European Journal of Chemistry

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

Crossmark


Main Article Content

Chandrakant Pawar
Dattatraya Pansare
Devanand Shinde

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.


icon graph This Abstract was viewed 1646 times | icon graph Article PDF downloaded 785 times

How to Cite
(1)
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, 13-21.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Wan, Y.; Wallinder, C.; Plouffe, B.; Beaudry, H.; Mahalingam, A. K.; Wu, X.; Johansson, B.; Holm, M.; Botoros, M.; Karlen, A.; Pettersson, A.; Nyberg, F.; Faendriks, L.; Gallo-Payet, N.; Hallberg, A.; Alterman, M. J. Med. Chem. 2004, 47, 5995-6008.
https://doi.org/10.1021/jm049715t

[2]. Caridha, D.; Kathcart, A. K.; Jirage, D.; Waters, N. C. Bioorg. Med. Chem. Lett. 2010, 20, 3863-3867.
https://doi.org/10.1016/j.bmcl.2010.05.039

[3]. Chen, Y.; Wan, X.; Long, G. Acc. Chem. Res. 2013, 46, 2645-2655.
https://doi.org/10.1021/ar400088c

[4]. Miao, Q.; Yan, X.; Zhao, K. Chin. J. Chem. 2010, 28, 81-85.
https://doi.org/10.1002/cjoc.201090039

[5]. Do, C. V.; Faouzi, A.; Barette, C.; Farce, A.; Fauvarque, M. O.; Colomb, E.; Catry, L.; Vergnes, O. B.; Haftek, M.; Barret, R.; Lomberget, T. Bioorg. Med. Chem. Lett. 2016, 26, 174-180.
https://doi.org/10.1016/j.bmcl.2015.11.010

[6]. Pandya, D. H.; Sharma, J. A.; Jalani, H. B.; Pandya, A. N.; Sudarsanam, V.; Kachler, K. N.; Klotz, K.; Vasu, K. Bioorg. Med. Chem. Lett. 2015, 25, 1306-1309.
https://doi.org/10.1016/j.bmcl.2015.01.040

[7]. Pilipati, L.; Sridevi, J. P.; Yogeeswari, P.; Sriram, D.; Kantevari, S. Bioorg. Med. Chem. Lett. 2016, 26, 3135-3140.
https://doi.org/10.1016/j.bmcl.2016.04.088

[8]. Deng, H.; Hu, J.; Hu, H.; He, M.; Fang, Y. Bioorg. Med. Chem. Lett. 2012, 22, 4148-4152.
https://doi.org/10.1016/j.bmcl.2012.04.057

[9]. Lindenschmidt, G.; Krane, D.; Vortherms, S.; Hilbig, L.; Prinz, H.; Muller, K. Eur. J. Org. Chem. 2016, 110, 280-290.

[10]. Nasr, T.; Bondock, S.; Eid, S. Eur. J. Org. Chem. 2014, 84, 491-504.

[11]. Mobkhot, Y. N.; Kheder, N. A.; Barakat, A.; Choudhary, M. I.; Yousuf, S.; Frey, W. Rsc. Adv. 2016, 6, 63724-63729.
https://doi.org/10.1039/C6RA09883E

[12]. Sharif, M.; Shoaib, K.; Ahmed, S.; Iqbal, J.; Abilov, Z. A.; Spannenbery, A.; Langer, P. Tetrahedron Lett. 2016, 57, 3060-3062.
https://doi.org/10.1016/j.tetlet.2016.05.041

[13]. Abe, T.; Mino, T.; Watanabe, K.; Sakamoto, M. Eur. J. Org. Chem. 2014, 31, 6983-6991.
https://doi.org/10.1002/ejoc.201402881

[14]. Kolli, S. K.; Nakhi, A.; Medishetti, R.; Yellanki, S.; Pal, M. Bioorg. Med. Chem. Lett. 2014, 24, 4460-4465.
https://doi.org/10.1016/j.bmcl.2014.07.096

[15]. Haidle, A. H.; Zabierek, A. A.; Childers, K. K.; Rosenstein, C.; Young, J. R. Bioorg. Med. Chem. Lett. 2014, 24, 1968-1973.
https://doi.org/10.1016/j.bmcl.2014.02.064

[16]. Badland, M.; Compere, D.; Courte, K.; Dublanchet, A. C.; Wrigglesworth, R. Bioorg. Med. Chem. Lett. 2011, 21, 528-530.
https://doi.org/10.1016/j.bmcl.2010.10.087

[17]. Parai, M. K.; Panda, G.; Chaturvedi, V.; Manju, Y. K.; Sinha, S. Bioorg. Med. Chem. Lett. 2008, 18, 289-292.
https://doi.org/10.1016/j.bmcl.2007.10.083

[18]. Ye, P.; Kuhn, C.; Juan, M.; Sharma, R.; Kablaoui, N. M. Bioorg. Med. Chem. Lett. 2011, 21, 849-852.
https://doi.org/10.1016/j.bmcl.2010.11.069

[19]. Laing, V. E.; Brookings, D. C.; Carbery, R. J.; Simorte, J. G.; Merriman, M. Bioorg. Med. Chem. Lett. 2012, 22, 472-475.
https://doi.org/10.1016/j.bmcl.2011.10.105

[20]. Romagnoli, R.; Baraldi, P. G.; Lopez, O. C.; Tolomeo, M.; Hamel, E. Bioorg. Med. Chem. Lett. 2011, 21, 2746-2751.
https://doi.org/10.1016/j.bmcl.2010.11.083

[21]. Klapars, A.; Buchwald, S. L. J. Am. Chem. Soci. 2002, 124, 14844-14845.
https://doi.org/10.1021/ja028865v

[22]. Fleckenstein, C. A.; Plenio, H. J. Org. Chem. 2008, 73, 3236-3244.
https://doi.org/10.1021/jo8001886

[23]. Pawar, C. D.; Sarkate, A. P.; Karnik, K. S.; Bahekar, S. S.; Pansare, D. N.; Shelke, R. N.; Jawale, C. S.; Shinde, D. B. Bioorg. Med. Chem. Lett. 2016, 26, 3525-3528.
https://doi.org/10.1016/j.bmcl.2016.06.030

[24]. Pawar, C. D.; Sarkate, A. P.; Karnik, K. S.; Pansare, D. N.; Shinde, D. B. Egyp. J. Basic Appl. Sci. 2017, 4(4), 310-314.
https://doi.org/10.1016/j.ejbas.2017.09.001

[25]. Pawar, C. D.; Shinde, D. B. Res. Rev. J. Chem. 2016, 5(3), 28-33.

[26]. Pawar, C. D.; Sarkate, A.; Karnik, K.; Pansare, D. N.; Shinde, D. B. Eur. J. Chem. 2017, 8(4), 384-390.
https://doi.org/10.5155/eurjchem.8.4.384-390.1635

[27]. Pawar, C.; Pansare, D.; Shinde, D. Eur. J. Chem. 2017, 8(4), 400-409.
https://doi.org/10.5155/eurjchem.8.4.400-409.1645

[28]. Skehan, P.; Storeng, R.; Scudiero. D.; Monks, A.; McMohan, J.; Vistica, D.; Warrem, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Nat. Cancer Inst. 1990, 82, 1107-1112.
https://doi.org/10.1093/jnci/82.13.1107

[29]. Vichai, V.; Kirtikara, K. Nat. Protoc. 2006, 1(3), 1112-1116.
https://doi.org/10.1038/nprot.2006.179

Supporting Agencies

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