Synthesis, Antifungal Activity, and Structure-activity Relationships of Coruscanone A Analogues.
From: National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences and Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
Journal of medicinal chemistry
- Publish Date: Dec 2006
- ISSN: 0022-2623
- Volume: 49
- Issue: 26
- Pages: 7877-86
- Medium: Print
- Language: English
- Citation (JAMA): Babu K Suresh, Li Xing-Cong, Jacob Melissa R, et al. Synthesis, Antifungal Activity, and Structure-activity Relationships of Coruscanone A Analogues.. J. Med. Chem. Dec 2006;49:7877-86
Abstract
Coruscanone A, a plant-derived cyclopentenedione derivative, showed potent in vitro antifungal activity against Candida albicans and Cryptococcus neoformans comparable to amphotericin B and fluconazole. A series of analogues have been synthesized by modification of the cyclopentenedione ring, the enolic methoxy functionality, and the side chain styryl moiety of this natural product lead. A structurally close 1,4-benzoquinone analogue was also prepared. All the compounds were examined for their in vitro activity against major opportunistic fungal pathogens including C. albicans, C. neoformans, and Aspergillus fumigatus and fluconazole-resistant C. albicans strains, with several analogues demonstrating potent antifungal activity. Structure-activity relationship studies indicate that the 2-methoxymethylenecyclopent-4-ene-1,3-dione structural moiety is the pharmacophore responsible for the antifungal activity of this class of compounds while the side chain styryl-like moiety plays an important complementary role, presumably contributing to target binding.
Mesh Headings (Keywords): Animals, Antifungal Agents, Candida albicans, Cell Survival, Cercopithecus aethiops, Cryptococcus neoformans, Cyclopentanes, Drug Resistance, Fungal, Fluconazole, LLC-PK1 Cells, Miconazole, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship, Swine, Vero Cells
Check for Full Text / PubMed Unique Identifier (PMID): 17181171
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