SYNTHESIS AND BIOLOGICAL EVALUATION OF AMINOTHIAZOLES, THIAZOLYLACETONITRILE, IMIDAZO[1,2-A]PYRIDINE, IMIDAZO[2,1-B]THIAZOLE, CHROMENE AND BENZO[F]CHROMENE DERIVATIVES CONTAINING NAPROXENOYL MOIETY AS POTENTIAL ANTI-INFLAMMATORY AGENTS

Document Type : Original Article

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Chemistry Department, Faculty of Science, Al-Azhar University, 11284 Nasr City, Cairo, Egypt.

Abstract

In the present investigation, a series of newly synthesized N-(4-(2-aminothiazol-2-yl) (4a,b), (2-hydrazinylthiazol-4-yl) (6) and (2-(cyanomethyl)thiazol-4-yl)phenyl-2-(6-methoxy-naphthalene-2-yl)propanamide (8) were synthesized from the cyclocondensation of 2-bromo-acetyl derivative (2) with reagents containing thioamide function. A one-pot synthesis of thiophene derivatives (10&11) was achieved from three-component reaction of 2 with malononitrile and/or ethyl acetoacetate and phenyl isothiocyanate catalyzed by DMF/KOH. Cyclocondensation of 2 with 2-aminopyridine and 2-aminothiazole gave imidazo[1,2-a]-pyridine and imidazo[2,1-b]thiazole derivatives (12&13), respectively. The reactivity of 8 toward some electrophilic reagents was investigated, where 2-iminochromenes (14, 15) were obtained, respectively. The structures of the newly compounds were confirmed on the basis of IR, 1HNMR, and mass spectral data. The synthesized compounds were screened for animal toxicity, analgesic, and anti-inflammatory studies.

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