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

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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 | Revised: 09 Sep 2010 | Accepted: 11 Oct 2010 | Published: 28 Mar 2011 | Issue Date: March 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.

2_1_94_99_800


Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


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

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.2.1.94-99.161

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 2582 times | icon graph PDF Article downloaded 809 times


Citations

/


[1]. Ibrahim Ozcan, Senem Akkoc, Hakan Alici, Seval Capanlar, Onur Sahin, Hakan Tahtaci
Novel Thioether‐Bridged 2,6‐Disubstituted and 2,5,6‐Trisubstituted Imidazothiadiazole Analogues: Synthesis, Antiproliferative Activity, ADME, and Molecular Docking Studies
Chemistry & Biodiversity  20(1), , 2023
DOI: 10.1002/cbdv.202200884
/

[2]. Amit B. Patel, Jignesh V. Rohit
Development of 1,3,4-Thiadiazole and Piperazine Fused Hybrid Quinazoline Derivatives as Dynamic Antimycobacterial Agents
Polycyclic Aromatic Compounds  42(9), 5991, 2022
DOI: 10.1080/10406638.2021.1970586
/

[3]. Mustafa Er, Buğracan Ergüven, Hakan Tahtaci, Abdurrahman Onaran, Tuncay Karakurt, Abdulilah Ece
Synthesis, characterization, preliminary SAR and molecular docking study of some novel substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives as antifungal agents
Medicinal Chemistry Research  26(3), 615, 2017
DOI: 10.1007/s00044-017-1782-4
/

[4]. Mustafa Er, Hakan Tahtaci, Tuncay Karakurt, Abdurrahman Onaran
Novel Substituted Imidazo[2,1‐ b ][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities
Journal of Heterocyclic Chemistry  56(9), 2555, 2019
DOI: 10.1002/jhet.3653
/

[5]. Tulika Anthwal, HariOm Singh, Sumitra Nain
1,3,4-Thiadiazole Scaffold: Anti-Microbial Agents
Pharmaceutical Chemistry Journal  55(12), 1345, 2022
DOI: 10.1007/s11094-022-02580-8
/

[6]. Ammankallu Sowmya, Gudibande N. Anil Kumar, Sujeet Kumar, Subhas S. Karki
Qualitative and Quantitative Study of Intermolecular Interactions in Imidazo[2,1‐b] [1,3,4] Thiadiazoles
ChemistrySelect  6(17), 4265, 2021
DOI: 10.1002/slct.202100552
/

[7]. A. Sowmya, G.N. Anil Kumar, Sujeet Kumar, Subhas S. Karki
Crystal structure, quantum chemical and theoretical charge density analysis of 5‑bromo-2-(4-methylbenzyl)-6-(4-nitrophenyl)imidazo[2,1-b][1,3,4] thiadiazole
Chemical Data Collections  25, 100326, 2020
DOI: 10.1016/j.cdc.2019.100326
/

[8]. Neena Neena, Vishwas Chaudhri, Fateh V. Singh, Hideyasu China, Toshifumi Dohi, Ravi Kumar
Synthetic Utility of the Vilsmeier–Haack Reagent in Organic Synthesis
Synlett  34(07), 777, 2023
DOI: 10.1055/s-0042-1751421
/

[9]. José S. Casas, M. Victoria Castaño, María D. Couce, Agustín Sánchez, José Sordo, M. Dolores Torres, Saulo A. Vázquez, Ezequiel M. Vázquez-López
Relevance of weak intermolecular forces on the supramolecular structure of free or DMSO solvated 5-(4-X-benzylidene)rhodanines (X = F, Cl, Br, I)
Journal of Molecular Structure  1120, 100, 2016
DOI: 10.1016/j.molstruc.2016.05.010
/

[10]. Sercan Askin, Hakan Tahtaci, Cüneyt Türkeş, Yeliz Demir, Abdulilah Ece, Gülşen Akalın Çiftçi, Şükrü Beydemir
Design, synthesis, characterization, in vitro and in silico evaluation of novel imidazo[2,1-b][1,3,4]thiadiazoles as highly potent acetylcholinesterase and non-classical carbonic anhydrase inhibitors
Bioorganic Chemistry  113, 105009, 2021
DOI: 10.1016/j.bioorg.2021.105009
/

[11]. Mustafa Er, Arif Özer, Şahin Direkel, Tuncay Karakurt, Hakan Tahtaci
Novel substituted benzothiazole and Imidazo[2,1-b][1,3,4]Thiadiazole derivatives: Synthesis, characterization, molecular docking study, and investigation of their in vitro antileishmanial and antibacterial activities
Journal of Molecular Structure  1194, 284, 2019
DOI: 10.1016/j.molstruc.2019.05.104
/

[12]. Hakan Tahtaci, Hatice Karacık, Abdulilah Ece, Mustafa Er, Mine Gül Şeker
Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents
Molecular Informatics  37(3), 1700083, 2018
DOI: 10.1002/minf.201700083
/

[13]. Bhoomendra A. Bhongade, Sirajunisa Talath, Ravikiran A. Gadad, Andanappa K. Gadad
Biological activities of imidazo[2,1-b][1,3,4]thiadiazole derivatives: A review
Journal of Saudi Chemical Society  20, S463, 2016
DOI: 10.1016/j.jscs.2013.01.010
/

[14]. Nadia S. El-Gohary, Mona I. Shaaban
Synthesis, antimicrobial, antiquorum-sensing, antitumor and cytotoxic activities of new series of fused [1,3,4]thiadiazoles
European Journal of Medicinal Chemistry  63, 185, 2013
DOI: 10.1016/j.ejmech.2013.02.010
/

[15]. Dhanusu Suresh, Kuppusamy Kanagaraj, Kasi Pitchumani
Microwave promoted one-pot synthesis of 2-aryl substituted 1,3,4-oxadiazoles and 1,2,4-oxadiazole derivatives using Al3+-K10 clay as a heterogeneous catalyst
Tetrahedron Letters  55(27), 3678, 2014
DOI: 10.1016/j.tetlet.2014.05.004
/

[16]. Hasan Tunel, Mustafa Er, Hakan Alici, Abdurrahman Onaran, Tuncay Karakurt, Hakan Tahtaci
Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2, 6‐disubstituted imidazothiadiazole analogues
Journal of Heterocyclic Chemistry  58(6), 1321, 2021
DOI: 10.1002/jhet.4260
/

[17]. Shigeki Sano, Keisuke Matsuura, Hayato Sumiyoshi, Akira Miki, Syuji Kitaike, Michiyasu Nakao
Reinvestigation of 1,3,4-Thiadiazol-2(3H)-iminium Bromide in the Two-Step Synthesis of Imidazo[2,1-b][1,3,4]thiadiazoles
HETEROCYCLES  89(4), 1041, 2014
DOI: 10.3987/COM-14-12938
/

[18]. Meltem Dagli, Mustafa Er, Tuncay Karakurt, Abdurrahman Onaran, Hakan Alici, Hakan Tahtaci
Synthesis, Characterization, Antimicrobial Evaluation, and Computational Investigation of Substituted Imidazo[2,1‐ b ][1,3,4]Thiadiazole Derivatives
ChemistrySelect  5(38), 11753, 2020
DOI: 10.1002/slct.202002821
/

[19]. Shankar G. Alegaon, Kallanagouda R. Alagawadi
New thiazolidine-2,4-diones as antimicrobial and cytotoxic agent
Medicinal Chemistry Research  21(10), 3214, 2012
DOI: 10.1007/s00044-011-9876-x
/

[20]. Mustafa Er, Farid Ahmadov, Tuncay Karakurt, Şahin Direkel, Hakan Tahtaci
A Novel Class Substituted Imidazo[2,1‐ b ][1,3,4]thiadiazole Derivatives: Synthesis, Characterization, In Vitro Biological Activity, and Potential Inhibitors Design Studies
ChemistrySelect  4(48), 14281, 2019
DOI: 10.1002/slct.201903886
/

[21]. Tryfon Zarganes-Tzitzikas, Constantinos G. Neochoritis, Julia Stephanidou-Stephanatou, Constantinos A. Tsoleridis, Gernot Buth, George E. Kostakis
Azodicarboxylates: valuable reagents for the multicomponent synthesis of novel 1,3,4-thiadiazoles and imidazo[2,1-b][1,3,4]thiadiazoles
Tetrahedron  69(24), 5008, 2013
DOI: 10.1016/j.tet.2013.03.096
/

[22]. Nadia S. El-Gohary, Mona I. Shaaban
Antimicrobial and Antiquorum-Sensing Studies. Part 3: Synthesis and Biological Evaluation of New Series of [1,3,4]Thiadiazoles and Fused [1,3,4]Thiadiazoles
Archiv der Pharmazie  348(4), 283, 2015
DOI: 10.1002/ardp.201400381
/

[23]. S Singh, Amandeep Kaur
SYNTHESIS AND ANTICANCER ACTIVITY OF NOVEL 2-BENZYL-6- (SUBSTITUTED PHENYL)-IMIDAZO[2,1-B] [1,3,4] THIADIAZOLE DERIVATIVES
INDIAN DRUGS  56(04), 13, 2019
DOI: 10.53879/id.56.04.11454
/

References


[1]. Tenover, F. C.; McDonald, L. C. Curr. Opin. Infect. Dis. 2005, 18, 300-305.
doi:10.1097/01.qco.0000171923.62699.0c
PMid:15985825

[2]. Pfeltz, R. F.; Wilkinson, B. J. Curr. Drug. Targets Infect. Disord. 2004, 4, 273-294.
doi:10.2174/1568005043340470
PMid:15578969

[3]. Roberts, M. C. Curr. Drug. Targets Infect. Disord. 2004, 4, 207-215.
doi:10.2174/1568005043340678
PMid:15379732

[4]. Dessen, A.; Di Guilmi, A. M.; Vernet, T.; Dideberg, O. Curr. Drug. Targets Infect. Disord. 2001, 1, 63-77.
doi:10.2174/1568005013343272
PMid:12455234

[5]. Muroi, H.; Nihei, K.; Tsujimoto, K, and Kubo, I. Bioorg. Med. Chem. 2004, 12, 583-587.
doi:10.1016/j.bmc.2003.10.046

[6]. Chopra, I.; Schofield, C.; Everett, M.; O’Neill, K.; Miller, K.; Wilcox, M. Lancet Infect, Dis. 2008, 8, 133-139.
doi:10.1016/S1473-3099(08)70018-5

[7]. Terzioglu, N.; Gursoy, A. Eur. J. Med. Chem. 2003, 38, 781-786.
doi:10.1016/S0223-5234(03)00138-7

[8]. Kolavi, G.; Hegde, V.; Khazi, I M.; Gadad, P. Bioorg. Med. Chem. 2006, 14, 3069-3080.
doi:10.1016/j.bmc.2005.12.020

[9]. Gadad, A. K.; Mahajanshetti, C. S.; Nimbalkar, S.; Raichurkar, A. Eur. J. Med. Chem. 2000, 35, 853-857.
doi:10.1016/S0223-5234(00)00166-5

[10]. Andotra, C. S.; Langer, T. C.; Kotha, A. J. Indian Chem Soc. 1997, 72, 125-127.

[11]. Kumar, P. Chinese J. Chem. 2010, 28, 250-254.
doi:10.1002/cjoc.201090061

[12]. Andreani, A.; Bonazzi, D.; Rambaldi, M.; Fabbri, G.; Rainsford, K. D. Eur. J. Med. Chem. 1982, 17, 271-274.

[13]. Bhovi, V. K.; Bodke, Y. D. Current Chem. Biol. 2010, 4, 145-150.

[14]. Khazi, I. A. M.; Mahajanshetti, C. S.; Gadad, A. K.; Tarnalli, A. D.; Sultanpur, C. M. Arzneimittelforschung. 1996, 46, 949-952.
PMid:8931885

[15]. Andreani, A.; Leonia, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Simon, W. A.; Senn-Bilfinger, J. Arzneimittelforschung. 2000, 50, 550-553.
PMid:10918949

[16]. Andreani, A.; Rambaldi, M.; Mascellani, G.; Bossa, R.; Galatulas, I. Eur. J. Med. Chem. 1986, 21, 451-453.

[17]. Andreani, A.; Rambaldi, M.; Mascellani, G.; Rugarli, P. Eur. J. Med. Chem. 1987, 22, 19-22.
doi:10.1016/0223-5234(87)90169-3

[18]. Andreani, A.; Rambaldi, M.; Locatelli, A.; Andreani, F. Collect. Czech. Chem. Commun. 1991, 56, 2436-2447.
doi:10.1135/cccc19912436

[19]. Terashima, H.; Hama, K.; Yamamoto, R.; Tsuboshima, M.; Kikkawa, I. and Shigata, Y. J. Pharmacol. Exp. Ther. 1984, 229, 226-230.

[20]. Yoshioka, T.; Fujita, T.; Kanai, T.; Aizawa,Y.; Kurumada, T.; Hasegawa, K.; Horikoshi, H. J. Med. Chem. 1989, 32, 421-428.
doi:10.1021/jm00122a022
PMid:2913302

[21]. Ayhan-Kilcigil, G.; Altanlar, N. Arzneimittelforschung. 2000, 50, 154-157.
PMid:10719619

[22]. Heerding, D. A.; Christmann, L. T.; Clark, T. J.; Holmes, D. J.; Rittenhouse, S. F.; Takata, D. T.; Venslavsky, J. W. Med. Chem. Lett. 2003, 13, 3771-3773.
doi:10.1016/j.bmcl.2003.07.010

[23]. Tuncbilek, M.; Altanlar N. Arch. Pharm. Chem. Life Sci. 2006, 339, 213-216.
doi:10.1002/ardp.200500180
PMid:16572478

[24]. Bozdag-Dundar, O.; Ozgen, O.; Mentese, A.; Altanlar, N.; Atli, O.; Kendi, E.; Ertan, R. Bioorg. Med. Chem. 2007, 15, 6012- 6017.
doi:10.1016/j.bmc.2007.06.049

[25]. Cantello, B. C. C.; Cawthorne, M. A.; Cottam, G. P.; Duff, P. T.; Haigh, D.; Hindley, R. M.; Lister, C. A.; Smith, S. A.; Thurlby, P. L. J. Med. Chem. 1994, 37, 3977-3985.
doi:10.1021/jm00049a017
PMid:7966158

[26]. Andreani, A.; Rambaldi, M.; Locatelli, A.; Leoin, A.; Bossa, R.; Chiericozzi, M.; Galatulas, I.; Salvatore, G. Eur. J. Med. Chem. 1993, 28, 825-829.
doi:10.1016/0223-5234(93)90118-X

[27]. De Lima, J. G.; Perrissin, M.; Chantegrel, J. Arzneimittelforschung. 1994, 44, 831-834.
PMid:7945517

[28]. Boschelli, D. H.; Connor, D. T.; Kuipers, P. J.; Wright, C. D. Bioorg. Med. Chem. Lett. 1992, 2, 705-708.
doi:10.1016/S0960-894X(00)80396-0

[29]. Al-Omar, M.; Al-Deeb, A.; Al-Khamees.; El-Emam, A. A. Phosphorus, Sulfur, and Silicon. 2004, 179, 2509-2517.
doi:10.1080/10426500490485525

[30]. Mazzone, G.; Bonina, F.; Puglisi, G.; Arrigo, R. R.; Cosentino, C.; Blandino, G. Farmaco Sci. 1982, 37, 685-700.
PMid:6982830

[31]. Maccari, R.; Ottana, R.; Curinga, C.; Vigorita, M. G.; Rakowitz, D.; Steindl, T.; Langer, T. Bioorg. Med. Chem. 2005, 13, 2809-2823.
doi:10.1016/j.bmc.2005.02.026

[32]. CLSI/NCCLS Guidelines: Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically; 7th Ed. Approved Standard document M-7:A5, Villanova, PA, NCCLS, 2006.


How to cite


Alegaon, S.; Alagawadi, K. Eur. J. Chem. 2011, 2(1), 94-99. doi:10.5155/eurjchem.2.1.94-99.161
Alegaon, S.; Alagawadi, K. Synthesis, characterization and antimicrobial activity evaluation of new imidazo [2,1-b][1,3,4]thiadiazole derivatives. Eur. J. Chem. 2011, 2(1), 94-99. doi: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: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. 3 Jun. 2023
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)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



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


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



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

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c)




© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.