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Synthesis and Biological Evaluation of Tricyclic Guanidine Analogues of Batzelladine K for Antimalarial, Antileishmanial, Antibacterial, Antifungal, and Anti‐HIV Activities
Author(s) -
Ahmed Nafees,
Brahmbhatt Keyur G.,
Khan Shabana I.,
Jacob Melissa,
Tekwani Babu L.,
Sabde Sudeep,
Mitra Debashis,
Singh Inder P.,
Khan Ikhlas A.,
Bhutani Kamlesh K.
Publication year - 2013
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.1427
Subject(s) - antimicrobial , leishmania donovani , plasmodium falciparum , tricyclic , chemistry , guanidine , stereochemistry , antimalarial agent , antifungal , in vitro , pharmacology , microbiology and biotechnology , biology , leishmaniasis , malaria , biochemistry , organic chemistry , visceral leishmaniasis , immunology
Fifty analogues of batzelladine K were synthesized and evaluated for in vitro antimalarial ( Plasmodium falciparum ), antileishmanial ( Leishmania donovani ), antimicrobial (panel of bacteria and fungi), antiviral (HIV‐1) activities. Analogues 14h and 20l exhibited potential antimalarial activity against chloroquine‐sensitive D6 strain with IC 50 1.25 and 0.88 μ m and chloroquine‐resistant W2 strain with IC 50 1.64 and 1.07 μ m , respectively. Analogues 12c and 14c having nonyl substitution showed the most potent antileishmanial activity with IC 50 2.39 and 2.78 μ m and IC 90 11.27 and 12.76 μ m , respectively. Three analogues 12c , 14c, and 14i were the most active against various pathogenic bacteria and fungi with IC 50 < 3.02 μ m and MIC/MBC/MFC <6 μ m . Analogue 20l having pentyl and methyl substituents on tricycle showed promising activities against all pathogens. However, none was found active against HIV‐1. Our study demonstrated that the tricyclic guanidine compounds provide new structural class for broad spectrum activity.