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Synthesis and Biological Screening of 4-Benzyl-2H-phthalazine Derivatives
Chemistry Department, Faculty of Science, Al-Azhar University, 11884, Nasr City, Cairo, Egypt
Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Saudi Arabia
Chemistry Department, Faculty of Medicine, Jazan University, 82621, Jazan, Saudi Arabia
Chemistry Department, Faculty of Science, King Khalid University, 9004, Abha, Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 20 June 2011; in revised form: 13 July 2011 / Accepted: 13 July 2011 / Published: 17 August 2011
Abstract: Preparation of 4-benzyl-2-substituted phthalazin-1-one derivatives 2-8 is reported. Condensation of 4-benzyl-1-chlorophthalazine (9) with a series of different nucleophiles gave 4-benzylphthalazin-1-ylamino derivatives (10-13 and 16) and 4-amino-2-[N'-(4-benzylphthalazin-1-yl)-hydrazino]-6-arylpyrimidine-5-carbonitriles (14a,b). Interaction of 9 with ambident anions was also studied. 5-Benzyl-6,6a,12-triazobenzo[a]-anthracen-7-one (15) is obtained from 9 and anthranilic acid derivatives. Treatment of 16 with (EtO)3CH/Ac2O under reflux afforded the corresponding ethoxymethylene derivative 17, while aqueous ammonium hydroxide treatment afforded carboxamide derivative 18. The structures of the newly synthesized derivatives were confirmed by their elemental analysis, IR, 1H NMR, 13C NMR and mass spectral studies. Antimicrobial activities of some selected compounds were also studied and some of these were found to exhibit promising effects against Gram-positive and Gram-negative bacteria and fungi.
Keywords: phthalazine derivatives; anthracene derivatives; synthesis; antimicrobial activity
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El-Wahab, A.H.A.; Mohamed, H.M.; El-Agrody, A.M.; El-Nassag, M.A.; Bedair, A.H. Synthesis and Biological Screening of 4-Benzyl-2H-phthalazine Derivatives. Pharmaceuticals 2011, 4, 1158-1170.
El-Wahab AHA, Mohamed HM, El-Agrody AM, El-Nassag MA, Bedair AH. Synthesis and Biological Screening of 4-Benzyl-2H-phthalazine Derivatives. Pharmaceuticals. 2011; 4(8):1158-1170.
El-Wahab, Ashraf H.F. Abd; Mohamed, Hany M.; El-Agrody, Ahmed M.; El-Nassag, Mohammed A.; Bedair, Ahmed H. 2011. "Synthesis and Biological Screening of 4-Benzyl-2H-phthalazine Derivatives." Pharmaceuticals 4, no. 8: 1158-1170.