Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 63, Issue -, Pages 435-443Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2013.02.024
Keywords
3,3 '-Diindolylmethanes; Antileishmanial; Antimalarial; Leishmania donovani; Antifungal; Fe-pillared interlayered clay
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Funding
- CSIR (India)
- United States Department of Agriculture (USDA), Agricultural Research Service [58-6408-2-0009]
- US Department of Defense CDMRP [W81XWH-09]
- NIH, NIAID, Division of AIDS [AI27094]
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An efficient protocol for synthesis of 3,3'-diindolylmethanes using recyclable Fe-pillared interlayered clay (Fe-PILC) catalyst under aqueous medium has been developed. All synthesized 3,3'-diindolylmethanes showed promising antileishmanial activity against Leishmania donovani promastigotes as well as axenic amastigotes. Structure-activity relationship analysis revealed that nitroaryl substituted diindolylmethanes showed potent antileishmanial activity. The 4-nitrophenyl linked 3,3'-diindolylmethane 8g was found to be the most potent antileishmanial analog showing IC50 values of 7.88 and 8.37 mu M against both L donovani promastigotes and amastigotes, respectively. Further, a pharmacophore based QSAR model was established to understand the crucial molecular features of 3,3'-diindolylmethanes essential for potent antileishmanial activity. These compounds also exhibited promising antifungal activity against Cryptococcus neoformans, wherein fluorophenyl substituted 3,3'-diindolylmethanes were found to be most potent antifungal agents. Developed synthetic protocol will be useful for economical and eco-friendly synthesis of potent antileishmanial and antifungal 3,3'-diindolylmethane class of compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.
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