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

Article Sidebar

PDF
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 2017-09-14
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.


icon graph This Abstract was viewed 1939 times | icon graph Article PDF downloaded 789 times

How to Cite
(1)
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.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
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

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).