Synthesis, characterization and molecular docking studies of novel  S-substituted phenacyl-1,3,4-thiadiazole-thiol derivatives  as antimicrobial agents

Shashidhar Kerur; Kallanagouda Alagawadi; Hailiang Zhu; Fakkirappa Manvi

doi:10.5155/eurjchem.3.3.293-297.613

European Journal of Chemistry 2012, 3(3), 293-297 | doi: https://doi.org/10.5155/eurjchem.3.3.293-297.613 | Get rights and content

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Synthesis, characterization and molecular docking studies of novel S-substituted phenacyl-1,3,4-thiadiazole-thiol derivatives as antimicrobial agents

Shashidhar Kerur ^(1,*)

, Kallanagouda Alagawadi ⁽²⁾

, Hailiang Zhu ⁽³⁾

, Fakkirappa Manvi ⁽⁴⁾

⁽¹⁾ Department of Pharmaceutical Chemistry, Karnataka Lingayath Education University College of Pharmacy, Belgaum, 580010, India
⁽²⁾ Department of Pharmaceutics, Karnataka Lingayath Education University College of Pharmacy, Hubli, 580031, India
⁽³⁾ State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, 210093, China
⁽⁴⁾ Department of Pharmaceutics, Karnataka Lingayath Education University College of Pharmacy, Hubli, 580031, India
^(*) Corresponding Author

Received: 13 Apr 2012 | Accepted: 25 Jun 2012 | Published: 30 Sep 2012 | Issue Date: September 2012

Abstract

In the present study, synthesis and antimicrobial activity of 2,5-disubstituted 1,3,4-thiadiazole derivatives 5a-f are described. The structures of the newly synthesized compounds were confirmed by FT-IR, ¹H NMR, ¹³C NMR, mass and elemental analysis. All compounds were screened for antitubercular and antimicrobial activity. Molecular modeling studies were performed to dock compounds into the ecKAS III binding site, which suggested probable inhibition mechanism. The results revealed that most of the compounds showed high to moderate biological activity against tested microorganisms.

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Keywords

1,3,4-Thiadiazole; Phenacyl bromide; Molecular docking; Antimicrobial activity; Antitubercular activity; Mycobacterium tuberculosis

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DOI: 10.5155/eurjchem.3.3.293-297.613

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Citations

[1]. Mahmoud R. Mahmoud, Manal M. El‐Shahawi, Fatma S. Abu El‐Azm, Mohamed Abdeen
Synthesis and Antimicrobial Activity of Polyfunctionally Substituted Heterocyclic Compounds Derived from 5‐Cinnamoylamino‐2‐Cyanomethyl‐1,3,4‐Thiadiazole
Journal of Heterocyclic Chemistry 54(4), 2352, 2017
DOI: 10.1002/jhet.2824

[2]. Parminder Kaur, Vimal Arora
Significance of Molecular Docking in Developing Potent Antimicrobial 1,3,4-Thiadiazole Derivatives
Letters in Organic Chemistry 20(5), 423, 2023
DOI: 10.2174/1570178619666220930144853

References

[1]. Soumya, S. Indian J. Tub. 2002, 49, 11-16.

[2]. Jolly, V. S.; Pathak, M. Indian J. Chem. 1993, 32B, 502-505.

[3]. Christensen, C. E.; Kragelund, B. B.; Von, P. W. K.; Henriksen, A. Protein Sci. 2007, 16, 261-267.
http://dx.doi.org/10.1110/ps.062473707
PMid:17242430 PMCid:2203288

[4]. De Jong, B. C.; Israelski, D. M.; Corbett, E. L.; Small, P. M. Annu. Rev. Med. 2004, 55, 280-304.
http://dx.doi.org/10.1146/annurev.med.55.091902.103753
PMid:14746522

[5]. Kemal, S.; Yasemin, U.; Mustafa, E. R. Turk. J. Chem. 2007, 31, 125-134.

[6]. Foroumadi, A. S.; Sharifzades, Z.; Hemmateenejod, B.; Moshafi, M. H. DARU 2007, 15, 218-226.

[7]. Sanmati, K. J.; Mishra, P. Indian J. Chem. 2004, 43B, 184-188.

[8]. Onkol, T.; Cakir, B.; Sahin, M. F.; Yildirim, E.; Ekol, K. Turk. J. Chem. 2004, 28, 461-468.

[9]. Fang, L.; Xiao-Qiong, L.; Pinaki, S.; Song, Y. Bioorg. Med. Chem. 2008, 16, 3632-3640.
http://dx.doi.org/10.1016/j.bmc.2008.02.006

[10]. Khalid, M.K.; Naheed, F.; Maimona, R.; Saima, J.; Shahnaz, P. M. Bioorg. Med. Chem. 2009, 12, 481- 486.

[11]. Padmavati, V.; Sudhakar, R. G.; Padmaja, A. Eur. J. Med. Chem. 2009, 44, 2106-2112.
http://dx.doi.org/10.1016/j.ejmech.2008.10.012
PMid:19036476

[12]. Kumar, N. D.; Kumar, N. M.; Kuei-Hua, C.; Kavita, S. Eur. J. Med. Chem. 2010, 45, 4664-4668.
http://dx.doi.org/10.1016/j.ejmech.2010.07.023
PMid:20692741

[13]. Talwar, M. B.; Desai, S, S.; Bennur, S, C. Indian J. Hetero. Chem. 1996, 5, 237-241.

[14]. Bhaskar, D.; Rajesh, H. D. Tetrahedron. Lett. 1996, 37(35), 6375-6378.
http://dx.doi.org/10.1016/0040-4039(96)01351-2

[15]. Joshi, S. D.; Vagdevi, H. M.; Vaidya, V. P.; Gadaginamath, G. S. Eur. J. Med. Chem. 2008, 43, 1989-1996.
http://dx.doi.org/10.1016/j.ejmech.2007.11.016
PMid:18207286

[16]. Stefania-Felicia, B.; Gabriela, L. A.; Ioanna, S.; Constantin, D.; Ana, I. T.; Gabriela, B. Eur. J. Med. Chem. 2009, 44, 4752-4757.
http://dx.doi.org/10.1016/j.ejmech.2009.06.021
PMid:19616347

[17]. Pattan, S. R.; Reddy, V. V. K.; Manvi, F. V.; Desai, B. G., Bhat, A. R. Indian J. Hetero. Chem. 2006, 45(B), 1778-1781.

[18]. Bauer, R. W.; Kirby, M. D. K.; Sherris, J. C.; Turck, M. Am. J. Clin. Pathol. 1966, 45, 493-496.
PMid:5325707

[19]. Paul, M. K.; Mukhopadhyay. A. K. Int. J. Med. Sci. 2004, 1, 101-106.
http://dx.doi.org/10.7150/ijms.1.101
PMid:15912202 PMCid:1074718

[20]. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson. A. J. J. Comput. Chem. 1998, 19, 1639-1642.
http://dx.doi.org/10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B

How to cite

Kerur, S.; Alagawadi, K.; Zhu, H.; Manvi, F. Eur. J. Chem. 2012, 3(3), 293-297. doi:10.5155/eurjchem.3.3.293-297.613

Kerur, S.; Alagawadi, K.; Zhu, H.; Manvi, F. Synthesis, characterization and molecular docking studies of novel S-substituted phenacyl-1,3,4-thiadiazole-thiol derivatives as antimicrobial agents. Eur. J. Chem. 2012, 3(3), 293-297. doi:10.5155/eurjchem.3.3.293-297.613

Kerur, S., Alagawadi, K., Zhu, H., & Manvi, F. (2012). Synthesis, characterization and molecular docking studies of novel S-substituted phenacyl-1,3,4-thiadiazole-thiol derivatives as antimicrobial agents. European Journal of Chemistry, 3(3), 293-297. doi:10.5155/eurjchem.3.3.293-297.613

Kerur, Shashidhar, Kallanagouda Alagawadi, Hailiang Zhu, & Fakkirappa Manvi. "Synthesis, characterization and molecular docking studies of novel S-substituted phenacyl-1,3,4-thiadiazole-thiol derivatives as antimicrobial agents." European Journal of Chemistry [Online], 3.3 (2012): 293-297. Web. 10 Dec. 2023

Kerur, Shashidhar, Alagawadi, Kallanagouda, Zhu, Hailiang, AND Manvi, Fakkirappa. "Synthesis, characterization and molecular docking studies of novel S-substituted phenacyl-1,3,4-thiadiazole-thiol derivatives as antimicrobial agents" European Journal of Chemistry [Online], Volume 3 Number 3 (30 September 2012)

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