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Synthesis and Investigation of Carbonic Anhydrase I and II Activity of Dihydrobenzo[h]Quinazolin-2-yl Thiourea Compounds

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Pharmaceutical Chemistry Journal Aims and scope

Thirteen novel compounds in a series of dihydrobenzo[h]quinazolin-2-yl thiourea compounds (7a–m) were synthesized and characterized using FT-IR, 1H, 13C NMR spectroscopy, and elemental analysis. Some inhibition parameters including IC50 and inhibition constant values (Ki) were determined for all the compounds. All studied compounds exhibited potent inhibition against carbonic anhydrases (CAs). They inhibited CAs with the IC50 values of 30.45 to 94.00 μM (Ki: 28.27–61.01 μM) for hCA I and 21.80 to 78.00 μM (Ki: 17.84–57.96 μM) for hCA II. The most active compounds were found to be compound 7m for hCA I (Ki: 28.27 μM) and compound 7d for hCA II (Ki : 17.84 μM). The absorption, distribution, metabolism, excretion, and toxicity (ADME-Tox) study revealed that all the derivatives had good oral bioavailability with respect to Lipinski’s rule of five and Jorgensen’s rule of three. All derivatives in the series can be considered as outstanding multitarget inhibitors for further investigations.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Art and Sciences, Sakarya University, Sakarya, Turkey

    Merve Taşcı & Mustafa Arslan

  2. Department of Chemistry, Faculty of Science, Balikesir University, Balikesir, Turkey

    Kübra Çıkrıkcı, Adem Ergun, Nahit Gençer & Oktay Arslan

  3. Department of Chemistry, Faculty of Art and Sciences, Balikesir University, Cagis Campus, 10145, Balikesir, Turkey

    Nahit Gençer

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  1. Merve Taşcı
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  2. Mustafa Arslan
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  3. Kübra Çıkrıkcı
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Correspondence to Nahit Gençer.

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Taşcı, M., Arslan, M., Çıkrıkcı, K. et al. Synthesis and Investigation of Carbonic Anhydrase I and II Activity of Dihydrobenzo[h]Quinazolin-2-yl Thiourea Compounds. Pharm Chem J 57, 899–906 (2023). https://doi.org/10.1007/s11094-023-02965-3

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  • DOI: https://doi.org/10.1007/s11094-023-02965-3

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