Synthesis, antitumor, antitrypanosomal and antileishmanial activities of benzo[4,5]canthin-6-ones bearing the N'-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide groups at C-2.

doi:10.1248/CPB.C12-00356

Paper

Synthesis, antitumor, antitrypanosomal and antileishmanial activities of benzo[4,5]canthin-6-ones bearing the N'-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide groups at C-2.

Published Nov 1, 2012 · C. L. Leite Silva, F. Garcia, J. H. Rodrigues

Chemical & pharmaceutical bulletin

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Abstract

A series of novel benzo[4,5]canthin-6-ones, bearing the N'-(substituted benzylidene)-carbohydrazide (11a-e) and N-alkylcarboxamide (13a-g) moieties at position-2, were synthesized and screened for their in vitro antitumor activity, against seven human cancer cell lines, and for antitrypanosomal and antileishmanial activities against Trypanosoma cruzi and Leishmania amazonensis. The results indicated that N-methylpiperazyl-6-oxobenzo[4,5]canthine-2-carboxamide (13f) displayed potent antitumor activity with IC(50) values in the range of 1.15-8.46 µM for all cell lines tested. Compounds 13f and 13g bearing an N-methylpiperazylcarboxamide and N-morpholylcarboxamide at C-2, respectively, showed potent activities towards both Trypanosoma cruzi and Leishmania amazonensis parasites, with IC(50) in the range of 0.4 to 16.70 µM.

In Vitro Study

Study Snapshot

Novel benzo[4,5]canthin-6-ones with N-methylpiperazylcarboxamide at C-2 show potent antitumor activity and antitrypanosomal and leishmanial activities against Trypanosoma cruzi and Leishmania amazonensis parasites.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis, antitumor, antitrypanosomal and antileishmanial activities of benzo[4,5]canthin-6-ones bearing the N'-(Substituted benzylidene)-carbohydrazide and N-Alkylcarboxamide groups at C-2.

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References

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Beta-carboline alkaloids exhibit diverse biological activities and pharmacological properties, including sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic, and antimicrobial properties.

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New beta-carboline alkaloids from Eurycoma longifolia roots show potential cytotoxic and antimalarial activities, with 9-methoxycanthin-6-one (4) showing significant cytotoxicity against human lung cancer and breast cancer cell lines.

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Canthin-6-one and 5-methoxycanthin-6-one, major constituents of Zanthoxylum chiloperone stem bark, show in vitro and in vivo activity against various Leishmania strains, but their effectiveness in vivo remains unclear.

Citations

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