European Journal of Chemistry

Synthesis and antiproliferative activity of 3-(substituted)-4,5,6,7-tetrahydro-6-(substituted)-1H-pyrazolo[3,4-c]pyridine derivatives

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Published: Dec 31, 2017
DOI: https://doi.org/10.5155/eurjchem.8.4.400-409.1645
Keywords:
Pd/C, Antiproliferative, Aurora-A kinases, 5, 6-Dihydropyrazole, Tetrahydropyridine, 4, 6, 7-Tetrahydropyrazole
Section
Research Article
Issue
Vol. 8 No. 4 (2017): December 2017
Dates
Received 2017-08-30
Accepted 2017-09-23
Published 2017-12-31


Main Article Content

Chandrakant Pawar
Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004, MS, India
Dattatraya Pansare
Department of Chemistry, Deogiri College, Aurangabad, 431005, MS, India
Devanand Shinde
Department of Chemistry, Shivaji University, Vidyanagar, Kolhapur, 416004, MS, India

Abstract

A series of new molecules having 3-(substituted)-4,5,6,7-tetrahydro-6-(substituted)-1H-pyrazolo[3,4-c]pyridine and 3-(substituted)-5,6-dihydro-6-(substituted)-1H-pyrazolo[3,4-c] pyridin-7(4H)-one derivatives were designed and synthesized in large scale (grams range). The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, 13C NMR, Mass spectra; and purity was also checked through LC/MS and HPLC analysis. The antiproliferative activity of the compounds was checked for lung cancer, cervical cancer, breast cancer and prostate cancer on panel of four cell lines. A few compounds (13c, 13g, 15g and 15h) showed promising antiproliferative activity in the range of 5.12-17.12 µM which were further tested for their inhibitory activity against panel of 8 human kinases at 10 µM concentrations. The compounds 13c, 13g, 15g and 15h shows prominent inhibitory activity against Aurora-A, Aurora-B, CDK5/P25 and mTOR kinases.


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Pawar, C.; Pansare, D.; Shinde, D. Synthesis and Antiproliferative Activity of 3-(substituted)-4,5,6,7-Tetrahydro-6-(substituted)-1H-pyrazolo[3,4-c]pyridine Derivatives. Eur. J. Chem. 2017, 8, 400-409.

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References

[1]. Alafeefy, A. M.; Ashour, A. E.; Prasad, O.; Sinha, L.; Pathak, S.; Alasmari, F. A.; Rishi, A. K.; Abdel-Aziz, H. A. Eur. J. Med. Chem. 2015, 92, 191-201.
https://doi.org/10.1016/j.ejmech.2014.12.048

[2]. Devegowda, V. N.; Seo, S. H.; Pae, A. N.; Nam, G.; Choi, K. I. Bull. Korean Chem. Soc. 2012, 33, 647-650.
https://doi.org/10.5012/bkcs.2012.33.2.647

[3]. Devegowda, V. N.; Hong, J. R.; Cho, S.; Lim, E. J.; Choo, H.; Keum, G.; Rhim, H.; Nam, G. Bioorg. Med. Chem. Lett. 2013, 23, 4696-4700.
https://doi.org/10.1016/j.bmcl.2013.05.100

[4]. Guo, Z.; Orth, P.; Zhu, Z.; Mazzola, R. D.; Chan, T. Y.; Vaccaro, H. A.; Brian, K.; Kozlowski, J. A.; Lavey, B. J.; Zhou, G.; Paliwal, S.; Wong, S. C.; Shih, N. Y.; Ting, P. C.; Rosner, K. E.; Shipps, G. W.; Siddiqui, M. A. Belanger, D. B.; Dai, C.; Li, D.; Girijavallabhan, V. M.; Popovici-Muller, J.; Yu, W.; Zhao, L. PCT Int. Appl., 2005121130, 22 Dec. 2005.

[5]. Chen, M.; Guo, Z.; Lanier, M. C.; Zhao, L.; Betz, S. F.; Huang, C. Q.; Loweth, C. J.; Ashweek, N. J.; Liu, X. J.; Struthers, R. S.; Bradbury, M. J.; Behan, J. W.; Wen, J.; Brien, Z. O.; Saunders, J.; Zhu, Y. F. Bioorg. Med. Chem. Lett. 2007, 17, 3845-3850.
https://doi.org/10.1016/j.bmcl.2007.05.009

[6]. Caruso, M.; Valsasina, B.; Ballinari, D.; Bertrand, J.; Brasca, M. G.; Caldarelli, M.; Cappella, P.; Fiorentini, F.; Gianellini, L. M.; Scolaro, A.; Beria, I. Bioorg. Med. Chem. Lett. 2012, 22, 96-101.
https://doi.org/10.1016/j.bmcl.2011.11.065

[7]. Wei, Z.; Yang, H.; Liu, Z.; Tremblay, M.; Jonstone, S.; Beha, S.; Yue, S. Y.; Srivastava, S.; Tomaszewaski, M. J.; Brown, W.; Walpole, C.; St-Onge, S.; Lessard, E.; Archambault, A. J.; Groblewski, T.; Page, D. Bioorg. Med. Chem. Lett. 2012, 22, 3884-3889.
https://doi.org/10.1016/j.bmcl.2012.04.128

[8]. Pinto, D. J. P.; Orwat, M. J.; Koch, S.; Rossi, K, A.; Alexander, R. S.; Smallwood, A.; Wong, P. C.; Rendina, A. R.; Luettgen, J. M.; Knabb, R. M.; He, K.; Xin, B.; Wexler, R. R.; Lam, P. Y. S. J. Med. Chem. 2007, 50, 5339-5356.
https://doi.org/10.1021/jm070245n

[9]. Duplantier, A. J.; Andersen, C. J.; Cheng, J. B.; Cohan, V. L.; Decker, C.; Dicapua, F. M.; Kraus, K. G.; Johnson, K. L.; Turner, C. R.; Umland, J. P.; Watson, J. W.; Wester, R. T.; Williams, A. S.; Williams, J. A. J. Med. Chem. 1998, 41, 2268-2277.
https://doi.org/10.1021/jm9800090

[10]. Khatri, C. J.; Indalkar, K. S.; Patil, C. R.; Goyal, S. N.; Chaturbhuj, G. U. Bioorg. Med. Chem. Lett. 2017, 27, 1721-1726.
https://doi.org/10.1016/j.bmcl.2017.02.076

[11]. Hafez, H. N.; El-Gazzar, A. R.; Al-Hussain, S. A. Bioorg. Med. Chem. Lett. 2016, 26, 2428-2433.
https://doi.org/10.1016/j.bmcl.2016.03.117

[12]. Bhide, R. S.; Neels, J.; Qin, L. Y.; Ruan, Z.; Stachura, S.; Weight, C.; Sack, J. S.; Stefanski, K.; Gu, X.; Xie, J. H.; Goldstine, C. B.; Skala, S.; Pedicord, D. L.; Ruepp, S.; MuraliDhar, T. G.; Carter, P. H.; Salter-Cid, L. M.; Poss, M. A.; Davies, P. Bioorg. Med. Chem. Lett. 2016, 26, 4256-4260.
https://doi.org/10.1016/j.bmcl.2016.07.047

[13]. Fukui, H.; Inoguchi, K.; Nakano, J. Heterocycles 2002, 56, 257-264.
https://doi.org/10.3987/COM-01-S(K)25

[14]. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J; Vistica, D.; Jonathan, T. W.; Heidi, B.; Susan, K.; Michael, R. B. J. Natl. Cancer Inst. 1990, 82, 1107-1112.
https://doi.org/10.1093/jnci/82.13.1107

[15]. Vichai, V.; Kirtikara, K. Nat. Protoc. 2006, 1, 1112-1116.
https://doi.org/10.1038/nprot.2006.179

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Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431004, MS, India
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