Synthesis of novel 4-oxo-N-(4-oxo-3-substituted-3,4-dihydroquinazolin-2-yl amino)-2-phenylquinazoline-3(4H)-carboxamidines as AntiHIV, antitubercular and antibacterial agents

  • Sulthana M.T Medicinal Chemistry Research Laboratory, MNR College of Pharmacy, Sangareddy, Hyderabad-502 294, Telangana, India
  • Chitra K Faculty of Pharmacy, Sri Ramachandra Institute of Higher education and Research (Deemed to be University), Porur, Chennai-600116, Tamil Nadu, India
  • Alagarsamy V Medicinal Chemistry Research Laboratory, MNR College of Pharmacy, Sangareddy, Hyderabad-502 294, Telangana, India

Abstract

A series of novel 4-oxo-N-(4-oxo-3-substituted-3,4-dihydroquinazolin-2-yl amino)-2-phenylquinazoline-3(4H)-carboxamidines are prepared from methyl 4-oxo-2-phenylquinazoline-3(4H)-carbthioimidate & 3-(substituted)-2-hydrazino-quinazoline-4(3H)-ones. The starting material 4-oxo-2-phenylquinazoline-3(4H)-carbthioimidates were prepared from anthranilic acid while the 3-(substituted)-2-hydrazino-quinazolin-4(3H)-one was prepared from a range of 1° amines using multistep preparation. Entire synthesized analogues were screened for their antitubercular, anti-HIV and antibacterial activity. Among the series, N-(3-(4-nitrophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl amino)-4-oxo-2-phenylquinazoline-3(4H)-carboxamidine (BQC7) and N-(3-(4-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl amino)-4-oxo-2-phenylquinazoline-3(4H)-carboxamidine (BQC9) showed most potent activity against S. epidermidis, S. aureus & B. subtilis with the MIC of 3 µg/mL. The compound BQC7 displayed the antitubercular potency at 12.5 µg/mL and anti-HIV activity at 8.53 µg/mL against HIV1 and HIV2. Thus, these derivatives are useful in the development of novel antitubercular & antiHIV agents. The results obtained from this study confirm that the synthesized and biologically evaluated quinazolines showed promising antimicrobial, antitubercular and anti-HIV activities and are new scaffolds for antimicrobial activity.

Keywords: Antibacterial, Anti-HIV, Antitubercular, Quinazoline

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Published
2019-07-19
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How to Cite
Sulthana M.T, Chitra K, & Alagarsamy V. (2019). Synthesis of novel 4-oxo-N-(4-oxo-3-substituted-3,4-dihydroquinazolin-2-yl amino)-2-phenylquinazoline-3(4H)-carboxamidines as AntiHIV, antitubercular and antibacterial agents. International Journal of Research in Pharmaceutical Sciences, 10(3), 2031-2037. https://doi.org/10.26452/ijrps.v10i3.1449
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Original Articles
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