Design and Therapeutic Potential of 2,5-substituted diphenyl-1,3,4-oxadiazole Derivatives
Abstract
In the present study, new class of 2,5-substituted diphenyl-1,3,4-oxadiazole derivatives were developed by combining substituted aromatic acids with hydrazine hydrate in the presence of POCl3 reagent under various reaction conditions. The compounds were also evaluated for their antimicrobial potential against some bacteria (E. coli and S. aureus) and fungi (C. albicans and A. Niger). As the result of the newly synthesized compounds were characterized as 2-(4-chlorophenyl) compounds-5-(4-nitrophenyl)-1,3,4-oxadiazole (13), 2-(4-methylphenyl)-5-(4-nitrophenyl)-1,3,4-oxadiazole (16), 2-(4-chlorophenyl)-5-(4-methoxyhenyl)-1,3,4-oxadiazole (17), 4-[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]phenol (18), and 2-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole (25). The results also revealed that these compounds have good potential to inhibit microbes. It may be concluded that oxadiazole nucleus may be a profitable source for the synthesis of drugs against infectious diseases.
Keywords:
Antibacterial activity, Antifungal activity, 1,3,4-oxadiazole derivatives, Substituted aromatic acids.DOI
https://doi.org/10.25004/IJPSDR.2023.150104References
Lanza FL. A guideline for the treatment and prevention of NSAID-induced ulcers. Official journal of the American College of Gastroenterology| ACG. 1998 Nov 1;93(11):2037-46. Available from: 10.1111/j.1572-0241.1998.00588.x
Ilango K, Valentina P. Textbook of medicinal chemistry. Chennai, Keerthi Publishers. 2007;1:336-52.
Aghekyan АА, Mkryan GG, Panosyan HA, Safaryan AS, Stepanyan HM. Synthesis and Antibacterial Activity of Novel (4-Methoxyphenyl)- tetrahydropyranyl-substituted 1, 3, 4-Oxadiazoles. Russian Journal of Organic Chemistry. 2020 Feb;56:281-6. Available from: https:// doi.org/10.1134/S1070428020020177
Upadhyay PK, Mishra P. Synthesis and antimicrobial screening of some 1, 3, 4-oxadiazoles and their molecular properties prediction through'rule of five'. Pakistan Journal of Pharmaceutical Sciences. 2019 May 1;32(3).
Rohand T, Ramli Y, Baruah M, Budka J, Das AM. Synthesis, structure elucidation and antimicrobial properties of new bis-1, 3, 4-oxadiazole derivatives. Pharmaceutical Chemistry Journal. 2019 May 5;53:150-4. Available from: https://doi.org/10.1007/ s11094-019-01969-2
Mummed B, Abraha A, Feyera T, Nigusse A, Assefa S. In vitro antibacterial activity of selected medicinal plants in the traditional treatment of skin and wound infections in eastern Ethiopia. BioMed research international. 2018 Jul 11;2018. Available from: https:// doi.org/10.1155/2018/1862401
Shi J, Luo N, Ding M, Bao X. Synthesis, in vitro antibacterial and antifungal evaluation of novel 1, 3, 4-oxadiazole thioether derivatives bearing the 6-fluoroquinazolinylpiperidinyl moiety. Chinese Chemical Letters. 2020 Feb 1;31(2):434-8. Available from: https://doi.org/10.1016/j.cclet.2019.06.037
Chawla R, Arora A, Parameswaran MK, Sharma PC, Michael S, Ravi TK. Synthesis of novel 1, 3, 4-oxadiazole derivatives as potential antimicrobial agents. Synthesis. 2010;181:23.
Patel RV, Patel PK, Kumari P, Rajani DP, Chikhalia KH. Synthesis of benzimidazolyl-1, 3, 4-oxadiazol-2ylthio-N-phenyl (benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents. European journal of medicinal chemistry. 2012 Jul 1;53:41-51. Available from: https://doi.org/10.1016/j.ejmech.2012.03.033
Küçükgüzel ŞG, Oruç EE, Rollas S, Şahin F, Özbek A. Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1, 3, 4-oxadiazoles and some related compounds. European journal of medicinal chemistry. 2002 Mar 1;37(3):197-206. Available from: https://doi.org/10.1016/S0223-5234(01)01326-5
Patel RV, Kumari P, Rajani DP, Chik halia KH. Synthesis of coumarin-based 1, 3, 4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides as antimicrobial and antituberculosis agents. Medicinal Chemistry Research. 2013 Jan;22:195-210. Available from: https:// doi.org/10.1007/s00044-012-0026-x
Sun J , Z hu H , Y ang Z M, Z hu H L. S ynthesis, m olecular m odeling and biological evaluation of 2-aminomethyl-5-(quinolin-2-yl)-1, 3, 4-oxadiazole-2 (3H)-thione quinolone derivatives as novel anticancer agent. European journal of medicinal chemistry. 2013 Feb 1;60:23-8. Available from: https://doi.org/10.1016/j. ejmech.2012.11.039
Omar FA, Mahfouz NM, Rahman MA. Design, synthesis and antiinflammatory activity of some 1, 3, 4-oxadiazole derivatives. European Journal of Medicinal Chemistry. 1996 Jan 1;31(10):819-25. Available from: https://doi.org/10.1016/0223-5234(96)83976-6
Ozyazici T, Gurdal EE, Orak D, Sipahi H, Ercetin T, Gulcan HO, Koksal M. Synthesis, anti‐inflammatory activity, and molecular docking studies of some novel Mannich bases of the 1, 3, 4‐oxadiazole‐2 (3H)‐thione scaffold. Archiv der Pharmazie. 2020 Jul;353(7):2000061. Available from: https://doi.org/10.1002/ardp.202000061
Omar MT. Synthesis of new xanthenone derivatives of expected antibilharzial activity. Archives of pharmacal research. 1997 Dec;20:602-9. Available from: https://doi.org/10.1007/BF02975219
Xu J, Wei L, Mathvink RJ, Edmondson SD, Eiermann GJ, He H, Leone JF, Leiting B, Lyons KA, Marsilio F, Patel RA. Discovery of potent, selective, and orally bioavailable oxadiazole-based dipeptidyl peptidase IV inhibitors. Bioorganic & Medicinal Chemistry Letters. 2006 Oct 15;16(20):5373-7. Available from: https://doi. org/10.1016/j.bmcl.2006.07.061
Jessen KA, English NM, Yu Wang J, Maliartchouk S, Archer SP, Qiu L, Brand R, Kuemmerle J, Zhang HZ, Gehlsen K, Drewe J. The discovery and mechanism of action of novel tumor-selective and apoptosis-inducing 3, 5-diaryl-1, 2, 4-oxadiazole series using a chemical genetics approach. Molecular cancer therapeutics. 2005 May;4(5):761-71. Available from: https://doi.org/10.1158/1535- 7163.MCT-04-0333
World Health Organization. Antibiotic-resistant bacteria are a genuine threat we must all fight, https://www.who.int/-news-room/fact-sheets/detail/antibiotic-resistance,
Sun XY, Wu R, Wen X, Guo L, Zhou CP, Li J, Quan ZS, Bao J. Synthesis and evaluation of antibacterial activity of 7-alkyloxy-4, 5-dihydro-imidazo [1, 2-a] quinoline derivatives. European Journal of Medicinal Chemistry. 2013 Feb 1;60:451-5. Available from: https:// doi.org/10.1016/j.ejmech.2012.12.034
Li S , W ang Z , Wei Y, W u C , G ao S , J iang H , Z hao X , Yan H , W ang X. Antimicrobial activity of a ferrocene-substituted carborane derivative targeting multidrug-resistant infection. Biomaterials. 2013 Jan 1;34(4):902-11. Available from: https://doi.org/10.1016/j. biomaterials.2012.10.069
Eicher T, Hauptmann S, Speicher A. The chemistry of heterocycles: structures, reactions, synthesis, and applications. John Wiley & Sons; 2013 Feb 26.
Dua R, Shrivastava S, Sonwane SK, Srivastava SK. Pharmacological significance of synthetic heterocycles scaffold: a review. Advances in Biological Research. 2011;5(3):120-44..
Zaidan MR, Noor Rain A, Badrul AR, Adlin A, Norazah A, Zakiah I. In vitro screening of five local medicinal plants for antibacterial activity using disc diffusion method. Trop biomed. 2005 Dec 1;22(2):165-70.
Sridhar SR, Rajagopal RV, Rajavel R, Masilamani S, Narasimhan S. Antifungal activity of some essential oils. Journal of agricultural and food chemistry. 2003 Dec 17;51(26):7596-9.
Salahuddin, Mazumder A, Yar MS, Mazumder R, Chakraborthy GS, Ahsan MJ, Rahman MU. Updates on synthesis and biological activities of 1, 3, 4-oxadiazole: A review. Synthetic Communications. 2017 Oct 18;47(20):1805-47. Available from: https://doi.org/10.10 80/00397911.2017.1360911
Rauf A, Sharma S, Gangal S. One-pot synthesis, antibacterial and antifungal activities of novel 2, 5-disubstituted-1, 3, 4-oxadiazoles. Chinese Chemical Letters. 2008 Jan 1;19(1):5-8. Available from: https://doi.org/10.1016/j.cclet.2007.11.026
Published

