133986-32-0

Basic information

• Product Name: 3-(cyclohexylmethyl)-1-(4-aminophenyl)-3-azabicyclo(3.1.0)hexane-2,4-dione
• Synonyms: 3-(cyclohexylmethyl)-1-(4-aminophenyl)-3-azabicyclo(3.1.0)hexane-2,4-dione
• CAS NO: 133986-32-0
• Molecular Formula: C₁₈H₂₂N₂O₂
• Molecular Weight: 298.38
• Mol File: 133986-32-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 505.8°C at 760 mmHg
• Flash Point: 259.7°C
• Appearance: /
• Density: 1.281g/cm³
• Vapor Pressure: 2.35E-10mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: 3-(cyclohexylmethyl)-1-(4-aminophenyl)-3-azabicyclo(3.1.0)hexane-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(cyclohexylmethyl)-1-(4-aminophenyl)-3-azabicyclo(3.1.0)hexane-2,4-dione(133986-32-0)
• EPA Substance Registry System: 3-(cyclohexylmethyl)-1-(4-aminophenyl)-3-azabicyclo(3.1.0)hexane-2,4-dione(133986-32-0)

Safety Data

• Hazardous Substances Data: 133986-32-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H22N2O2/c19-14-8-6-13(7-9-14)18-10-15(18)16(21)20(17(18)22)11-12-4-2-1-3-5-12/h6-9,12,15H,1-5,10-11,19H2

Upstream product

• 3218-02-8 cyclohexylmethylamine 
• 63162-65-2 1-phenylcyclopropanedicarboxylic acid 
• 93579-32-9 3-cyclohexylmethyl-1-(4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione 
• 133986-33-1 3-Cyclohexylmethyl-1-phenyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 

Relevant articles and documents

Synthesis and aromatase inhibitory activity of novel 1-(4-aminophenyl)-3-azabicyclo[3.1.0[hexane- and -[3.1.1]heptane-2,4- diones

The synthesis of 3-(cyclohexylmethyl)-1-(4-aminophenyl)-3-azabicyclo [3.1.0]hexane-2,4-dione (1h), with its optical enantiomers, and a series of novel achiral 1-(4-aminophenyl)-3- azabicyclo[3.1.1]haptane-2,4-diones (2a-i,k) is described. These compounds were tested in vitro for inhibition of human placental aromatase, a cytochrome-P450-dependent enzyme responsible for the conversion of androgens to estrogens. All of them displayed enzyme-inhibiting activity, and 3-cyclohexyl derivative 2g and 3-cyclohexylmethyl derivative 1h both proved more potent (>140-fold) than the clinically effective agent aminoglutethimide [3-(4-aminophenyl)- 3-ethylpiperidine-2,6-dione, AG]. As with AG and its derivatives, the 1R-(+)-enantiomer of 1h was responsible for the enzyme inhibitory activity. These novel compounds are of interest as potential drugs for endocrine therapy of hormone-dependent tumors, e.g. breast cancer.