75655-57-1Relevant academic research and scientific papers
Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides
Conole, Daniel,Beck, Thorsten M.,Jay-Smith, Morgan,Tingle, Malcolm D.,Eason, Charles T.,Brimble, Margaret A.,Rennison, David
supporting information, p. 2220 - 2235 (2014/04/17)
A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia - with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed within each series, with 1,2,4-oxadiazole 3 (metHb% = 61.0 ± 3.6) and 1,3,4-oxadiazole 10 (metHb% = 52.4 ± 0.9) demonstrating the greatest activity. Of the 5 candidates (compounds 3, 10, 11, 13 and 23) evaluated in vivo, failure to induce a lethal end-point at doses of 120 mg/kg was observed in all cases. Inadequate metabolic stability, particularly towards hepatic enzymes such as the CYPs, was postulated as one reason for their failure.
A mild and efficient one pot synthesis of 1,3,4-oxadiazoles from carboxylic acids and acyl hydrazides
Rajapakse, Hemaka A.,Zhu, Hong,Young, Mary Beth,Mott, Bryan T.
, p. 4827 - 4830 (2007/10/03)
A convenient one pot method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from acids and acyl hydrazides is reported. Acid activation with CDI, followed by coupling with the desired acylhydrazide and dehydration in the same pot with Ph3P and CBr4 affords the corresponding 1,3,4-oxadiazoles in good yield. The scope of the acid and acylhydrazide components is presented.
DISILYLATED COMPOUNDS AS PRECURSORS OF HETEROCYCLES: A NEW AND EASY OXADIAZOLE SYNTHESIS
Rigo, Benoit,Fasseur, Dominique,Cauliez, Pascal,Couturier, Daniel
, p. 2321 - 2336 (2007/10/02)
Silyl diacylhydrazines have been synthesized.When they are treated with a slight amount of a variety of catalyst (nucleophiles, F-, true or Lewis acids, Pd, Pt...), 1,3,4-oxadiazoles are obtained.This cyclization can be performed in one step by
ACID CATALYZED CYCLIZATION OF BIS SILYL DIACYLHYDRAZINES : A NEW 1,3,4-OXADIAZOLE SYNTHESIS
Rigo, Benoit,Cauliez, Pascal
, p. 1247 - 1252 (2007/10/02)
Diacylhydrazines are converted in good yields into 1,3,4-oxadiazoles with dichlorodimethylsilane and trifluoromethane sulfonic acid.
