Synthesis and biological evaluation of new benzo[ d ][1,2,3]triazol-1-yl-pyrazole-based dihydro-[1,2,4]triazolo[4,3- a ]
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Synthesis and biological evaluation of new benzo[d][1,2,3] triazol‑1‑yl‑pyrazole‑based dihydro‑[1,2,4]triazolo[4,3‑a] pyrimidines as potent antidiabetic, anticancer and antioxidant agents Vinay Pogaku1 · R. Krishnan2 · Srinivas Basavoju1 Received: 29 May 2020 / Accepted: 26 September 2020 © Springer Nature B.V. 2020
Abstract A series of new benzo[d][1,2,3]triazol-1-yl-pyrazole-based dihydro-[1,2,4] triazolo[4,3-a]pyrimidine derivatives 4a-p were synthesized and well characterized by using IR, 1H, 13C NMR and mass spectral data. Finally, the structure of the compound 4l was solved unambiguously by single-crystal X-ray diffraction (SXRD) which confirms all the structures 4a–p. The in vitro α-glucosidase inhibition, anticancer (A549 and MCF-7 cell lines) and antioxidant studies of the title compounds 4a–p were screened. Among all the compounds, 4g, 4h and 4n exhibited significant α-glucosidase inhibition activity with the IC50 values 20.12 ± 0.19 µM, 21.55 ± 0.46 µM and 24.92 ± 0.98 µM. Similarly, the compounds 4h, 4d and 4e showed potent anticancer activity against A549 (human lung carcinoma) cell line with IC50 values 3.64 µM, 4.73 µM and 4.56 µM, respectively, whereas the compounds 4c and 4o displayed potent anticancer activity against human breast cancer (MCF-7) cell line with IC50 values of 2.66 µM and 2.11 µM. In addition, the antioxidant activity revealed that the compounds 4e and 4h exhibited potent antioxidant activity (IC50: 4.25 µM and 5.40 µM). To determine the safety profile of the most active compounds 4c, 4d, 4e, 4g, 4h, 4n and 4o were tested against non-cancer HEK293 cell line (human embryonic kidney 293), results in the lower toxicity of these compounds.
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116 4-020-04285-7) contains supplementary material, which is available to authorized users. * Srinivas Basavoju [email protected] 1
Department of Chemistry, National Institute of Technology, Warangal, Telangana 506 004, India
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Department of Chemistry, Birla Institute of Technology and Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500 078, India
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Graphic abstract New benzo[d][1,2,3]triazol-1-yl-pyrazole-based dihydro-[1,2,4]triazolo[4,3-a] pyrimidines were synthesized. The target compounds were showed significant α-glucosidase inhibition, anticancer and antioxidant activities.
Keywords Pyrazole · Triazolopyrimidine · α-glucosidase inhibition activity · Anticancer activity · Antioxidant activity
Introduction Pyrazole scaffolds have shown potent anticancer activity, and for instance, pyrazole derivatives such as Barasertib and Tozasertib have exhibited potent anticancer activity in the literature [1–3]. Some pyrazole-based molecules Danusertib and ENMD2076 are under clinical trials for the treatment of cancer disease, and Crizotinib has been approved for the treatment of NSCLC (non-small cell lung carcinoma) (Fig. 1) [4]. Similarly, pyrazole derivatives have also been
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