- Synthesis and biological evaluation of coumarin-1,3,4-oxadiazole hybrids as selective carbonic anhydrase IX and XII inhibitors
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With an aim to develop novel heterocyclic hybrids as potent anticancer agents, we synthesized a series of coumarin-1,3,4-oxadiazole hybrids (7a-t) and evaluated for their inhibitory activity against the four physiologically relevant human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms CA I, CA II, CA IX and CA XII. The CA inhibition results clearly indicated that the coumarin-1,3,4-oxadiazole derivatives (7a-t) exhibited selective inhibition of the tumor associated isoforms, CA IX and CA XII over CA I and II isoforms. Among all, compound 7b, exhibited significant inhibition in lower micromolar potency against hCA XII, with a Ki of 0.16 μM and compound 7n, exhibited significant inhibition in lower micromolar potency against hCA IX, with a Ki of 2.34 μM respectively. Therefore, compound 7b and 7n could be the potential leads for development of selective anticancer agents by exhibiting a novel mechanism of action through hCA IX and XII inhibition.
- Narella, Sridhar Goud,Shaik, Mohammed Ghouse,Mohammed, Arifuddin,Alvala, Mallika,Angeli, Andrea,Supuran, Claudiu T.
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p. 765 - 772
(2019/04/13)
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- Synthesis and biological evaluation of new thiosubstituted oxadiazole derivatives of coumarin under solvent-free conditions
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A series of new thiosubstituted 1,3,4-oxadiazole derivatives of coumarin were synthesised by reaction of 7-((5- mercapto-1,3,4-oxadiazol-2-yl)methoxy)-4- methyl-2H-chromen-2-one and α-haloketones by grinding, in solvent-free conditions at room temperature. The reaction was also carried out in ethanol in reflux conditions. Shorter reaction time and better yields were observed in solvent-free conditions. The structures of the compounds were characterised by IR, NMR, elemental analysis and mass spectral data. The synthesised compounds were evaluated for their in vitro antimicrobial screening on different strains of bacteria and fungi. Most of the compounds showed good to moderate activities.
- Bobade, Vivek D.,Patil, Sachin V.,Gaikwad, Nitin D.
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experimental part
p. 25 - 28
(2012/04/04)
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