European Journal of Chemistry 2014, 5(3), 550-556 | doi: https://doi.org/10.5155/eurjchem.5.3.550-556.1059 | Get rights and content

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


Ganesh Samala (1) , Chunduri Madhuri (2) , Jonnalagadda Padma Sridevi (3) , Radhika Nallangi (4) , Yogeeswari Perumal (5) , Sriram Dharmarajan (6,*)

(1) Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
(2) Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
(3) Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
(4) Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
(5) Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
(6) Antitubercular Drug Discovery Laboratory, Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad, 500078, India
(*) Corresponding Author

Received: 25 Mar 2014 | Revised: 29 Apr 2014 | Accepted: 30 Apr 2014 | Published: 30 Sep 2014 | Issue Date: September 2014

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.


Keywords


Cytotoxicity; Antitubercular activity; Thiazolidine derivatives; Mycobacterium tuberculosis; Structure activity relationship; Minimum inhibitory concentration

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DOI: 10.5155/eurjchem.5.3.550-556.1059

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Funding information


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

Citations

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[1]. Nazar Trotsko
Antitubercular properties of thiazolidin-4-ones – A review
European Journal of Medicinal Chemistry  215, 113266, 2021
DOI: 10.1016/j.ejmech.2021.113266
/


[2]. Nadezhda N. Kolos, Nikolai V. Nazarenko, Svetlana V. Shishkina, Andrey O. Doroshenko, Elena G. Shvets, Maksim A. Kolosov, Fedor G. Yaremenko
Synthesis, study of the structure, and modification of the products of the reaction of 4-aryl-4-oxobut-2-enoic acids with thiourea
Chemistry of Heterocyclic Compounds  56(9), 1202, 2020
DOI: 10.1007/s10593-020-02798-y
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How to cite


Samala, G.; Madhuri, C.; Sridevi, J.; Nallangi, R.; Perumal, Y.; Dharmarajan, S. Eur. J. Chem. 2014, 5(3), 550-556. doi:10.5155/eurjchem.5.3.550-556.1059
Samala, G.; Madhuri, C.; Sridevi, J.; Nallangi, R.; Perumal, Y.; Dharmarajan, S. Synthesis and antitubercular evaluation of 2-iminothiazolidine-4-ones. Eur. J. Chem. 2014, 5(3), 550-556. doi:10.5155/eurjchem.5.3.550-556.1059
Samala, G., Madhuri, C., Sridevi, J., Nallangi, R., Perumal, Y., & Dharmarajan, S. (2014). Synthesis and antitubercular evaluation of 2-iminothiazolidine-4-ones. European Journal of Chemistry, 5(3), 550-556. doi:10.5155/eurjchem.5.3.550-556.1059
Samala, Ganesh, Chunduri Madhuri, Jonnalagadda Padma Sridevi, Radhika Nallangi, Yogeeswari Perumal, & Sriram Dharmarajan. "Synthesis and antitubercular evaluation of 2-iminothiazolidine-4-ones." European Journal of Chemistry [Online], 5.3 (2014): 550-556. Web. 24 Oct. 2021
Samala, Ganesh, Madhuri, Chunduri, Sridevi, Jonnalagadda, Nallangi, Radhika, Perumal, Yogeeswari, AND Dharmarajan, Sriram. "Synthesis and antitubercular evaluation of 2-iminothiazolidine-4-ones" European Journal of Chemistry [Online], Volume 5 Number 3 (30 September 2014)

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