Hydrolysis and Oxidation of 1H‐Benzotriazole‐carboxylic Acid Esters by Rat Liver Microsomes

Abstract

The 1H-benzotriazole-carboxylic acid esters under investigation were almost - with the exception of the tert.-butylester - completely hydrolyzed by rat liver microsomes. Some substrates were metabolically oxidized to a very small extent (less than 1%) yielding small amounts of possibly toxic metabolites after inhibition of the esterases with paraoxone.

Convenient Synthesis of tert‐Butyl Esters of Indole‐5‐carboxylic Acid and Related Heterocyclic Carboxylic Acids

“…The mixture was stirred for 30 min, diluted with aqueous NaHCO 3 solution (5%), and extracted with ethyl acetate. The organic layer was dried with tert-Butyl 1H-Benzotriazole-5-carboxylate (11) [11] Compound 10 (157 mg, 0.6 mmol) was dissolved in ethanol (10 ml tert-Butyl 1H-Benzimidazole-5-carboxylate (12) 1H-Benzimidazole-5-carboxylic acid (3 mmol, 486 mg) was reacted with acetic anhydride in the same way as described for the synthesis of 9 to yield a mixture of 1-acetyl-1H-benzimidazole-5-carboxylic acid and 1-acetyl-1H-benzimidazole-6-carboxylic acid (546 mg). A part of this mixture (204 mg) was treated with tert-butyl trichloroacetimidate and BF 3 -etherate as described for the preparation of 10.…”