Synthesis of derivatives of NK109, 7-OH benzo[c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction-resistant properties

Authors
Nakanishi, T Masuda, A Suwa, M Akiyama, Y Hoshino-Abe, N Suzuki, M
Citation
T. Nakanishi et al., Synthesis of derivatives of NK109, 7-OH benzo[c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction-resistant properties, BIOORG MED, 10(20), 2000, pp. 2321-2323
Citations number
11
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
10
Issue
20
Year of publication
2000
Pages
2321 - 2323
Database
ISI
SICI code
0960-894X(20001016)10:20<2321:SODON7>2.0.ZU;2-D
Abstract
The N-5-C-6 double bond of NK109 (an antitumor benzo[c]phenanthridine alkal oid) is easily reduced under biological environment. To suppress the inacti vation caused by reduction, we synthesized 5-, 6-, and 8-substituted NK109. 5-Substituted derivatives (4a-c) were reduced more easily than NK109. 6-Su bstituted ones (10a-f) inhibited biological reduction, but showed weak cyto toxic activity. 8-O-Substituted ones (13a-h), especially 8-O-hydroxyethyl N K109 (13d), suppressed biological reduction and exhibited strong cytotoxic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.