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Design, Synthesis, and Structure–Activity Relationships of Novel 1-(Substituted)-2-Methyl-3-(4-Oxo-2-Methylquinazolin-3(4H)-yl) Isothioureas for Their Anti-HIV and Antibacterial Activities

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Abstract

In this study, a novel quinazolinone analogue was designed and synthesized by substituting the thiourea group and phenyl ring at N-3 and C-2 positions of the quinazoline ring, respectively. The prepared analogue was tested for its antibacterial, antitubercular and anti-HIV potencies. The agar dilution method was used to test the antibacterial potency of entire prepared derivatives against various gram-positive and gram-negative microorganism strains. Compound 1-(3-chlorophenyl)-2-methyl-3-(4-oxo-2-methylquinazolin-3(4H)-yl)isothioureas (Xi) shown most potent activity against Klebsiella pneumoniae, Proteus vulgaris, and Staphylococcus epidermidis at 1.6 µg/mL. The compound (Xi) exhibited the antitubercular activity at the minimum microgram of 6.25 µg/mL and anti-HIV activity at 1.17 µg/mL against HIV1 and HIV2. The compound (Xi) offers a potential lead for further optimization and development to new antitubercular and anti-HIV agents. The results obtained from this study confirm that the synthesized and biologically evaluated quinazolines showed promising antimicrobial, antitubercular, and anti-HIV activities and new scaffolds for antimicrobial activity.

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Authors and Affiliations

  1. Medicinal Chemistry Research Laboratory, MNR College of Pharmacy, 502294, Sangareddy, Gr. Hyderabad, India

    V. Alagarsamy, M. T. Sulthana, V. Raja Solomon & G. Saravanan

  2. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Sri Ramachandra Medical College and Research Institute (Deemed University), 600116, Porur, Chennai, India

    K. Chitra

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  1. V. Alagarsamy
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Correspondence to V. Alagarsamy.

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Alagarsamy, V., Sulthana, M.T., Chitra, K. et al. Design, Synthesis, and Structure–Activity Relationships of Novel 1-(Substituted)-2-Methyl-3-(4-Oxo-2-Methylquinazolin-3(4H)-yl) Isothioureas for Their Anti-HIV and Antibacterial Activities. Russ J Bioorg Chem 48, 548–556 (2022). https://doi.org/10.1134/S1068162022030025

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