1016275-12-9

Basic information

• Product Name: C₁₄H₁₄N₂O₂
• Synonyms: C₁₄H₁₄N₂O₂
• CAS NO: 1016275-12-9
• Molecular Weight: 242.277
• Mol File: 1016275-12-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₁₄H₁₄N₂O₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₄H₁₄N₂O₂(1016275-12-9)
• EPA Substance Registry System: C₁₄H₁₄N₂O₂(1016275-12-9)

Safety Data

• Hazardous Substances Data: 1016275-12-9(Hazardous Substances Data)

Upstream product

• 25501-32-0 (S)-indanol 
• 17325-26-7 1H-imidazole-5-carboxylic acid methyl ester 

Relevant articles and documents

New selective inhibitors of steroid 11β-hydroxylation in the adrenal cortex. Synthesis and structure-activity relationship of potent etomidate analogues

Derivatives of etomidate were evaluated as inhibitors of adrenal steroid 11β-hydroxylations. Stereoselective coupling by Mitsunobu produced chirally pure analogues to study the effect of configuration, modification of the ester, and substitution in the phenyl ring, with the aim to probe specific sites for introducing a radionuclide. Iodophenyl metomidate (IMTO) labeled with iodine-131 served as radioligand for structure-affinity relationship studies. We have characterized the kinetic parameters of specific 131I-IMTO binding on rat adrenal membranes and used the displacement of 131I-IMTO binding to evaluate functionalized MTO analogues. Our results indicated that (1) (R)-configuration is essential for high affinity, (2) highest potency resides in the ethyl, 2-propyl, and 2-fluoroethyl esters, and (3) substitution of the phenyl ring is well tolerated. The clinically used inhibitors metyrapone and ketoconazole inhibited 131I-IMTO binding with low affinity. Incubation of selected analogues with human adrenocortical NCI-h295 cells demonstrated a high correlation with the inhibitory effect on cortisol secretion.