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Molecules 2017, 22(1), 148; doi:10.3390/molecules22010148

Synthesis of Some New Pyridazine Derivatives for Anti-HAV Evaluation

1
Department of Chemistry, College of Science, Taibah University, Al-Madinah Al-Monawarah 1343, Saudi Arabia
2
Department of Photochemistry, Chemical Industries Research Division, National Research Centre, 33 EL-Bohouth St., Dokki 12622, Giza, Egypt
3
Department of Water Pollution, Environmental Research Division, National Research Centre, 33 EL-Bohouth St., Dokki 12622, Giza, Egypt
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 9 December 2016 / Revised: 9 January 2017 / Accepted: 10 January 2017 / Published: 17 January 2017
(This article belongs to the Section Bioorganic Chemistry)
View Full-Text   |   Download PDF [1181 KB, uploaded 17 January 2017]   |  

Abstract

4-(2-(4-Halophenyl)hydrazinyl)-6-phenylpyridazin-3(2H)-ones 1a,b were prepared and treated with phosphorus oxychloride, phosphorus pentasulphide and ethyl chloroformate to give the corresponding chloropyridazine, pyridazinethione, oxazolopyridazine derivatives 24, respectively. Compound 2 reacted with hydrazine hydrate to afford hydrazinylpyridazine 7. The reaction of 4-(2-(4-chlorophenyl)hydrazinyl)-3-hydrazinyl-6-phenylpyridazine (7) with acetic anhydride, p-chlorobenzaldehyde and carbon disulphide gave the corresponding pyridazinotriazine derivatives 810. On the other hand, 5-(4-chlorophenylamino)-7-(3,5-dimethoxybenzylidene)-3-phenyl-5H-pyridazino[3,4-b][1,4]thiazin-6(7H)-one (11) was prepared directly from the reaction of compound 3 with chloroacetic acid in presence of p-chlorobenzaldehyde. Compound 11 reacted with nitrogen nucleophiles (hydroxylamine hydrochloride, hydrazine hydrate) and active methylene group-containing reagents (malononitrile, ethyl cyanoacetate) to afford the corresponding fused compounds 1215, respectively. Pharmacological screening for antiviral activity against hepatitis A virus (HAV) was performed for the new compounds. 4-(4-Chlorophenylamino)-6-phenyl-1,2-dihydropyridazino[4,3-e][1,2,4]triazine-3(4H)-thione (10) showed the highest effect against HAV. View Full-Text
Keywords: pyridazine; fused pyridazine derivatives; hepatitis A virus (HAV) pyridazine; fused pyridazine derivatives; hepatitis A virus (HAV)
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MDPI and ACS Style

Flefel, E.M.; Tantawy, W.A.; El-Sofany, W.I.; El-Shahat, M.; El-Sayed, A.A.; Abd-Elshafy, D.N. Synthesis of Some New Pyridazine Derivatives for Anti-HAV Evaluation. Molecules 2017, 22, 148.

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