Synthesis of Some New Pyridazine Derivatives for Anti-HAV Evaluation
Abstract4-(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 2–4, 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 8–10. 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 12–15, 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
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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.
Flefel EM, Tantawy WA, El-Sofany WI, El-Shahat M, El-Sayed AA, Abd-Elshafy DN. Synthesis of Some New Pyridazine Derivatives for Anti-HAV Evaluation. Molecules. 2017; 22(1):148.Chicago/Turabian Style
Flefel, Eman M.; Tantawy, Waled A.; El-Sofany, Walaa I.; El-Shahat, Mahmoud; El-Sayed, Ahmed A.; Abd-Elshafy, Dina N. 2017. "Synthesis of Some New Pyridazine Derivatives for Anti-HAV Evaluation." Molecules 22, no. 1: 148.
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