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Synthesis, Characterization, and Antifungal Activity of Some New Thieno[2,3-b]pyridines Incorporating Quinazoline or Benzimidazole Moiety

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Abstract

Reaction of 4,6-dimethyl-3-cyanopyridine-2(1H)-thione (IIIa) or 4,5,6-trisubstituted-3-cyanopyridine-2(1H)-thiones (IIIb–d) with 2-chloromethylquinazoline-4(3H)-one (IVa) furnished the corresponding 3-amino-2-(4-oxo-3,4-dihydroquinazolin-2-yl)thieno[2,3-b]pyridines (VIa–d). Reaction of aminothieno-pyridines (VIa, b, d) were reacted with triethyl orthoformate, acetic anhydride or nitrous acid to furnish pyridothienopyrimidoquinazolines (VIIIa, b, d), (IXa, b, d) or pyridothienotriazinoquinazolines (Xa, b, d). The new compound, 3-cyano-5-acetyl-6-methyl-4-styrylpyridine-2(1H)-thione (IIIe) was synthesized and reacted with 2-chloromethyl-1H-benzimadazole to give 5-acetyl-3-amino-2-(1H-benzimidazol-2-yl)-6-methyl-4-styryl-thieno[2,3-b]pyridine (XII) which was used as a key intermediate for synthesizing pyridothienopyrimidobenzimidazoles (XIII, XIV). All newly synthesized compounds were characterized on the basis of their elemental and spectral analyses. Also, most of the synthesized compounds were screened in vitro for their antifungal activity.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Assiut University, Assiut, 71515, Egypt

    O. F. Ibrahim, E. A. Bakhite, S. A. M. Metwally & Y. A. El-Ossaily

  2. Chemistry Department, College of Science, Jouf University, Sakaka, 2014, Saudi Arabia

    Y. A. El-Ossaily

  3. Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Assiut University, 71515, Assiut, Egypt

    H. H. M. Abdu-Allah

  4. Department of Chemistry, Faculty of Science, Sana’a University, Sana’a, Yemen

    E. A. Al-Taifi

  5. Department of Biomedical Sciences, College of Veterinary Medicine, King Faisal University, 31982, Al-Ahsa, Kingdom of Saudi Arabia

    M. Kandel

  6. Department of Pharmacology, Faculty of Veterinary Medicine, Kafrelsheikh University, 33516, Kafrelsheikh, Egypt

    M. Kandel

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  1. O. F. Ibrahim
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Correspondence to E. A. Bakhite.

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Ibrahim, O.F., Bakhite, E.A., Metwally, S.A. et al. Synthesis, Characterization, and Antifungal Activity of Some New Thieno[2,3-b]pyridines Incorporating Quinazoline or Benzimidazole Moiety. Russ J Bioorg Chem 47, 918–928 (2021). https://doi.org/10.1134/S1068162021040117

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