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Current Organic Synthesis

Author(s): Hany M. Mohamed and Ashraf H.F. Abd El-Wahab*

DOI: 10.2174/1570179416666190719101727

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Heteroaromatization with 4-Phenyldiazenyl-1-naphthol. Part IV: Synthesis of Some New Heterocyclic Compounds with Potential Biological Activity

Page: [931 - 938] Pages: 8

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Abstract

Background: Synthetic azo compounds and their derivatives have been studied extensively due to their biological and pharmacological activities. Pyranopyridines, pyranopyrimidines and tetrazoles derivatives have emerged as a promising and attractive scaffold in the development of potent biological and pharmacological agents.

Objectives: To design a series of new benzochromeno(pyridine/pyrimidine/tetrazole) derivatives and evaluate their antimicrobial activity against some bacterial strains (Gram-positive and Gram-negative) and some fungal strains.

Materials and Methods: The (E)-7-(4-chlorophenyl)-5-(phenyldiazenyl)-10-thioxo-7,9,10,11-tetrahydro-8Hnaptho[ 1,2-b]pyrano[2,3-d]pyrimidin-8-one (4) was synthesized by the reaction of 4H-naphtho[1,2-b]pyran-3- carbonitrile (3) with carbon disulfide in alcoholic potassium hydroxide solution. Reaction of 3 with sodium azide in DMF and in presence of ammonium chloride afforded 6-(phenyldiazenyl)-3-(1H-tetrazol-5-yl)-4Hbenzo[ h]chromen-2-amine (7) while with malononitrile, thiourea or urea gave chromeno[2,3-b]pyridine-9- carbonitrile (8), chromeno[2,3-d]pyrimidine-10-thione (9) and chromeno[2,3-d]pyrimidin-10-one (10), respectively. The assignment structures were established on the basis of spectral data.

Results: In this study, the antimicrobial activity of the synthesized compounds 3-12 was examined for their in vitro antimicrobial activity by using agar diffusion method such as Mueller-Hinton agar medium for bacteria and Sabouraud’s agar medium for fungi. Ampicillin and mycostatine were included in the experiments as reference drugs.

Conclusion: A series of new benzochromeno(pyridine/pyrimidine/tetrazole) derivatives were synthesized in this work. All compounds were evaluated in antimicrobial activities.

Keywords: 4-Phenyldiazenyl-1-naphthol, aromatic aldehyde, malononitrile, thiourea, urea, antimicrobial activity.

Graphical Abstract

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