Subscribe to RSS
DOI: 10.1055/s-0043-1775446
Design and Synthesis of a Novel 1,2,4-Oxadiazole Derivative: 3-(3-(5-((4-Phenylpiperazin-1-yl)methyl)-1,2,4-oxadiazol-3-yl) phenoxy)propan-2-olamines

Abstract
The synthesis of novel heterocyclic 3-(3-(5-((4-phenylpiperazin-1-yl)methyl)-1,2,4-oxadiazol-3-yl)phenoxy)propan-2-olamine derivatives, in particular piperazine and piperidine derivatives of 1,2,4-oxadiazole, is reported. These compounds are a distinguished motif for biological studies. An effective piperazine and piperidine derivative methodology on 1,2,4-oxadiazole substrates has been developed. This pathway, along with good yields and clean reactions, has a broad substrate scope and provides new biologically useful moieties that can be further investigated for their applicability.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775446. Included are copies of 1H NMR and HRMS spectra of compounds 9.
- Supporting Information
Publication History
Received: 24 November 2024
Accepted after revision: 19 January 2025
Article published online:
01 April 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Pace A, Pierro P. Org. Biomol. Chem. 2009; 7: 4337
- 2 Jones RM, Leonard JN, Buzard DJ, Lehmann J. Expert Opin. Ther. Pat. 2009; 19: 1339
- 3 Bray GA. J. Med. Chem. 2006; 49: 4001
- 4 Likhite N, Lakshminarasimhan T, Rao MH. V. R, Shekarappa V, Sidar S, Subramanian V, Fraunhoffer KJ, Leung S, Vaidyanathan R. Org. Process Res. Dev. 2016; 20: 1328
- 5 Zhang H.-Z, Kasibhatla S, Kuemmerle J, Kemnitzer W, Ollis-Mason K, Qiu L, Crogan-Grundy C, Tseng B, Drewe J, Cai SX. J. Med. Chem. 2005; 48: 5215
- 6 Cottrell DM, Capers J, Salem MM, DeLuca-Fradley K, Croft SL, Werbovetz KA. Bioorg. Med. Chem. 2004; 12: 2815
- 7 Crich G, Cabella C, Barge A, Belfiore S, Ghirelli C, Lattuada L, Lanzardo S, Mortillaro A, Tei L, Visigalli M, Forni G, Aime S. J. Med. Chem. 2006; 49: 4926
- 8 Ono M, Haratake M, Saji H, Nakayama M. Bioorg. Med. Chem. 2008; 16: 6867
- 9 Orlek BS, Blaney FE, Brown F, Clark MS. G, Hadley MS, Hatcher J, Riley GJ, Rosenberg HE, Wadsworth HJ, Wyman P. J. Med. Chem. 1991; 34: 2726
- 10 Goldberg K, Groombridge S, Hudson J, Leach AG, MacFaul PA, Pickup A, Poultney R, Scott JS, Svensson PH, Sweeney J. MedChemComm 2012; 3: 600
- 11 Patani GA, LaVoie EJ. Chem. Rev. 1996; 96: 3147
- 12 Warmus JS, Flamme C, Zhang LY, Barrett S, Bridges A, Chen H, Gowan R, Kaufman M, Sebolt-Leopold J, Leopold W, Merriman R, Ohren J, Pavlovsky A, Przybranowski S, Tecle H, Valik H, Whitehead C, Zhang E. Bioorg. Med. Chem. Lett. 2008; 18: 6171
- 13 McBriar MD, Clader JW, Chu I, Del Vecchio RA, Favreau L, Greenlee WJ, Hyde LA, Nomeir AA, Parker EM, Pissarnitski DA, Song L, Zhang L, Zhao Z. Bioorg. Med. Chem. Lett. 2008; 18: 215
- 14 Bethge K, Pertz HH, Rehse K. Arch. Pharm. 2005; 338: 78
-
15 Asian Journal of Chemistry, 17(4), 2063–2075
- 16 Desai N, Monapara J, Jethawa A, Khedkar V, Shingate B. Arch. Pharm. 2022; 355: e2200123
- 17 Hirao I, Kato Y, Hirota T. Bull. Chem. Soc. Jpn. 1971; 44: 1923
-
18 Schlecker, R.; Thletie, P. C. 1987.
- 19 Bala S, Kamboj S, Kumar A. J. Pharm. Res. 2010; 3: 2993
- 20 Elzein E, Ibrahim P, Koltun DO, Rehder K, Shenk KD, Marquart TA, Jiang B, Li X, Natero R, Li Y, Nguyen M, Kerwar S, Chu N, Soohoo D, Hao J, Maydanik VY, Lustig DA, Zeng D, Leung K, Zablocki JA. Bioorg. Med. Chem. Lett. 2004; 14: 6017
- 21 Haranahalli K, Lazzarini C, Sun Y, Zambito J, Pathiranage S, McCarthy JB, Mallamo J, Del Poeta M, Ojima I. J. Med. Chem. 2019; 62: 8249