European Journal of Chemistry 2017, 8(4), 400-409 | doi: https://doi.org/10.5155/eurjchem.8.4.400-409.1645 | Get rights and content






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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 | Issue Date: December 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

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DOI: 10.5155/eurjchem.8.4.400-409.1645

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Funding information


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

Citations

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[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
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[2]. Dattatraya D. Gaikwad, Umakant D. Pawar, Sadhana L. Chavan, Chandrakant D. Pawar, Dattatraya N. Pansare, Rohini N. Shelke, Santosh L. Chavan, Ashok M. Zine
Synthesis and anti‐proliferative activity studies of 2‐(2‐(trifluoromethyl)‐6‐(substituted)imidazo[1,2‐ b ]pyridazin‐3‐yl)‐ N ‐(substituted)acetamide derivatives
Journal of Heterocyclic Chemistry  57(4), 1925, 2020
DOI: 10.1002/jhet.3920
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[3]. 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
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[4]. Chandrakant Dhondiram Pawar, Dattatraya Navnath Pansare, Devanand Baburao Shinde
(Substituted)-benzo[b]thiophene-4-carboxamide Synthesis and Antiproliferative Activity Study
Letters in Drug Design & Discovery  17(5), 563, 2020
DOI: 10.2174/1570180815666181004114125
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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. 24 Oct. 2020
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)

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

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