- Design, synthesis, modelling studies and biological evaluation of 1,3,4-oxadiazole derivatives as potent anticancer agents targeting thymidine phosphorylase enzyme
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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.
- Bajaj, Shalini,Kumar, Maushmi S.,Tinwala, Hussain,YC, Mayur
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- Catalytic application of electrochemically prepared nickel oxide nanoparticles to synthesize 2, 5–disubstituted-1,3,4–oxadiazoles
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The present work aims to synthesize 2,5–disubstituted-1,3,4–oxadiazoles using electrochemically prepared nanoparticles of nickel oxide as catalyst.The nanoparticles thus prepared using electrochemical syntheses are in appreciable yield.The tetrabutyl phosphonium bromide has been used for capping followed by UV, FTIR, XRD, SEM EDS andTEM SAED studies for the characterization. The 2,5-disubstituted-1,3,4-oxadiazoles were synthesized from substituted benzoic acids and their hydrazides in microwave synthesis system using prepared nanoparticles as a catalyst.
- Dare, Sushama B.,Gaikwad, Suresh T.,Rajbhoj, Anjali S.,Sawant, Manisha R.
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p. 300 - 308
(2020/07/03)
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- 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
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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.).
- Kotipalli, Trimurtulu,Kavala, Veerababurao,Konala, Ashok,Janreddy, Donala,Kuo, Chu-Wei,Yao, Ching-Fa
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p. 2652 - 2660
(2016/09/03)
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- Efficient oxidative cyclisation of acid hydrazides to 2,5-disubstituted 1,3,4-oxadiazoles catalysed by Bu4NI with t-BuOOH as oxidant
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Acid hydrazides or araldehyde N-acylhydrazones can be converted in good yields to, respectively, symmetrical or unsymmetrical, 2,5-disubstituted 1,3,4-oxadiazoles at 60 °C by a Bu4NI-catalysed procedure which requires the presence of a base and 2.5 equiv. of t-butyl hydroperoxide.
- Gao, Peng,Wei, Yunyang
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p. 506 - 510
(2013/09/12)
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- A new efficient one-pot synthesis of 2,5-diaryl-1,3,4-oxadiazoles
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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.
- Chiriac, Constantin I.,Tanasa, Fulga,Nechifor, Marioara
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experimental part
p. 1113 - 1117
(2012/08/13)
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- Rapid synthesis of 2,5-disubstituted 1,3,4-oxadiazoles under microwave irradiation
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A number of symmetrically 2,5-disubstituted 1,3,4-oxadiazoles are quickly prepared by the reaction of aromatic acids with hydrazine dihydrochloride in a mixture of orthophosphoric acid and phosphorus pentoxide under microwave irradiation.
- Bentiss, Fouad,Lagrenee, Michel,Barbry, Didier
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p. 935 - 938
(2007/10/03)
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- A new synthesis of symmetrical 2,5-disubstituted 1,3,4- oxadiazoles
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Several new 2,5-disubstituted 1,3,4-oxadiazoles have been synthesized in good yields by reaction of aromatic acids with hydrazine dihydrochloride in a mixture of orthophosphoric acid, phosphorus pentoxide and, in general, with addition of phosphorus oxychloride to the reaction mixture. The structures of new oxadiazoles derivatives were confirmed by analytical and spectral data.
- Bentiss, Fouad,Lagrenee, Michel
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p. 1029 - 1032
(2007/10/03)
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