The derivation of 1a-demethylmitomycin G from mitomycin C
| Autor: | Masaji Kasai, Makoto Morimoto, Motomichi Kono, Kunikatsu Shirahata |
|---|---|
| Rok vydání: | 1990 |
| Předmět: |
Pharmacology
Antitumor activity Antibiotics Antineoplastic Chemical Phenomena Molecular Structure Stereochemistry Mitomycin Mitomycin C Biological activity Aziridine Chemical synthesis Mitomycins Chemistry Mice Structure-Activity Relationship chemistry.chemical_compound chemistry Porfiromycin Yield (chemistry) Drug Discovery Animals 1a-demethylmitomycin G Sarcoma 180 |
| Zdroj: | The Journal of Antibiotics. 43:383-390 |
| ISSN: | 1881-1469 0021-8820 |
| DOI: | 10.7164/antibiotics.43.383 |
| Popis: | Mitomycin G (2) was derived from porfiromycin (10b) in 3 steps via the methanesulfonate (14b) in an overall yield of 39%. On the basis of the established method for the introduction of an exomethylene group in mitomycins with a 9a-methoxy group, the preparation of biologically more important 1a-demethylmitomycin G (5) from mitomycin C (1) was accomplished by the use of a protective acetyl group on the aziridine in an overall yield of 57%. 1a-Demethylmitomycin K (6) was obtained from 5 in a yield of 42%. In a preliminary evaluation of their antitumor activity, compound 5 showed superior activity against sarcoma 180 (sc-ip) to its 1a-methyl congener, i.e., mitomycin G (2). |
| Databáze: | OpenAIRE |
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