Grinding and Microwave‐assisted Synthesis of Heterocyclic Molecules in High Yields and Their Biological Evaluation |
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| Authors: | Sandeep Kumar Anuj Kumar Nikhil Kumar Partha Roy Sham M. Sondhi |
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| Affiliation: | 1. Department of Chemistry, Indian Institute of Technology‐Roorkee, Roorkee, Uttarakhand, India;2. Department of Biotechnology, Indian Institute of Technology‐Roorkee, Roorkee, Uttarakhand, India |
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| Abstract: | Cis‐cyclohexane1,2‐dicarboxylic acid ( 1a ), phthalic acid ( 1b ), and pyrazine 2,3‐ dicarboxylic acid ( 1c ) on grinding with hydrazine hydrate ( 2a ) gave 2‐aminohexahydro‐1H‐isoindole‐1,3(2H)‐dione ( 3a ), 2‐amino‐1H‐isoindole‐1,3(2H)‐dione ( 3b ), and 6‐amino‐5H‐pyrrolo[3,4‐b]pyrazine‐5,7(6H)‐dione ( 3c ), respectively. Condensation of ( 3a , 3b , 3c ) with aldehydes ( 4x , 4y , 4z ) and 2‐cyanopyridine, 4‐cyanopyridine, 2‐cyanopyrazine ( 5x , 5y , 5z ) under microwave irradiation gave corresponding azomethine ( 6ax , 6ay , 6az , 6bx , 6by , 6bz , 6cx , 6cy , 6cz ) and amidine ( 7ax , 7ay , 7az , 7bx , 7by , 7bz , 7cx , 7cy , 7cz ) derivatives, respectively. Fully characterized azomethine ( 6ax , 6ay , 6az , 6bx , 6by , 6bz , 6cx , 6cy , 6cz ) and amidine ( 7ax , 7ay , 7az , 7bx , 7by , 7bz , 7cx , 7cy , 7cz ) derivatives were screened for anti‐inflammatory and anticancer activity against five human cancer cell lines. Compound 7cx exhibited 35% anti‐inflammatory activity at a dose of 50 mg/kg p.o. whereas standard drug ibuprofen showed 39% activity at a dose of 50 mg/kg p.o. Compounds 6bz , 7cx , 7cz (breast T47D), 6bz , 6cy (lung NCI H‐522), 6bx , 7bz (colon HCT‐15), 6bz (ovary PA‐1) and 6bx , and 6cz (liver HepG‐2) exhibited good (35–41% inhibition at 10 μM c) anticancer activity. IC50 values of 6bx , 6bz , 6cy , 6cz , 7bz , 7cx , and 7cz against various cancer cell lines and normal cell (COS‐1) are also reported. |
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