European Journal of Chemistry 2021, 12(3), 279-283 | doi: https://doi.org/10.5155/eurjchem.12.3.279-283.2118 | Get rights and content

Issue cover




Crossmark

  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Synthesis of substituted pyridine based sulphonamides as an antidiabetic agent


Gautam Sadawarte (1) orcid , Samadhan Jagatap (2) orcid , Mukesh Patil (3) orcid , Vasant Jagrut (4) orcid , Jamatsing Darbarsing Rajput (5,*) orcid

(1) Department of Chemistry, Faculty of B.P. Arts, S.M.A. Science and K.K.C. Commerce College Chalisgaon, Maharashtra, 424101, India
(2) Department of Chemistry, Faculty of B.P. Arts, S.M.A. Science and K.K.C. Commerce College Chalisgaon, Maharashtra, 424101, India
(3) Department of Zoology, Faculty of B.P. Arts, S.M.A. Science and K.K.C. Commerce College, Chalisgaon Maharashtra, 424101, India
(4) Department of Chemistry, Swami Vivekanand College, Mantha Jalna, 431504 India
(5) Department of Chemistry, Faculty of B.P. Arts, S.M.A. Science and K.K.C. Commerce College Chalisgaon, Maharashtra, 424101, India
(*) Corresponding Author

Received: 07 Apr 2021 | Revised: 11 Jun 2021 | Accepted: 15 Jul 2021 | Published: 30 Sep 2021 | Issue Date: September 2021

Abstract


This research work describes the synthesis of a new series of heterocyclic compounds, namely sulfonamide derivatives. Sulfonamides are a diverse class of organic compounds having significant and potent biological activities. Diverse synthetic methods have been engaged to build up its various derivatives for different biological functions. In this study, the production of novel pyridine-based heterocyclic compounds having sulfonamide moieties has been elaborated. The obtained sulfonamide-based pyridine scaffold was used to investigate their alpha-amylase inhibition activity. The structures of freshly prepared compounds were described using 1H NMR, 13C NMR, and IR spectroscopic techniques. The molecular docking of sulfonamides performed against porcine pancreatic alpha-amylase using PDB file 1LP was used for generation of grid. All the new synthesized compounds were shown notable anti-diabetic activity.


Keywords


Acarbose; Sulfonamides; Alpha-amylase; Antidiabetic activity; Medicinal chemistry; N-Isopropyl-4-methylpyridine-2,6-diamine

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.12.3.279-283.2118

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 214 times | icon graph PDF Article downloaded 69 times


References


[1]. Hansch C., Sammes P. G., Taylor J. B. Comprehensive Medicinal Chemistry, Vol. 2, Pergamon Press, Oxford, 1990.

[2]. Kanda, Y.; Kawanishi, Y.; Oda, K.; Sakata, T.; Mihara, S. I.; Asakura, K.; Kanemasa, T.; Ninomiya, M.; Fujimoto, M.; Konoike, T. Bioorg. Med. Chem. 2001, 9 (4), 897-907.
https://doi.org/10.1016/S0968-0896(00)00305-9

[3]. Stokes, S. S.; Albert, R.; Buurman, E. T.; Andrews, B.; Shapiro, A. B.; Green, O. M.; McKenzie, A. R.; Otterbein, L. R. Bioorg. Med. Chem. Lett. 2012, 22 (23), 7019-7023.
https://doi.org/10.1016/j.bmcl.2012.10.003

[4]. Chibale, K.; Haupt, H.; Kendrick, H.; Yardley, V.; Saravanamuthu, A.; Fairlamb, A. H.; Croft, S. L. Bioorg. Med. Chem. Lett. 2001, 11 (19), 2655-2657.
https://doi.org/10.1016/S0960-894X(01)00528-5

[5]. Ezabadi, I. R.; Camoutsis, C.; Zoumpoulakis, P.; Geronikaki, A.; Soković, M.; Glamocilija, J.; Cirić, A. Bioorg. Med. Chem. 2008, 16 (3), 1150-1161.
https://doi.org/10.1016/j.bmc.2007.10.082

[6]. Kennedy, J. F.; Thorley, M.: Pharmaceutical Substances, 3rd ed., Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D.; Thieme: Stuttgart, 1999.

[7]. Gal, C. S.-L. Cardiovasc. Drug Rev. 2006, 19 (3), 201-214.
https://doi.org/10.1111/j.1527-3466.2001.tb00065.x

[8]. Natarajan, A.; Guo, Y.; Harbinski, F.; Fan, Y.-H.; Chen, H.; Luus, L.; Diercks, J.; Aktas, H.; Chorev, M.; Halperin, J. A. J. Med. Chem. 2004, 47 (21), 4979-4982.
https://doi.org/10.1021/jm0496234

[9]. Vullo, D.; De Luca, V.; Scozzafava, A.; Carginale, V.; Rossi, M.; Supuran, C. T.; Capasso, C. Bioorg. Med. Chem. 2013, 21 (15), 4521-4525.
https://doi.org/10.1016/j.bmc.2013.05.042

[10]. Wilson, C. O.; Gisvold, O.; Block, J. H., Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 11th ed.; Block, J., Beale, J., Wilson, C. O., Eds.; Lippincott Williams and Wilkins: Philadelphia, PA, 2004.

[11]. Levin, J. I.; Chen, J. M.; Du, M. T.; Nelson, F. C.; Killar, L. M.; Skala, S.; Sung, A.; Jin, G.; Cowling, R.; Barone, D.; March, C. J.; Mohler, K. M.; Black, R. A.; Skotnicki, J. S. Bioorg. Med. Chem. Lett. 2002, 12 (8), 1199-1202.
https://doi.org/10.1016/S0960-894X(02)00136-1

[12]. Kim, D.-K.; Lee, J. Y.; Lee, N.; Ryu, D. H.; Kim, J.-S.; Lee, S.; Choi, J.-Y.; Ryu, J.-H.; Kim, N.-H.; Im, G.-J.; Choi, W.-S.; Kim, T.-K. Bioorg. Med. Chem. 2001, 9 (11), 3013-3021.
https://doi.org/10.1016/S0968-0896(01)00200-0

[13]. Hu, B.; Ellingboe, J.; Han, S.; Largis, E.; Lim, K.; Malamas, M.; Mulvey, R.; Niu, C.; Oliphant, A.; Pelletier, J.; Singanallore, T.; Sum, F.-W.; Tillett, J.; Wong, V. Bioorg. Med. Chem. 2001, 9 (8), 2045-2059.
https://doi.org/10.1016/S0968-0896(01)00114-6

[14]. Ma, T.; Fuld, A. D.; Rigas, J. R.; Hagey, A. E.; Gordon, G. B.; Dmitrovsky, E.; Dragnev, K. H. Chemotherapy 2012, 58 (4), 321-329.
https://doi.org/10.1159/000343165

[15]. Adkins, J. C.; Faulds, D. Amprenavir. Drugs 1998, 55, 837-842.
https://doi.org/10.2165/00003495-199855060-00015

[16]. Roush, W. R.; Gwaltney, S. L.; Cheng, J.; Scheidt, K. A.; McKerrow, J. H.; Hansell, E. J. Am. Chem. Soc. 1998, 120 (42), 10994-10995.
https://doi.org/10.1021/ja981792o

[17]. Hoehn, H.; Polacek, I.; Schulze, E. J. Med. Chem. 1973, 16 (12), 1340-1346.
https://doi.org/10.1021/jm00270a006

[18]. Purohit, S. S.; Veerapur, V. P. Sch. Acad. J. Pharm. 2014, 3 (1), 26-37. https://saspublishers.com/media/articles/SAJP3126-37.pdf (accessed Jul 15, 2021).

[19]. Ma, F.; Liu, J.; Zhou, T.; Lei, M.; Chen, J.; Wang, X.; Zhang, Y.; Shen, X.; Hu, L. Eur. J. Med. Chem. 2018, 152, 307-317.
https://doi.org/10.1016/j.ejmech.2018.04.028

[20]. Williams, D. R. Chem. Rev. 1972, 72 (3), 203-213.
https://doi.org/10.1021/cr60277a001

[21]. Fathalla, O. A.; Awad, S. M.; Mohamed, M. S. Arch. Pharm. Res. 2005, 28 (11), 1205-1212.
https://doi.org/10.1007/BF02978199

[22]. Domagk, G. Angew. Chem. Weinheim Bergstr. Ger. 1935, 48 (42), 657-667.
https://doi.org/10.1002/ange.19350484202

[23]. Abdul Qadir, M.; Ahmed, M.; Aslam, H.; Waseem, S.; Shafiq, M. I. J. Chem. 2015, 2015, 1-8.
https://doi.org/10.1155/2015/524056

[24]. Casini, A.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. Curr. Cancer Drug Targets 2002, 2 (1), 55-75.
https://doi.org/10.2174/1568009023334060

[25]. Scozzafava, A.; Owa, T.; Mastrolorenzo, A.; Supuran, C. Curr. Med. Chem. 2003, 10 (11), 925-953.
https://doi.org/10.2174/0929867033457647

[26]. Thun, M. J.; Henley, S. J.; Patrono, C. J. Natl. Cancer Inst. 2002, 94 (4), 252-266.
https://doi.org/10.1093/jnci/94.4.252

[27]. Dalloul, H. M. MOJ Bioorg. Org. Chem. 2017, 1 (7), 255-260.
https://doi.org/10.15406/mojboc.2017.01.00044

[28]. Singh, V.; Kaushik, N. K.; Singh, R. Asian J. Res. Chem. 2011, 4, 339-347.

[29]. Sharma, R.; Soman, S. S. Eur. J. Med. Chem. 2015, 90, 342-350.
https://doi.org/10.1016/j.ejmech.2014.11.041

[30]. Kumar Parai, M.; Panda, G.; Srivastava, K.; Kumar Puri, S. Bioorg. Med. Chem. Lett. 2008, 18 (2), 776-781.
https://doi.org/10.1016/j.bmcl.2007.11.038

[31]. Mirian, M.; Zarghi, A.; Sadeghi, S.; Tabaraki, P.; Tavallaee, M.; Dadrass, O.; Sadeghi-Aliabadi, H. Iran. J. Pharm. Res. 2011, 10 (4), 741-748.

[32]. Kolaczek, A.; Fusiarz, I.; Lawecka, J.; Branowska, D. Institute of Chemistry, Siedlce University, Siedlce, Poland. https://www.researchgate.net/profile/Rafik_Karaman/post/im_working_on_sulphonamids_antibacterial_does_any_one_prepear_any_analogs_for_sulphonamids_and_which_rout_he_use_paper_are_needed_thanks/attachment/59d6355a79197b8077992ee6/AS%3A383878217912320%401468535107273/download/Sulfonamides+1.pdf (accessed Jul 15, 2021).

[33]. Bagul, S. D.; Rajput, J. D.; Tadavi, S. K.; Bendre, R. S. Res. Chem. Intermed. 2017, 43 (4), 2241-2252.
https://doi.org/10.1007/s11164-016-2759-5

[34]. Liu, Y.; Lu, Y.; Prashad, M.; Repic, O.; Blacklock, T. J. Adv. Synth. Catal. 2005, 347 (2-3), 217-219.
https://doi.org/10.1002/adsc.200404236

[35]. Akhter, F.; Hashim, A.; Khan, M. S.; Ahmad, S.; Iqbal, D.; Srivastava, A. K.; Siddiqui, M. H. S. Afr. J. Bot. 2013, 88, 265-272.
https://doi.org/10.1016/j.sajb.2013.06.024

[36]. Rajput, J. D.; Bagul, S. D.; Hosamani, A. A.; Patil, M. M.; Bendre, R. S. Res. Chem. Intermed. 2017, 43 (10), 5377-5393.
https://doi.org/10.1007/s11164-017-2933-4

[37]. Gilles, C.; Astier, J.-P.; Marchis-Mouren, G.; Cambillau, C.; Payan, F. C. Eur. J. Biochem. 1996, 238 (2), 561-569.
https://doi.org/10.1111/j.1432-1033.1996.0561z.x


How to cite


Sadawarte, G.; Jagatap, S.; Patil, M.; Jagrut, V.; Rajput, J. Eur. J. Chem. 2021, 12(3), 279-283. doi:10.5155/eurjchem.12.3.279-283.2118
Sadawarte, G.; Jagatap, S.; Patil, M.; Jagrut, V.; Rajput, J. Synthesis of substituted pyridine based sulphonamides as an antidiabetic agent. Eur. J. Chem. 2021, 12(3), 279-283. doi:10.5155/eurjchem.12.3.279-283.2118
Sadawarte, G., Jagatap, S., Patil, M., Jagrut, V., & Rajput, J. (2021). Synthesis of substituted pyridine based sulphonamides as an antidiabetic agent. European Journal of Chemistry, 12(3), 279-283. doi:10.5155/eurjchem.12.3.279-283.2118
Sadawarte, Gautam, Samadhan Jagatap, Mukesh Patil, Vasant Jagrut, & Jamatsing Darbarsing Rajput. "Synthesis of substituted pyridine based sulphonamides as an antidiabetic agent." European Journal of Chemistry [Online], 12.3 (2021): 279-283. Web. 1 Dec. 2021
Sadawarte, Gautam, Jagatap, Samadhan, Patil, Mukesh, Jagrut, Vasant, AND Rajput, Jamatsing. "Synthesis of substituted pyridine based sulphonamides as an antidiabetic agent" European Journal of Chemistry [Online], Volume 12 Number 3 (30 September 2021)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



DOI Link: https://doi.org/10.5155/eurjchem.12.3.279-283.2118

CrossRef | Scilit | GrowKudos | Researchgate | Publons | Microsoft | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2021, 12(3), 279-283 | doi: https://doi.org/10.5155/eurjchem.12.3.279-283.2118 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c) 2021 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/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 (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).



© Copyright 2010 - 2021  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 2010-2021 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.