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Studies Directed toward Synthesis of the Structure Proposed for Stereocalpin A

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Chinese Journal of chemistry 2011年第6期29卷 1185-1191页

作者： Huang, Yixian Wu, Yikang State Key Laboratory of Bioorganic and natural products chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

Some synthetic efforts directed to the proposed structure of stereocalpin A are disclosed. The stereogenic centers in the aldol unit were installed using the method of Evans and the intermediates obtained through a reliable route helped to reveal that the spectroscopic data reported earlier in the literature for the same structures were either erroneous or irrelevant.

关键词： peptide natural product aldol reaction amino acid condensation

Syntheses and Anti-cancer Activities of Glycosylated Derivatives of Diosgenin

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Chemical research in Chinese Universities 2017年第1期33卷 80-86页

作者： TAN Yonghua XIAO Xiao YAO Jianing HAN Fei LOU Huayong LUO Heng LIANG Guangyi BEN-DAVID Yaacov PAN Weidong Key Laboratory of chemistry for natural products of Guizhou Province and Chinese Academy of Sciences Guiyang 550002 P R. China Key Laboratory of chemistry for natural products of Guizhou Medical University Guiyang 550001 P. R. China

In order to obtain better anti-cancer compounds, nine glycosylated derivatives were designed and synthe- sized using diosgenin as starting material. Their structures were confn-med by 1H NMR, 13C NMR and MS spectra. The anti-cancer activities of intermediate compounds 5a-5i and the target compounds 6a-6i were investigated against human leukemia HEL, K562, HL60 and melanoma WM9 cell lines via MTT method. The bioassay results show that these derivatives possess good inhibitory activities against the four cancer cell lines. Furthermore, these derivatives show better inhibitory activities against K562 than against other cell lines, and most derivatives show better inhibitory activities than the parental material. Moreover, compounds 6a--6i are more active than their inter- mediates 5a--5i when against these ceils. The above results demonstrate the effects of glycosylation on 3-OH of di- osgenin and acetylation of the sugar moiety on their antitumor activities.

关键词： Diosgenin Glycosylation Anti-cancer activity

Synthesis and Crystal Structure of (E)-2-phenyl-6,7dihydrobenzofuran-4(5H)-one O-cyanomethyl Oxime

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Chinese Journal of Structural chemistry 2013年第9期32卷 1334-1338页

作者：金蕾方胡彪曹成桥黄年玉邹坤汪鋆植 Hubei Key Laboratory of natural products research and Development College of Chemistry and Life Sciences China Three Gorges University Hubei Tujia Institute of Medicine

A pair of E/Z-isomers of 2-phenyl-6,7-dihydrobenzofuran-4（5H）-one O-cyanomethyl oxime,C16H14N2O2,as potential drugs for treating peptic ulcer and other acid-related diseases have been synthesized and characterized by IR,MS and NMR ***,the crystal of IIIa was obtained and determined by X-ray single-crystal *** data： monoclinic system,space group P21 /c,a = 8.423（8）,b = 19.596（16）,c = 8.770（8）,β = 107.750（12）°,V = 1379（2）3,Z = 4,F（000） = 560,Dc = 1.283 g/cm3,μ = 0.086 mm 1,R = 0.0681 and wR = 0.2029 for 14472 independent reflections（Rint = 0.0782） and 2428 observed ones（I 2σ（I））.

关键词： X-ray diffraction crystal structure oxime ether H+/K+-ATPase inhibitory activity cytotoxic activity

Transport properties of dilute ammonia-noble gas mixtures from new intermolecular potential energy functions

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Chinese Journal of Chemical Engineering 2017年第12期25卷 1727-1734页

作者： Farshid Zargari Delara Mohammad-Aghaie Maryam Lotfi Masoume Ghorbanipour Mohammad Mehdi Alavianmehr Omolbanin Shahraki Department of chemistry Shiraz University of Technology Shiraz Iran Medicinal and natural products chemistry research Center Shiraz University of Medical Sciences Shiraz Iron Department of Physical chemistry University of Tabriz Tabriz Iran Zahedan University of Medical Sciences Zahedan Iran

Previously we have determined the dilute mixture transport properties of slightly polar fluorocarbons using the inverted intermolecular potential energies(Ind. Eng. Chem. Res. 45(2006) 9211–9223). In the present paper, the corresponding states correlations for reduced viscosity collision integrals were employed to obtain effective unlike interaction potential models for dilute binary mixtures of highly polar molecule ammonia with noble *** inverted potentials were fitted to the Morse–Spline–van der Waals(MSV), model potential. The method of least-squares fitting was then applied to identify best consistence force parameters for each ammonia-noble gas mixture, taking advantage of experimental viscosities, diffusion coefficients and thermal *** proposed potential models were compared with those obtained from other sources, in order to assess the extent of their *** potentials were later employed to calculate transport properties of the studied mixtures. Then, results were compared with those reported in the literature, which led to the acceptable agreement.

关键词： lntermolecular potential energy Transport properties Inversion pmcedure Mixture Ammonia Noble gas

Studies on the Physicochemical Properties, Structure and Antitumor Activity of an Oligosaccharide Homologue SnS-2 from the Root of Scrophularia ningpoensis Hemsl.

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Chinese Journal of chemistry 2004年第5期22卷 492-497页

作者：邓军娥张健陈晓明柯炜田庚元 State Key Laboratory of Bio-organic & natural products chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

An oligosaccharide homologue named SnS-2 was isolated from the root of Scrophularia ningpoensis Hemsl. SnS-2 was purified by means of gel-permeation chromatography and ion-exchange chromatography. Its physico-chemical properties, including carbohydrate content and molecular weight were determined. The structure of SnS-2 was elucidated by chemical methods along with 1H and 13C NMR spectroscopy, including two-dimensional DQCOSY and H-detected 1H, 13C HMQC experiments. These results show that SnS-2 possesses a backbone con-sisting of terminal a-Galp-(1, a-Galp-(16), a-Glcp-(16) and nonreducing end -Fruf-(2. The bioactive as-say showed that it could inhibit the growth of Lewis pulmonary carcinoma implanted in mice.

关键词： Scrophularia ningpoensis Hemsl. physicochemical property structure antitumor activity oligosaccharide homologue

Synthesis of 15-Demethyl Brefeldin A and Its 7-epi Isomer

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Chinese Journal of chemistry 2007年第6期25卷 802-807页

作者：沈鑫杨永青胡祺黄嘉慧高剑伍贻康 State Key Laboratory of Bio-organic and natural products chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

Synthesis of 15-demethyl brefeldin A and its 7-epimer is detailed. X-ray crystallographic structure for 15-demethyl brefeldin A is also disclosed.

关键词： antibiotics asymmetric synthesis analogue lactone

Synthesis of chiral phosphine derivatives through a copper（I）-catalyzed desymmetric SNAr reaction

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Science China chemistry 2025年

作者： Shuai Zhang Pei-Zhi Liu Yan-Bo Li Qi Zhang Jun-Zhao Xiao Yi-Fan Wang Tian-Yu Wei Jia-Wei Jiang Ye Wang Qian Peng Liang Yin Key Laboratory of Fluorine and Nitrogen chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences State Key Laboratory of Elemento-Organic chemistry and Tianjin Key Laboratory of Biosensing and Molecular Recognition College of Chemistry Frontiers Science Center for New Organic Matter Nankai University Haihe Laboratory of Sustainable Chemical Transformations

Axially chiral phosphines are a class of extremely important ligands in asymmetric catalysis. Herein, an unprecedented copper（I）-catalyzed asymmetric SNAr reaction with HP（S）R2is uncovered, which delivers a series of axially chiral phosphine derivatives in high yields with excellent enantioselectivity. Furthermore, the diastereoselective reaction with the kinetic resolution of racemic HP（S）ArR proceeds smoothly, providing the products with moderate diastereoselectivity and excellent enantioselectivity. Control experiments indicate that HP（S）Ph2is much more active than HPPh2and HP（O）Ph2as the pronucleophile in the present reaction. It is found that the SNAr reaction （the first SNAr） proceeds in a desymmetric manner, providing the desired chiral products while a continued SNAr reaction （the second SNAr） slightly occurs in a kinetic resolution manner in the present catalytic system, which enhances the ee of the desired chiral products. DFTcalculations support a concerted reaction pathway rather than a step-wise mechanism. Finally, axially chiral olefin-phosphines produced by the present method work as suitable ligands in Pdcatalyzed asymmetric allylic substitution with C-, N-, and O-nucleophiles and Rh-catalyzed asymmetric addition of arylboronic acid to benzil.

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Synthesis of propyl O-(α-L-rhamnopyranosyl)-(1→3)-[2,4-di-O-(2s-methylbutyryl)-α-L-rhamno-pyranosyl]-(1→2)-(3-O-acetyl-β-D-glucopyranosyl)-(1→2)-β-D-fucopyranoside,the tetrasaccharide moiety of Tricolorin A

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Chinese Journal of chemistry 1998年第1期16卷 78-89页

作者：卢寿福欧阳琴琴郭忠武俞飚惠永正 State Key Laboratory of Bio-organic and natural products chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

Propyl O-(α-L-rhamncpyranosyl)-(1→3)-[2,4-di-O-(2s-methylbutyryl)-α-L-rham-nopyranosyl]-(1→2)-(3-O-acetyl-β-D-glucopyranosyl)-(1→2)-β-D-fucopyranoside (1), the tetrasac-charide moiety of Tricolorin A, was synthesized in total 23 steps with a longest linear sequence of 10 steps, and overall yield of 3.7% from D-Glucose. The isomerization of the dioxolane-type berzyli-dene in the presence of NIS/AgOTf was observed. Tetrasaccharide 1 exhibited no activity against the cultured P388 cell as Tricolorin A did.

关键词： Propyl O-(α-L-rhamnopyranosyl)-(1→3)-[2,4-di-O-(2s-methylbutyryl)-α-L-rham-nopyranosyl]-(1→2)-(3-O-acetyl-β-D-glucopyranosyl)-(1→2)-β-D-fucopyranoside synthesis dioxo-lane-type benzylidene Tricolorin A

Synthesis of 1,2-Dioxane Type Antimalarial Peroxides

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Chinese Journal of chemistry 2006年第9期24卷 1180-1189页

作者：刘鹤华张琦金红霞沈鑫伍贻康 State Key Laboratory of Bio-organic and natural products chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

Synthesis of five simple analogues of peroxyplakoric acid by using Kobayashi＇s method to construct the key 1,2-dioxane core is detailed.

关键词： peroxide cyclization hemiketal antimalarial