Synthesis and biological activity of structural analogs of the anticancer benzophenanthridine alkaloid nitidine chloride

The indenoisoquinoline analogue 9 of nitidine (1) has been prepared and found to possess significant anticancer activity against L1210 lymphoid leukemia, P388 lymphocytic leukemia, and B16 melanocarcinoma. Analogue 14, which lacks the B ring of nitidine (1), has also been synthesized. Compound 14 re...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1984-04, Vol.27 (4), p.544-547
Main Authors: Cushman, Mark, Mohan, Prem, Smith, Edward C. R
Format: Article
Language:English
Subjects:
Animals
Antineoplastic Agents - chemical synthesis
Benzophenanthridines
Carcinoma
Cell Line
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Humans
Indicators and Reagents
Isoquinolines - chemical synthesis
Isoquinolines - therapeutic use
Isoquinolines - toxicity
Mice
Mouth Neoplasms
Neoplasms, Experimental - drug therapy
Organic chemistry
Phenanthridines - chemical synthesis
Phenanthridines - therapeutic use
Phenanthridines - toxicity
Preparations and properties
Structure-Activity Relationship
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Summary:The indenoisoquinoline analogue 9 of nitidine (1) has been prepared and found to possess significant anticancer activity against L1210 lymphoid leukemia, P388 lymphocytic leukemia, and B16 melanocarcinoma. Analogue 14, which lacks the B ring of nitidine (1), has also been synthesized. Compound 14 retains the in vitro toxicity associated with nitidine (1) but is devoid of antileukemic activity. The structural factors that may contribute to the difference in biological activity between the two closely related analogues 9 and 14 are discussed.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00370a021