Novel 1,3,4-oxadiazole motifs bearing a quinoline nucleus: synthesis, characterization and biological evaluation of their antimicrobial, antitubercular, antimalarial and cytotoxic activities

Abstract

A series of quinoline based 1,3,4-oxadiazole derivatives 8a-l were synthesized by chloro-amine coupling reaction approach with different catalyst and solvents. The substituted 1,3,4-oxadiazole intermediates 7a-c were obtained from 2-sustituted-N-phenylhydrazinecarbothioamide 6a-c by cyclization with different cyclizing reagents like mercuric acetate, lead dioxide, iodobenzenediacetate (IBD) and aqueous sodium hydroxide with iodine in aqueous potassium iodide to isolate the most effective reaction condition by using iodobenzenediacetate as extremely good catalyst. The structure of the title compounds were confirmed by FT-IR, 1 H NMR, 13 C NMR and mass spectrometry. The synthesized molecules were evaluated for their antibacterial, antifungal, antituberculosis and antimalarial activities. The brine shrimp bioassay was carried out to study the in vitro cytotoxic properties for the highly active compounds of in vitro biological evaluation. antifungal 34 . Quinoline scaffolds have been selected due to their diverse therapeutic and pharmacological properties, such as antitumor, antiatherosclerotic, vasodilator, geroprotective, bronchodilator and hepatoprotective activity 35 .

Recent Developments on Pharmacological Potential of 1,3,4-Oxadiazole Scaffold

“…Ladania GG et al synthesized new series of hits by coupling 1,3,4-oxadiazole with substituted quinoline moiety using molecular hybridization using different catalyst and solvents. 26 Primary screening of obtained compounds were performed against Mycobacterium tuberculosis H37Rv strain using Lowenstein-Jensen medium. The result showed that compounds 27(a-d) ( Figure 24) were found to possess excellent activity.…”

Synthesis of 4-azo-butenolides

“…[1][2][3] Several of these compounds containing the quinoline nucleus display innumerous biological properties and are used as drugs against malaria, cardiovascular diseases, allergies, and vasodilators. [4][5][6][7][8][9][10][11][12][13][14][15] The search for new drugs more potent and with less side effects requires chemical strategies of synthesis that facilitate the obtaining of intermediates for the construction of heterocycles in a quick way and in smaller reaction times, speeding up the process of the synthesis until the biological evaluation. [16] 4-Azo-butenolides are synthons for the synthesis of quinolines, dihydroquinolines, lactones, and a large amount of derivatives of great pharmacological interest.…”

Synthesis, structural characterization and cytotoxic activity of heterocyclic compounds containing the furoxan ring

“…Various derivatives of these types of heterocycle have previously revealed cytotoxic activity: 1,2,4-oxadiazole, 31 1,2,4-triazine, 32,33 1,2,3-triazole, 34 and furoxan itself. 13,14 Heterocyclic motifs, namely quinolines 35 and pyridines, 36 connected to the furoxan ring through O-bridges, are also found in compounds possessing cytotoxic activity.…”