European Journal of Chemistry

Synthesis, characterization and in vitro evaluation of some new 5-benzylidene-1,3-thiazolidine-2,4-dione analogs as new class of α-glucosidase inhibitors

Article Sidebar

PDF
Published: Mar 31, 2014
DOI: https://doi.org/10.5155/eurjchem.5.1.144-149.925
Keywords:
α-Glucosidase, Structure activity relationship, Aromatic/heteroaromatic ketone, Thiazolidine-2, 4-dione derivatives, Minimum inhibitory concentration, 5-Benzylidene-1, 3-thiazolidine-2, 4-dione
Section
Research Article
Issue
Vol. 5 No. 1 (2014): March 2014
Dates
Received 2013-09-10
Accepted 2013-10-06
Published 2014-03-31


Main Article Content

Divakara Laxman Somayajulu Nori
Department of Chemistry, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
Kasapu Vishnu Veera Venkata Satyanarayan
Department of Chemistry, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
Vasudeva Rao Avupati
Pharmaceutical Chemistry Division, Andhra University College of Pharmaceutical Sciences, Andhra University, Visakhapatnam-530003, Andhra Pradesh, India
Bharat Kumar Bugata
Department of Biochemistry and Bioinformatics, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
Subhash Yenupuri
Department of Chemistry, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India

Abstract

A series of 5-benzylidene-1,3-thiazolidine-2,4-dione derivatives (5a-u) were synthesized and tested against α-glucosidase. Preparation of the titled compounds was achieved by reaction of (Z)-4-((2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl)benzaldehyde (4) and aromatic/hetero aromatic ketone. Among the compounds tested, (5p) and (5o) were identified as the most active in vitro with minimum inhibitory concentration (MIC) of 6.56±0.81 and 8.92±0.21 µg/mL against α-glucosidase, respectively. Evaluation of the structure activity relationship of substituents within these series has followed the discovery of a variety of compounds.


icon graph This Abstract was viewed 1244 times | icon graph Article PDF downloaded 839 times

How to Cite
(1)
Nori, D. L. S.; Satyanarayan, K. V. V. V.; Avupati, V. R.; Bugata, B. K.; Yenupuri, S. Synthesis, Characterization and in Vitro Evaluation of Some New 5-Benzylidene-1,3-Thiazolidine-2,4-Dione Analogs As New Class of α-Glucosidase Inhibitors. Eur. J. Chem. 2014, 5, 144-149.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Fujisawa, T.; Ikegami, H.; Inoue, K.; Kawabata, Y.; Ogihara, T. Metabolism. 2005, 54, 387-390.
http://dx.doi.org/10.1016/j.metabol.2004.10.004

[2]. Sou, S.; Takahashi, H.; Yamasaki, R.; Kagechika, H.; Endo, Y.; Hashimoto, Y. Chem. Pharm. Bull. 2001, 49, 791-793.
http://dx.doi.org/10.1248/cpb.49.791

[3]. Liu, Y.; Zou, L.; Ma, L.; Chen, W. H.; Wang, B.; Xu, Z. L. Bioorgan. Med. Chem. 2006, 14, 5683-5690.
http://dx.doi.org/10.1016/j.bmc.2006.04.014

[4]. Pandey, J.; Dwivedi, N.; Singh, N.; Srivastava, A. K.; Tamarkarb, A.; Tripathi, R. P. Bioorg. Med. Chem. Lett. 2007, 17, 1321-1325.
http://dx.doi.org/10.1016/j.bmcl.2006.12.002

[5]. Look, G. C.; Fotsh, C. H.; Wong, C. H. Acc. Chem. Res. 1993, 26, 182-190.
http://dx.doi.org/10.1021/ar00028a008

[6]. Roth, J.; Ziak, M.; Zuber, C. Biochimie. 2003, 85, 287-294.
http://dx.doi.org/10.1016/S0300-9084(03)00049-X

[7]. Kaushal, G. P.; Pastuszak, I.; Hatanaka, K. I.; Elbein, A. D. J. Biol. Chem. 1990, 265, 16271-16279.

[8]. Hammond, C.; Braakman, I.; Helenius, A. Proc. Natl. Acad. Sci. U. S. A. 1994, 91, 913-917.
http://dx.doi.org/10.1073/pnas.91.3.913

[9]. Alonso, J. M.; Santa-Cecilia, A.; Calvo, P. Eur. J. Biochem. 1993, 215, 37-42.
http://dx.doi.org/10.1111/j.1432-1033.1993.tb18004.x

[10]. Takeda, Y.; Totoni, K.; Matsuo, I.; Ito, Y. Bioorg. Med. Chem. Lett. 2010, 20, 5357-5359.
http://dx.doi.org/10.1016/j.bmcl.2009.05.125

[11]. Momose, Y.; Meguro, K.; Ikeda, H.; Hatanaka, C.; Oi, S.; Sohda, T. Chem. Pharm. Bull. 1991, 39, 1440-1445.
http://dx.doi.org/10.1248/cpb.39.1440

[12]. Bruno, G.; Costantino, L.; Curinga, C.; Maccari, R.; Monforte, F.; Nicolo, F.; Ottana, R.; Vigorita, Bioorgan. Med. Chem. 2002, 10, 1077-1084.
http://dx.doi.org/10.1016/S0968-0896(01)00366-2

[13]. Jung, S. H.; Park, S. Y.; Kim-Pak, Y.; Lee, H. K.; Park, S. Y.; Shin, K. H.; Ohuchi, K.; Shin, H. K.; Keum, S. R.; Lim, S. S. Chem. Pharm. Bull. 2006, 54, 368-371.
http://dx.doi.org/10.1248/cpb.54.368

[14]. Liu, X. F.; Zheng, C. J.; Sun, L. P.; Liu, X. K.; Piao, H. R. Eur. J. Med. Chem. 2011, 46, 3469-3473.
http://dx.doi.org/10.1016/j.ejmech.2011.05.012

[15]. Zuping, X.; Christian, K.; Jian, M.; Zanna, M.; Beharry, C. M.; Wenxue, W.; Andrew, S. K.; Charles D. S. J. Med. Chem. 2009, 52, 74-86.
http://dx.doi.org/10.1021/jm800937p

[16]. Patil, V.; Tilekar, K.; Munj, S. M.; Mohan, R.; Ramaa, C. S. Eur. J. Med. Chem. 2010, 45, 4539-4544.
http://dx.doi.org/10.1016/j.ejmech.2010.07.014

[17]. Bonde, C. G.; Gaikwad, N. J. Bio. Org. Med. Chem. 2004, 12, 2151-2161.
http://dx.doi.org/10.1016/j.bmc.2004.02.024

[18]. Fan, Y. H.; Chen, H.; Natarajan, A.; Guo, Y.; Harbinski, F.; Iyasere, J.; Christ, W.; Aktasa, H.; Halperina, J. A. Bioorg. Med. Chem. Lett. 2004, 14, 2547-2550.
http://dx.doi.org/10.1016/j.bmcl.2004.02.087

[19]. Jeon, R.; Park, S. Y. Arch. Pharm. Res. 2004, 27, 1099-1105.
http://dx.doi.org/10.1007/BF02975111

[20]. Hafez, H. N.; ElGazzar, A. R. B. A. Bioorg. Med. Chem. Lett. 2009, 19, 4143-4147.
http://dx.doi.org/10.1016/j.bmcl.2009.05.126

[21]. Madhavan, G. R.; Chakrabarti, R.; Reddy, K. A.; Rajesh, B. M.; Balraju, V.; Rao, P. B.; Rajagopalan, R.; Iqbal, J. Bioorgan. Med. Chem. 2006, 14, 584-591.
http://dx.doi.org/10.1016/j.bmc.2005.08.043

[22]. Sambasivarao, S. V.; Soni, L. K.; Gupta, A. K.; Hanumantharao, P.; Kaskhedikar, S. G. Bioorg. Med. Chem. Lett. 2006, 16, 512-520.
http://dx.doi.org/10.1016/j.bmcl.2005.10.069

[23]. Wu, Y.; Tai, H. H.; Cho, H. Bio. Org. Med. Chem. 2010, 18, 1428-1433.
http://dx.doi.org/10.1016/j.bmc.2010.01.016

[24]. Komatsu, T.; Hirano, T.; Songkram, C.; Kawachi, E.; Kagechika, H. Bio. Org. Med. Chem. 2007, 15, 3115-3126.
http://dx.doi.org/10.1016/j.bmc.2007.02.053

[25]. Hu, B.; Ellingboe, J.; Gunawan, I.; Han, S.; Largis, E.; Li, Z.; Malamas, M.; Mulvey, R.; Oliphant, A.; Sum, F.; Tillett, J.; Wong, V. Bioorg. Med. Chem. Lett. 2001, 11, 757-760.
http://dx.doi.org/10.1016/S0960-894X(01)00063-4

[26]. Koide, Y.; Tatsui, A.; Hasegawa, T.; Murakami, A.; Satoh, S.; Yamada, H.; Kazayamaa, S.; Takahashia, A. Bioorg. Med. Chem. Lett. 2003, 13, 25-29.
http://dx.doi.org/10.1016/S0960-894X(02)00853-3

[27]. Li, Q.; AlAyoubi, A.; Guo, T.; Zheng, H.; Sarkar, A.; Nguyen, T.; Eblen, S. T.; Grant, S.; Kellogg, G. E.; Zhang, S. Bioorg. Med. Chem. Lett. 2009, 19, 6042-6046.
http://dx.doi.org/10.1016/j.bmcl.2009.09.057

[28]. Peyrot, V.; Leynadier, D.; Sarrazin, M.; Briand, C.; Rodriquez, A.; Nieto, J. M.; Andreu, J. M., J. Biol. Chem. 1989, 264, 21296-21301.

[29]. Vasudeva, R. A.; Rajendra, P. Y.; Annapurna, A.; Girija, S. G.; Bhagya, R. D.; Venkata, R. V.; Suvarna, R. A.; Lakshmana, S. A.; Aruna, K. V. Bioorg. Med. Chem. Lett. 2012, 22, 6442-6450.
http://dx.doi.org/10.1016/j.bmcl.2012.08.052

[30]. Pierre, C.; Roland, R.; Tremblay, D. J. Clin. Chem. 1978, 24, 208–211.

[31]. Peyrot, V.; Leynadier, D.; Sarrazin, M.; Briand, C.; Menendez, M.; Laynez, J.; Andreu, J. M. Biochemistry 1992, 31, 11125-11132.
http://dx.doi.org/10.1021/bi00160a024

[32]. Assia, S.; Kaddour, L.; Mahieddine, M.; Nouara, Z.; Paul, M. Eur. J. Chem. 2011, 2(3), 311-313.
http://dx.doi.org/10.5155/eurjchem.2.3.311-313.414

[33]. Mohammed, R. A.; Mohammed, H. R. K.; Vedula, G. S.; Nasreen, B.; Syed, A.; Yejella, R. P. Eur. J. Chem. 2012, 3(2), 186-190.
http://dx.doi.org/10.5155/eurjchem.3.2.186-190.554

[34]. Mohammed, S. B.; Aly, A. A.; Ashraf, F. W.; Marwa, M. R. Eur. J. Chem. 2013, 4(2), 92-97.
http://dx.doi.org/10.5155/eurjchem.4.2.92-97.615

[35]. Ashutosh, B.; Malleshappa, N.; Niharika, S.; Vishnu, D. G.; Gaurav, B. Eur. J. Chem. 2011, 2(3), 388-393.
http://dx.doi.org/10.5155/eurjchem.2.3.388-393.184

[36]. Du, Z. Y.; Liu, R. R.; Shao, W. Y.; Mao, X. P.; Ma, L.; Gu, L. Q.; Huang, Z. S.; Chan, A. S. Eur. J. Med. Chem. 2006, 41(2), 213-218.
http://dx.doi.org/10.1016/j.ejmech.2005.10.012

Most read articles by the same author(s)

Most read articles by the same author(s)

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).