A Convenient Synthesis and Cytotoxic Activity of 3-Aryl-5-Pentyl-1,2,4-Oxadiazoles From Carboxylic Acid Esters and Arylamidoximes Under Solvent-Free Conditions

N‐arylthiophene‐2‐carboxamidoxime derivatives (a‐e) were synthesized by using two methods and then subjected to thermolysis at 200–250 °C for 2 h under nitrogen atmosphere either alone or in the presence of tetralin and/or naphthalene as radical scavengers yielded imidazole, oxazole, triazine and amide derivatives. The pyrolysates from both reactions were separated with their constituents by column chromatography and analyzed then identified 1H NMR, 13C NMR and GC‐MS. A plausible mechanism is suggested through two competitive pathways involving the homolysis of N‐O and/or C‐N bonds to account for the thermolysis products.

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Investigation of Thermolysis Products of Some N‐Arylthiophene‐2‐carboxamidoximes by Analytical and Spectroscopic Analyses

Gaber

Aly

Mekhemer

2019

ChemistrySelect

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Design, synthesis of novel pyranotriazolopyrimidines and evaluation of their anti-soybean lipoxygenase, anti-xanthine oxidase, and cytotoxic activities

Said¹,

Romdhane²,

Elie

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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The synthesis of 14-(aryl)-14H-naphto[2,1-b]pyrano[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-2-yl) acetamidoximes 2a-e has been accomplished by reaction of 2-acetonitrile derivatives 1a-e with hydroxylamine. Cyclocondensation reaction of precursors 2a-e with some elctrophilic species such as ethylorthoformate, acetic anhydride, and methyl-acetoacetate provided the new oxadiazole derivatives 3a-e, 4a-e, and 5a-e, respectively. On the other hand, the reaction of precursors 2a-e with 2-chloropropanoyl chloride afforded the new acetimidamides 6a-e which evolve under reflux of toluene to the new oxadiazoles 7a-e. The synthetic compounds were screened for their anti-xanthine oxidase, anti-soybean lipoxygenase, and cytotoxic activities. Moderate to weak xanthine oxidase and soybean lipoxygenase inhibitions were obtained but significant cytotoxic activities were noted. The most cytotoxic activities were recorded mainly (i) 5a was the most active (IC50 = 4.0 μM) and selective against MCF-7 and (ii) 2a was cytotoxic against the four cell lines with selectivity for MCF-7 and OVCAR-3 (IC50 = 17 and 12 μM, respectively) while 2e is highly selective against OVCAR-3 (IC50 = 10 μM).

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A Convenient Synthesis and Cytotoxic Activity of 3-Aryl-5-Pentyl-1,2,4-Oxadiazoles From Carboxylic Acid Esters and Arylamidoximes Under Solvent-Free Conditions

Cited by 2 publications

References 32 publications

Investigation of Thermolysis Products of Some N‐Arylthiophene‐2‐carboxamidoximes by Analytical and Spectroscopic Analyses

Investigation of Thermolysis Products of Some N‐Arylthiophene‐2‐carboxamidoximes by Analytical and Spectroscopic Analyses

Design, synthesis of novel pyranotriazolopyrimidines and evaluation of their anti-soybean lipoxygenase, anti-xanthine oxidase, and cytotoxic activities

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