Generic placeholder image

Current Drug Research Reviews


ISSN (Print): 2589-9775
ISSN (Online): 2589-9783

Review Article

Significance of 1,3,4-Oxadiazole Containing Compounds in New Drug Development

Author(s): Kavita Rana*, Salahuddin and Jagdish K. Sahu

Volume 13, Issue 2, 2021

Published on: 21 December, 2020

Page: [90 - 100] Pages: 11

DOI: 10.2174/2589977512666201221162627

Price: $65


Background: Oxadiazole core displays various pharmacological properties among five membered nitrogen heterocyclic compounds, specially 1,3,4-oxadiazole containing molecules that have occupied a particular place in the field of synthetic medicinal chemistry as surrogates (bioisosteres) of carboxylic acids, carboxamides and esters. Moreover, they are having widespread kind of applications in numerous zones as polymers, as luminescence producing materials and as electron- transporting materials and corrosion inhibitors.

Methods: This study contains comprehensive and extensive literature survey on chemical reactivity and biological properties associated with 1,3,4-oxadiazole containing compounds.

Results: This review summarises 1,3,4-oxadiazole moiety in numerous compounds with reported pharmacological activity such as antiviral, analgesic and anti-inflammatory, antitumor, antioxidant, insecticidal and anti-parasitic, etc. Nevertheless, ring opening reactions of the 1,3,4-oxadiazole core have also made great attention, as they produce new analogues containing an aliphatic nitrogen atom and to other ring systems.

Conclusion: In relation to the occurrence of oxadiazoles in biologically active molecules, 1,3,4- oxadiazole core emerges as a structural subunit of countless significance and usefulness for the development of new drug aspirants applicable to the treatment of many diseases. It concludes that 1,3,4-oxadiazole core compounds are more efficacious and less toxic medicinal agents with respect to new opinions in the search for rational strategies.

Keywords: 1, 3, 4-oxadiazole, heterocyclic, anticancer, antimicrobial, anti-tubercular, analgesic, anti-inflammatory.

Graphical Abstract
Li JJ. Heterocyclic Chemistry in Drug Discovery. 1st ed. New York, USA: Wiley 2013.
Vitaku E, Smith DT, Njardarson JT. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals. J Med Chem 2014; 57(24): 10257-74.
[] [PMID: 25255204]
Ko D, Patel HA, Yavuz CT. Synthesis of nanoporous 1,2,4-oxadiazole networks with high CO2 capture capacity. Chem Commun (Camb) 2015; 51(14): 2915-7.
[] [PMID: 25585204]
Ongungal RM, Sivadas AP, Kumar NS, Menon S, Das S. Self-assembly and mechanochromic luminescence switching of trifluoromethyl substituted 1,3,4-oxadiazole derivatives. J Mater Chem 2016; 4(40): 9588-97.
Shih CH, Rajamalli P, Wu CA, Chiu MJ, Chu LK, Cheng CH. A high triplet energy, high thermal stability oxadiazole derivative as the electron transporter for highly efficient red, green and blue phosphorescent OLEDs. J Mater Chem C Mater Opt Electron Devices 2015; 3(7): 1491-6.
Bouanis M, Tourabi M, Nyassi A, Zarrouk A, Jama C, Bentiss F. Corrosion inhibition performance of 2,5-bis(4-dimethylaminophenyl)-1,3,4-oxadiazole for carbon steel in HCl solution: Gravimetric, electrochemical and XPS studies. Appl Surf Sci 2016; 389: 952-66.
Nobeli I, Price SL, Lommerse JPM, Taylor R. Hydrogen bonding properties of oxygen and nitrogen acceptors in aromatic heterocycles. J Comput Chem 1997; 18(16): 2060-74.
Lima LM, Barreiro EJ. Bioisosterism: a useful strategy for molecular modification and drug design. Curr Med Chem 2005; 12(1): 23-49.
[] [PMID: 15638729]
Boström J, Hogner A, Schmitt S. Do structurally similar ligands bind in a similar fashion? J Med Chem 2006; 49(23): 6716-25.
[] [PMID: 17154502]
Tiemann F, Kruger P. Ueber Amidoxime und Azoxime. Ber Dtsch Chem Ges 1884; 17(2): 1685-98.
Gupta RR, Kumar M, Gupta V. Heterocyclic chemistry: Five membered heterocycles. 1st ed. India: Springer 2005.
Clapp LB. 1, 2, 4-oxadiazoles. Adv Heterocycl Chem 1976; 20: 65-116.
Elderfield RC. Heterocyclic compounds. 1961; pp. 525.
Grignard V, Baud P, Dupont G, Locquin R. Traite de chimie organique. 1953; pp. 997.
Gan X, Hu D, Chen Z, Wang Y, Song B. Synthesis and antiviral evaluation of novel 1,3,4-oxadiazole/thiadiazole-chalcone conjugates. Bioorg Med Chem Lett 2017; 27(18): 4298-301.
[] [PMID: 28838690]
Rathore A, Sudhakar R, Ahsan MJ, et al. In vivo anti-inflammatory activity and docking study of newly synthesized benzimidazole derivatives bearing oxadiazole and morpholine rings. Bioorg Chem 2017; 70: 107-17.
[] [PMID: 27923497]
Porta F, Facchetti G, Ferri N, et al. An in vivo active 1,2,5-oxadiazole Pt(II) complex: A promising anticancer agent endowed with STAT3 inhibitory properties. Eur J Med Chem 2017; 131: 196-206.
[] [PMID: 28324784]
Mihailović N, Marković V, Matić IZ, et al. Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids. RSC Advances 2017; 7(14): 8550-60.
Tok F, Kocyigit-Kaymakcioglu B, Tabanca N, et al. Synthesis and structure-activity relationships of carbohydrazides and 1,3,4-oxadiazole derivatives bearing an imidazolidine moiety against the yellow fever and dengue vector, Aedes aegypti. Pest Manag Sci 2018; 74(2): 413-21.
[] [PMID: 28869331]
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. Bioorg Med Chem 2017; 25(15): 4064-75.
[] [PMID: 28634040]
Dewangan D, Pandey A, Sivakumar T, Rajavel R, Dubey RD. Synthesis of some novel 2, 5- disubstituted 1, 3, 4-oxadiazole and its analgesic, antiinflammatory, anti-bacterial and anti-tubercular activity. Int J Chemtech Res 2010; 2(3): 1397-412.
Sahoo BM, Kumar RBVV, Kumara PBUBP. Synthesis, characterisation and biological evaluation of novel oxadiazole derivatives. Int J Pharm Sci Res 2011; 2(2): 344-50.
Amir M, Saifullah K, Akhtar W. Design, synthesis and biological evaluation of 1,3,4-oxadiazole derivatives of aryl acetic acid as anti-inflammatory and analgesic agents. Indian J Chem 2011; 50B: 1107-11.
Murti Y, Mehrotra V, Pathak D. Design, synthesis and biological evaluation of some novel 2,5-disubstituted-1,3,4-oxadiazole derivatives. Inter J Dr Desi and Disc 2011; 2(4): 659-65.
Biju CR, Ilango K, Prathap M, Rekha K. Design and microwave-assisted synthesis of 1,3,4-oxadiazole derivatives for analgesic and anti-inflammatory activity. J you Phar 2012; 4(1): 33-7.
Kumar Singh A, Lohani M, Parthsarthy R. Synthesis, characterization and anti-inflammatory activity of some 1, 3,4 -oxadiazole derivatives. Iran J Pharm Res 2013; 12(2): 319-23.
[PMID: 24250606]
Jain SK, Mishra P. Appraisal of analgesic and anti-inflammatory activity of some 2,5-disubstituted-1,3,4-thiadiazoles. Int J Curr Microbiol Appl Sci 2014; 3(10): 849-55.
Khan SA, Imam SM, Ahmad A, Basha SH, Hussain A. Synthesis, molecular docking with COX I & II enzyme, ADMET screening and in vivo anti-inflammatory activity of oxadiazole, thaidiazole and triazole analogs of felbinac. J Sau Chem Soci 2017; 1-16.
Mogilaiah K, Prasad DH, Rao AN, Jyothi S, Babu HR. Hypervalent Iodine mediate solid state synthesis and biological activity of some new 1-[(5-aryl-1,3,4-oxadiazole-2-yl)methyl]-3-(4-nitrophenyl)-1,2-dihydro[1,8]naphthyridine-2-ones. Indian J Chem 2017; 56B: 656-62.
Sahin G, Palaska E, Ekizoğlu M, Ozalp M. Synthesis and antimicrobial activity of some 1,3,4-oxadiazole derivatives. Farmaco 2002; 57(7): 539-42.
[] [PMID: 12164209]
Bharadwaj N, Saraf SK, Sharma P, Kumar P. Syntheses, evaluation and characterization of some 1, 3, 4-oxadiazoles as antimicrobial agents. E-J Chem 2009; 6(4): 1133-8.
Kanthiah S, Kalusalingam A, Velayutham R, Vimala AT, Beyatricks J. 5-(2-aminophenyl)-1,3,4-oxadiazole-2(3h)-thione derivatives: synthesis, characterization and antimicrobial evaluation. Int J Phar Sci Rev & Res 2011; 6(1)
Desai NC, Dodiya AM, Rajpara KM, Rupala YM. Synthesis and antimicrobial screening of 1,3,4-oxadiazole and clubbed thiophene derivatives. J Saudi Chem Soc 2014; 18: 255-61.
Bala S, Kamboj S, Kajal A, Saini V, Prasad DN. 1,3,4-oxadiazole derivatives: synthesis, characterization, antimicrobial potential, and computational studies. BioMed Res Int 2014; 2014
[] [PMID: 25147788]
Raju GN, Prathyusha TG, Sowmya PL, Mounika SJ, Nadendla RR. Synthesis, characterization and biological activity of some 1,3,4-oxadiazole derivatives with benzothiazole moiety. Pharm Sin 2015; 6(6): 1-8.
Sengupta P, Dash DK, Yeligar VC, et al. Evaluation of anticancer activity of some 1,3,4-oxadiazole derivatives. Indian J Chem 2008; 47B: 460-2.
Gudipati R, Anreddy RNR, Manda S. Synthesis, characterization and anticancer activity of certain 3-{4-(5-mercapto-1,3,4-oxadiazole-2-yl)phenylimino}indoline-2-one derivatives. Saudi Pharm J 2011; 19: 153-8.
[] [PMID: 23960753]
Jisha MV, Kamalabhai AVK, Babu G, Viju CR. Synthesis, characterization and invitro anticancer screening of novel thiazole1,3,4-oxadiazole hybrid analogues. J Chem & Phar Res 2013; 5(6): 64-70.
Salahuddin , Shaharyar M, Mazumder A, Ahsan MJ. Synthesis, Characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1-[5-(substituted phenyl)-[1,3,4]oxadiazole-2-ylmethyl]-1Hbenzimidazole. Arbi J Chem 2014; 7: 418-24.
Mochona B, Mazzio E, Gangapurum M, Mateeva N, Redda KK. Synthesis of some benzimidazole derivatives bearing 1,3,4-oxadiazole moiety as anticancer agents. Chem Sci Trans 2015; 4(2): 534-40.
[PMID: 26451350]
Roy PP, Bajaj S, Maity TK, Singh J. Synthesis and evaluation of anticancer activity of 1, 3, 4-oxadiazole derivatives against Ehrlich Ascites Carcinoma bearing mice and their correlation with histopathology of liver. Ind J Phar Edu 2017; 51(2): 260-9.
Kavitha S, Kannan K, Gnanavel S. Synthesis, characterization and biological evaluation of novel 2,5 substituted-1,3,4 oxadiazole derivatives. Saudi Pharm J 2017; 25(3): 337-45.
[] [PMID: 28344487]
Tabatabai SA, Lashkari SB, Zarrindast MR, Gholibeikian M, Shafiee A. Design, synthesis and anticonvulsant activity of 2-(2-Phenoxy) phenyl- 1,3,4-oxadiazole derivatives. Iran J Pharm Res 2013; 12(Suppl.): 105-11.
[PMID: 24250678]
Zarghi A, Hajimahdi Z, Mohebbi S, et al. Design and synthesis of new 2-substituted-5-[2-(2-halobenzyloxy)phenyl]-1,3,4-oxadiazoles as anticonvulsant agents. Chem Pharm Bull (Tokyo) 2008; 56(4): 509-12.
[] [PMID: 18379099]
Gilani SJ, Alam O, Khan SA, Siddiqui N, Kumar H. Synthesis of some derived thiazolidin-4-one, azetidin-2-one and 1,3,4-oxadiazole ring systems from Isoninicotinic acid hydrazide: A novel class of potential anticonvulsant agents. Der Pharmacia Letter 2009; 1(2): 1-8.
Pattan SR, Rabara P, Pattan JS, et al. Synthesis and evaluation of some novel substituted 1, 3, 4-oxadiazole and pyrazole derivatives for antitubercular activity. Indian J Chem B 2009; 48: 1453-6.
Rane RA, Bangalore P, Borhade SD, Khandare PK. Synthesis and evaluation of novel 4-nitropyrrole-based 1,3,4-oxadiazole derivatives as antimicrobial and anti-tubercular agents. Eur J Med Chem 2013; 70: 49-58.
[] [PMID: 24140916]
Sun J, Li M-H, Qian S-S, et al. Synthesis and antitumor activity of 1,3,4-oxadiazole possessing 1,4-benzodioxan moiety as a novel class of potent methionine aminopeptidase type II inhibitors. Bioorg Med Chem Lett 2013; 23(10): 2876-9.
[] [PMID: 23582273]
Shahzad SA, Yar M, Bajda M, et al. Synthesis and biological evaluation of novel oxadiazole derivatives: a new class of thymidine phosphorylase inhibitors as potential anti-tumor agents. Bioorg Med Chem 2014; 22(3): 1008-15.
[] [PMID: 24411198]
Malhotra V, Pathak SR, Nath R, Mukherjee D, Shanker K. Substituted imidazole derivatives as novel cardiovascular agents. Bioorg Med Chem Lett 2011; 21(3): 936-9.
[] [PMID: 21232951]
Cheptea C, Şunel V, Holban M, Desbrieres J, Popa M, et al. Enhanced antipyretic activity of new 2, 5-substituted 1, 3, 4-oxadiazoles encapsulated in alginate/gelatin particulated systems. Cellul Chem Technol 2012; 46: 19.

Rights & Permissions Print Export Cite as
© 2022 Bentham Science Publishers | Privacy Policy