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Synthesis of novel N-aryl-4-[6-(2-fluoropyridin-3-yl)quinazolin-2-yl]-piperazine-1-carboxamide or -carbothioamide derivatives and their antimicrobial activity

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Chemistry of Heterocyclic Compounds Aims and scope

A series of novel N-aryl-4-[6-(2-fluoropyridin-3-yl)quinazolin-2-yl]-piperazine-1-carboxamide or -carbothioamide derivatives was synthesized by cyclization of 5-bromo-2-fluorobenzaldehyde and guanidine carbonate in the presence of dimethylacetamide followed by treatment with isoamylnitrite and diiodomethane in the presence of copper iodide to afford 6-bromo-2-iodoquinazoline. The latter was treated with piperazine in the presence of triethylamine followed by (2-fluoropyridin-3-yl)boronic acid in the presence of Pd(PPh3)2Cl2 to afford 6-(2-fluoropyridin-3-yl)-2-(piperazin-1-yl)quinazoline which was further treated with various substituted arylisocyanates and arylisothiocyanates to obtain the title compounds. The chemical structures of the synthesized compounds were confirmed by means of LC-MS, 1H, 13C NMR, IR, and mass spectra and elemental analysis. All the synthesized compounds were evaluated for their in vitro antibacterial activity against two Gram-positive and two Gram-negative bacterial species, as well as two different strains of antibiotic-resistant E. coli and for antifungal activity against two fungal strains. Some of the compounds have shown potential antimicrobial activity.

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The authors express their gratitude to IISC, Bangalore, for providing spectral data and to DST-PURSE center, Sri Venkateswara University, Tirupati, for evaluating the antibacterial and antifungal activities.

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Authors and Affiliations

  1. Sri Venkateswara University, Tirupati, 517502, Andhra Pradesh, India

    D. Suresh Babu, Doddaga Srinivasulu & Venkata S. Kotakadi

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  1. D. Suresh Babu
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  2. Doddaga Srinivasulu
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  3. Venkata S. Kotakadi
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Correspondence to Doddaga Srinivasulu.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(1), 60–66

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Babu, D.S., Srinivasulu, D. & Kotakadi, V.S. Synthesis of novel N-aryl-4-[6-(2-fluoropyridin-3-yl)quinazolin-2-yl]-piperazine-1-carboxamide or -carbothioamide derivatives and their antimicrobial activity. Chem Heterocycl Comp 51, 60–66 (2015). https://doi.org/10.1007/s10593-015-1660-2

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