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

Pak J Pharm Sci. 2021 Jan;34(1(Special)):441-446.

Abstract

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.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Escherichia coli / drug effects
  • Hemolytic Agents / chemical synthesis
  • Hemolytic Agents / chemistry*
  • Hemolytic Agents / pharmacology
  • Klebsiella pneumoniae / drug effects
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Morpholines / chemical synthesis
  • Morpholines / chemistry*
  • Morpholines / pharmacology
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry*
  • Oxadiazoles / pharmacology
  • Pseudomonas aeruginosa / drug effects
  • Salmonella typhi / drug effects
  • Spectrophotometry, Infrared
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Bacterial Agents
  • Hemolytic Agents
  • Morpholines
  • Oxadiazoles