137623-89-3

Basic information

• Product Name: 2,6-Piperidinedione, 3-(4-aminophenyl)-3-cyclohexyl-, (S)-
• CAS NO: 137623-89-3
• Molecular Formula: C17H22N2O2
• Molecular Weight: 286.374
• Mol File: 137623-89-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,6-Piperidinedione, 3-(4-aminophenyl)-3-cyclohexyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Piperidinedione, 3-(4-aminophenyl)-3-cyclohexyl-, (S)-(137623-89-3)
• EPA Substance Registry System: 2,6-Piperidinedione, 3-(4-aminophenyl)-3-cyclohexyl-, (S)-(137623-89-3)

Safety Data

• Hazardous Substances Data: 137623-89-3(Hazardous Substances Data)

Usage

Commonly known as

S-Cyclohexyl-S-phenylsultam

Physical properties

white solid at room temperature, soluble in organic solvents

Use

chiral building block in organic synthesis

Function

acts as a chiral auxiliary in asymmetric synthesis

Industry applications

pharmaceutical and agrochemical industries

Importance

key intermediate in the production of optically active compounds

Role in medicinal chemistry

used in the production of drugs

Key attribute

chiral nature is crucial for creating enantiomerically pure products

Upstream product

• 108-85-0 1-bromocyclohexane 
• 115883-24-4 3-cyclohexyl-3-(4-nitrophenyl)piperidine-2,6-dione 
• 140-29-4 phenylacetonitrile 
• 115883-23-3 3-cyclohexyl-3-phenylpiperidine-2,6-dione 
• 20881-44-1 2-cyclohexyl-2-phenylglutarodinitrile 
• 3893-23-0 cyclohexyl phenyl acetonitrile 
• 115883-22-2 Cyclohexylaminoglutethimide 

Relevant articles and documents

Synthesis and aromatase inhibition of 3-cycloalkyl-substituted 3-(4- aminophenyl)piperidine-2,6-diones

The synthesis of 3-cycloalkyl-substituted 3-(4-aminophenyl)piperidine-2,6- diones is described [cyclopentyl (1), cyclohexyl (2)]. The enantiomers of 2 were separated either by using HPLC on optically active sorbent or by crystallization of the brucine salt of the phthalamic acid of 2. The absolute configuration of the (+)- and (-)-enantiomers of 2 were assigned as S and R, respectively, by comparing the CD spectra to those of the enantiomers of aminoglutethimide (AG, 3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione). The compounds were tested in vitro for inhibition of human placental aromatase, the cytochrome P450-dependent enzyme which is responsible for the conversion of androgens to estrogens. Compounds 1 and 2 inhibited aromatase by 50% at 1.2 and 0.3 μM, respectively (IC50 AG = 37 μM). According to the findings with AG, the (+)-enantiomer of 2 was responsible for the inhibitory activity, being a 240-fold more potent aromatase inhibitor in vitro than racemic AG. On the other hand, (+)-2 displayed a strongly reduced inhibition of desmolase (cholesterol side-chain cleavage enzyme) compared to AG (relative activity = 0.3). Thus (+)-2 is of interest as a potential drug for the treatment of estrogen-dependent diseases, e.g. mammary tumors.