European Journal of Chemistry 2014, 5(1), 144-149 | doi: https://doi.org/10.5155/eurjchem.5.1.144-149.925 | Get rights and content

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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


Divakara Laxman Somayajulu Nori (1,*) , Kasapu Vishnu Veera Venkata Satyanarayan (2) , Vasudeva Rao Avupati (3) , Bharat Kumar Bugata (4) , Subhash Yenupuri (5)

(1) Department of Chemistry, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
(2) Department of Chemistry, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
(3) Pharmaceutical Chemistry Division, Andhra University College of Pharmaceutical Sciences, Andhra University, Visakhapatnam-530003, Andhra Pradesh, India
(4) Department of Biochemistry and Bioinformatics, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
(5) Department of Chemistry, Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India
(*) Corresponding Author

Received: 10 Sep 2013 | Revised: 18 Oct 2013 | Accepted: 29 Oct 2013 | Published: 31 Mar 2014 | Issue Date: March 2014

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.


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

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DOI: 10.5155/eurjchem.5.1.144-149.925

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Gitam University, Rushikonda, Visakhapatnam-530045, Andhra Pradesh, India

Citations

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[1]. Danylo Kaminskyy, Anna Kryshchyshyn, Roman Lesyk
5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry
European Journal of Medicinal Chemistry  140, 542, 2017
DOI: 10.1016/j.ejmech.2017.09.031
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[2]. Subbarayal Reddy Dwarampudi, Gowri Sankar Dannana, Vasudeva Rao Avupati, Venkata Satyanarayana Murthy Bendi
Synthesis, characterization and in vitro biological evaluation of some new 1,3,5-triazine-chalcone hybrid molecules as Mycobacterium tuberculosis H37Rv inhibitors
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DOI: 10.5155/eurjchem.5.4.570-576.1098
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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


How to cite


Nori, D.; Satyanarayan, K.; Avupati, V.; Bugata, B.; Yenupuri, S. Eur. J. Chem. 2014, 5(1), 144-149. doi:10.5155/eurjchem.5.1.144-149.925
Nori, D.; Satyanarayan, K.; Avupati, V.; Bugata, B.; 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(1), 144-149. doi:10.5155/eurjchem.5.1.144-149.925
Nori, D., Satyanarayan, K., Avupati, V., Bugata, B., & Yenupuri, S. (2014). 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. European Journal of Chemistry, 5(1), 144-149. doi:10.5155/eurjchem.5.1.144-149.925
Nori, Divakara, Kasapu Vishnu Veera Venkata Satyanarayan, Vasudeva Rao Avupati, Bharat Kumar Bugata, & Subhash Yenupuri. "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." European Journal of Chemistry [Online], 5.1 (2014): 144-149. Web. 2 Mar. 2021
Nori, Divakara, Satyanarayan, Kasapu, Avupati, Vasudeva, Bugata, Bharat, AND Yenupuri, Subhash. "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" European Journal of Chemistry [Online], Volume 5 Number 1 (31 March 2014)

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European Journal of Chemistry 2014, 5(1), 144-149 | doi: https://doi.org/10.5155/eurjchem.5.1.144-149.925 | Get rights and content

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