1. Synthesis and biological evaluation of caracasine acid derivatives.
- Author
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Chávez K, Compagnone RS, Álvarez A, Figarella K, Galindo-Castro I, Marsiccobetre S, Triviño J, Arocha I, Taddei A, Orsini G, Tillett S, and Suárez AI
- Subjects
- Amides chemistry, Anti-Bacterial Agents pharmacology, Antineoplastic Agents pharmacology, Antiprotozoal Agents pharmacology, Bacillus cereus drug effects, Bacillus cereus growth & development, Carboxylic Acids pharmacology, Cell Line, Tumor, Cell Survival drug effects, Epoxy Compounds chemistry, Escherichia coli drug effects, Escherichia coli growth & development, Esters chemistry, Humans, Inhibitory Concentration 50, Leishmania mexicana drug effects, Leishmania mexicana growth & development, MCF-7 Cells, Phenanthrenes pharmacology, Pseudomonas aeruginosa drug effects, Pseudomonas aeruginosa growth & development, Staphylococcus aureus drug effects, Staphylococcus aureus growth & development, Structure-Activity Relationship, Trypanosoma cruzi drug effects, Trypanosoma cruzi growth & development, Anti-Bacterial Agents chemical synthesis, Antineoplastic Agents chemical synthesis, Antiprotozoal Agents chemical synthesis, Carboxylic Acids chemical synthesis, Phenanthrenes chemical synthesis
- Abstract
A series of caracasine acid (1) derivatives were synthesized and evaluated for their in vitro cytotoxicity on human cancer-derived cell lines MCF-7 and PC-3, as well as for other activities such as antibacterial, antileishmanial and antitrypanosomal activity. Compound 1 was more effective than any of its derivatives against tested human cancer cell lines. PC-3 cells were more sensitive than MCF-7 to all compounds, particularly the methyl ester (2), the amide (9) and the epoxide (10). The evaluation of antiparasitic activity revealed that ester derivatives (2-8) and the amide derivative (9) were the most effective antileishmanial and antitrypanosomal compounds, even though their effect on Trypanosoma cruzi was modest. Finally, compound 1 and the derivatives evidenced a broad spectrum of antibacterial activity, as assayed against Gram-positive and Gram-negative bacteria., (Copyright © 2015 Elsevier Ltd. All rights reserved.)
- Published
- 2015
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