18886-71-0Relevant academic research and scientific papers
Grinding and Microwave-assisted Synthesis of Heterocyclic Molecules in High Yields and Their Biological Evaluation
Kumar, Sandeep,Kumar, Anuj,Kumar, Nikhil,Roy, Partha,Sondhi, Sham M.
, p. 1761 - 1770 (2016/11/23)
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. IC50values of 6bx, 6bz, 6cy, 6cz, 7bz, 7cx, and 7cz against various cancer cell lines and normal cell (COS-1) are also reported.
One-step ring condensation of hydrazine derivatives and cyclic anhydrides
Katrusiak, Anna,Katrusiak, Andrzej
, p. 28 - 36 (2015/03/05)
Hydroxypyridazinone and pyrroledione rings condensation in the reactions of hydrazine hydrate with citraconic, 2,3-dimethylmaleic, succinic and cis-cyclohexanedicarboxylic anhydrides have been conducted in the HCl aqueous solution. The pyridazine-ring condensation yields products unexpected for these conditions. They have been identified by 1H/13C NMR and X-ray diffraction. The course of the reaction toward the five- and six-membered ring condensation strongly depends on methyl and other substituents in the anhydrides and in hydrazine. The obtained products indicate that the ring condensation is controlled by the molecular strains and steric hindrances between the substituents in anhydrides and pyridazinone products. The condensation of cyclic anhydrides with hydrazines has been reduced to one-step reaction and its yield significantly increased.
