Synthesis and biological activities of [N-MeLeu(5)]- and [N-MePhe(5)]-didemnin B

Authors
Pfizenmayer, AJ Ramanjulu, JM Vera, MD Ding, XB Xiao, D Chen, WC Joullie, MM
Citation
Aj. Pfizenmayer et al., Synthesis and biological activities of [N-MeLeu(5)]- and [N-MePhe(5)]-didemnin B, TETRAHEDRON, 55(2), 1999, pp. 313-334
Citations number
36
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
2
Year of publication
1999
Pages
313 - 334
Database
ISI
SICI code
0040-4020(19990108)55:2<313:SABAO[>2.0.ZU;2-K
Abstract
Based on information from X-ray, NMR, and SAR data, the N,O-diMeTyr(5) unit of didemnin B was believed to be important for biological activity. To det ermine the importance of aromaticity and the role of the methoxy group in t his unit, two analogs were synthesized in which the N,O-diMeTyr(5) moiety w as replaced with N-MeLeu and N-MePhe. Preliminary testing showed that the a nalogs retained antitumor activity and the ability to inhibit protein biosy nthesis ill vitro. (C) 1998 Elsevier Science Ltd. All rights reserved.