European Journal of Chemistry

Synthesis and antitubercular evaluation of 2-iminothiazolidine-4-ones

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Published: Sep 30, 2014
DOI: https://doi.org/10.5155/eurjchem.5.3.550-556.1059
Keywords:
Cytotoxicity, Antitubercular activity, Thiazolidine derivatives, Mycobacterium tuberculosis, Structure activity relationship, Minimum inhibitory concentration
Section
Short Communication
Issue
Vol. 5 No. 3 (2014): September 2014
Dates
Received 2014-03-25
Accepted 2014-04-30
Published 2014-09-30


Main Article Content

Ganesh Samala
Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
Chunduri Madhuri
Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
Jonnalagadda Padma Sridevi
Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
Radhika Nallangi
Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
Yogeeswari Perumal
Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
Sriram Dharmarajan
Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India

Abstract

In the present manuscript, we report synthesis of new 3 and 5 substituted 2-imino thiazolidine-4-ones by three step synthetic protocols from 3-trifluormethyl aniline or 2-amino heterocycle. The compounds were evaluated for in vitro activities against Mycobacterium tuberculosis (MTB) in presence and absence of efflux pump inhibitor, cytotoxicity against RAW 264.7 cells. Among the thirty six compounds, 2-imino-3-(5-nitrothiazol-2-yl)-5-(3,4,5-trimethoxybenzylidene)thiazolidin-4-one (5g) was found to be the most active compound in vitro with MICs of 3.31 µM against log-phase culture of MTB and also non-toxic up to 100 µM. Compound 5g showed minimum inhibitory concentration (MIC) of 0.82 µM against MTB in presence of efflux pump inhibitor verapamil.


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How to Cite
(1)
Samala, G.; Madhuri, C.; Sridevi, J. P.; Nallangi, R.; Perumal, Y.; Dharmarajan, S. Synthesis and Antitubercular Evaluation of 2-Iminothiazolidine-4-Ones. Eur. J. Chem. 2014, 5, 550-556.

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References

[1]. World Health Organization, 2011/2012 Tuberculosis Global Facts, Geneva, Switzerland, 2011.

[2]. Berry, M.; Kon, O. M. Eur. Respir. Rev. 2009, 18, 195-197.
http://dx.doi.org/10.1183/09059180.00005209

[3]. Koul, A.; Arnoult, E.; Lounis, N.; Guillemont, J.; Andries, K. Nature 2011, 469, 483-490.
http://dx.doi.org/10.1038/nature09657

[4]. Choi, J. Y.; Plummer, M. S.; Starr, J.; Desbonnet, C. R.; Soutter, H.; Chang, J.; Miller, J. R.; Dillman, K.; Miller, A. A.; Roush, W. R. J. Med. Chem. 2012, 55, 852-870.
http://dx.doi.org/10.1021/jm201349f

[5]. Payne, D. J.; Gwynn, M. N.; Holmes, D. J.; Pompliano, D. L. Nat. Rev. Drug. Discov. 2007, 6, 29-40.
http://dx.doi.org/10.1038/nrd2201

[6]. Norbert, H.; Kurt, M.; Richard, W.; available online at http://merian.pch.univie.ac.at/pch/pub/nh7.pdf.

[7]. Reynolds, R. C.; Ananthan, S.; Faaleolea, E.; Hobrath, J. V.; Kwong, C. D.; Maddox, C.; Rasmussen, L.; Sosa, M. I.; Thammasuvimol, E.; White, E. L.; Zhang, W.; Secrist, J. A. Tuberculosis 2012, 92, 72-83.
http://dx.doi.org/10.1016/j.tube.2011.05.005

[8]. Ananthan, S.; Faaleolea, E. R.; Goldman, R. C.; Hobrath, J. V.; Kwong, C. D.; Laughon, B. E.; Maddry, J. A.; Mehta, A.; Rasmussen, L.; Reynolds, R. C.; Secrist, J. A. 3rd.; Shindo, N.; Showe, D. N.; Sosa, M. I.; Suling, W. J.; White, E. L. Tuberculosis 2009, 89, 334-353.
http://dx.doi.org/10.1016/j.tube.2009.05.008

[9]. Maddry, J. A.; Ananthan, S.; Goldman, R. C.; Hobrath, J. V.; Kwong, C. D.; Maddox, C.; Rasmussen, L.; Reynolds, R. C.; Secrist, J. A.; Sosa, M. I.; White, E. L.; Zhang, W. Tuberculosis 2009, 89, 354-363.
http://dx.doi.org/10.1016/j.tube.2009.07.006

[10]. Sriram, D.; Yogeeswari, P.; Senthilkumar, P.; Sangaraju, D.; Nelli, R.; Banerjee, D.; Bhat, P.; Manjashetty, T. H. Chem. Biol. Drug. Des. 2010, 75, 381-391.
http://dx.doi.org/10.1111/j.1747-0285.2010.00947.x

[11]. Kulkarni, A. A.; Wankhede, S. B.; Dhawale, N. D.; Yadav, P. B.; Deore, V. V.; Gonjari, I. D. Arabian. J. Chem. In press, DOI: 10.1016/j.arabjc.2012.07.020
http://dx.doi.org/10.1016/j.arabjc.2012.07.020

[12]. Franzblau, S. G.; Witzig, R. S.; McLaughlin, J. C.; Torres, P.; Madico, G.; Hernandez, A.; Degnan, M. T.; Cook, M. B.; Quenzer, V. K.; Ferguson, R. M.; Gilman, R. H. J. Clin. Microbiol. 1998, 36, 362-366.

[13]. Weir-Torn. J.; Tsu, A. H.; Wen, H. L.; Yu, S. C. US 2012/0225880 A1.

[14]. De Rossi, E.; Ainsa, J. A.; Riccardi, G. FEMS. Microbiol. Rev. 2006, 30, 36-52.
http://dx.doi.org/10.1111/j.1574-6976.2005.00002.x

[15]. Rodrigues, L.; Ainsa, J. A.; Amaral, L.; Viveiros, M. Recent. Pat. Anti-Infect Drug. Discovery. 2011, 6, 118-127.

[16]. Pages, J. M.; Amaral, L. Biochim. Biophys. Acta. 2009, 1794, 826-833.

Supporting Agencies

Department of Science & Technology (SR/S1/OC-70/2010), New Delhi, India and Council of Scientific & Industrial Research, India
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