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Synthesis, docking study, and DNA photocleavage activity of some pyrimidinyl hydrazones and 3-(quinolin-3-yl)-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidine derivatives

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Abstract

In the present study, synthesis of a series of some novel 3-(Quinolin-3-yl)-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidine derivatives (4a–e) has been achieved by oxidative cyclization of new pyrimidinyl hydrazone intermediates (3a–e) using hypervalent iodine reagent(III) under mild conditions. The structures of all synthesized compounds were established on the basis of IR, NMR (1H and 13C), mass spectral data, and elemental analysis. All compounds were evaluated for their DNA photocleavage activity. Compounds 4a, 4b, 4d and 3a–e were found to possess good activity at 40 μg/μl concentration and were mainly responsible for the conversion of supercoiled form of DNA into open circular form. Further, docking study was carried out using Molegro Virtual Docker version 2010.4.2.0 using PDB (1AB4) in support of the results obtained.

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Notes

  1. inter-convertible between 5′ and 7′.

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Authors and Affiliations

  1. Department of Chemistry, Maharishi Markandeshwar University, Mullana, Ambala, 133207, Haryana, India

    Ajay Sharma, Vinod Kumar & Rajshree Khare

  2. Department of Pharmaceutical Chemistry, Maharishi Markandeshwar College of Pharmacy, Maharishi Markandeshwar University, Mullana, Ambala, 133207, Haryana, India

    Girish Kumar Gupta

  3. Department of Biotechnology, Maharishi Markandeshwar University, Mullana, Ambala, 133207, Haryana, India

    Vikas Beniwal

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  1. Ajay Sharma
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Correspondence to Vinod Kumar.

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Sharma, A., Kumar, V., Khare, R. et al. Synthesis, docking study, and DNA photocleavage activity of some pyrimidinyl hydrazones and 3-(quinolin-3-yl)-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidine derivatives. Med Chem Res 24, 1830–1841 (2015). https://doi.org/10.1007/s00044-014-1265-9

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