Synthesis, characterization of some novel 1,3,4-oxadiazole compounds containing 8-hydroxy quinolone moiety as potential antibacterial and anticancer agents

  • Vinayak Mahadev Adimule Mount Carmel Centre for Scientific Research and Advanced Learning, Mount Carmel College, Palace Road, Bangalore, India
  • Sudha Medapa Department of Chemistry, Mount Carmel College (Autonomous),Vasanthnagar, Bengaluru- 560 052, Karnataka
  • Adarsha Haraballi Jagadeesha Inorganic and Physical Chemistry, IISc, Bengaluru, Karnataka,
  • Padmashree Kulkarni Department of Microbiology, Mount Carmel College(Autonomous), Bangalore
  • Lalita Sanjeev Kumar Department of Chemistry, School of Sciences, IGNOU, New-Delhi,
  • Prakash Kumar Rao Mount Carmel Centre for Scientific Research and Advanced Learning, Mount Carmel College, Vasanthnagar, Bengaluru-560 052, Karnataka,

Abstract

In the present work a series of novel derivatives of 8-hydroxy quinolone substituted 1,3,4-oxadiazole compounds were synthesized by convergent synthetic method and studied for their antibacterial and anticancer properties. The cell lines used for cytotoxic evaluation were HeLa , Caco-2 and MCF7 . The synthetic chemistry involved conversion of various substituted aromatic acids into ethyl ester 2a-e . The ethyl ester was converted into corresponding carbohydrazide 3a-e . Carbohydrazides are reacted with chloroacetic acid, phosphorous oxytrichloride and irradiated with microwave in order to obtain the various key intermediates 2-(chloromethyl)-5-(substituted phenyl)-1,3,4-oxadiazole 4a-e . The 2-(chloromethyl)-5-(substituted phenyl)-1,3,4-oxadiazole was reacted with 8-hydroxy quinolone in presence of sodium hydride and obtained a series of 8-hydroxy quinoline substituted 1,3,4-oxadiazoles 5a-e . Among the synthesised compounds, the cytotoxicity of the compound 5b i.e. 8-{[5-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2-yl]methoxy}quinoline against MCF7 with IC 50 of 5.3M and the compound 5e i.e. 8-{[5-(4-bromophenyl)-1,3,4-oxadiazol-2-yl]methoxy}quinoline showed MIC of 6.25g/mL against Staphylococcus aureus which is comparable with the known standards. The standards used for cytotoxic evaluation was 5-fluorouracil and for antibacterial was nitrofurazone

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Published
2014-12-30
How to Cite
1.
Adimule V, Medapa S, Jagadeesha A, Kulkarni P, Kumar L, Rao P. Synthesis, characterization of some novel 1,3,4-oxadiazole compounds containing 8-hydroxy quinolone moiety as potential antibacterial and anticancer agents. IJPR [Internet]. 30Dec.2014 [cited 24Mar.2019];4(4):180-5. Available from: https://ssjournals.com/index.php/ijpr/article/view/1479
Section
Research Articles