Synthesis and Crystal Structure of (Z)-Methyl-3-methoxy-2-{2-[(4-(E-3-p-tolylacryloyl)phenoxy)methyl]phenyl}acrylate

The title compound,(Z)-methyl-3-methoxy-2-{2-[(4-(E-3-p-tolylacryloyl)phenoxy)-methyl]phenyl}acrylate,was synthesized and determined by X-ray single-crystal diffraction.The crystal belongs to the triclinic system,space group P1 with a=8.0157(8),b=12.5748(13),c=13.3768(14)Å,α=64.770(2),β=75.720(2),γ=89.784(2)°,μ=0.085 mm^(-1),Mr=442.49,V=1174.1(2)Å3,Z=2,Dc=1.252 g/cm^(3),F(000)=468,T=294(2)K,R=0.0603 and wR=0.1498 for 2644 observed reflections with I〉2σ(I).X-ray diffraction analysis reveals that the single crystal contains strong non-classical hydrogen bonds.The preliminary bioassay showed that the title compound exhibits inhibitory activity against the Pseudoperoniospora cubensis and Rhizoctonia solani at the test concentration of 200 mg/L.

Stereoselective Synthesis of 2-(4-Hydroxyphenyl)-3-hydroxymethyl-1,4-benzodioxane-6-aldehyde—The Key Intermediate of Sinaiticin

2-(4-Hydroxyphenyl)-3-hydroxymethyl-1,4-benzodioxane-6-aldehyde 8,the key intermediate of sinaiticin 10,was synthesized in 6 step from caffeic acid 4 and 4- hydroxybenzsaldehyde 1.the coupling reaction is the key step.

Synthesis and Crystal Structure of a New Quinazolinone Compound 2,3-Dihydro-2-(2-hydroxyphenyl)-3-phenyl-quinazolin-4(1H)-one

A new quinazolinone compound 2,3-dihydro-2-(2-hydroxyphenyl)-3-phenyl- quinazolin-4(1H)-one 3 ([C20H16O2N2]?C2H5OH, Mr = 362.42) and compound 2-(2-hydroxy- benzylidene-amino)-N-phenyl-benzamide 2 (C20H16O2N2, Mr = 316.34) were prepared from a precursor of 2-amino-N-phenyl-benzamide 1 (C13H12ON2, Mr = 212.25). Compound 3 was characterized by single-crystal X-ray diffraction analysis. The crystal belongs to orthorhombic, space group Pbca with a = 1.2889(11), b = 1.6170(14), c = 1.7729(15) nm, V = 3.695(6) nm3, Z = 8, F(000) = 1536, Mr = 362.42, Dc = 1.303 g/cm3, μ(MoKα) = 0.087 mm-1, R = 0.0447 and wR = 0.0879. The crystal structure analysis indicates that the title compound has a two-dimensional network structure formed by hydrogen bonds and electrostatic interactions.

Synthesis, Crystal Structure and Antitumor Activity of (E)-1-(7-Methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5- yl)-3-(2-methoxyphenyl)-2-(1H-1,2,4-triazol-1-yl)propenol

The title compound, （E）-1-（7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl）- 3-（2-methoxyphenyl）-2-（1H-1,2,4-triazol-1-yl）propenol （3a）, was synthesized by the Aldol con- densation reaction of 1-（7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl）-2-（1,2,4-triazol- 1-yl）ethanone with 2-methoxybenzaldehyde and then reduced with NaBH4, and its crystal structure was determined by single-crystal X-ray diffraction： monoclinic system, space group P21 with a = 6.2002（3）, b = 12.8452（7）, c = 13.2257（7） ？, Z = 2, V = 1031.23（9） ？3, Mr = 407.46, Dc = 1.312 Mg/m3, S = 1.054, μ = 0.091 mm-1, F（000） = 432, the final R = 0.0353 and wR = 0.0769 for 3161 observed reflections （I 〉 2σ（I））. X-ray analysis displays that the title compound adopts an E configuration for the C（7）=C（8） double bond and S configuration for the chirality center with the specific rotation of –63.75°. Furthermore, the stability of the crystal was maintained through the intermolecular hydrogen bond O（1）–H？？？N（3）. The antitumor assay exhibits that the title compound 3a （E configuration） has a good antitumor activity against the Hela cell line with the IC50 value of 36.9 μM, which is better than that of 3b （Z configuration）.

Effect of Temperature on the Reaction of 2-(N-acetylamine)-3-(3,5-di-<i>tert</i>-butyl-4-hydroxyphenyl)-propionic Acid with Oxygen in an Alkaline Condition

Results of oxidation 2-(N-acetylamine)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid oxygen depend on temperature. At 55℃?- 60℃, 2,4-di-tert-butylbicyclo(4,3,1)deca-4,6-dien-8-(N-acetylamine)-3,9-dion-1-oxa is formed. The constitution is based on dates of spectrums 1Н and 13С NMR. At 95℃?- 97℃, mixtures of 2,4-di-tert-butylbicyclo(4,3,1)deca-4,6-dien-8-(N-acetylamine)-3,9-dion-1-oxa and of 6,8-di-tert-butyl-3-(N-acetylamine)spiro(4,5)deca-1-oxa-5,8-dien-2,7-dione are produced. Structures are calculated by the method of Hartrii-Foka. Values of enthalpies and of entropies allow to assume dynamic isomerism.

Synthesis and Crystal Structure of(E)-Ethyl 2-(4-(2,4-dimethoxybenzylideneamino)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-3-ylthio)acetate

The crystal structure of the title compound(E)-ethyl 2-(4-(2,4-dimethoxy benzylide-neamino)-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazol-3-ylthio)acetate(4,C_(24)H_(28)N_(4)O_(7)S,Mr=516.17)was synthesized and determined by X-ray single-crystal diffraction.The crystal belongs to the monoclinic system,space group P2_(1)/n with a=13.162(2),b=8.4506(13),c=22.602(4)Å,β=99.888(3)°,μ=0.183 mm^(-1),V=2476.5(7)Å^(3),Z=4,D_(c)=1.385 g/cm^(3),F(000)=1088,T=110(2)K,R=0.0426 and wR=0.1216 for 3859 observed reflections with I 2σ(Ⅰ).

Synthesis of 3-(4-hydroxyphenyl)-4-methyl-6-methoxy-7-hydroxycoumarin and its analogues as angiogenesis inhibitors

3-（4-Hydroxyphenyl）-4-methyl-6-methoxy-7-hydroxycoumarin （2a） and its analogues with different substituents at the p-position of 3-phenyl group were designed and synthesized as the non-steroidal analogues of 2-methoxyestradiol （2-ME 1）. The desired compounds were synthesized via a novel and simple route and the effects of specific substituents on their antiangiogenesis activities were investigated with Human umbilical vein endothelial cells （HUVECs） proliferation assays. Preliminary biological screening showed that compounds 2a and 2d （IC50 = 61.0 and 76.7 ktM, respectively） have potential anti-angiogenesis activities. The bulk of the group at the p-position of 3-phenyl group likely play an important role in their activities.

Apoptotic effect and mechanisms of AHPN on human skin malignant melanoma cell A375

Objective： To study apoptotic effects of synthetic retinoic acid 6-[3-（1-adamantyl）-4-hydroxyphenyl]-2-naphthalene carboxylic acid（AHPN） on human skin malignant melanoma A375 cells in comparison with the natural ligand all-trans-retinoic acid（ATRA） in vitro and the mechanisms related to the actions of AHPN. Methods：MTT assay was used to determine the anti-proliferative effects of AHPN and ATRA on A375 cells. Flow cytometry was performed to investigate the influence of AHPN and ATRA on cell cycle and cell apoptosis. In addition, transfection and luciferase activity assays were employed to explore the mechanisms of how AHPN executes its proapoptotic function. Results：Firstly, AHPN promoted apoptosis and GI arrest in A375 cells compared with ATRA. Secondly, the activity of NF-K B in A375 cells treated with AHPN increased 2-3 times compared with solvent DMSO treatment. Conclusion：AHPN, in comparison with ATRA, is a more effective alternative for therapy of malignant melanoma. The potentially proapoptotic function of AHPN requires activation of NF-K B.

冰糖草化学成分的分离与鉴定

目的研究冰糖草(Scoparia dulcis L.)全草乙醇提取物的正丁醇萃取部位的化学成分。方法运用硅胶、Sephadex LH-20和半制备HPLC等各种方法进行分离纯化,根据理化性质和波谱数据等鉴定化合物结构。结果分离得到16个化合物,分别鉴定为(2S)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-O-β-glucopyranoside(1)、(2R)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-O-β-glucopyranoside(2)、对羟基苯甲酸甲酯(3)、对羟基苯甲醛(4)、2-唑啉酮(5)、对羟基苯乙酮(6)、薏苡素(7)、苯甲酸(8)、对羟基肉桂酸甲酯(9)、黑麦草内酯(10)、异黑麦草内酯(11)、橙酰胺乙酸酯(12)、apigenin 7-O-rutinoside(13)、hispidulin-7-O-rutinoside(14)、isoschaftoside(15)和schaftoside(16)。结论化合物1为新化合物,化合物13~16为首次从冰糖草中分离得到。

A New Quinolizidine Alkaloid from Boehmeria siamensis

A new quinolizidine alkaloid. 3-(4-hydroxyphenyl)-4-(3-methoxy-4-hydroxyphenyl)-3,4-dihydroquinolizidine (1). was isolated from the ethanol extract of the whole plants of Boehmeria siamensis Craib. Its structure was elucidated on the analysis of ID NMR and 2D NMR spectrum.

A New Chromone Derivative from Stellera chamaejasme L

A new chromone derivative, 3-[1- (2, 4, 6-trihydroxyphenyl) 3-di-(4-hydroxyphenyl) 1-propanone-2-yl] 5,7-dihydroxy-8-di(4-hydroxyphenyl)methyl-4H-1-benzopyran-4-one, named as isomohsenone was isolated from the roots of Stellera chamaejasme L. together with known chamaechromone. Its structure was determined by the analysis of MS and NMR data, especially 2D NMR spectra.

匙叶八角中的酚性成分

目的研究匙叶八角Illicium spathulatum枝叶的化学成分。方法匙叶八角枝叶的甲醇提取物经醋酸乙酯和正丁醇萃取部分经过反复的硅胶柱色谱、反相柱色谱及Sephadex LH-20凝胶色谱等方法分离,用波谱分析法鉴定化合物结构。结果分离得到了13个酚性化合物,分别鉴定为苏式-(1,2-二羟基丙基)-3,5-二甲氧基苯-4-O-β-D-葡萄糖苷(1)、5,7,3′,4′-tetrahydroxy-2-methoxy-3-flavanone-3-hydrate(2)、4-O-(2-hydroxy-1-hydroxymethylethyl)-dihydroconierylalcohol(3)、2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone(4)、槲皮素(5)、槲皮素-3-O-α-L-吡喃鼠李糖苷(6)、山柰酚(7)、山柰酚-3-O-α-L-吡喃鼠李糖苷(8)、儿茶素(9)、丁香酸-4-O-β-D-吡喃葡萄糖苷(10)、丁香酸甲酯-4-O-β-D-吡喃葡萄糖苷(11)、3,4-二羟基苯甲酸(12)、羟基酪醇(13),同时还分离到大量的莽草酸(14)。结论化合物1是一个新苯丙素葡萄糖苷类化合物,命名为匙叶八角苷。化合物2是首次从植物中分离得到的黄酮醇类物质氧化的水合物,可能是一人工产物,其余化合物均为首次从匙叶八角中分离得到。

Constituents from the Roots of Semiaquilegia adoxoides

In present literature search, some cyano-containing compounds, which are very rare in plants, from the traditional anticancer herb Tiankuizi were reported. To find more cyano-containing compounds in the important plant Semiaquilegia adoxoides （DC） Makino （Chinese name Tiankuizi）, the isolation of the chemical constituents was investigated for advancing the research. Two new compounds, a new alkaloid, 1,2,3,4-tetrahydro-6-hydroxy-1[（3,4-dihydroxyphenyl）methyl]-7-methoxy-2,2-dimethyl-isoquinolinium, named Semiaquilegine A （1）, and a new ester, 3-（4＇-hydroxyphenyl）-2-propenoic acid （4＂-carboxyl）-phenyl ester （2）, and four cyano-containing compounds, （Z）-6a-（β-D-glucosyloxy）-4a,5a-dihydroxy-2-cyclohexene-△^1,a-acetonitrile （3）, （L0-6α-（β-D-glucosyloxy）-4α-hydroxy-2-cyclohexene-△^1,α-acetonitrile （4）, lithospermoside （5）, ehretioside B （6）, as well as eleven known compounds, were isolated from the roots of Semiaquilegia adoxoides. The structures of new compounds 1 and 2 were elucidated mainly by 1D/2D-NMR techniques. Very unusual cyano-containing compounds 3 and 4 were first isolated from Ranunculaceae family. Hitherto, there were six cyano-containing compounds found in the herb.

New Isoflavonoid Glycosides from the Rhizomes of Iris leptophylla Lingelsh.

Two new isoflavonoid glucosides, 5-hydroxy-6,7-methylenedioxy-isoflavone-4＇-O-D-glucopyranosyl （2→〉l）-L-rhamnoside （irilone-bioside） （compound 1） and 5,4＇-methoxy-6,7-methylenedioxyisoflavone-3＇-O-β-D-glucoside （irisleptophyllidin） （compound 2）, together with five known compounds, nigricanin- 4＇-O-β-D-glucoside （compound 3）, irifloside （compound 4）, irigenin （compound 5）, 5, 3＇, 4＇-trimethoxy-6,7-methylenedioxyisoflavone （compound 6）, and nigricanin （compound 7） were isolated from the alcoholic extract of rhizomes of Iris leptophylla Lingelsh. Their structures were elucidated by spectroscopic methods.