Synthesis and antitumor activity of structural analogs of the anticancer benzophenanthridine alkaloid fagaronine chloride
- 31 July 1985
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 28 (8) , 1031-1036
- https://doi.org/10.1021/jm00146a010
Abstract
The indenoisoquinoline analog 4 of fagaronine chloride was prepared, as well as its positional isomer 20 [2,3,10-trimethoxy-6-methyl-9-hydroxy-11H-indeno[1,2-c]isoquinoline chloride] and the corresponding mesylated derivatives 16 [2,3,8-trimethoxy-6-methyl-9-[(methylsulfonyl)oxy]-11H-indeno [1,2,c]isoquinolin chloride]. Compounds 4, 16, and 20 were tested against P388 lymphocytic leukemia and possessed significant activity. A tricyclic analog was also synthesized and was devoid of cytotoxicity in the KB cancer cell culture system. The change in the substitution pattern of the A-ring on going from 4 to 20 was tolerated without producing a significant decrease in antitumor activity.This publication has 11 references indexed in Scilit:
- Interaction of the antileukemic alkaloid, 2-hydroxy-3,8,9-trimethoxy-5-methylbenzo[c]phenanthridine (fagaronine), with nucleic acidsChemico-Biological Interactions, 1983
- Synthesis and biological activity of benzothiazolo- and benzoxazolo[3,2-a]quinolinium saltsJournal of Medicinal Chemistry, 1982
- Quino[1,2‐c]quinazolines. I. Synthesis of quino[1,2‐c]quinazolinium derivatives and the related indazolo[2,3‐a]quinoline derivatives as analogs of the antitumor benzo[c]phenanthridine alkaloidsJournal of Heterocyclic Chemistry, 1980
- INVIVO CHARACTERISTICS OF RESISTANCE AND CROSS-RESISTANCE OF AN ADRIAMYCIN-RESISTANT SUBLINE OF P388 LEUKEMIA1978
- Total synthesis of nitidine chlorideThe Journal of Organic Chemistry, 1978
- Absence of Mutagenicity of Coralyne and Related Antileukemic Agents: Structural Comparison with the Potent Carcinogen 7,12-Dimethylbenz[a]anthraceneJournal of Pharmaceutical Sciences, 1977
- Inhibition of Catechol O-Methyltransferase and Transfer RNA Methyltransferases by Coralyne, Nitidine, and Related CompoundsJournal of Pharmaceutical Sciences, 1977
- Condensation of imines with homophthalic anhydrides. A convergent synthesis of cis- and trans-13-methyltetrahydroprotoberberinesThe Journal of Organic Chemistry, 1977
- INHIBITION OF MAMMALIAN AND ONCORNAVIRUS NUCLEIC-ACID POLYMERASE ACTIVITIES BY ALKOXYBENZOPHENANTHRIDINE ALKALOIDS1976
- Propagation in a Fluid Medium of a Human Epidermoid Carcinoma, Strain KBExperimental Biology and Medicine, 1955