European Journal of Chemistry 2011, 2(1), 94-99. doi:https://doi.org/10.5155/eurjchem.2.1.94-99.161

Synthesis, characterization and antimicrobial activity evaluation of new imidazo [2,1-b][1,3,4]thiadiazole derivatives


Shankar Gaddeppa Alegaon (1,*) , Kallanagouda Ramappa Alagawadi (2)

(1) Department of Pharmaceutical Chemistry, Karnataka Lingayat Education University’s College of Pharmacy, Belgaum, Karnataka, IN-590010, India
(2) Department of Pharmaceutical Chemistry, Karnataka Lingayat Education University’s College of Pharmacy, Belgaum, Karnataka, IN-590010, India
(*) Corresponding Author

Received: 09 Jun 2010, Accepted: 11 Oct 2010, Published: 28 Mar 2011

Abstract


Imidazo[2,1-b][1,3,4]thiadiazoles (4a-g) were synthesized from 3,4,5-trimethoxy benzoic acid and thiosemicarbazide. Reaction of 4 with Vilsmeier-Haack reagent yielded imidazo [2,1-b][1,3,4] thiadiazole–5-carbaldehyde derivatives (5a-g). Obtained imidazo[2,1-b][1,3,4] thiadia zoles-5-carbaldehydes were subjected to Knoevenagel condensation with 2-(2,4-dioxothia zolidin-3-yl)acetic acid (1) and 2-(4-oxo-2-thioxothiazolidin-3-yl)acetic (2) in the presence of catalytic amount of piperidine and acetic acid to afford imidazo[2,1-b][1,3,4]thiadiazoles (6a-g) and (7a-g), respectively. The structures of the newly synthesized compounds were confirmed by IR, NMR and elemental analyses. All compounds were screened for their antibacterial and antifungal activities. Some of the compounds displayed good antibacterial and antifungal activity.

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Keywords


Thiazolidinedione; Thiadiazole; Imidazo[2,1-b][1,3,4]thiadiazoles; Antibacterial activity; Antifungal activity; Rhodanine

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DOI: 10.5155/eurjchem.2.1.94-99.161

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Citations

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Tetrahedron  69(24), 5008, 2013
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[4]. Mustafa Er, Buğracan Ergüven, Hakan Tahtaci, Abdurrahman Onaran, Tuncay Karakurt, Abdulilah Ece
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Medicinal Chemistry Research  26(3), 615, 2017
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[5]. Nadia S. El-Gohary, Mona I. Shaaban
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[6]. Hakan Tahtaci, Hatice Karacık, Abdulilah Ece, Mustafa Er, Mine Gül Şeker
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[7]. Shigeki Sano, Keisuke Matsuura, Hayato Sumiyoshi, Akira Miki, Syuji Kitaike, Michiyasu Nakao
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[8]. Shankar G. Alegaon, Kallanagouda R. Alagawadi
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[9]. Bhoomendra A. Bhongade, Sirajunisa Talath, Ravikiran A. Gadad, Andanappa K. Gadad
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How to cite


Alegaon, S.; Alagawadi, K. Eur. J. Chem. 2011, 2(1), 94-99. doi:https://doi.org/10.5155/eurjchem.2.1.94-99.161
Alegaon, S.; Alagawadi, K. Eur. J. Chem. Synthesis, characterization and antimicrobial activity evaluation of new imidazo [2,1-b][1,3,4]thiadiazole derivatives. 2011, 2(1), 94-99. doi:https://doi.org/10.5155/eurjchem.2.1.94-99.161
Alegaon, S., & Alagawadi, K. (2011). Synthesis, characterization and antimicrobial activity evaluation of new imidazo [2,1-b][1,3,4]thiadiazole derivatives. European Journal of Chemistry, 2(1), 94-99. doi:https://doi.org/10.5155/eurjchem.2.1.94-99.161
Alegaon, Shankar, & Kallanagouda Ramappa Alagawadi. "Synthesis, characterization and antimicrobial activity evaluation of new imidazo [2,1-b][1,3,4]thiadiazole derivatives." European Journal of Chemistry [Online], 2.1 (2011): 94-99. Web. 18 Jun. 2018
Alegaon, Shankar, AND Alagawadi, Kallanagouda. "Synthesis, characterization and antimicrobial activity evaluation of new imidazo [2,1-b][1,3,4]thiadiazole derivatives" European Journal of Chemistry [Online], Volume 2 Number 1 (28 March 2011)

DOI: https://doi.org/10.5155/eurjchem.2.1.94-99.161

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