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Synthesis of phenyl thiazole hydrazones and their activity against glycation of proteins

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Abstract

Phenyl thiazole hydrazone derivatives 1–21 have been synthesized and screened for their in vitro antiglycation activity. Hydrazones 1–21 displayed assorted antiglycation activities having IC50 values in the range of 187.61 ± 1.12–886.98 ± 5.29 µM as compared to standard rutin (IC50 = 269.07 ± 3.79 µM). Compounds 5 (IC50 = 187.61 ± 1.12 µM), 3 (IC50 = 191.92 ± 3.08 µM), 4 (IC50 = 193.77 ± 3.06 µM), 6 (IC50 = 217.90 ± 2.48 µM), 15 (IC50 = 221.98 ± 2.34 µM), 2 (IC50 = 226.59 ± 1.19 µM), 21 (IC50 = 229.67 ± 1.95 µM), 18 (IC50 = 231.09 ± 0.38 µM), 12 (IC50 = 242.94 ± 2.05 µM), and 1 (IC50 = 264.22 ± 5.60 µM), respectively, showed excellent antiglycation activities superior to standard rutin. Compound 17 (IC50 = 269.94 ± 1.11 µM) demonstrated a comparable activity to the standard. Compounds 7, 8, 9, 10, 11, 13, 14, and 16 exhibited weaker activities than standard. However, compounds 19 and 20 showed no activity. When evaluated for cytotoxicity against rat fibroblast cell line (3T3 cell line), all compounds were found to be non-toxic in cellular model.

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Acknowledgments

Authors would like to acknowledge the Higher Education Commission (HEC), Pakistan, Project No. 20-2073 under the National Research Program for Universities and the Organization for Prohibition of Chemical Weapons (OPCW), The Netherlands (Project No. L/ICA/ICB/173681/12), for financial supports.

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Authors and Affiliations

  1. International Center for Chemical and Biological Sciences, H. E. J. Research Institute of Chemistry, University of Karachi, Karachi, 75270, Pakistan

    Khalid Mohammed Khan, Muhammad Irfan, Mahwish Ashraf, Syed Muhammad Saad & M. Iqbal Choudhary

  2. Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300, Bandar Puncak Alam, Selangor D. E., Malaysia

    Muhammad Taha

  3. Faculty of Applied Science, Universiti Teknologi MARA, 40450, Shah Alam, Malaysia

    Muhammad Taha

  4. PCSIR Laboratories Complex, Karachi, Shahrah-e-Dr. Salimuzzaman Siddiqui, Karachi, 75280, Pakistan

    Shahnaz Perveen

  5. Department of Biochemistry, Faculty of Science, King Abdulaziz University, Jeddah, 22254, Saudi Arabia

    M. Iqbal Choudhary

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  1. Khalid Mohammed Khan
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  2. Muhammad Irfan
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  3. Mahwish Ashraf
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  4. Muhammad Taha
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  5. Syed Muhammad Saad
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  6. Shahnaz Perveen
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  7. M. Iqbal Choudhary
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Correspondence to Khalid Mohammed Khan.

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Khan, K.M., Irfan, M., Ashraf, M. et al. Synthesis of phenyl thiazole hydrazones and their activity against glycation of proteins. Med Chem Res 24, 3077–3085 (2015). https://doi.org/10.1007/s00044-015-1349-1

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  • DOI: https://doi.org/10.1007/s00044-015-1349-1

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