Synthesis, spectral analysis and biological evaluation of 2-{[(morpholin-4-yl)ethyl]thio}-5-phenyl/aryl-1,3,4-oxadiazole derivatives

• Main Authors: Ahmad, M. (Author), Akhtar, N. (Author), Aziz-Ur-Rehman (Author), Batool, S. (Author), Bokhari, T.H (Author), Irfan, M. (Author), Khan, S.G (Author), Naqvi, S.A.R (Author), Rasool, S. (Author), Shah, S.A.A (Author), Shahid, M. (Author), Usman, A. (Author)
• Format: Article
• Language: English
• Published: Pakistan Journal of Pharmaceutical Sciences 2021
• Series: Pakistan Journal of Pharmaceutical Sciences
• Subjects: 1,3,4-oxadiazole; 2 [[(morpholin 4 yl)ethyl]thio] 5 aryl 1,3,4 oxadiazole derivative; 2 [[(morpholin 4 yl)ethyl]thio] 5 phenyl 1,3,4 oxadiazole derivative; antibacterial activity; Antibacterial activity; antiinfective agent; Article; catalyst; controlled study; drug screening; drug synthesis; Gram negative bacterium; Gram positive bacterium; hemolysis; Hemolytic activity; hemolytic agent; minimum inhibitory concentration; Morpholine; nonhuman; nucleophilicity; spectroscopy; substitution reaction; sulfuric acid; unclassified drug
• Online Access: View Fulltext in Publisher; View in Scopus
• ISBN: 1011601X (ISSN)
• DOI: 10.36721/PJPS.2021.34.1.SP.441-446.1

A series of new derivatives of 4-(2-chloroethyl)morpholine hydrochloride (5) were efficiently synthesized. Briefly, different aromatic organic acids (1a-f) were refluxed to acquire respective esters (2a-f) using conc. H2SO4 as catalyst. The esters were subjected to nucleophillic substitution by monohydrated hydrazine to acquire hydrazides (3a-f). The hydrazides were cyclized with CS2 in the presence of KOH to yield corresponding oxadiazoles (4a-f). Finally, the derivatives, 6a-f, were prepared by reacting oxadiazoles (4a-f) with 5 using NaH as activator. Structures of all the derivatives were elucidated through 1D-NMR EI-MS and IR spectral data. All these molecules were subjected to antibacterial and hemolytic activities and showed good antibacterial and hemolytic potential relative to the reference standards. © 2021 Pakistan Journal of Pharmaceutical Sciences. All rights reserved.