European Journal of Chemistry 2018, 9(1), 13-21 | doi: https://doi.org/10.5155/eurjchem.9.1.13-21.1669 | Get rights and content

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Synthesis of new 3-(substituted-phenyl)-N-(2-hydroxy-2-(substituted-phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives as antiproliferative agents


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

(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 Chemistry, Shivaji University, Vidyanagar, Kolhapur, 416004 (MS), India
(*) Corresponding Author

Received: 11 Nov 2017 | Revised: 06 Dec 2017 | Accepted: 14 Dec 2017 | Published: 31 Mar 2018 | Issue Date: March 2018

Abstract


In the present work, we report the synthesis of a series of 3-(substituted phenyl)-N-(2-hydroxy-2-(substituted-phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives through Suzuki and Buchwald reaction. We have optimized methodology for targets from milligram to multi-gram scale. The newly synthesized compounds were characterized by 1H NMR, 19F NMR, 13C NMR, LC-MS techniques and purity was further checked by HPLC. The compounds were evaluated for their in-vitro antiproliferative activity against MCF-7, HeLa, A-549 and Du-145 cancer cell lines by CCK-8 assay. The preliminary bioassay suggests that most of the compounds show antiproliferation with different degrees and 5-fluorouracil was used as positive control. Among these compounds 2d, 2g, 2i, 4e, 4h and 4k are most active compared to the standard. All the synthesized compounds show IC50 values from 1.82-9.52 µM in different cell lines. Amongst these, compounds 2d, 2g, 2i, 4e, 4h and 4k were most potent, with IC50 values ranging from 1.82-4.28 µM in different cell lines.


Keywords


Suzuki reaction; Buchwald reaction; Antiproliferation activity; Thiophene-2-sulfonamide; N-N-Dimethylethylenediamine; 2-(Methylamino)-1-phenylethanol

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DOI: 10.5155/eurjchem.9.1.13-21.1669

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Funding information


Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431004, MS, India.

Citations

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[1]. 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
/


[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
/


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How to cite


Pawar, C.; Pansare, D.; Shinde, D. Eur. J. Chem. 2018, 9(1), 13-21. doi:10.5155/eurjchem.9.1.13-21.1669
Pawar, C.; Pansare, D.; Shinde, D. Synthesis of new 3-(substituted-phenyl)-N-(2-hydroxy-2-(substituted-phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives as antiproliferative agents. Eur. J. Chem. 2018, 9(1), 13-21. doi:10.5155/eurjchem.9.1.13-21.1669
Pawar, C., Pansare, D., & Shinde, D. (2018). 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), 13-21. doi:10.5155/eurjchem.9.1.13-21.1669
Pawar, Chandrakant, 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 [Online], 9.1 (2018): 13-21. Web. 15 Jan. 2021
Pawar, Chandrakant, Pansare, Dattatraya, AND Shinde, Devanand. "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 [Online], Volume 9 Number 1 (31 March 2018)

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