Journal of medicinal chemistry p. 31 - 37 (1978)
Update date:2022-08-16
Topics:
Kupchan
Sneden
Branfman
Howie
Rebhun
McIvor
Wang
Schnaitman
In an effort to determine the structural requirements for the significant antileukemic, cytotoxic, antitubulin, and antimitotic activity exhibited by the novel ansa macrolide, maytansine (1), four new C-3 ester and six new C-9 ether homologues were synthesized. The biological activities of these compounds were assayed and compared to the activities of previously reported, naturally occurring maytansinoids. From the data, it is apparent that presence of the C-3 ester is necessary for significant activity, and variations in the ester group are not accompanied by marked changes in activity. However, elimination of the ester group, as in maytansinol (7), maysine (8), normaysine (9), and maysenine (10), results in a significant decrease in biological activity. Blockage of the C-9 carbinolamide via etherification markedly reduces antileukemic and cytotoxic activity and slightly reduces antitubulin activity but has relatively little effect on antimitotic activity against sea urchin eggs. Thus, a free carbinolamide at C-9 is advantageous for optimal activity.
View MoreShenzhen JYMed Technology Co.,Ltd.
website:http://www.jymedtech.com
Contact:+86-755-26612112
Address:1#8,9/F, Biomedicine innovation Industrial Park, No.14, Jinhui Road, Pingshan Sistrict, Shenzhen, China
Suzhou Health Chemicals Co., Ltd.
website:http://www.healthchems.com
Contact:13776257979
Address:No. 338, Jingang Avenue,
Beijing Mashi Fine Chemical Co.,Ltd.
Contact:+86-10-61271592
Address:Room 506, Section B, Kaichi Mansion, Industrial Development
Contact:86-21-34622192,13917187091,21-34622765
Address:No. 500 Caobao Road Shanghai P.R China
Chengdu Yunyi International Trade Co., Ltd
Contact:0411-39894967
Address:china
Doi:10.1021/jo00314a057
(1981)Doi:10.1016/j.ejmech.2020.112253
(2020)Doi:10.1007/s00706-005-0421-9
(2006)Doi:10.1007/s11172-016-1642-2
(2016)Doi:10.1002/ejoc.201601549
(2017)Doi:10.1039/c8dt03056a
(2018)