Factors affecting the accumulation of 9-methoxycanthin-6-one in callus cultures of Eurycoma longifolia

A study was conducted to improve 9-methoxycanthin-6-one productivity （potential anti-tumour compound） from callus cultures of Emycorna longifolia （Tongkat All）. Several factors affecting 9-methoxycanthin-6-one production in callus cultures such as different medium compositions and physical factors were investigated and analyzed. Results show that a higher production of 9-methoxycanthin-6-one （3.84 mg-g-1 DW （Dry Weight）） is obtained from callus cultured in 1/4 MS basal media. At fructose of 2% （w/v）, the production of 9-methoxycanthin-6-one （4.59 mgg-1DW） is promoted to gain the highest yield, compared to other carbon sources tested. The addition of 2.0-mg·L^-1 dicamba also increases 9-methoxycanthin-6-one production （12.3 mg·g^-1 DW）. Higher production of 9-methoxycanthin-6-one was obtained at pH 5.5 （1.53 mg·g^-1 DW）. Production of 9-methoxycanthin-6-one （2.34 mg-g^-1 DW） in callus cultures is also increased when the medium is added with 1×10 ^-1μM phenylalanine. This study suggests that the successful production of 9-methoxycanthin-6-one in vitro cultures has a potential in large-scale production using bioreactor technology.

Synthesis, Crystal Structure and Properties of Ethyl 3,9-Dimethyl-7-phenyl-6H-dibenzo[b,d]pyran-6-one-8-carboxylate

ABSTRACT Ethyl 3,9-dimethyl-7-phenyl-6It-dibenzo[b,d]pyran-6-one-8-carboxylate （C24H20O4, Mr = 372.40） has been synthesized and its structure was determined by ^1H and ^1C NMR, ESI-MS, elemental analysis, and X-ray single-crystal diffraction. The crystal belongs to the monoclinic system, space group P21/n, with a = 8.3674（11）, b = 10.6683（14）, c = 11.3817（15） A, a = 95.596（2）, β = 109.866（2）, γ = 94.495（2）°, V= 944.2（2）A^3, Z= 2, Dc = 1.310 g/cm3, μ= 0.089 mm^-1, F（000） = 392, R = 0.0482 and wR = 0.1281 for 2916 observed reflections with I 〉 2σ（I）. In the crystal structure, the fused tricyclic nucleus of the title compound is not fully coplanar. Analysis of the crystal packing indicates aromatic π-π stacking interactions occurring between the fused tricyclic aromatic rings of neighboring molecules in which a maximum overlap of the x-electron systems was achieved. Fluorescence and thermal studies indicate that compound 3 has good optical properties and thermal stability.

Crystal Structure and Antiproliferative Activity of Ethyl 3,9-Dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6Hdibenzo[b,d]pyran-6-one-8-carboxylate

Ethyl 3,9-dihydroxy-9-methyl-7-phenyl-7,8,10-trihydro-6H-dibenzo[b,d]pyran-6-one-8-carboxylate（C（23）H（22）O6,Mr = 394.42） has been synthesized and its structure was determined by ~1H and ^（13）C NMR,ESI-MS,elemental analysis,and X-ray single-crystal diffraction.The crystal belongs to the triclinic system,space group P1,with a = 8.8220（17）,b = 9.881（2）,c = 12.157（2） A,α= 90.488（3）,β= 102.664（4）,γ= 98.799（3）°,V= 1020.8（3） A^3,Z= 2,Dc = 1.342 g/cm^3,μ= 0.099mm^（-1）,F（000） = 436,R = 0.0615 and wR = 0.2501 for 2592 observed reflections with（I2σ（I））.In the crystal structure,the coumarin ring system is planar and the 3：4 fused cyclohexane ring adopts distorted half-chair conformation.Rich hydrogen bonding interactions are formed between compound 2 and lattice water molecules.These interactions assemble molecules of 2 into 2D layered networks in an AB stacking sequence.Its in vitro antiproliferative activities against three human cancer cell lines were evaluated by MTT assay.

STUDY ON THE SYNTHESIS OF A NEW TYPE OF PHOSPHORUS HETEROCYCLIC COMPOUNDS-PYRAZOLO[3,4-d]-1,3,2-DIAZAPHOSPHORIN-6-ONE

1-substituted-5-benzoylamino-4-pyrazolecarboxamides(2)were prepared by the reaction of 1-substituted pyrazolo[3,4-d]-oxazinone(1) with amines in benzene.The compound 2 was refluxed with excess LiAlH_4 in a mixture of THF and ether,one of the two carbamoyl groups in the molecule 2 was reduced selectively.As the results,1-substituted-5- benzylamino-4-pyrazolecarboxamides(3)were obtained.Compounds 3 reacted with Cl_2PPh-X,or P(NET_2)_3,producing the title compounds(4). The conditions of the reactions were studied.

An Efficient Approach to 6, 7-Disubstituted-1H-quinoxalin-2-ones

A novel approach to the synthesis of 6, 7-disubstituted-1H-quinoxalin-2-ones is described.The title compounds were regioselectively prepared by starting from substituted phenylamines andchloroacetyl chloride through the efficient sequence of acylation, nitration, reduction, intramolecular alkylation, and oxidation.

PREVOST-WOODWARD HYDROXYLATION OF 3,5-CYCLO-24S-ETHYL-CHOLEST-22-EN-6-ONE

Preost-Woodward hydroxylation of 2 gave the 22S,23S-glycol(3), contrary to expectation.It is suggested that the formation of the two possible iodonium ions(4a and 4b)are reversible,thus allowing the discriminatory acetoxy group to follow the less hindered route,reacting with 4a virtually exclusively.

SYNTHESIS OF 4,6-DISUBSTITUTED 5-THIOXO-1,2,4-TRIAZIN-3-ONE FROM BENZOTHIOFORMANILIDE

A method of synthesis of 4,6-disubstituted 5-thioxo-1,2,4-triazin- 3-ones from benzothioformanilides and semicarbazide is described.And six new compounds were synthesized by this method.

STEREOCHEMISTRY OF THE BENZILIC ACID-TYPE REARRANGEMENT IN BASE-CATALYZED AUTOXIDATION OF 3α,5-CYCLO-5α-CHOLESTANE-6-ONE

The configuration of the hydroxy acid 2, a product from base-catalyzed autoxidation of 3α,5-cyclo-5α-cholestane-6-one,was established on the basis of NMR techniques and the mechanism of the formation of 2 was discussed.

A Facile Synthesis of 6β-Hydroxy-7α(H)-eudesma-4-en-3-one

A stereoselective total synthesis of 6β-hydroxy-7α(H)-eudesma-4-en-3- 1startingfrom (+)-dihydrocarvone 7 has been described.

The First Total Synthesis of Natural 6β-Cinnamoyloxy-1α- hydroxy-5, 10-bis-epi-eudesm-4-en-3-one

The first total synthesis of natural 6β-cinnamoyloxy-1α-hydroxy-5, 10-bis-epi- eudesm-4-en-3-one （1）, a highly complex natural eudesmane, was described.

H_3PMo_(12)O_(40) catalyzed three-component one-pot synthesis of 4,6-diarylpyrimidin-2(1H)-ones under solvent-free conditions

4,6-Diarylpyrimidin-2(1H)-one derivatives have been synthesized from three-component one-pot condensation of acetophe-none derivatives,aldehydes and urea in the presence of trimethylsilyl chloride and a catalytic amount of HPMoOunder solvent-free conditions.

Facile synthesis of[1,2,4]triazino[4,3-b][1,2,4,5]tetrazepin derivatives by a one-pot reactions using 4-amino-3-hydrazinyl-6-methyl-1,2,4-triazin-5(4H)-one

4-Amino-3-mercapto-6-methyl-l,2,4-triazin-5（4H）-one 1 converted to 4-amino-6-methy-3-（methylthio）-1,2,4-triazin-5（4H）-one by methylation with methyl iodide.Controlled hydrazination of the resulting compound afforded 4-amino-3-hydrazinyl-6- methyl-l,2,4-triazin-5（4H）-one 2 as a building block,to the synthesis of some novel derivatives of[1,2,4]triazino- [4,3,b][1,2,4,5]tetrazepine 3-6,by the reaction with 3-chloropentane-2,4-dione,chloro acetonitrile,1,3-dichloroacetone,and methyl bromoacetate.This general synthetic procedure can be extended to the preparation of wide variety of tetrazepines using 1,2- bielectrophiles derivatives.

A Facile Synthesis of 9,10-Dimethoxybenzo[6,7]- ox-epino[3,4-<i>b</i>]quinolin-13(6<i>H</i>)-one and Its Derivatives

A concise and efficient method for the synthesis of novel 9,10-imethoxybenzo[6,7]oxepino[3,4-b]quinolin13(6H)-one and its derivatives 7a-p has been developed via the intramolecular Friedel-Crafts acylation reactions of 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylic acids 6a-p with polyphosphoric acid (PPA) as catalyst and solvent under mild conditions. The key intermediates 6a-p were prepared through the in situ formation of ethyl 6,7-dimethoxy-2-(phenoxymethyl)quinoline-3-carboxylates 5a-p followed by hydrolysis with aqueous ethanolic sodium hydroxide solution. The novel synthetic method has the advantages of good yields, easy work-up, and environmentally friendly character, which may provide a novel highly efficient process for making quinoline and related azaheterocycle libraries.

Spontaneous Changes of Solid 5,7-di-<i>tert</i>-butylspiro(2,5)octa-4,7-diene-6-one in Storage Conditions at Room Temperature

On an example of spontaneous changes 5,7-di-tert-butylspiro (2,5) octa-4,7-diene-6-one at room temperature, a new example of condensations in a solid station is opened. The single crystal of 2-(3’, 5'-di-tert-butyl-4'-hydroxy-phenyl)-ethyloxy-p-cresole is produced as result of a structure transformation 5,7-di-tert-butylspiro (2,5) octa-4,7-diene-6-one in a solid phase at room temperature except a single crystal at transformation 5,7-di-tert-butylspiro (2,5) octa-4,7-diene-6-one a new substance is formed too. Spectrums 1Н and 13С NMR differ from similar spectrums of initial compound and the single crystal. New substance represents an admixture of isomeric compounds, capable reversible to be transformed in initial 5,7-di-tert-butylspiro(2,5) octa-4,7-diene-6-one and 2-(3’, 5'-di-tert-butyl-4'-hydroxyphenyl)-ethyloxy-p-cresole.

Synthesis, Reactions and Characterization of 1,1’-(1,4-Phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(ethan-1-one)

Reaction of 4,4’-(1,4-phenylene)bis(5-acetyl-6-methyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile) (1) with methyl iodide afforded the 4,4’-(1,4-phenylene)bis(5-acetyl-6-methyl-2-(methylthio)nicotinonitrile) (2). The reaction of 2 with hydrazine hydrate followed by diazotization reaction af-forded the 1,1’-(1,4-phenylenebis(3-amino-6-methyl-1H-pyrazolo[3,4-b]pyridine-4,5-diyl))bis(e-than-1-one) (3) and 1,1’-(1,4-phenylenebis(3-(chlorodiazenyl)-6-methyl-1H-pyrazolo[3,4-b]-pyridine-4,5-diyl))bis(ethan-1-one) (4) respectively. On the other hand, reaction of 4 with malononitrile, 2-cyanoethanethioamide, ethyl acetoacetate, acetyl acetone, ethyl benzoylacetate, diethylmalonate, ethyl cyanoacetate and phenacylbromide aiming to build up pyrazolotriazine or pyrazole ring on the ring system of 4. Structures of all newly synthesized heterocyclic compounds in the present study were confirmed by considering the data of IR, 1H NMR, mass spectra as well as that of elemental analyses.

Quantum Chemical Studies on the Corrosion Inhibition of Mild Steel by Piperidin-4-One Derivatives in 1 M H₃PO₄

The corrosion inhibition properties of 2,6-diphenylpiperidin-4-one (DPP) (1A) and 2,6-diphenyldihydro-2H-thiopyran-4(3H)-one (DPDT) (1B) for mild steel in 1 M phosphoric acid were studied using weight loss, potentiodynamic polarization and electrochemical impedance spectroscopic techniques. The effect of temperature on the corrosion behavior of mild steel has been examined in the temperature range 303 - 328 K. The inhibition efficiency increases with increasing inhibitor concentration but decreases with increasing temperature. Potentiodynamic polarization studies indicated the mixed nature of inhibitors. The adsorption of the inhibitors on mild steel surface obeyed the Langmuir adsorption isotherms. The density functional theory (DFT) at the B3LYP/6- 31G (d) basis set level was performed on 1A and 1B to investigate the correlation between molecular structure and the corresponding inhibition efficiency (%). The quantum chemical parameters such as EHOMO, ELUMO, the energy gap (E), hardness (η), softness (S), dipole moment (μ), electron affinity (A), ionization potential (I), the absolute electronegativity (χ), the fraction of electron transferred (N), electrophilicity index (ω), the back-donation (EBack-donation) and Mulliken population analysis have been calculated.

Visible-light-induced radical-cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole:Access to benzoimidazo[2,1-a]isoquinolin-6(5H)-ones

A metal-free visible-light-induced synthesis of aza-polycyclic aromatic hydrocarbons via cascade alkylation/cyclization of N-methacryloyl-2-phenylbenzimidazole was developed.The reaction was carried out with inactive alkanes and cyclic ethers as alkylation reagents,and phenanthrenequinone(PQ)as a direct hydrogen-atom transfer(HAT)photocatalyst.The desired products were obtained in moderate to good yields at room temperature under air.

Synthesis,Crystal Structure and Anti-tumor Activity of Ethyl 3-(4-methoxyphenyl)-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylate

The title compound（ethyl 3-（4-methoxyphenyl）-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylate） has been synthesized,and its crystal structure was characterized by X-ray single-crystal diffraction.The crystal belongs to monoclinic,space group P21/n,with a = 10.124（4）,b = 11.754（4）,c = 13.792（5） ,β = 111.533（3）o,V = 1526.6（10） 3,Z = 4,C17H19O6,Mr = 319.32,Dc = 1.389 g/cm3,F（000） = 676,λ（MoKα） = 0.71073 ,μ = 0.105 mm-1,R = 0.0660 and wR = 0.2027 for 2993 observed reflections（I 2σ（I））.The compound shows potent anti-tumor activity in vitro.

Synthesis, Characterization, and Antioxidation Evaluation of Novel Spiro-5-(fluoren-9’-yl)-6-azauracil and Their <i>N</i>,<i>N</i>-Dialkyl Derivatives

In search for new antioxidant agents derived from 6-azauracil, the spiro-5-(flurin-9’-yl)-6-azauracil 3 and their N,N-disubstituted-6-azauracils 4 - 17 have been synthesized using various methods and reaction conditions. Structure of the new synthesized compounds was deduced from elemental analysis and spectral measurements, for example IR, 1H/13C NMR and mass spectroscopy. The antioxidant evaluation of the new targets showed that the activity increases in the order of 8 > 10 > 6 > 7 > 9 in comparison with 2,2-Diphenyl-1-picrylhydrazyl (DPPH) and ascorbic acid as standards.

花椒属植物对口腔致病菌的抗菌活性(英文)

目的:比较6种花椒属(Zanthoxylum)植物乙醇提取物对口腔致病菌的抗菌活性,从中寻找抗菌的活性物质。方法:用于抗菌活性实验的口腔致病菌是变形链球菌(StreptococcusmutansATCC25175),放线菌(Actinomycesnaeslundii ATCC12104)和嗜血放线伴生杆菌(ActinobacillusactinomycetemicomtansATCC43717)。抗菌实验为琼脂扩散法(agardiffusion assays)和最低抑菌浓度法(MIC)。结果:拟蚬壳花椒(Z.lactum)的根对这些口腔致病菌表现出最强的抗菌活性,其次是两面针(Z.nitidum)和异叶花椒(Z.dimorphyllum)的根。进而对异叶花椒(Z.dimorphyllum)的根进行化学成分研究,分离到4个已知化合物,其中化合物Canthin 6 one对这三种口腔致病菌均有很强的抗菌能力,最低抑菌浓度(MIC)在15.6和62.5 μg/mL之间。结论:Canthin 6 one可能是异叶花椒抗菌活性的物质基础。