Synthesis of Some New 1,3,4-Thiadiazole Derivatives Derived from Cholic Acid and Evaluation of their Biological Activity

Year 2024, , 425 - 432, 15.05.2024

Intisar Q M Alaraj , Rana A. Saeed Linda Reyadh , Amena A. Ahmed

https://doi.org/10.18596/jotcsa.1371936

Abstract

In this work, several oxadiazole, thiadiazole, and triazole derivatives, as well as new Schiff bases, were prepared. Cholic acid was used as a starting material to prepare the five-membered heterocyclic compounds. The synthesized compounds were identified by FTIR and 1H,13C-NMR spectroscopy, which elucidated and confirmed the structure of the target molecules. Estimation of the biological activity of the newly produced compounds has been conducted against two types of Gram-positive and Gram-negative pathogenic bacteria.

Keywords

Cholic acid, heterocyclic, Schiff bases, thiadiazoles, oxadiazoles, pathogenic bacteria

References

• 1. Sievänen E. Exploitation of Bile Acid Transport Systems in Prodrug Design. Molecules [Internet]. 2007 Aug 16;12(8):1859–89. Available from: <URL>
• 2. Lee S, Lee MS, Chang E, Lee Y, Lee J, Kim J, et al. Mulberry Fruit Extract Promotes Serum HDL-Cholesterol Levels and Suppresses Hepatic microRNA-33 Expression in Rats Fed High Cholesterol/Cholic Acid Diet. Nutrients. 2020 May 21;12(5):1499. <URL>
• 3. Sahoo S, Ghosh P, Banerjee S, De P. Recent Advances in Biomedical Applications of Cholic Acid-Based Macromolecules. ACS Appl Polym Mater. 2021 Apr 9;3(4):1687–706. <URL>
• 4. Anwar S, Shamsi A, Kar RK, Queen A, Islam A, Ahmad F, et al. Structural and biochemical investigation of MARK4 inhibitory potential of cholic acid: Towards therapeutic implications in neurodegenerative diseases. Int J Biol Macromol. 2020 Oct;161:596–604. <URL>
• 5. Yadav K, Kumar S, Mishra D, Asad M, Mitra M, Yavvari PS, et al. Deciphering the Role of Intramolecular Networking in Cholic Acid–Peptide Conjugates on the Lipopolysaccharide Surface in Combating Gram-Negative Bacterial Infections. J Med Chem. 2019 Feb 28;62(4):1875–86. <URL>
• 6. Pheiffer F, Schneider Y, Hansen E, Andersen J, Isaksson J, Busche T, et al. Bioassay-Guided Fractionation Leads to the Detection of Cholic Acid Generated by the Rare Thalassomonas sp. Mar Drugs. 2022 Dec 20;21(1):2. <URL>
• 7. Kumar S, Thakur J, Yadav K, Mitra M, Pal S, Ray A, et al. Cholic Acid-Derived Amphiphile which Combats Gram-Positive Bacteria-Mediated Infections via Disintegration of Lipid Clusters. ACS Biomater Sci Eng. 2019 Sep 9;5(9):4764–75. <URL>
• 8. Uchida N, Yanagi M, Hamada H. Anionic Technol PG-Based Nanoparticles Prepared Using Cholic Acid-Derived Surfactants. Nat Prod Commun. 2022 May 13;17(5) <URL>
• 9. Knudtson CA, Dias JR. Recent methods for diversification of bile acids and related steroids towards supramolecular. Steroids. 2019 Nov;151:108442. <URL>
• 10. Shetnev A, Baykov S, Kalinin S, Belova A, Sharoyko V, Rozhkov A, et al. 1,2,4-Oxadiazole/2-Imidazoline Hybrids: Multi-target-directed Compounds for the Treatment of Infectious Diseases and Cancer. Int J Mol Sci. 2019 Apr 5;20(7):1699. <URL>
• 11. Li Z, Zhan P, Liu X. 1,3,4-Oxadiazole: A Privileged Structure in Antiviral Agents. Mini-Reviews in Medicinal Chemistry. 2011;11(13). <URL>
• 12. Ahmed AA, Mahmood IQ, Aziz HS. Synthesis and Characterization of Few New Substituted 1,3,4-Oxadiazoles 1,2,4-Triazoles and Schiff Bases via Chalcone Compounds. INTERNATIONAL JOURNAL OF DRUG DELIVERY TECHNOLOGY. 2022 Jun 30;12(03):1087–92. <URL>
• 13. Luczynski M, Kudelko A. Synthesis and Biological Activity of 1,3,4-Oxadiazoles Used in Medicine and Agriculture. Applied Sciences. 2022 Apr 8;12(8):3756. <URL>
• 14. Nazar S, Siddiqui N, Alam O. Recent progress of 1,3,4‐oxadiazoles as anticonvulsants: Future horizons. Arch Pharm (Weinheim). 2020 Jul 21;353(7):1900342. <URL>
• 15. Rezki N, Al-Yahyawi A, Bardaweel S, Al-Blewi F, Aouad M. Synthesis of Novel 2,5-Disubstituted-1,3,4-thiadiazoles Clubbed 1,2,4-Triazole, 1,3,4-Thiadiazole, 1,3,4-Oxadiazole and/or Schiff Base as Potential Antimicrobial and Antiproliferative Agents. Molecules. 2015 Sep 2;20(9):16048–67. <URL>
• 16. Torosyan, S. A., et al. "Synthesis of New 1, 3, 4-Oxadiazole and 1, 2, 3-Triazole Derivatives of Thieno [3, 2-b] pyrrolecarboxylic Acid." Russian Journal of Organic Chemistry 59.2 (2023): 328-331. <URL>
• 17. K. Ajay Kumar* PJGVK. International Journal of ChemTech Research CODEN( USA): IJCRGG ISSN : 0974-4290 Vol.4, No.4, pp 1782-1791, Oct-Dec 2012 Comprehensive Review On The Chemistry Of 1,3,4- Oxadiazoles And Their Applications. Int J Chemtech Res. <URL>
• 18. Ebenezer O, Shapi M, Tuszynski JA. A Review of the Recent Developments of Molecular Hybrids Targeting Tubulin Polymerization. Int J Mol Sci. 2022 Apr 4;23(7):4001. <URL>
• 19. Sonar JP, Pardeshi SD, Dokhe SA, Kharat KR, Zine AM, Kotai L, et al. SYNTHESIS AND ANTIPROLIFERATIVE SCREENING OF NEW THIAZOLE COMPOUNDS. European Chemical Bulletin. 2020 Apr 20;9(4–6):132. <URL>
• 20. Dhotre B et al. An Efficient and One Spot Synthesis of Silica Supported Synthesis of Fluorinated 1, 3, 4-Thiadiazole Derivative Under Microwave Irradiation. Chem. J. 2020;2. <URL>
• 21. Ibraheem H, Al-Majedy Y, Al-Amiery A. 4-Thiadiazole: The Biological Activities. Systematic Reviews in Pharmacy. 2018 Jul 31;9(1):36–40.<URL>
• 22. Alminderej, Elganzory, El-Bayaa, Awad, El-Sayed. Synthesis and Cytotoxic Activity of New 1,3,4-Thiadiazole Thioglycosides and 1,2,3-Triazolyl-1,3,4-Thiadiazole N-glycosides. Molecules. 2019 Oct 16;24(20):3738. <URL>
• 23. Çevik UA, Osmaniye D, Levent S, Sağlik BN, Çavuşoğlu BK, Özkay Y, et al. Synthesis and characterization of a new series of thiadiazole derivatives as potential anticancer agents. Heterocycl Comm. 2020 Mar 10;26(1):6–13. <URL>
• 24. Hussain SJS and MA. Synthesis and antimicrobial activities of 1, 2, 4-triazole and 1, 3, 4-thiadiazole derivatives of 5-amino-2-hydroxybenzoic acid. E-Journal of Chemistry . <URL>
• 25. Abu-Hashem AA, Al-Hussain SA. Design, Synthesis of New 1,2,4-Triazole/1,3,4-Thiadiazole with Spiroindoline, Imidazo[4,5-b]quinoxaline and Thieno[2,3-d]pyrimidine from Isatin Derivatives as Anticancer Agents. Molecules. 2022 Jan 27;27(3):835. <URL>
• 26. Cai BG, Bao YP, Pei C, Li Q, Li L, Koenigs RM, et al. Photochemical synthesis of 1,2,4-triazoles via addition reaction of triplet intermediates to diazoalkanes and azomethine ylide intermediates. Chem Sci. 2022;13(44):13141–6. <URL>
• 27. Zazharskiy V et al. Synthesis, structure, physicochemical properties and antibacterial activity of 1,2,4-triazoles-3-thiols and furan derivatives. Voprosy Khimii i Khimicheskoi Tekhnologii. 2019 Nov;(6):74–82. <URL>
• 28. Aggarwal R, Sumran G. An insight on medicinal attributes of 1,2,4-triazoles. Eur J Med Chem. 2020 Nov;205:112652. <URL>
• 29. Asif M. Antiviral and antiparasitic activities of various substituted triazole derivatives: A mini. Chem Int. <URL>
• 30. Gupta O, Pradhan T, Chawla G. An updated review on diverse range of biological activities of 1,2,4-triazole derivatives: Insight into structure activity relationship. J Mol Struct. 2023 Feb;1274:134487. <URL>
• 31. El‐Sebaey SA. Recent Advances in 1,2,4‐Triazole Scaffolds as Antiviral Agents. ChemistrySelect. 2020 Oct 8;5(37):11654–80. <URL>
• 32. Tawfik SS, Liu M, Farahat AA. Antiviral activity of thiadiazoles, oxadiazoles, triazoles and thiazoles. Arkivoc. 2020 Aug 18;2020(1):180–218. : <URL>
• 33. Iacopetta D, Ceramella J, Catalano A, Saturnino C, Bonomo MG, Franchini C, et al. Schiff Bases: Interesting Scaffolds with Promising Antitumoral Properties. Applied Sciences. 2021 Feb 20;11(4):1877. <URL>
• 34. Mukhtar S, Hassan A, Morsy N, Hafez T, Hassaneen H, Saleh F. Overview on Synthesis, Reactions, Applications, and Biological Activities of Schiff Bases. Egypt J Chem. 2021 Jun 19;0(0):0–0. <URL> 35. Troschke EMO and IKI. Schiff‐bases for sustainable battery and supercapacitor electrodes. Exploration. <URL>
• 36. Panda J et al. Retracted: Green Chemistry Approach for Efficient Synthesis of Schiff Bases of Isatin Derivatives and Evaluation of Their Antibacterial Activities. Journal of Nanoparticles. 2015 Dec 17;2015:1–1. <URL>
• 37. Ibrahim MN, and SES. Synthesis, characterization and use of Schiff bases as fluorimetric analytical reagents. E-journal of Chemistry. <URL>
• 38. Surendar P et al. Organic Quasi-Liquid Schiff Bases from Biomolecules: Synthesis, Structure and Quantum Mechanical Studies. Biointerface Res Appl Chem. 2022 Mar 24;13(2):107. <URL>
• 39. Sani U, Na’ibi HU, Dailami SA. In vitro antimicrobial and antioxidant studies on N-(2-hydroxylbenzylidene) pyridine-2-amine and its M (II) complexes. Nigerian Journal of Basic and Applied Sciences. 2017;25(1):81-8. <URL>