Synthesis of cyclopentanthraquinones: Analogues of mitomycin C Journal Article
| Authors: | Köhler, B.; Su, T. L.; Chou, T. C.; Jiang, X. J.; Watanabe, K. A. |
| Article Title: | Synthesis of cyclopentanthraquinones: Analogues of mitomycin C |
| Abstract: | 2,3-Dihydro-1H-cyclopent[α]anthracene-6,11-dione (cyclopentanthraquinone) derivatives bearing a mustard side chain at C-4 and an aziridine ring at the cyclopentene moiety were synthesized. Such a compound may be viewed as an analogue of mitomycin C (MC) and may exhibit bitfunctional DNA-alkylating and DNA-intercalating agent. The key intermediate, 4-hydroxy-2,3-di-O-substituted cyclopentanthraquinone, was synthesized by Deils-Alder reaction of naphthoquinone with various 4,5-dihydroxy-1-vinylcyclopent-1-ene derivatives. Introduction of a mustard side chain to the OH group at C-4 and subsequent construction of an aziridine-ring on C2–C3 of the cyclopentanthraquinone molecule furnished the target compound, 2,3-aziridino-4-[2-[N,N-bis(2-chloroethyl)amino]ethoxy]-2,3-dihydro-1H-cyclopent[a] anthracene-6,11-dione (37). It was found that both the aziridine function and the mustard side chain play a significant role in their cytotoxicity against leukemic L1210 and HL-60 cell growth in culture and the inhibition of topoisomerase II kDNA decatenation. © 1993, American Chemical Society. All rights reserved. |
| Keywords: | controlled study; human cell; nonhuman; animal cell; mouse; cytotoxicity; drug synthesis; tumor cell; anthraquinone derivative; human; article; mitomycin c derivative; leukemia l 1210 |
| Journal Title: | Journal of Organic Chemistry |
| Volume: | 58 |
| Issue: | 7 |
| ISSN: | 0022-3263 |
| Publisher: | American Chemical Society |
| Date Published: | 1993-03-01 |
| Start Page: | 1680 |
| End Page: | 1686 |
| Language: | English |
| DOI: | 10.1021/jo00059a014 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Source: Scopus |
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