European Journal of Chemistry 2017, 8(4), 400-409. doi:10.5155/eurjchem.8.4.400-409.1645

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


Chandrakant Pawar (1,*) , Dattatraya Pansare (2) , Devanand Shinde (3)

(1) Department of Chemical Technology, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad, 431004, MS, India
(2) Department of Chemistry, Deogiri College, Aurangabad, 431005, MS, India
(3) Department of Chemistry, Shivaji University, Vidyanagar, Kolhapur, 416004, MS, India
(*) Corresponding Author

Received: 30 Aug 2017, Accepted: 23 Sep 2017, Published: 31 Dec 2017

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.


Keywords


Pd/C; Antiproliferative; Aurora-A kinases; 5,6-Dihydropyrazole; Tetrahydropyridine; 4,5,6,7-Tetrahydropyrazole

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.8.4.400-409.1645

Article Metrics


This Abstract was viewed 554 times | PDF Article downloaded 206 times

Citations

/


[1]. Chandrakant Pawar, Dattatraya Pansare, Devanand Shinde
Synthesis of new 3-(substituted-phenyl)-N-(2-hydroxy-2-(substituted-phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives as antiproliferative agents
European Journal of Chemistry  9(1), 13, 2018
DOI: 10.5155/eurjchem.9.1.13-21.1669
/

[2]. Chandrakant D. Pawar, Sadhana L. Chavan, Umakant D. Pawar, Dattatraya N. Pansare, Santosh V. Deshmukh, Devanand B. Shinde
Synthesis, anti-proliferative activity, SAR, and kinase inhibition studies of thiazol-2-yl- substituted sulfonamide derivatives
Journal of the Chinese Chemical Society  66(3), 257, 2019
DOI: 10.1002/jccs.201800312
/

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


How to cite


Pawar, C.; Pansare, D.; Shinde, D. Eur. J. Chem. 2017, 8(4), 400-409. doi:10.5155/eurjchem.8.4.400-409.1645
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(4), 400-409. doi:10.5155/eurjchem.8.4.400-409.1645
Pawar, C., Pansare, D., & Shinde, D. (2017). Synthesis and antiproliferative activity of 3-(substituted)-4,5,6,7-tetrahydro-6-(substituted)-1H-pyrazolo[3,4-c]pyridine derivatives. European Journal of Chemistry, 8(4), 400-409. doi:10.5155/eurjchem.8.4.400-409.1645
Pawar, Chandrakant, Dattatraya Pansare, & Devanand Shinde. "Synthesis and antiproliferative activity of 3-(substituted)-4,5,6,7-tetrahydro-6-(substituted)-1H-pyrazolo[3,4-c]pyridine derivatives." European Journal of Chemistry [Online], 8.4 (2017): 400-409. Web. 21 Oct. 2019
Pawar, Chandrakant, Pansare, Dattatraya, AND Shinde, Devanand. "Synthesis and antiproliferative activity of 3-(substituted)-4,5,6,7-tetrahydro-6-(substituted)-1H-pyrazolo[3,4-c]pyridine derivatives" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

DOI Link: https://doi.org/10.5155/eurjchem.8.4.400-409.1645

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c)



© Copyright 2019 • Atlanta Publishing House LLC • All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.