Synthesis and Biological Screening of 4-Benzyl-2H-phthalazine Derivatives

Ashraf H.F.Abd El-Wahab, Hany M. Mohamed, Ahmed M. El-Agrody, Mohammed A. El-Nassag, Ahmed H. Bedair

Research output: Contribution to journalJournal articlepeer-review

15 Scopus citations

Abstract

Preparation of 4-benzyl-2-substituted phthalazin-1-one derivatives 2-8 isreported. Condensation of 4-benzyl-1-chlorophthalazine (9) with a series of differentnucleophiles gave 4-benzylphthalazin-1-ylamino derivatives (10-13 and 16) and4-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 16with (EtO)3CH/Ac2O under reflux afforded the corresponding ethoxymethylene derivative17, while aqueous ammonium hydroxide treatment afforded carboxamide derivative 18.The structures of the newly synthesized derivatives were confirmed by their elementalanalysis, IR, 1H NMR, 13C NMR and mass spectral studies. Antimicrobial activities ofsome selected compounds were also studied and some of these were found to exhibitpromising effects against Gram-positive and Gram-negative bacteria and fungi.

Original languageEnglish
Pages (from-to)1158-1170
Number of pages13
JournalPharmaceuticals
Volume4
Issue number8
DOIs
StatePublished - 2011
Externally publishedYes

Keywords

  • Anthracene derivatives
  • Antimicrobial activity
  • Phthalazine derivatives
  • Synthesis

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