The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity 英文参考文献.docVIP

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The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity 英文参考文献.doc

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The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)-Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity 英文参考文献

Molecules 2003, 8, 322-332 molecules ISSN 1420-3049 / The Use of 4-(3,4-Dichlorophenyl)-4-Oxo-2-(4-Antipyrinyl)- Butanoic Acid in the Preparation of Some New Heterocyclic Compounds With Expected Biological Activity G.H. Sayed Chemistry Department, Faculty of Science, Ain Shams University, Abbassia, Cairo, Egypt. Author to whom correspondence should be addressed; E-mail: g_hosni45@. * , A.A. Hamed, G.A. Meligi, W.E. Boraie and M. Shafik * Received: 18 December 2002; in revised form: 29 March 2003/ Accepted: 30 March 2003 / Published: 31 March 2003 Abstract: Reaction of 4-oxo-4-(3,4-dichlorophenyl)-2-butenoic acid (1) with antipyrin (2) gave the corresponding butanoic acid 3. Reaction of 3 with hydrazines gave the pyridazinone derivatives 5a,b. Compounds 5a,b were used to prepare the corresponding dithio derivatives. Reaction of 5a with POCl3 unexpectedly gave the chloropyridazine derivative 7, which is used to prepare the corresponding thio derivative. The hitherto unknown reactions of this chloro derivative with 2-amino-3-carbethoxy-4,5- dimethylthiophene and 2-amino-3-carbethoxy tetrahydrobenzothiophene have now been described. The behaviour of the chloro derivative toward hydrazine hydrate, sodium azide and anthranilic acid was also studied. Some of the new compounds showed antimicrobial and antifungal activities . Keywords: Substituted pyridazinones, chloropyridazine, substituted thiophenes Introduction Antipyrin derivatives are reported to exhibit analgesic and anti-inflammatory effects [1-3], antiviral [4], antibacterial [5] and herbicidal [6] activities and have also been used as hair colour additives [7] and to potentiate the local anesthetic effect of lidocaine [8]. This prompted us to synthesize a new Molecules 2003, 8 323 series of heterocyclic compounds containing the antipyrinyl moiety. The antimicrobial activities of several of the compounds wer