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Synthesis of S-(5-aryl-1,3,4-oxadiazol-2-yl) O-alkyl carbonothioate and alkyl 2-((5-aryl-1,3,4-oxadiazol-2-yl)thio) acetate, and their antimicrobial properties

Year 2023, Volume: 10 Issue: 3, 599 - 604, 30.08.2023
https://doi.org/10.18596/jotcsa.1250629

Abstract

The S-(5-aryl-1,3,4-oxadiazol-2-yl) O-alkyl carbonothioate (4-9) and the alkyl 2-((5-aryl-1,3,4-oxadiazol-2-yl)thio) acetate (10-15) were synthesized by interaction of 5-aryl-1,3,4-oxadiazole-2-thiones with alkyl esters of chloroformic acid and chloroacetic acid. The yields of target compounds (7-9) obtained with isobutyl chloroformate were 69-73%, compounds (4-6) with propyl chloroformate - 74-79% and compounds (10-15) with alkyl esters of chloroacetic acid - 86-92%, respectively. The structures of the synthesized compounds were confirmed by IR, UV, 1H and 13C NMR spectra. The antibacterial and antifungal activities of these compounds were investigated. The results of in vitro antimicrobial activity tests showed that S-(5-phenyl(2-chlorophenyl)-1,3,4-oxadiazol-2-yl) O-propyl carbonothioate (4-5) and S-(5-phenyl(2-chlorophenyl)-1,3,4-oxadiazol-2-yl) O-isobutyl carbonothioate (7-8) exhibited weak, but selective antibacterial activity against gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus). At the same time, no activity was shown by compounds with two chlorine atoms in the aromatic ring (13-15) and alkyl 2-((5-aryl-1,3,4-oxadiazol-2-yl) thio) acetate (10-15).

Thanks

Financial support (Ф-ФА-2021-360 grant) from Ministry of Innovative Development of the Republic of Uzbekistan is gratefully acknowledged.

References

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  • 12. Tozhiev IF, Ziyaev AA, Shakhidoyatov KhM. Alkylation of 5-aryl-1,3,4-оxadiazol-2(3Н)-thions with allyl- and benzylhalogens. Chemistry and chemical technology. 2012;4:17-20.
  • 13. Ziyaev AA, Tozhiev IF, Shakhidoyatov KhM. 5-Aryl-1,3,4-oxadiazolin-2(3H)-thiones in reactions with alkyl haloacetates. Chem Heterocycl Compd. 2012;48:488-491.
  • 14. Ziyaev AA, Ismailova DS. Synthesis of 5-phenoxymethyl-1,3,4-oxadiazolin-2(3H)-thion and its alkylation. Uzbek Chem J. 2015;1:15-18.
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  • 16. Koparır M, Çetin A, Cansız A. 5-Furan-2yl[1,3,4]oxadiazole-2-thiol, 5-Furan-2yl-4H [1,2,4] triazole-3-thiol and Their Thiol-Thione Tautomerism. Molecules. 2005;10(2):475-480.
  • 17. Rozhkova N, Sabirov K, Seytanidi KL. Reaction of benzothiazolin-2-thione with 1-chloro-2,3-epoxypropane. Chem Heterocycl Compd. 1983;11:1170-1173.
  • 18. Eshimbetov AG, Tojiev IF, Ziyaev AA. DFT and TD-DFT study of isomeric 5-(pyridyl)-1,3,4-oxadiazol-2-thiones and 2-methylthio-5-(pyridyl)-1,3,4-oxadiazoles. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Dec 5;187:191-197.
Year 2023, Volume: 10 Issue: 3, 599 - 604, 30.08.2023
https://doi.org/10.18596/jotcsa.1250629

Abstract

References

  • 1. Glomb T, Świątek P. Antimicrobial Activity of 1,3,4-Oxadiazole Derivatives. Int. J. Mol. Sci. 2021;22:6979.
  • 2. Glomb T, Szymankiewicz K, Swiatek P. Anti-Cancer Activity of Derivatives of 1,3,4-Oxadiazole. Molecules. 2018;23:3361.
  • 3. Rubina B, Dharam PP, Garima K, Ravi K, Manni D. Recent Developments on Pharmacological Potential of 1,3,4-Oxadiazole Scaffold. Ind. J. Pharm. Edu. Res. 2019;53(2S):1-16.
  • 4. Tantray MA, Khan I, Hamid H, Alam MS, Dhulap A, Kalam A. Synthesis of Benzimidazole-Linked-1,3,4-Oxadiazole Carboxamides as GSK-3β Inhibitors with in Vivo Antidepressant Activity. Bioorg Chem. 2018;77:393-401.
  • 5. Akram M, Rauf A, Saeed A, Ahmed F, Mubeen S, Ashraf M, Hussain S, Qureshi AM. Synthesis, biological evaluation and molecular docking studies of Mannich bases derived from 1,3,4-oxadiazole-2-thiones as potential urease inhibitors. Trop J Pharm Res. 2018;17(1):127-134.
  • 6. Kumar D, Kumar V, Marwaha R, Singh G. Oxadiazole-An Important Bioactive Scaffold for Drug Discovery and Development Process Against HIV and Cancer- A Review. Current Bioactive Compounds. 2019;15(3):271-279.
  • 7. Alam MM. 1,3,4-Oxadiazole as a Potential Anti-Cancer Scaffold: A Review. Biointerface Research in Applied Chemistry. 2022;12(4):5727-5744.
  • 8. Thakkar SS, Thakor P, Doshi H, Ray A. 1,2,4-Triazole and 1,3,4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities. Bioorganic & Medicinal Chemistry. 2017;25(15):4064-4075.
  • 9. Espinosa AV, Costa DS, Tunes LG, do Monte-Neto RL, Grazul RM, de Almeida MV, Silva H. Anticancer and antileishmanial in vitro activity of gold (I) complexes with 1,3,4-oxadiazole-2(3H)-thione ligands derived from δ-D-gluconolactone. Chem Biol Drug Des. 2021;97(1):41-50.
  • 10. Verma SK, Verma R, Verma S, Vaishnav Y, Tiwari SP, Rakesh KP. Antituberculosis activity and its structure-activity relationship (SAR) studies of oxadiazole derivatives: A key review. Eur J Med Chem. 2021;209:112886.
  • 11. Ziyaev AA, Galust’yan GG. Reaction of 5-aryl-1,3,4-oxadiazole-2(3H)-thiones with chloromethyl alkyl ethers. Chem Heterocycl Compd. 1999;35:1104-1106.
  • 12. Tozhiev IF, Ziyaev AA, Shakhidoyatov KhM. Alkylation of 5-aryl-1,3,4-оxadiazol-2(3Н)-thions with allyl- and benzylhalogens. Chemistry and chemical technology. 2012;4:17-20.
  • 13. Ziyaev AA, Tozhiev IF, Shakhidoyatov KhM. 5-Aryl-1,3,4-oxadiazolin-2(3H)-thiones in reactions with alkyl haloacetates. Chem Heterocycl Compd. 2012;48:488-491.
  • 14. Ziyaev AA, Ismailova DS. Synthesis of 5-phenoxymethyl-1,3,4-oxadiazolin-2(3H)-thion and its alkylation. Uzbek Chem J. 2015;1:15-18.
  • 15. Performance Standards for Antimicrobial Disk Susceptibility Tests. CLSI document M02. 13th Edition. Wayne, PA, USA; 2018. ISBN 1-56238-834-7.
  • 16. Koparır M, Çetin A, Cansız A. 5-Furan-2yl[1,3,4]oxadiazole-2-thiol, 5-Furan-2yl-4H [1,2,4] triazole-3-thiol and Their Thiol-Thione Tautomerism. Molecules. 2005;10(2):475-480.
  • 17. Rozhkova N, Sabirov K, Seytanidi KL. Reaction of benzothiazolin-2-thione with 1-chloro-2,3-epoxypropane. Chem Heterocycl Compd. 1983;11:1170-1173.
  • 18. Eshimbetov AG, Tojiev IF, Ziyaev AA. DFT and TD-DFT study of isomeric 5-(pyridyl)-1,3,4-oxadiazol-2-thiones and 2-methylthio-5-(pyridyl)-1,3,4-oxadiazoles. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Dec 5;187:191-197.
There are 18 citations in total.

Details

Primary Language English
Subjects Organic Chemistry
Journal Section RESEARCH ARTICLES
Authors

Abdukhakim Ziyaev 0000-0002-8612-3540

Sobirdjan Sasmakov 0000-0003-1863-7117

Turdibek Toshmurodov 0000-0002-3715-931X

Mavluda Zıyaeva 0000-0002-0688-1123

Jaloliddin Abdurakhmanov 0000-0002-3954-3251

Shukhrat Khasanov 0000-0003-4773-7117

Shakhnoz Azimova 0000-0003-1803-7728

Publication Date August 30, 2023
Submission Date February 15, 2023
Acceptance Date May 13, 2023
Published in Issue Year 2023 Volume: 10 Issue: 3

Cite

Vancouver Ziyaev A, Sasmakov S, Toshmurodov T, Zıyaeva M, Abdurakhmanov J, Khasanov S, Azimova S. Synthesis of S-(5-aryl-1,3,4-oxadiazol-2-yl) O-alkyl carbonothioate and alkyl 2-((5-aryl-1,3,4-oxadiazol-2-yl)thio) acetate, and their antimicrobial properties. JOTCSA. 2023;10(3):599-604.