1095565-81-3

Basic information

• Product Name: (5S)-2-[(1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino]-5-methyl-5-(1-methylethyl)-4(5H)-thiazolone
• Synonyms: (5S)-2-[(1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino]-5-methyl-5-(1-methylethyl)-4(5H)-thiazolone;AMG-221
• CAS NO: 1095565-81-3
• Molecular Formula: C14H22N2OS
• Molecular Weight: 266
• Mol File: 1095565-81-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.35
• CAS DataBase Reference: (5S)-2-[(1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino]-5-methyl-5-(1-methylethyl)-4(5H)-thiazolone(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-2-[(1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino]-5-methyl-5-(1-methylethyl)-4(5H)-thiazolone(1095565-81-3)
• EPA Substance Registry System: (5S)-2-[(1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino]-5-methyl-5-(1-methylethyl)-4(5H)-thiazolone(1095565-81-3)

Safety Data

• Hazardous Substances Data: 1095565-81-3(Hazardous Substances Data)

Usage

General Description

"(5S)-2-[(1S,2S,4R)-Bicyclo[2.2.1]hept-2-ylamino]-5-methyl-5-(1-methylethyl)-4(5H)-thiazolone" is a complex organic compound with a thiazolone ring structure. It contains a bicyclic heptane ring, an amino group, and a thiazolone ring. The compound also has a methyl and isopropyl group attached to the thiazolone ring. This chemical has potential uses in medicinal chemistry and the pharmaceutical industry, although it may require further investigation and research to determine its specific properties and applications.

Upstream product

• 75-30-9 2-iodo-propane 
• 870708-58-0 2-((1S,2S,4R)bicyclo[2.2.1]heptan-2-ylamino)-5-methylthiazol-4(5H)-one 
• 1095565-87-9 (S)-2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-isopropyl-5-methylthiazol-4(5H)-one methanesulfonate 
• 84235-33-6 (+)-(1S,2S,4R)-2-norbornylamine 
• 870708-65-9 1-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-yl)thiourea 
• 3639-20-1 (+/-)-2-hydroxy-2,3-dimethylbutanoic acid 
• 74-88-4 methyl iodide 
• 870708-93-3 2-(exo-bicyclo[2.2.1]heptan-2-ylamino)-5-isopropylthiazol-4(5H)-one 

Relevant articles and documents

Asymmetric alkylation of 5-alkyl-2-aminothiazolones using a C 2-symmetric chiral tetraamine base

The diastereoselective alkylation of a series of 5-alkyl-2-aminothiazolones utilizing a C2-symmetric chiral tetraamine base is reported.

Discovery of a potent, orally active 11β-hydroxysteroid dehydrogenase type 1 inhibitor for clinical study: Identification of (S)-2-((1 S,2 S,4 R)-Bicyclo[2.2.1]heptan-2-ylamino)-5-isopropyl-5-methylthiazol-4(5 H)-one (AMG 221)

Thiazolones with an exo-norbornylamine at the 2-position and an isopropyl group on the 5-position are potent 11β-HSD1 inhibitors. However, the C-5 center was prone to epimerization in vitro and in vivo, forming a less potent diastereomer. A methyl group was added to the C-5 position to eliminate epimerization, leading to the discovery of (S)-2-((1S,2S,4R)-bicyclo[2.2.1] heptan-2-ylamino)-5-isopropyl-5-methylthiazol-4(5H)-one (AMG 221). This compound decreased fed blood glucose and insulin levels and reduced body weight in diet-induced obesity mice.

Two asymmetric syntheses of AMG 221, an inhibitor of 11β- hydroxysteroid dehydrogenase type 1

(Chemical Equation Presented) Two asymmetric syntheses of AMG 221 (2), an inhibitor of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) discovered in our laboratories, are reported. One of the syntheses utilizes chiral trimethylsilyl cyanohydrin 12 as s