2492-02-6Relevant articles and documents
Design, synthesis, modelling studies and biological evaluation of 1,3,4-oxadiazole derivatives as potent anticancer agents targeting thymidine phosphorylase enzyme
Bajaj, Shalini,Kumar, Maushmi S.,Tinwala, Hussain,YC, Mayur
, (2021/04/12)
A series of novel 1,3,4-oxadiazole derivatives with substituted phenyl ring were designed and synthesized with an objective of discovering newer anti-cancer agents targeting thymidine phosphorylase enzyme (TP). The 1,3,4-oxadiazole derivatives were synthesized by simple and convenient methods in the lab. Chemical structure of the all the synthesized compounds were characterized by IR, 1H NMR and mass spectral methods and evaluated for cytotoxicity by MTT method against two breast cancer cell lines (MCF-7 and MDA-MB-231). Further, results of TP assay identified that 1,3,4-oxadiazole molecules displayed anti-cancer activity partially by inhibition of phosphorylation of thymidine. The TP assay identified SB8 and SB9 as potential inhibitors with anti-cancer activity against both the cell lines. The molecular docking studies recognized the orientation and binding interaction of molecule at the active site amino acid residues of TP (PDB: 1UOU). Acute toxicity studies of compound SB8 at the dose of 5000 mg/kg has identified no signs of clinical toxicity was observed. The SARs study of synthesized derivatives revealed that the substitution of phenyl ring with electron withdrawing group at ortho position showed significant TP inhibitory activity compared to para substitution. The experimental data suggests that 1,3,4-oxadiazole with substituted phenyl can be taken as a lead for the design of efficient TP inhibitors and active compounds which can be taken up for further studies.
Reagent/Substituent Switching Approach for the Synthesis of Substituted 1,3,4-Oxadiazole/1,3,4-Oxadiazoline and 1,2,4-Triazole Derivatives from N-Substituted Hydrazides
Kotipalli, Trimurtulu,Kavala, Veerababurao,Konala, Ashok,Janreddy, Donala,Kuo, Chu-Wei,Yao, Ching-Fa
, p. 2652 - 2660 (2016/09/03)
A metal-free method for the synthesis of substituted 1,3,4-oxadiazole/1,3,4-oxadiazoline and 1,2,4-triazole derivatives from a common starting material via reagent/substituent switching is reported. In the presence of 2-fluoropyridine/triflic anhydride, 1,3,4-oxadiazole derivatives were exclusively formed from N′-tert-butylhydrazides and 1,3,4-oxadiazoline derivatives were produced from N-phenylhydrazides. On the other hand, when using pyridine/triflic anhydride, salts of 1,2,4-triazoles were the sole products. (Figure presented.).
A new efficient one-pot synthesis of 2,5-diaryl-1,3,4-oxadiazoles
Chiriac, Constantin I.,Tanasa, Fulga,Nechifor, Marioara
experimental part, p. 1113 - 1117 (2012/08/13)
Symmetrically substituted 2,5-diaryl-1,3,4-oxadiazoles have been prepared in 81-92% yields by a new direct one-pot synthesis from arenecarboxylic acids, hydrazine dihydrochloride, anhydrous phosphoric acid and sodium borohydride in the absence of a solvent at 170-180°C for 5-6h.
