Synthesis, Bioactivity, and Crystal Structure Analysis of 2-(3-Oxobenzo[d]isothiazol-2(3H)-yl)ethyl Benzoates

Fifteen novel 2-（3-oxobenzo[d]isothiazol-2（3H）-yl）ethyl benzoates were synthesi- zed by the condensation of 2-（2-hydroxyethyl）benzo[d]isothiazol-3（2H）-one with substituted benzoic acids in dichloromethane. All the compounds were characterized by elemental analysis, IR, ESI-MS and 1H NMR. The crystal structures for 2-（2-hydroxyethyl）benzo[d]isothiazol-3（2H）-one （2） and 2-（3-oxobenzo[d]isothiazol-2（3H）-yl）ethyl 2-methoxybenzoate （30） have been determined by X-ray crystal structure analysis. Compound 2 （C9H9NO2S） crystallizes in the monoclinic system, space group Pn with a = 10.552（3）, b = 7.849（2）, c = 10.765（4） A, β = 103.128（4）°, V= 868.3（5） A3, Mr = 195.24, Dc = 1.493 Mg.m-3, μ = 0.33 mm-1, F（000） = 408, Z = 4, R= 0.0314 and wR= 0.0628. Compound 30 （C17H15NO4S） crystallizes in the triclinic system, space group P1 with a = 8.028（2）, b = 9.300（2）, c = 10.430（3）A, V= 752.1（3）A3, Mr = 329.36, D,= 1.454 Mg.m-3, p = 0.24 mm-1, F（000） = 344, Z = 2, R = 0.0377 and wR = 0.0904. The preliminary biological test indicated that the title compounds show better growth inhibitory activity against the gram-positive bacteria than the gram-negative bacteria.

Hydrothermal Synthesis and Thermal Decomposition Mechanism of Alkaline Earth Benzoates

Alkaline earth benzoates were synthesized using hydrothermal reaction. The complexes were characterized by elemental analysis, IR, X ray powder diffraction. All of them are monoclinic and have layered structure. The mechanism of thermal decomposition of alkaline earth benzoates was studied by using TG, DTA, IR and gas chromatography mass spectrometry. The thermal decomposition of alkaline earth benzoates in nitrogen proceeded in one or two stages: they decomposed to form MCO 3 (M=Ca,Sr,Ba) or MgO and organic compounds, respectively. The organic compounds obtained from decomposition reaction are mainly benzophenone, triphenylmethane and so on.

Synthesis and Thermal Decomposition Mechanism of Rare Earth Benzoates

The rare earth metal benzoates were synthesized using hydrothermal reaction. The complexes were characterized by elemental analysis, IR and X-ray powder diffraction. They can be represented by general formula RE (C6H5COO)(3)(RE = La, Nd, Sm, Eu, Gd, Dy and Er). All of them are monoclinic and have layered structure. The mechanism of thermal decomposition of rare earth metal benzoates was studied by using TG, DTA, IR, and gas chromatography-mass spectrometry. The thermal decomposition of the rare earth benzoates in nitrogen proceeded in two stages; firstly it decomposed to form RE2O(CO3)(2) and organic compounds, then RE2O(CO3)(2) decomposed further to form rare earth metal oxides and carbon dioxide. The organic compounds obtained from the first step of the reaction are mainly benzophenone, 9,10-anthraquinone, 1, 3-Diphenylisobenzofuran and so on.

RUTHENIUM CARBENE INITIATED RING-OPEN METATHESIS POLYMERIZATION OF ENDO-BICYCLO[3.2.0]HEPT-6-EN-3-YL BENZOATES WITH TACTICITY STUDIES

After tentative ring-opening cross metathesis （ROCM） of endo-bicyclo[3.2.0]hept-6-en-3-yl 4-bromobenzoate with PhCH = CH2 initiated by （Cy3P）2Cl2Ru = CHPh in CH2Cl2, ring-opening metathesis polymerization （ROMP） of a series of endo-bicyclo[3.2.0]hept-6-en-3-yl benzoates was achieved under the same conditions, furnishing a variety of the corresponding polymers. Then some of them were selected to hydrogenate the C=C double bonds in their backbone with p-tosylhydrazide, affording saturated and thus more flexible polymers. All of these polymers were well characterized by spectroscopic means including GPC, UV-Vis, NMR and IR, based on which the tacticity of these polymers was investigated together with nonlinear optical （electric-field-induced second-harmonic generation, EFISH）） analysis.

Synthesis and anti-inflammatory-analgesic activity of 2',4'-difluoro-3-(carbamoyl)biphenyl-4-yl benzoates

Eighteen 2′,4′-difluoro-3-（carbamoyl）biphenyl-4-yl benzoates were synthesized from diflunisal in three steps with total yields from 72% to 86%. All compounds were identified by IR, 1^H NMR, MS and elemental analysis. The anti-inflammatory activity and analgesic activity for 18 compounds were evaluated. The preliminary assay results showed that compounds 4a and 4p exhibited potent anti-inflammatory-analgesic activity.

Synthesis and Crystal Structure of Tetra Benzoates Bridged Binuclear Sm(III) Complex

The binuclear complex Sm2(C12H8N2)2(C6H5COO)6 has been prepared and structurally analyzed by single crystal Xray diffraction. The complex crystallizes in the triclinic system, space group P1 , with a=10.833(2), b=11.937(2), c=12.448(3) , = 104.97(3), = 93.63(3), = 113.27(3), V=1403.5 3, Dc=1.64g/cm3, =21.42cm-1, F(000)=690, Z=1, final R=0.037, Rw=0.077 for 4855 observed reflections I>2(I) and 5703 independent reflections. In the molecule, each Sm atom is coordinated by seven O atoms and two N atoms forming an irregular coordination polyhedron.

Two 2-(quinonylcarboxamino)benzoates from the lateral roots of Aconitum carmichaelii

Two new 2-（quinonylcarboxamino）benzoates, named aconicarmiquinamides A （1） and B （2）, were isolated from an aqueous extract of the lateral roots of Aconitum carmichaelii. Their structures were determined by spectroscopic data analysis, and confirmed by comparison with synthetic methyl 3.6- bis（ diethylamino ）benzoqunonylcarboxylate （3）.

Kinetic Evidence for the Solvent Intervention in the Solvolysis of Tertiary Benzylic Benzoates

Rates of solvolyses of 2-（4-methylphenyl）-2-propyl benzoate （2b）, 2-（4-methylthiopheny1）-2-propyl benzoate （3b） and 2,2-dimethy1-1-（4-methoxypheny1）-1-phenyl-1-propy1 benzoate （4b） were measured, respectively, in ten or more different solvent systems. Additional YBnOPXB and Y, BnOPNB values in binary trifluoroethanol-water systems were determined, Grunwald-Winstein type correlation analysis showed that YBaIOBB values were applicable to benzylic benzoates. The rate ratio, koPNB/KOBZ, was found to be solvent-dependent in the range of 29 for 4 in ethanol to 4 for 2 in trifluoroethanol-water. Non-limiting mechanism, including both nucleophilic and electrophilic solvent assistance, in the solvolysis of 2b was discussed,

Enantioresolution of a Series of Chiral Benzyl Alcohols by HPLC on a Dinitrobenzoylphenylglycine Stationary Phase after Achiral Pre-Column Derivatization

High performance liquid chromatography method for the separation of a series of chiral benzyl alcohols on N-(3,5-dinitrobenzoyl)-D-phenylglycine stationary phase (Macherey Nagel, Chiral-2) after pre-column achiral derivatization was developed. Cheap and easy available aromatic acid chlorides were used as derivatization agents. Good to excellent separations of the enantiomers were achieved in all cases in relatively short analytical runs. It was shown that the enantiorecognition depends on the substituents both in the starting alcohol and in the acid chloride. The method presents an efficient alternative to the direct analyses on polysaccharide and cyclodextrine-derived stationary phases.

尼泊尔水东哥的化学成分研究(英文)

从尼泊尔水东哥树皮的95%乙醇提取物中首次分离到12个化合物,应用波谱方法或与已知品对照的手段鉴定为auranamide(1)、aurantiamide benzoate(2)、齐墩果酸(3)、β-谷甾醇(4)、β-胡萝卜甙(5)、乌苏酸(6)、2α,3α-二羟基-12-烯-28-乌苏酸(7)、2α,3β,24-三羟基-12-烯-28-乌苏酸(8)、(2S,3S,4R,10E)-2-[(2′R)-2′-hydroxytetracosanoylamino]-10-octadecene-1,3,4-triol(9)、2α,3α,24-三羟基-12-烯-28-齐墩果酸(10)、2α,3β-二羟基-12-烯-28-乌苏酸(11)和2α,3α,24-三羟基-12-烯-28-乌苏酸(12)。

2-羟基-4-(5,6-二硝基-1H-苯并[2,3-d]咪唑-2-基)苯甲酸甲酯的合成探索

以4,5-二硝基邻苯二胺和2-羟基对苯二甲酸单甲酯为起始原料,设计并成功采用一锅法合成出2-羟基-4-(5,6-二硝基-1H-苯并[2,3-d]咪唑-2-基)苯甲酸甲酯(MHDIB)。以50 mL二乙二醇二甲醚为溶剂,1.5 g的2-羟基对苯二甲酸单甲酯和2.5 g SOCl2在80℃反应2 h制2-羟基-4-氯羰基苯甲酸甲酯。室温下快速向反应体系中加入1.56 g 4,5-二硝基邻苯二胺,并于85℃反应1 h后加入3.52 g多聚磷酸,回流反应1 h后水析出粗产品,经乙醇重结晶得到纯度为93.67%的黄色针状产物,产率为17.82%。产物经IR、MS、1H NMR的准确定性和表征,作为AB型新单体的前体可应用于羟基改性PBI纤维即聚2-羟基-1,4-亚苯基-2,6-苯并[2,3-d:5',6'-d']二咪唑(H-PBI)的创新研究。

Rizatriptan benzoate influences the endogenous pain modulatory system in a rat model of migraine

The present study utilized a nitroglycerin-induced rat model of migraine to detect the effects of rizatriptan benzoate on proenkephalin and substance P gene expression in the midbrain using real-time quantitative polymerase chain reaction and investigate whether rizatriptan benzoate can regulate the endogenous pain modulatory system. The results showed that rizatriptan benzoate significantly reduced expression of the mRNAs for proenkephalin and substance P. Rizatriptan benzoate may inhibit the analgesic effect of the endogenous pain modulatory system.

Anaerobic benzene biodegradation by a pure bacterial culture of Bacillus cereus under nitrate reducing conditions

A pure culture using benzene as sole carbon and energy sources was isolated by screening procedure from gasoline contaminated soil.The analysis of the 16S rDNA gene sequence,morphological and physiological characteristics showed that the isolated strain was a member of genus Bacillus cereus.The biodegradation performance of benzene by B.cereus was evaluated,and the results showed that benzene could be efficiently biodegraded when the initial benzene concentration was below 150 mg/L.The metabolites of anaerobic nitrate-dependent benzene oxidation by strain B.cereus were identified as phenol and benzoate.The results of substrate interaction between binary combinations for benzene,phenol and benzoate showed that the simultaneous presence of benzene stimulated the degradation of benzoate,whereas the addition of benzene inhibited the degradation of phenol.Benzene degradation by B.cereus was enhanced by the addition of phenol and benzoate,the enhanced effects were more pronounced at higher concentration.To our knowledge,this is the first report that the isolated bacterial culture of B.cereus can efficiently degraded benzene under nitrate reducing conditions.

Emamectin benzoate 9.7%SL as a new formulation for a trunkinjections against pine wood nematode,Bursaphelenchus xylophilus

In this study,we investigated the preventive effects of emamectin benzoate 9.7%SL,which was newly developed to reduce the injection volume and number of injection holes required to protect against pine wood nematode.None of the Pinus thunbergii trees injected with emamectin benzoate 9.7%SL at 0.3 mL/cm diameter at breast height(DBH)died within 2 years of inoculation with pine wood nematodes.Emamectin benzoate 9.7%SL injected at 0.6 mL/cm DBH resulted in no tree mortality for 3 years.Mean residue of emamectin benzoate 9.7%SL in pine twigs injected with 0.3 mL/cm DBH was 0.490μg/g at 1 year after injection and 0.303μg/g after 2 years.These residues values are greater than 0.031μg/g,previously determined IC95 value for emamectin benzoate against the pine wood nematode.Our field experiment and residue analysis showed that emamectin benzoate 9.7%SL could be a substitute agent for emamectin benzoate 2.15%EC,which is widely used to prevent pine wood nematode in the field and that injection volume and number of injection holes can be greatly educed using this new formulation,which will reduce injury to the cambium,interruption of water movement,and infection of inoculation wounds by wood-decay or blue stain fungi.

A developed HPLC method for the determination of Alogliptin Benzoate and its potential impurities in bulk drug and tablets

Alogliptin(AGLT),active ingredient of Alogliptin Benzoate(AGLT-BZ),is a new dipeptidyl peptidase-4(DPP-4)inhibitor for the treatment of type 2 diabetes.This study aimed to build a suitable method to determine the potential related substances in AGLT-BZ bulk drug and tablets.Seven related substances in Alogliptin Benzoate substances were synthetized and identified by ^(1)H-NMR and ESI-MS.In addition,the impurities were detected by a gradient reverse-phase high performance liquid chromatography(RP-HPLC)with UV detection.The chromatographic system consisted of an Angilent Zobax SB-CN column(250×4.6 mm;5 μm).The mobile phase consisted of water/acetonitrile/trifluoroacetic acid 1900:100:1 v/v/v(solution A)and acetonitrile/water/trifluoroacetic acid 1900:100:1 v/v/v(solution B)using a gradient program at a flow rate of 1.0 ml/min with 278 nm detection and an injection volume of 20 ml.Additionally,selectivity,the limit of quantitation(LOQ)and limit of detection(LOD),linearity,accuracy,precision and robustness were determined.Linearity was good over the concentration range 50-1000 ng/ml and the coefficient of determination(R^(2))were 0.9991-0.9998.RSD% of the determination of precision were <2%(n=6).The method of RP-HPLC for the determination of impurities in AGLT-BZ was proved to be precise,accurate,robust and reliable.Three batches of self-made bulk drug and three dosages of commercial tablets were detected with this method.

STUDY ON THE THERMODYNAMIC PROPERTIES OF ADSORPTION OF ETHYL BENZOATE AND DIETHYL PHTHALATE BY PHENOLIC RESIN ADSORBENTS

This paper presents experimental observations on the adsorption of individual solutes by a simple thermodynamic framework, and the equilibrium adsorption of ethyl benzoate and diethyl phthalate on phenolic resin adsorbent in hexane solutions within the temperature range of 293-313 K. The experimental results show that the Freundlich adsorption law is applicable to the adsorption of ethyl benzoate and diethyl phthalate on the adsorbent, since all the correlative factors R' are larger than 0.99. The negative values of all the isosteric adsorption enthalpies for ethyl benzoate and diethyl phthalate indicate that they undergo exothermic processes, while their magnitudes (19-28 kJ/mol) manifest a hydrogen bonding sorption process. Other thermodynamic properties: the free energy changes and the entropy change associated with the adsorption have been calculated from the Gibbs adsorption equation and the Gibbs-Helmholtz equation

Synthesis, Crystal Structure and Antitumor Activity in Vitro of a New Benzoate Binuclear Cupper(Ⅱ ) Complex

The title compound, [Cu2（C7H5O2）4（C2H6O）2], was synthesized by the reaction of benzoic acid, copper acetate and ethanol in an aqueous solution. Trypan blue dye exclusion method was used in experiment. X-ray single-crystal analysis has revealed that compound 1 （C32H32Cu2O10） crystallizes in the monoclinic system, space group C2/c, Mr = 703.66, a = 47.340（5）, b = 6.6613（4）, c = 22.028（2）A,β = 113.284（4）°, V = 6380.6（10） A^3, Z = 8, Dc= 1.465 g/cm^3, F（000） = 2896,μ = 1.388 mm^-11, the final R = 0.0515 and wR = 0.1172 for 5712 observed reflections with I 〉 2σ（I）. X-ray crystal structure analysis suggests that compound [CH2（C7H5O2）4（C2H6O）2] has a binuclear structure with two Cu（II） atoms coordinated by four benzoate groups and two ethanol molecules. The crystal packing is stabilized by intermolecular O-H...O hydrogen bonds. The compound inhibits the proliferation of K562 cells （chronic myeloid leukemic cells） significantly and dose-dependently in 48 h, and IC50 of K562 is 17.3μg/mL by trypan blue dye exclusion method.

Release performance and sustained-release efficacy of emamectin benzoate-loaded polylactic acid microspheres

High-performance liquid chromatography （HPLC） was employed to determine drug release rates based on emamectin benzoate concentrations in the medium. Release kinetics equations were used to fit the drug release behavior. The effects of particle size and release medium pH on the release rate were also investigated. The indoor toxicity of emamectin benzoate-loaded polylactic acid microspheres on the diamondback moth larva （Plutella xylostella） was studied to explore drug sustained-release performance. In acidic and neutral media, the drug release behavior of the microspheres was in accord with the first-order kinetics equation. Increasing the spray dosage of emamectin benzoate-loaded polylactic acid microspheres initially resulted in an equivalent insecticidal efficacy with the conventional emamectin benzoate microemulsion. However, the drug persistence period was four-fold longer than that observed using the conventional formulation. The developed emamectin benzoate-loaded polylactic acid microspheres showed dramatic sustained-release performance. A treatment threshold of greater than 35 mg mL-1 was established for an efficient accumulated release concentration of emamectin benzoate-loaded microspheres.

Three new compounds from the leaves of Acanthopanax senticosus Harms

Three new compounds named (2E)prenyl benzoate-4-O-α-L-arabinopyranosyl (1→6) β-D-glucopyranoside (1), 7-methoxy-8-O-β-D-glucopyranosyl coumarin (2), and 3,4'-dihydroxy-3'-methoxy benzenepentanoic acid (3) were isolated from the leaves of Acanthopanax senticosus Harms. The structures of new compounds were determined by means of 2D NMR experiments and chemical methods.

Effects of sodium benzoate on growth and physiological characteristics of wheat seedlings under compound heavy metal stress

In this study, we investigated the effect of exogenous sodium benzoate on wheat seedlings(Yangmai 16) grown under heavy metal stress. The results showed that 2.4 mmol kg-1 of heavy metals significantly inhibited growth and delayed emergence of wheat seedlings. Under compound heavy metal stress, application of 2-4 g L^-1 sodium benzoate significantly increased(P<0.01) chlorophyll content and chlorophyll fluorescence parameters Fv/Fm and Fv/Fo of wheat, compared to the control(water treatment). Further analysis showed that application of 2-4 g L^-1 sodium benzoate alleviated osmotic stress by promoting the accumulation of osmolytes such as soluble proteins and free proline, increased the activity of superoxide dismutase(SOD) and reduced malondialdehyde content(MDA). In contrast, higher concentrations of sodium benzoate solution(>6 g L^-1) inhibited the growth of wheat seedlings and even caused damage to seedlings. Correlation analysis showed that when the sodium benzoate concentration was in the range of 1.97-3.12 g L^-1(2016) and 1.58-3.27 g L^-1(2017), values of chlorophyll and its components, root activity, SOD activity, soluble protein, and free proline content were the highest. When the sodium benzoate concentration was raised to 2.59 g L^-1(2016) or 3.02 g L^-1(2017), MDA content was the lowest. Ultimately, exogenous sodium benzoate(2-4 g L^-1) facilitates root development and improves the root activity of wheat seedlings grown under compound heavy metals stress, thereby effectively alleviating the damage of compound heavy metal stress in wheat seedlings.