Synthesis and evaluation of some novel heterocyclic compounds containing an oxadiazole moiety

Anjali Bakshi; Sowmyasree Kammari; Archana Awasthi; Shweta Bhutada; Saritha Pola; Bhagvan Raju Mantripragada

doi:10.30574/gscbps.2019.6.2.0166

Authors

Anjali Bakshi Department of Pharmaceutical Analysis and Quality Assurance, Sri Venkateshwara College of Pharmacy, Osmania University, Hyderabad -500081
Sowmyasree Kammari Department of Pharmaceutical Analysis and Quality Assurance, Sri Venkateshwara College of Pharmacy, Osmania University, Hyderabad -500081
Archana Awasthi Department of Pharmaceutical Analysis and Quality Assurance, Sri Venkateshwara College of Pharmacy, Osmania University, Hyderabad -500081.
Shweta Bhutada Department of Pharmaceutical Analysis and Quality Assurance, Sri Venkateshwara College of Pharmacy, Osmania University, Hyderabad -500081.
Saritha Pola Pulla Reddy institute of pharmacy, Medak.
Bhagvan Raju Mantripragada Department of Pharmaceutical Analysis and Quality Assurance, Sri Venkateshwara College of Pharmacy, Osmania University, Hyderabad -500081.

DOI:

https://doi.org/10.30574/gscbps.2019.6.2.0166

Keywords:

Heterocyclic compounds, 1, 3, 4-oxadiazoles, Pharmacological activities

Abstract

Heterocyclic compounds analog have attracted wide attention due to their useful biological properties. Among them, 1,3,4-oxadiazoles have exhibited a wide range of biological properties including anti-bacterial, anti-viral, anti-fungal, anti-cancer, anti-tumor, anti-inflammatory, anti-hypertensive, anti-convulsant and anti-diabetic properties. The purpose of this study was to collect the literature work reported by researchers on oxadiazole derivatives for their various pharmacological activities and also efforts made on this moiety. This study covers the work reported on various biological activities of oxadiazole derivatives.

Metrics

Metrics Loading ...

References

Sengupta P, Mal M, Mandal S, Singh J and Maity TK. (2008). Evaluation of antibacterial and antifungal activity of some 1,3,4 oxadiazoles. Iranian Journal of Pharmacology and Therapeutics, 7(2), 165–167.

Bhardwaj N, Saraf SK, Sharma P and Kumar P. (2009). Syntheses, evaluation and characterization of some 1,3,4-oxadiazoles as antimicrobial agents. E-Journal of Chemistry, 6(4), 1133–1138.

Kadi AA, El-Brollosy NR, Al-Deeb OA, Habib EE, Ibrahim TM and El-Emam AA. (2007). Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. European Journal of Medicinal Chemistry, 42(2), 235–242.

Singh R and Chouhan A. (2014). Various approaches for synthesis of 1,3,4-oxadiazole derivatives and their pharmacological activity. World Journal of Pharmacy and Pharmaceutical Sciences, 3(10), 1474-1505.

Bachwani M, Sharma V and Kumar R. (2011). Biological Activities of 1,3,4-oxadiazole: A review. International Research Journal of Pharmacy, 2(12), 84-89.

Ingole SP, Mohane SR and Berad BN. (2007). Synthesis and antimicrobial activity of 2-alkyl –aryl -5-(Pyrid-4-yl)-1,3,4-oxadiazole. Asian Journal of Chemistry, 19, 2683–2686.

Franski R. (2005). Biological activities of the compounds bearing 1,3,4-oxa (thia) diazole ring. Asian Journal of Chemistry, 17, 2063–75.

Amir M, Javed SA and Kumar H. (2007). Synthesis of some 1,3,4 oxadiazole derivatives as potential anti-inflammatory agents. Indian Journal of Chemistry, 46B, 1014–9.

Mishra A, Singh DV and Mishra RM. (2005). Synthesis, antifungal activity of new 1,3,4 oxadiazole(3,2-b)-s-triazine-5-ones and their thiones analogues. Indian Journal of Heterocyclic Chemistry, 14, 289–292.

Siddiqui N, Khan SA and Bhat MA. (2005). Synthesis and antibacterial activity of coumarin incorporated 1,3,4 oxadiazoles. Indian Journal of Heterocyclic Chemistry, 14, 271–2.

Agarwal M, Singh V, Sharma SK, Sharma P, Ansari MY, Jadav SS and Ahsan MJ. (2016). Design and synthesis of new 2,5-disubstituted-1,3,4-oxadiazole analogues as anticancer agents. Medicinal Chemistry Research, 25(10), 2289–2303.

Reddy VM, Reddy PS, Reddy PC and Ratmanc V. (1997). Cyclisation by dehydrosulfuration of 1-(2-amino benzoyl) -4-aryl-3 thiosemicarbazides. Formation of 1,3,4 benzotriazepinones, 1,3,4 thiadiazoles and 1,3,4 oxadiazoles. Indian Journal of Heterocyclic Chemistry, 7, 17–20.

Singh P and Jangra PK. (2010). Oxadiazoles: A novel class of anti-convulsant agents. Pelagia Research Library, 1(3), 118-123.

Bala S, Kamboj S and Kumar A. (2010). Heterocyclic 1,3,4-oxadiazole compounds with diverse biological activities: A comprehensive review. Journal of Pharmacy Research, 3(12), 2993-2997.

James ND and Growcott JW. (2009). Zibotentanendothelin ETA receptor antagonist oncolytic. Drugs of the Future, 34(8), 624-633.

Jones AM and Helm JM. (2009). Emerging treatments in cystic fibrosis. Drugs, 69, 1903−1910.

Summa V, Petrocchi A, Bonelli F, Crescenzi B, Donghi M, Ferrara M, Fiore F, Gardelli C, Gonzalez Paz O, Hazuda DJ and Jones P. (2008). Discovery of raltegravir, a potent, selective orally bioavailable HIV-integrase inhibitor for the treatment of HIV-AIDS infection. Journal of medicinal chemistry, 51(18), 5843-5855.

Brandenberger H and Maes RA. (Eds.). (2011). Analytical toxicology for clinical, forensic and pharmaceutical chemists (Vol. 5). Walter de Gruyter.

Ducharme Y, Blouin M, Brideau C, Châteauneuf A, Gareau Y, Grimm EL, Juteau H, Laliberté S, MacKay B, Massé F and Ouellet M. (2010). The discovery of setileuton, a potent and selective 5-lipoxygenase inhibitor. ACS medicinal chemistry letters, 1(4), 170-174.

Adelstein GW, Yen CH, Dajani EZ and Bianchi RG. (1976). 3, 3-Diphenyl-3-(2-alkyl-1,3,4-oxadiazol-5-yl) propylcycloalkylamines, a novel series of antidiarrheal agents. Journal of medicinal chemistry, 19(10), 1221-1225.

Ouyang X, Piatnitski EL, Pattaropong V, Chen X, He HY, Kiselyov AS, Velankar A, Kawakami J, Labelle M, Smith II L, Lohman J. (2006). Oxadiazole derivatives as a novel class of antimitotic agents: Synthesis, inhibition of tubulin polymerization, and activity in tumor cell lines. Bioorganic & medicinal chemistry letters, 16(5), 1191-1196.

Ichiro H. (1967). Synthesis of 5-C2-(5-Initro-2-fury1)-1-(2-furyl) vinylJ-2-amino-1,3,4-OXadia2Ole. NAwKagairZassi, 88, 574-575.

Ogata M, Atobe H, Kushida H and Yamamoto K. (1971). In vitro sensitivity of mycoplasmas isolated from various animals and sewage to antibiotics and nitrofurans. The Journal of antibiotics, 24(7), 443-451.

Kadi AA, El-Brollosy NR, Al-Deeb OA, Habib EE, Ibrahim TM and El-Emam AA. (2007). Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles. European Journal of Medicinal Chemistry, 42(2), 235–242.

Mickevičius V, Vaickelioniene R and Sapijanskaite B. (2009). Synthesis of substituted 1,3,4-oxadiazole derivatives. Chemistry of Heterocyclic Compounds, 45(2), 215–218.

Bentiss F and Lagrenee M. (1999). A new synthesis of symmetrical 2,5-disubstituted 1,3,4-oxadiazoles. Journal of Heterocyclic Chemistry, 36(4), 1029–1032.

Liras S, Allen MP and Segelstein BE. (2000). A mild method for the preparation of 1,3,4-oxadiazoles: triflic anhydride promoted cyclization of diacylhydrazines. Synthetic Communications, 2000, 30(3), 437–443.

Gomes D, Borges CP and Pinto JC. (2001). Study of the synthesis of poly(4,4′-diphenylether-1,3,4-oxadiazole) in solutions of poly(phosphoric acid). Polymer, 42(3), 851–865.

Souldozi A and Ramazani A. (2007). The reaction of (N-isocyanimino) triphenylphosphorane with benzoic acid derivatives: a novel synthesis of 2-aryl-1,3,4-oxadiazole derivatives. Tetrahedron Letters, 48(9), 1549–1551.

Ramazani A, Abdian B, Nasrabadi FZ and Rouhani M. (2013). The reaction of N-isocyaniminotriphenylphosphorane with biacetyl in the presence of (E)-cinnamic acids: synthesis of fully substituted 1,3,4-oxadiazole derivatives via intramolecular aza -wittig reactions of in situ generated iminophosphoranes. Phosphorus, Sulfur and Silicon and the Related Elements, 188(5), 642–648.

Ramazani A, ZeinaliaNasrabadi F and Ahmadi Y. (2011). One-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from (Isocyanoimino) triphenylphosphorane, a primary amine, an aromatic carboxylic acid, and chloroacetone. Helvetica ChimicaActa, 94(6), 1024–1029.

Ramazani A and Souldozi A. (2008). Iminophosphorane-mediated one-pot synthesis of 1,3,4-oxadiazole derivatives. Arkivoc, 16, 235–242.

Pitasse-Santos P, Sueth-Santiago V and Lima ME. (2018). 1,2,4- and 1,3,4-Oxadiazoles as scaffolds in the development of antiparasitic agents. Journal of the Brazilian Chemical Society, 29(3), 435–456.

de Oliveira CS, Lira B, Barbosa-Filho JM, Lorenzo JG and de Athayde-Filho PF. (2012). Synthetic approaches and pharmacological activity of 1, 3, 4-oxadiazoles: a review of the literature from 2000–2012. Molecules, 17(9), 10192-10231.

Zheng X, Li Z, Wang Y, Chen W, Huang Q, Liu C and Song G. (2003). Syntheses and insecticidal activities of novel 2,5-disubstituted 1,3,4-oxadiazoles. Journal of Fluorine Chemistry, 123(2), 163–169.

Kumar R, Yar MS, Rai AK and Chaturvedi S. (2013). Synthesis and biological evaluation of some novel 1,3,4-oxadiazoles derived from bi phenyl 4- carboxylic acid. Der Pharmacia Lettre, 5(1), 366–370.

Maslat AO, Abussaud M, Tashtoush H and Al-Talib M. (2002). Synthesis, antibacterial, antifungal and genotoxic activity of bis-1,3,4-oxadiazole derivatives. Polish Journal of Pharmacology, 2002, 54, 55–59.

Grewal AS and Redhu S. (2014). Synthesis, antibacterial and antifungal activity of 2, 5-disubstituted-1, 3, 4-oxadiazole derivatives. Synthesis, 6(7), 2015-2021.