed,synthesized and assayed for inhibitory activity against carboxypeptidase A(CPA,EC 3.4.17.1).To verify the role of the terminal hydroxyl group in 1 binding to CPA,2-benzyl-5- benzyloxy-4-oxopentanoic acid 2 was also synthesized and evaluated.The inhibition constants show that both L-1 and D-1 were shown to have strong binding affinity with L-1 being more potent than its enantiomer by 165-fold.On the other hand,the inhibition constant ...
基金supported by grants from the National Natural Science Foundation of China(No.31471668)。
文摘Trans-4-hydroxy-2-hexenal(4-HHE) and trans-4-hydroxy-2-nonenal(4-HNE) are secondary lipid peroxidation products in edible oils, which are cytotoxic and genotoxic. They could covalently bind with protein, phospholipids and DNA, further disrupting the normal function of liver, lung and brain.Derivation process was generally conducted during pretreatment before detection and quantification of 4-HHE and 4-HNE. However, the derivation procedures were time consuming and chemical degradation may occur during the process. Hence, this paper aims to establish a simple solid phase extractionhigh performance liquid chromatography(SPE-HPLC) method to determine the 4-HHE and 4-HNE contents in thermally treated soybean oil. C18 solid phase extraction was applied in the pretreatment process. Firstly, the reliability of the method was evaluated. Good linearity was observed in the range of 0.1–0.5 μg/m L and 0.5–10 μg/m L for 4-HHE and 4-HNE. The limit of detection(LOD) of 4-HHE and 4-HNE were 0.0486 and 0.0129 μg/m L, respectively. And the limit of quantitation(LOQ) of4-HHE and 4-HNE were 0.1458 and 0.0431 μg/m L, respectively. Recovery rate were in the range of89.11%–91.58% and 71.83%–79.40% for 4-HHE and 4-HNE, respectively. The method achieved the extraction, purification and detection of 4-HHE and 4-HNE simultaneously and had the advantages of simple operation, effectiveness, high precision, good repeatability. Then, the method was applied to monitor the concentrations of 4-HHE and 4-HNE in soybean oil heated at 180 °C for 40 h. The contents of 4-HHE and 4-HNE were 0–0.32 μg/g and 0–6.97 μg/g, respectively, which provided guidance for evaluating health risks of thermally treated soybean oil during heating.
基金This project was supported by the National Natural Science Foundation of China(No.30271548).
文摘Novel hexadecyl 3- { 4-[2-hydroxy-3(isopropylamino)propoxy]phenyl }propionate (HPP)was synthesized and its effect on delivery of liposomes into cultured cardiomyocytes was examined. The structure of HPP was characterized by IH NMR, 1R and MS. The amount of cardiomyocytes uptake of HPP-liposome was 3.9-fold higher than plain-liposome, and the increase was 6.2-fold when hypoxia happens. It indicated that HPP was a potential ligand for liposome targeting to ischemic myocardium.
基金supported by the National Undergraduate Training Programs for Innovation and Entrepreneurship of Hunan Universitythe Natural Science Foundation of Hunan Province(No.12jj3012)
文摘The title compound, 4-(tert-butyl)-5-(1 H- 1,2,4-triazol- 1 -yl)-N-(2-hydroxy-3,5-diio- dinebenzyl)thiazol-2-amine, was synthesized via the reduction of 4-(tert-butyl)-5-(1H-l,2,4- triazol-l-yl)-N-benzylidene-thiazol-2-amine with NaBH4, and its crystal structure was determined by single-crystal X-ray diffraction. The compound crystallizes in monoclinic system, space group P21/c with a = 7.91944(19), b = 10.5250(3), c = 24.4985(6) A, Z = 4, V = 2041.66(9) A3, Mr = 599.22, Dc = 1,949 Mg/m3, S = 1.120, p = 3.203 mm-1, F(000) = 1152, the final R = 0.0283 and wR = 0.0592 for 3490 observed reflections (I 〉 2σ(I)). X-ray analysis displays that the crystal water takes part in three intermolecular hydrogen bonds of O(2)-H(2A)…O(1), O(2)-H(2B)…N(I) and N(5)-H(5)…O(2), and an octatomic ring R^(8) is formed via intramolecular hydrogen bond of O(I)-H(IA)…N(4). Furthermore, the I…I contacts are involved in stabilizing the overall three-dimensional network structure. The preliminary biological test shows the title compound has good antitumor activity with the IC50 value of 26 μM against the Hela cell line.
文摘(+)-(4S,5R)-and (-)-(4R,5S)-osmundalactones as well as (+)-(4R,5S)- and (-)-(4S,5R)- 5-hydroxy-2-hexen-4-olides were synthesized by a concise and efficient synthesis method starting from 4-benzyloxy-5-hydroxy-2(E)-hexenoate in good yield with over 99% e.e..
基金supported financially by the National Science Fund for Distinguished Young Scholars(31525005)the NSFC-Yunnan Joint Fund (U1202263)+1 种基金the National Basic Research Program of China (973 Program) on Biological Control of Key Crop Pathogenic Nematodes (2013CB127505)the "Hundred Talents Program" of the Chinese Academy of Sciences (awarded to S.-H. Li)
文摘Glandular trichomes of plants produce a wide variety of secondary metabolites which are considered as major defensive chemicals. The capitate glandular trichomes of Oenothera glazioviana(Onagraceae) were collected with laser microdissection and analyzed by gas chromatography-mass spectrometry. The volatile compound 4-hydroxy-4-methylpentan-2-one(1) was identified. We found that compound 1 displays antimicrobial, insecticidal, and phytotoxic activities. These results suggest that compound 1 might function as a defensive compound in the capitate glandular trichomes of O. glazioviana against pathogens, insect herbivores, and presumably competitive plants as well.
基金supported by the Seoul Research and Business Development Program(No.10524).One of theauthors M.N.A.Khan is a recipient of Post-Doctoral fellowship from the post-BK2 1 program,Korea.
文摘A synthesis of methyl 2-hydroxy-4-oxo-4-(substituted phenyl)butanoates has been accomplished using Friedel-Crafts acylation of substituted benzenes with 2-acetoxybutanoyl chloride. The key feature of this strategy is that various 4-arylbutanoates can be obtained conveniently, which are important intermediates for the synthesis of biologically active compounds including ACE inhibitors.?2009 Yong Sup Lee. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
基金Financial supports from the National Key R&D Program of China(2018YFC1604100)the National Natural Science Foundation of China(NSFC)[21676120,31872891]+8 种基金the 111 Project[111-2-06]the Highend Foreign Experts Recruitment Program[G20190010083]the Program for Advanced Talents within Six Industries of Jiangsu Province[2015-NY007]the National Program for Support of Top-notch Young Professionalsthe Fundamental Research Funds for the Central Universities[JUSRP51504]the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education InstitutionsTop-notch Academic Programs Project of Jiangsu Higher Education Institutionsthe Jiangsu Province“Collaborative Innovation Center for Advanced Industrial Fermentation”Industry Development Programthe National First-Class Discipline Program of Light Industry Technology and Engineering[LITE2018-09]。
文摘(R)-1,3-butanediol is an important pharmaceutical intermediate, and the synthesis of(R)-1,3-butanediol using green biological methods has recently been of interest for industrial application. Here, a novel strain QC-1 that efficiently transforms 4-hydroxy-2-butanone to(R)-1,3-butanediol was isolated from soil samples. Based on morphological, physiological, and biochemical tests and 5.8 S-internal transcribed spacer sequencing, the strain was identified as Pichia kudriavzevii QC-1. The reaction conditions were optimized to 35 ℃, pH 8.0, rotation speed 200 rpm, and 6:5 mass ratio of glucose to 4-hydroxy-2-butanone. Evaluation of the effects of 4-hydroxy-2-butanone concentrations on yield and cell survival rate showed that 85.60 g·L^-1 product accumulated, with an enantiomeric excess of more than 99%, when 30 g·L^-14-hydroxy-2-butanone was added at 0, 10, and 30 h in a 3-L bioreactor. Thus, strain QC-1 showed excellent catalytic activity and stereoselectivity for the synthesis of(R)-1,3-butanediol from 4-hydroxy-2-butanone.
基金supported by the Russian Foundation for Basic Research (Grant No. 20-04-00526А)
文摘Liver diseases with the central pathogenetic mechanism of oxidative stress are one of the main causes of mortality worldwide.Therefore,dihydroquinoline derivatives,which are precursors of hepatoprotectors and have antioxidant activity,are of interest.We have previously found that some compounds in this class have the ability to normalize redox homeostasis under experimental conditions.Here,we initially analyzed the hepatoprotective potential of the dihydroquinoline derivative 1-benzoyl-6-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline(BHDQ)for carbon tetrachloride(CCl4)-induced liver injury in rats.Results suggested that BHDQ normalized the alanine aminotransferase,aspartate aminotransferase,and gamma-glutamyl transpeptidase in serum.We also observed an improvement in liver tissue morphology related to BHDQ.Animals with CCl4-induced liver injuries treated with BHDQ had less oxidative stress compared to animals with CCl4-induced liver injury.BHDQ promoted activation changes in superoxide dismutase,catalase,glutathione peroxidase,glutathione reductase,and glutathione transferase on control values in animals with CCl4-induced liver injury.BHDQ also activated gene transcription in Sod1 and Gpx1 via nuclear factor erythroid 2-related factor 2 and forkhead box protein O1 factors.Therefore,the compound of concern has a hepatoprotective effect by inhibiting the development of necrotic processes in the liver tissue,through antioxidation.
基金supported by the Project for Distinguished Young Scholars from Hubei Provincial Department of Education (No. Q20082601)
文摘The title compound [2-hydroxy-5-(4-hydroxy-3-phenyliminomethyl-benzyl)-benzylidene]-phenyl-amine (C27H22N2O2, Mr = 406.47) was synthesized by 5,5′-methylene-bissalicylal- dehyde with aminobenezene, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to the monoclinic system, space group C2/c with a = 4.4026(6), b = 1.501(13), c = 0.95818(12) nm, β = 90.868(2)°, V= 4.2813(9) nm^3, Z= 8, Dc= 1.292 g/cm^3,μ = 0.010, F(000) = 1744, R = 0.0576 and wR = 0.1450 for 3766 observed reflections with I 〉 2σ(I). X-ray analysis reveals that the molecule has a pair of intramolecular OH…N hydrogen bonds.
文摘It is demonstrated that (3Z)-nonenal (NON) and (3Z)-hexenal (HEX) are oxidized in a cascade by lipoxygenase (LOX) and hydroperoxide peroxygenase (HP peroxygenase) into (2E)-4-hydroxy-2- nonenal (HNE) and (2E)-4-hydroxy-2-hexenal (HHE), respectively. In turn, HNE inactivates LOX terminating the cascade. The hydroxy-alkenals produced serve to inhibit plant pathogens, which initiated the cascade. In addition to LOX, other unknown oxygenases may be involved in the cascade.
文摘Degradation of oxidized or oxidatively modified proteins is an essential part of the cellular antioxidant defense system. 4-Hydroxy-2-nonenal (HNE), a major reactive aldehyde formed by lipid peroxidation, causes many types of cellular damage. HNE-modified proteins are degraded by the ubiquitin-proteasome pathway or the lysosomal pathway. However, our previous studies using U937 cells showed that HNE-modified glyceraldehyde-3-phosphate dehydrogenase (GAPDH) is degraded by cathepsin G. In the present study, we examined whether GAPDH in U937 cells treated with HNE in culture is degraded similarly to that incubated with HNE and U937 cell extract. Treatment with HNE for 10 min in culture decreased GAPDH activity in a concentration dependent manner, but did not affect GAPDH degradation. The proteasome activities were not affected by HNE, but culturing with HNE decreased cathepsin G activity and protein level in a concentration dependent manner. These results suggest that HNE-induced oxidative stress leads to decreased cathepsin G activity and results in the loss of GAPDH degradation. Taken together, our findings indicate that cathepsin G has an important role in the degradation of oxidatively modified GAPDH in U937 cells.
文摘<span style="font-family:Verdana;">Coordination compounds of 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one with </span><span style="font-family:Verdana;">iron(III), cobat(III) and chromium(III) were synthesized with M:L (1:2)</span><span style="font-family:Verdana;">. Mixed ligand coordination compounds of 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one and 1,2-diaminocyclohexane using the same metal ions were also synthesized </span><b><span style="font-family:Verdana;">M:L1</span></b><span style="font-family:Verdana;">:</span><b><span style="font-family:Verdana;">L2</span></b><span style="font-family:Verdana;"> (1:1:1) where </span><b><span style="font-family:Verdana;">L1</span></b><span style="font-family:Verdana;"> is 3-hydroxy-2-methyl-4</span><i><span style="font-family:Verdana;">H</span></i><span style="font-family:Verdana;">-pyran-4-one and </span><b><span style="font-family:Verdana;">L2</span></b><span style="font-family:Verdana;"> is 1,2-diaminocyclohexane. The coordination compounds obtained were characterized using electronic and infrared spectral analyses, magnetic susceptibility and percentage metal analysis. They were also evaluated for their cytotoxic and antioxidant activities. The result obtained suggested that octahedral geometry was obtained for all the compounds, as a result of additional two molecules of the solvent coordinated to the metal ions. Both the primary and secondary ligands coordinated in a bidentate fashion. The synthesized compounds exhibited moderate cytotoxicity, although none was as active as the standard. The cobalt(III) mixed ligand complex elicited the highest activity. The synthesized compounds all exhibited good to moderate antioxidant activity.</span>
基金supported by the National Key Research and Development Program of China(No.2019YFA0706900)the National Natural Science Foundation of China(Nos.22022703 and 22177108)the Collaborative Innovation Program of Hefei Science Center,CAS(No.2022HSC-CIP013).
文摘The 2-hydroxy-4-methoxybenzyl(Hmb)backbone modification can prevent amide bond-mediated sidereactions(e.g.,aspartimide formation,peptide aggregation)by installing the removable Hmb group into a peptide bond,thus improving the synthesis of long and challenging peptides and proteins.However,its use is largely precluded by the limited Hmb’s installation sites.In this report,an improved installation of Hmb(iHmb)method was developed to achieve the flexible installation and the convenient removal of Hmb.The iHmb method involves two critical steps:(1)oxidative diazotization of the readily installed 2-hydroxy-4-methoxy-5-amino-benzyl(Hmab)to give 2-hydroxy-4-methoxy-5-diazonium-benzyl(Hmdab)by combining soamyl nitrite(IAN)/HBF_(4),and(2)reductive elimination of Hmdab to give the desired Hmb by 1,2-ethanedithiol(EDT).The iHmb method enables the installation of Hmb at any primary amino acid including the highly sterically hindered amino acids(e.g.,valine and isoleucine).The practicality and utility of the iHmb method was demonstrated by one-shot solid-phase synthesis of a challenging aspartimide-prone peptide,the mirror-image version of a hydrophobic peptide and a long-chain peptide up to 76-residue.Furthermore,the iHmb method can be utilized to facilitate chemical protein ligation,as exemplified by the synthesis of the single-spanning membrane protein sarcolipin.The iHmb method expands the toolkit for peptide synthesis and ligation and facilitates the preparation of peptides/proteins.
基金This work was supported by the foundation of Natural Science Research of Jiangsu Education Department (02KJB150007)
文摘The title complex [Cu3L3(H2O)]DMFH2O (H2L = 4-(3-hydroxy-2-ethyl-4- pyridinone-1-yl)-aniline condensation salicylaldehyde) was obtained. The single-crystal X-ray study shows that it is a trinuclear compound [Cu3(C20H15N2O3)3(H2O)]DMFH2O. The coordi- nation sphere about each copper ion in the complex consists of two oxygen atoms from hydroxylpyridinone moiety of one ligand and one oxygen and one nitrogen atoms from salicyladehyde Schiff-base moiety of another ligand arranged in a slightly distorted square planar geometry. Among the three copper ions, one (Cu(2)) is coordinated by the other oxygen atom of water molecule on the fifth coordinate position to form a distorted square pyramid geometry. The crystal is of monoclinic, space group P21/c with a = 12.9202(5), b = 27.197(1), c = 17.0116(7) ? b = 100.588(1), V = 5875.9(4) 3, Z = 4, C63H57N7O12Cu3, Mr = 1294.78, Dc = 1.464 g/cm3, m = 1.146 mm-1, F(000) = 2668, R = 0.0784 and wR = 0.1546 for 6926 observed reflections with I > 2s(I). The differences of coordinate bond lengths are observed between anhydrous and hydrous units: in the former unit, the average bond lengths are 1.978 ?for CuN (azomethine), 1.883 ?for CuO (phenolic) in Schiff-base moiety, 1.959 ?for CuO (keto), and 1.919 ?for CuO (hydroxy) in hydroxypyridinone moiety; while those in the latter are longer with the following corresponding values: 1.985(5), 1.908(5), 1.993(5) and 1.919(4) ? respectively. The Cu(2)O (water) bond length is 2.375(6) ?
文摘Nine 3,3’-(arylmethylene)bis(2-hydroxynaphthalene-1,4-dione) derivatives were synthesized through the reaction between 2-hydroxy-1,4-naphthalen-1,4-dione and different aromatic alde-hydes in water applying ultrasonic irradiation for 5 min at room temperature and microwave irradiation for 15 min at 70°;C. Two of the nine derivatives, compounds 3-e and 3-i, obtained from 3-bromo-hydroxybenzaldehyde and 5-methylfuran-2-carbaldehyde, respectively, are previously unpublished. The structures of all compounds were established on the basis of their spectral data and mass analysis. The attractive features of this synthesis protocol include mild conditions, high atom-economy and excellent yields with the elimination of water as the only by-product.
文摘The title compound 4 methyl 4 hydroxy 2 pentone is obtained by the condensed reaction of acetone, and co crystallized with octamolybdate anion and tetra butyl ammonium cation. The crystal structure belongs to triclinic system, space group P1 , Mo 8C 44 H 98 O 30 N 2 M r=1902.77, a=11.512(6), b=12.790(3), c=13.395(4), α=65.22(2), β=78.26(4), γ=71.12(3), V=1689(1) 3, Z=1, D x =1\^869g/cm 3, F(000)=950, μ =14.79 cm -1 , final R =0.053 and R w =0.067. The orbital hybridization of C(53) and C(55) are sp 3 and sp 2 separately in (CH 3) 2COHCH 2COCH 3 and the catalysis of β octamolybdate anion might be present for the condensed reaction of acetone.
基金the Natural Science Foundation of Jiangsu Education Department (No. 02KJB15007)
文摘The complex MoO2(C7H7O3)2 has been prepared by the reaction of 3-hydroxy- 2-ethyl-4-pyranone with (NH4)6Mo7O244H2O. The single-crystal X-ray study shows that the coordination sphere about the molybdenum atom in the complex consists of six oxygen atoms arranged in a distorted octahedral geometry with the dioxo ligands in cis positions. The crystal is of monoclinic, space group P21/c with a = 8.3968(2), b = 12.7534(4), c = 14.5443(4) ? b = 96.277(1), V = 1548.18(7) ?, Z = 4, C14H14O8Mo, Mr = 406.19, Dc = 1.743g/cm3, m = 0.886mm-1, F(000) = 816, R = 0.0444 and wR = 0.1091 for 2336 observed reflections with I>2s(I). The average Mo=O bond length is 1.695(4) ? The two ketonic oxygen atoms of the pyranone moieties are trans to the oxo ligands and the hydroxy oxygen atoms are trans to each other. The average MoO bond lengths are 2.248(4) ?for the ketone oxygens and 2.005(3) ?for the hydroxy oxygens. The average ligand bite angle of OMoO is 75.2(2) and the bond angle between two Mo=O is 105.1(2). The dihedral angle is 79.16(2)?between two chelate ring planes.