Antimicrobial, anti-inflammatory, and antinociceptive activities of triazole, pyrazole, oxadiazine, oxadiazole, and sugar hydrazone-5-nitroindoline-2-one derivatives and a study of their computational chemistry

Bassyouni, Fatma A.; Abdel All, Amira S.; Haggag, Wafaa M.; Mahmoud, Madiha; Sarhan, Mamoun M.A.; Abdel-Rehim, Mohamed

doi:10.7123/01.EPJ.0000422114.91245.38

Antimicrobial, anti-inflammatory, and antinociceptive activities of triazole, pyrazole, oxadiazine, oxadiazole, and sugar hydrazone-5-nitroindoline-2-one derivatives and a study of their computational chemistry

Authors

10.7123/01.EPJ.0000422114.91245.38

Abstract

Objective
The aim of this study (part II) is to evaluate the antibacterial, anti-inflammatory, and antinociceptive activities of a series of 1H-1,2,4-triazol-3-yl)phenylimino)(methylbenzyl)-5-nitroindolin-2-ones, 1H-pyrazole-1-carbonyl)phenylimino)-1-(-methylbenzyl)-5-nitroindolin-2-ones, 3-(4-(1,3,4-oxadizine-6-one)phenylimino)-1-(-methylbenzyl)-5-nitroindolin-2-ones, 1,3,4-oxadiazol-2-yl)phenylimino)-1-(-methylbenzyl)-5-nitroindolin-2-ones and 4-(-1-(-methylbenzyl)-5-nitro-2-oxoindolin-3-ylideneamino) sugar hydrazone derivatives () and, in addition, to investigate their computational chemistry.
Methods
The synthesized compounds in (part I) were evaluated for their antibacterial and antifungal activities using different strains of Gram-positive bacteria (), Gram-negative bacteria (, yeast (), and four mold fungi (, , , and ). The anti-inflammatory and antinociceptive activities of compounds were evaluated using a hot-plate test, acetic acid-induced writhing in mice, formalin-induced nociception, a tail immersion test, and carrageenan-induced hind paw edema. For computational chemistry, a semiempirical MNDO method (Modified Neglect of Differential Overlap is a semi-empirical method for the quantum calculation of molecular electronic structure in computational chemistry) associated with HyperChem professional 7.5 programs was adapted.
Results and conclusion
Compounds 4-[(1-(-methylbenzyl)-5-nitro-2-oxoindolin-3-ylideneamino)] benzohydrazide () and 3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenylimino)-1-(-methylbenzyl)-5-nitroindolin-2-one () showed the highest antibacterial and antifungal activities compared with clotrimazole and sulfamethoxazole as reference drugs. In contrast, compounds ethyl 4-(5-nitro-2-oxoindolin-3-ylideneamino) benzoate (), 3-(4-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbonyl) phenylimino)-1-(-methylbenzyl)-5-nitroindolin-2-one (), D-glucose-4-(-1-(-methylbenzyl)-5-nitro-2-oxoindolin-3-ylideneamino) hydrazone derivative (), and D-arabinose-4-(-1-(-methylbenzyl)-5-nitro-2-oxoindolin-3-ylideneamino) hydrazone derivative () showed significantly high anti-inflammatory and antinociceptive activities when compared with indomethacin and morphine as reference drugs. From the computational chemistry compounds, ethyl 4-(5-nitro-2-oxoindolin-3-ylideneamino) benzoate (), ethyl 4-[(1-(-methylbenzyl)-5-nitro-2-oxoindolin-3-ylideneamino)] benzoate (), and 4-[(1-(-methylbenzyl)-5-nitro-2-oxoindolin-3-ylideneamino)] benzohydrazide () yielded the lowest values of total energy and heat of formation, and had higher stability than other molecules.

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