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Synthesis of novel benzo[b]pyrimido[4',5':5,4]thieno[2,3-e][1,6]naphthyridine-8-ones via pictet–spengler cyclization

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Chinese Chemical Letters 2016年第2期27卷 261-264页

作者： Dao-Lin Wang Xiao-Ce Shi Yong-Yang Wang Jian Ma College of Chemistry and Chemical Engineering Liaoning Key Laboratory of Synthesis and Application of Functional Compound Bohai University

An efficient method for the synthesis of novel benzo[b]pyrimido[4′,5′：5,4]thieno[2,3e]-[1,6]naphthyridine-8-one derivatives via pictet-spengler cyclization is reported. The reaction of 4-（3-aminopyrimido[4,5-d]thieno-2-yl）quinoline-2-ones, which could be obtained from Thorpe-Ziegler isomerization of 4-bromomethylquinoline-2-ones and 5-cyano-1,6-dihydro-4-methyl-2-phenyl-6-thioxopyrimidine,with aromatic aldehydes in the presence of BF3·OEt2 gives pyrimidothieno[1,6]naphthyridines in good yields.

关键词： 4-Bromomethylquinoline-2-one 5-Cyano-6-thioxopyrimidine Pyrimido[4′,5′:5,4]thieno[2-3e]naphthyridine Thorpe-Ziegler reaction pictet-spengler reaction

Strictosidine synthase,an indispensable enzyme involved in the biosynthesis of terpenoid indole andβ-carboline alkaloids

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Chinese Journal of Natural Medicines 2021年第8期19卷 591-607页

作者： CAO Ning WANG Chang-Hong The MOE Key Laboratory for Standardization of Chinese Medicines Shanghai R&D Centre for Standardization of Chinese MedicinesInstitute of Chinese Materia MedicaShanghai University of Traditional Chinese MedicineShanghai 201203China

Terpenoid indole(TIAs)andβ-carboline alkaloids(BCAs),such as suppressant reserpine,vasodilatory yohimbine,and antimalarial quinine,are natural compounds derived from *** compounds can exert powerful pharmacological effects but be obtained from limited source in *** whole biosynthetic pathway of TIAs and BCAs,The pictet–spengler reaction catalyzed by strictosidine synthase(STR;EC:4.***.3.2)is the rate-limiting ***,it is necessary to investigate their biosynthesis pathways,especially the role of STR,and related findings will support the biosynthetic generation of natural and unnatural *** review summarizes the latest studies concerning the function of STR in TIA and BCA biosynthesis,and illustrates the compounds derived from *** substrate specificity of STR based on its structure is also *** that contain sixbladed four-strandedβ-propeller folds in many organisms,other than plants,are *** presence of these folds may lead to similar functions among *** expression of STR gene can greatly influence the production of many *** is mainly applied to product various valuable drugs in plant cell suspension culture and biosynthesis in other carriers.

关键词： Biosynthesis pictet-spengler reaction β-Carboline alkaloids Strictosidine synthase Terpenoid indole

Diversity-oriented synthesis of marine sponge derived hyrtioreticulins and their anti-inflammatory activities

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Chinese Journal of Natural Medicines 2022年第1期20卷 74-80页

作者： CHEN Bo-Ru GAO Cheng-Long LIU Jin GUO Yue-Wei JIANG Jian-Lan PANG Tao LI Xu-Wen School of Chemical Engineering and Technology Tianjin UniversityTianjin 300350China State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China State Key Laboratory of Natural Medicines New Drug Screening CenterChina Pharmaceutical UniversityNanjing 210009China Open Studio for Druggability Research of Marine Natural Products Qingdao National Laboratory for Marine Science and TechnologyQingdao 266237China

Diversity-oriented synthesis is aimed to increase the chemical diversity of target natural products for extensive biological activity *** ring is an important functional group in a large number of drugs and other biologically active agents,and indole-containing natural products have been frequently isolated from marine sources in recent *** this paper,a series of indole-containing marine natural hyrtioreticulin derivatives,including 19 new ones,were designed,synthesized through a key pictet-spengler reaction,and evaluated for their inflammation related *** 13b displayed the most promising activity by inhibiting TNF-αcytokine release with an inhibitory rate of 92%at a concentration of 20μmol·L^(−1).A preliminary structure-activity relationship analysis was also *** research may throw light on the discovery of marine indole alkaloid derived anti-inflammatory drug leads.

关键词： Indole alkaloid pictet-spengler reaction Inflammation Hyrtioreticulin

First total synthesis of marine alkaloid hyrtiosulawesine

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Chinese Chemical Letters 2010年第11期21卷 1307-1309页

作者： Pu Yong Zhang Sheng Biao Wan Su Mei Ren Tao Jiang School of Medicine and Pharmacy Key Laboratory of Marine DrugsMinistry of EducationOcean University of ChinaQingdao 266003China

Hyrtiosulawesine was isolated from Indonesian specimens of the marine sponges Hyrtios erectus and *** in *** report here the first total synthesis of hyrtiosulawesine using an efficient and convenient synthetic strategy which could be widely used in the synthesis of otherβ-carboline *** structures of new compounds were confirmed by 1H NMR,13C NMR and HRMS.

关键词： β-Carboline Hyrtiosulawesine pictet-spengler reaction Tryptamine Total synthesis

First Total Synthesis of the Proposed Structures of Orisuaveolines A and B

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Chinese Journal of Chemistry 2013年第1期31卷 123-126页

作者： Jie Zhang Shijun Da Xiaolin Feng Xiaoyi Chen Jianhui Jiang Ying Li State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering Lanzhou University Lanzhou Gansu 730000 China

First total synthesis of the proposed structures of β-indoloquinazoline alkaloids orisuaveolines A and B is re- ported. The key steps of the synthesis included a pictet-spengler reaction to build a six-member lactam which fur- ther transformed into target molecular by a one-pot condensation. This synthesis provided an access to the proposed structures of orisuaveolines A and B in a short and convenient manner from inexpensive, commercially available starting materials. The structures of our synthesized products were confirmed by 2D-NMR experiments.

关键词： orisuaveolines A and B indoloquinazoline alkaloids pictet-spengler reaction one-pot condensation

Synthesis of new chiral 1,2,3,4-tetrahydroisoquinoline β-amino alcohols from L-DOPA

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Chinese Chemical Letters 2008年第11期19卷 1271-1273页

作者： Geng Xu Zhan Zhu Liu Institute of Materia Medica Peking Union Medical College ＆ Chinese Academy of Medical Science Beijing 100050 China

Four new chiral 1,2,3,4-tetrahydroisoquinoline-derived β-amino alcohols were synthesized from L-DOPA in good yields. The structures of the target compounds were confirmed by ^1H NMR, ^13C NMR and MS.

关键词： β-Amino alcohol Tetrahydroisoquinoline L-DOPA pictet-spengler reaction

First total synthesis of eudistalbin A

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Chinese Chemical Letters 2010年第8期21卷 889-891页

作者： Pu Yong Zhang Jun Lei Wang Sheng Biao Wan Tao Jiang School of Medicine and Pharmacy Key Laboratory of Marine DrugsMinistry of Education Ocean University of ChinaQingdao 266003China

Eudistalbin A was isolated from marine tunicate eudistoma album and possess cytotoxic activity（ED_（50）3.2μg/mL） in vitro against the growth of KB human buccal carinoma *** synthetic eudistalbin A showed potent inhibitory activity against the breast carcinoma cell line MDA-231 with an IC_（50） value of 2.1μmol/L using the metabolic assay *** structures of new compounds were confirmed by ~1H NMR,^（13）C NMR,HRMS and optical rotation.

关键词： β-Carboline Eudistalbin A pictet-spengler reaction Henry reaction Total synthesis