European Journal of Chemistry 2017, 8(4), 384-390 | doi: https://doi.org/10.5155/eurjchem.8.4.384-390.1635 | Get rights and content

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Synthesis and antiproliferative evaluation of new (4-substituted-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methane substituted sulfonamide derivatives


Chandrakant Dhondiram Pawar (1) , Aniket Sarkate (2) , Kshipra Karnik (3) , Dattatraya Navnath Pansare (4) , Devanand Baburao Shinde (5,*)

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

Received: 01 Aug 2017 | Accepted: 23 Sep 2017 | Published: 31 Dec 2017 | Issue Date: December 2017

Abstract


A series of new molecules having 4-substituted-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methane substituted sulfonamide derivatives were synthesized. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, 13C NMR, Mass spectra, and the purity was checked through HPLC analysis. The compounds were also evaluated for their in vitro antiproliferative activity against MCF-7, HeLa, A-549 and DU-145 cancer cell lines by MTT assay. Compounds 4d, 7c and 7d were tested for their activity against a panel of eight human kinase at 10 µM concentrations. Among them the compounds 4d and 7d showed very promising activity against CDK5/P25 kinase with 66 and 70% inhibitions, respectively. Compound 7c also showed promising activity of 59% inhibition. The preliminary bioassay showed that most of the compounds were antiproliferative with different degrees, and some compounds showed better activity than 5-fluorouracil which was used as positive control.


Keywords


Benzoxazine; Human kinase; Antiproliferative; Sulfonyl chlorides; Phenylmethanethiol; CDK5/P25 kinase inhibitors

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DOI: 10.5155/eurjchem.8.4.384-390.1635

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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 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
/

[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
/

[3]. Namdeo Bhujbal, Dattatray Gaikwad, Yuvraj Jagdale, Chandrakant Pawar
Synthesis, antimicrobial and anti‐tubercular activity study of N‐(substituted‐benzyl)‐4‐(trifluoromethyl)thiazole‐2‐sulfonamide and 2‐(N‐(substituted‐benzyl)sulfamoyl)thiazole‐4‐carboxylic acid
Journal of the Chinese Chemical Society  68(8), 1563, 2021
DOI: 10.1002/jccs.202000421
/

[4]. 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
/

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How to cite


Pawar, C.; Sarkate, A.; Karnik, K.; Pansare, D.; Shinde, D. Eur. J. Chem. 2017, 8(4), 384-390. doi:10.5155/eurjchem.8.4.384-390.1635
Pawar, C.; Sarkate, A.; Karnik, K.; Pansare, D.; Shinde, D. Synthesis and antiproliferative evaluation of new (4-substituted-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methane substituted sulfonamide derivatives. Eur. J. Chem. 2017, 8(4), 384-390. doi:10.5155/eurjchem.8.4.384-390.1635
Pawar, C., Sarkate, A., Karnik, K., Pansare, D., & Shinde, D. (2017). Synthesis and antiproliferative evaluation of new (4-substituted-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methane substituted sulfonamide derivatives. European Journal of Chemistry, 8(4), 384-390. doi:10.5155/eurjchem.8.4.384-390.1635
Pawar, Chandrakant, Aniket Sarkate, Kshipra Karnik, Dattatraya Navnath Pansare, & Devanand Baburao Shinde. "Synthesis and antiproliferative evaluation of new (4-substituted-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methane substituted sulfonamide derivatives." European Journal of Chemistry [Online], 8.4 (2017): 384-390. Web. 20 Jan. 2022
Pawar, Chandrakant, Sarkate, Aniket, Karnik, Kshipra, Pansare, Dattatraya, AND Shinde, Devanand. "Synthesis and antiproliferative evaluation of new (4-substituted-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methane substituted sulfonamide derivatives" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

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