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Synthesis of (2R,3aR,8aR)-6-Chloro-3a-hydroxy-1,2,3,3a,8,8a- hexahydropyrrolo[2,3-b]indole-2-carboxylic Acid Methyl Ester by Reductive Cyclization

引用

Chinese Journal of Chemistry 2004年第4期22卷 365-370页

作者：洪文旭姚祝军 State Key Laboratory of Bioorganic and Natural Products Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences

A synthesis of (2R,3aR,8aR)-6-chloro-3a-hydroxy-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylic acid methyl ester (1) was achieved. An aldol reaction with Garner aldehyde, a hydroxyl introduction by Davis re-agent, and a reductive intramolecular ring-closure reaction were served as the key steps. This piece of work pro-vides a new way to synthesize the analogues of hexahydropyrrolo[2,3-b]indole, starting from readily available chemical substrates and inexpensive reagents.

关键词： aldol reaction Davis oxidation reductive ring-closure reaction indole derivative anticancer activity

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Immobilization of Chiral Catalyst on Amorphous Al2O3 for the Selective Hydrogenation of Ethyl 1H-indole-2-carboxylate

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Chemical Research in Chinese Universities 2014年第2期30卷 284-288页

作者： GUAN Ruqi CHAO Guoku YE Caiping WANG Yuxiang LIU Yanmei LI Haihua ZHAO Yajuan TAI Yulei College of Chemistry and Materials Engineering Wenzhou University Wenzhou 325027 P.R.China

Ru-B/γ-Al2O3 catalyst was prepared by reductant impregnation method,which was applied in the selective hydrogenation of ethyl 1H-indole-2-carboxylate for producing ethyl 2,3,3a,7a-tetrahydro-1H-indole-2-carboxylate with hydrogen as ***,we discussed the influences of substrate concentration,reaction solvent,hydrogenation temperature,initial hydrogen pressure and reaction time on the catalytic performance of the as-prepared *** obtained Ru-B/γ-Al2O3 catalyst showed a high-efficiency for the selective hydrogenation of ethyl 1H-indole-2-carboxylate（＞99％ conversion and selectivity） in i-propanol used as solvent at a concentration of 10％（mass fraction） of ethyl 1H-indole-2-carboxylate,a pressure of hydrogen of 6 MPa and a reaction temperature of 373 K.

关键词： Selective hydrogenation Supported amorphous catalyst Ru-B/γ-Al2O3 indole derivative

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Ester-Derivatized indoles as Fluorescent and Infrared Probes for Hydration Environments

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Chinese Journal of Chemical Physics 2018年第4期31卷 477-484,614页

作者： Xin-yue Huang MinYou Guang-liu Ran Hao-ran Fan Wen-kai Zhang Department of Physics and Applied Optics Beijing Area Major Laboratory Center for Advanced Quantum StudiesBelling Normal UniversityBelling 100875China Department of Chemistry Belling Normal UniversityBelling 100875China

Tryptophan derivatives have long been used as site-specific biological probes. 4-Cyanotrypto- phan emits in the visible region and is the smallest blue fluorescent amino acid probe for bio- logical applications. Other indole or tryptophan analogs may emit at even longer wavelengths than 4-cyanotryptophan. We performed FTIR, UV-Vis, and steady-state and time-resolved fluorescence spectroscopy on six ester-derivatized indoles in different solvents. Methyl indole- 4-carboxylate emits at 450 nrn with a long fluorescence lifetirne, and is a promising candidate for a fluorescent probe. The ester-derivatized indoles could be used as spectroscopic probes to study local protein environments. Our measurements provide a guide for choosing esterderivatized indoles to use in practice and data for computational modeling of the effect of substitution on the electronic transitions of indole.

关键词： Infrared probe Fluorescent probe Typtophan derivative indole derivative

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