Total synthesis and cytotoxic activities of longamide B, longamide B methyl ester, hanishin, and their analogues. Issue 1 (1st January 2016)

• Record Type: Journal Article
• Authors: Zhao, Deng-Gao; Ma, Yan-Yan; Peng, Wei; Zhou, Ai-Yu; Zhang, Yu; Ding, Liugang; Du, Zhiyun; Zhang, Kun
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 26:Issue 1(2016)
• Page Start: 6
• Page End: 8
• Publication Date: 2016-01-01
• Subjects: NBS N-bromosuccinimide -- rt room temperature -- TFA trifluoroacetate -- TsOH p-toluenesulfonic acid -- DCM dichloromethane -- THF tetrahydrofuran; Longamide B -- Longamide B methyl ester -- Hanishin -- Total synthesis -- Cytotoxic activity; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2015.11.069
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: The marine alkaloids, longamide B (1 ), longamide B methyl ester (2 ), hanishin (3 ), and a series of non-naturally occurring analogues were synthesized in an efficient manner from inexpensive commercially availabledl -aspartic acid dimethyl ester. The cytotoxicities of these natural products (1 –3 ) and their analogues (9 –15 ) were evaluated against human lung adenocarcinoma (A549) and human prostate cancer (PC3) cells. This is the first evaluation of the cytotoxicities of these alkaloids in these cancer cell lines and it revealed that analogue15 had comparable cytotoxic activity to its natural parent compound, (±)-hanishin (3 ). This study provides useful information for further structural modification of these alkaloids in order to develop novel antitumor agents.