Adriamycin analogs. Preparation of 9,10-anhydrodaunorubicin, 9,10-anhydroadriamycin, and some related compounds
- 1 April 1982
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 25 (4) , 478-481
- https://doi.org/10.1021/jm00346a027
Abstract
The title compounds, as well as 9,10-anhydro-N-(trifluoroacetyl)adriamycin 14-valerate (9,10-anhydro-AD 32), were prepared starting from daunorubicin, adriamycin, and N-(trifluoroacetyl)adriamycin 14-valerate (AD 32), respectively. In addition, 9-deoxydaunorubicin and 9-deoxy-AD 32 were obtained by catalytic hydrogenation of the appropriate olefin. All of the products were significantly less active than the parent drugs in inhibiting the growth of CCRF-CEM (human lymphoblastic leukemic) cells in culture. The results suggest the importance of the tertiary alcohol function, as found in the parent compounds at the anthracycline 9 position, in contributing to the expression of biological activity of these agents.This publication has 5 references indexed in Scilit:
- Adriamycin analogs. Preparation and biological evaluation of some N-perfluoroacyl analogs of daunorubicin, adriamycin, and N-(trifluoroacetyl)adriamycin 14-valerate and their 9,10-anhydro derivativesJournal of Medicinal Chemistry, 1982
- A regiospecific synthesis of the anthracycline aglycons, daunomycinone and adriamycinoneJournal of the American Chemical Society, 1978
- N-TRIFLUOROACETYLADRIAMYCIN-14-VALERATE - ADDITIONAL MOUSE ANTI-TUMOR AND TOXICITY STUDIES1978
- COMPARATIVE ANTI-NEOPLASTIC ACTIVITY OF ADRIAMYCIN AND N-TRIFLUOROACETYLADRIAMYCIN-14-VALERATE1978
- The response in vitro, of continuous cultures of human lymphoblasts (CCRF-CEM cells) to chemotherapeutic agentsBiochemical Pharmacology, 1967