922727-93-3

Basic information

• Product Name: (1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate
• Synonyms: (1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate;(1S,2R)-ethyl 1-((1R,2R,4S)-2-(hex-5-enyl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate;(1R,2S)-2-Ethenyl-1-[[[(1R,2R,4S)-2-[(5-hexen-1-ylmethylamino)carbonyl]-4-hydroxycyclopentyl]carbonyl]amino]cyclopropanecarboxylic acid ethyl ester;(1R,2S)-1-{[(1R,2R,4S)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester
• CAS NO: 922727-93-3
• Molecular Formula: C₂₂H₃₄N₂O₅
• Molecular Weight: 406.51576
• Mol File: 922727-93-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 601.2±55.0 °C(Predicted)
• Appearance: /
• Density: 1.14±0.1 g/cm3(Predicted)
• PKA: 13.21±0.40(Predicted)
• CAS DataBase Reference: (1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate(922727-93-3)
• EPA Substance Registry System: (1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate(922727-93-3)

Safety Data

• Hazardous Substances Data: 922727-93-3(Hazardous Substances Data)

Usage

General Description

The chemical (1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate is a compound with a complex structure that consists of multiple functional groups. It contains an ethyl ester, a carboxamide, a vinyl group, a cyclopropane ring, and a hydroxyl group. The compound is a derivative of cyclopentanecarboxamide and cyclopropanecarboxylate, and it is also substituted with an alkene and a methyl group. This chemical may have potential applications in pharmaceuticals, agrochemicals, and materials science due to its unique structure and functional groups. Further research and analysis are required to fully understand its potential uses and properties.

Upstream product

• 259214-54-5 ethyl (1R,2S)-1-amino-2-vinylcyclopropanecarboxylate hydrochloride 
• 922727-92-2 (1R,2R,4R)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentane carboxylic acid 
• 862174-98-9 (1R,4R,5R)-N-(hex-5-en-1-yl)-N-methyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide 
• 862174-60-5 (1R,4R,5R)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid 
• 922520-05-6 2,2,2-trifluoro-N-(hex-5-enyl)-N-methylacetamide 
• 55863-02-0 N-methylhex-5-en-1-amine 
• 2695-47-8 6-Bromo-1-hexene 
• 862259-02-7 trans-(3R,4R)-3,4-bis(methoxycarbonyl)cyclopentanol 
• 67885-98-7 (1R,2R)-4-hydroxycyclopentane-1,2-dicarboxylic acid 
• 28269-02-5 cis-4-oxo-1,2-cyclopentanedicarboxylic acid bis(methyl ester) 

Downstream Products

• 862175-03-9 1-{[4-(4-bromo-benzensulphonyloxy-2-(hex-5-enyl-methyl-carbamoyl)-cyclopentanecarbonyl)]-amino}2-vinyl-cyclopropanecarboxylic acid ethyl ester 
• 923604-56-2 ethyl (1R,2S)-2-ethenyl-1-({[(1R,2R,4R)-2-[hex-5-en-1-yl-(methyl)carbamoyl]-4-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)cyclopentyl]carbonyl}-amino)cyclopropanecarboxylate 

Relevant articles and documents

Macrocylic Inhibitors of Hepatitis C Virus

Compounds of the formula I: and N-oxides, salts, and stereoisomers thereof wherein A is OR1, NHS(═O)pR2; wherein; R1 is hydrogen, C1-C6alkyl, C0-C3alkylenecarbocyclyl, C0-C3alkylene-heterocyclyl;R2 is C1-C6alkyl, C0-C3alkylenecarbocyclyl, C0-C3alkyleneheterocyclyl;p is independently 1 or 2;n is 3, 4, 5 or 6; — denotes an optional double bond;L is N or CRz; Rz is H or forms a double bond with the asterisked carbon;Rq is H or when L is CRz, Rq can also be C1-C6alkyl;Rr is quinazolinyl, optionally substituted with one two or three substituents each independently selected from C1-C6 alkyl, C1-C6alkoxy, hydroxyl, halo, haloC1-C6alkyl, amino, mono- or dialkylamino, mono- or dialkylaminocarbonyl, C1-C6alkyl-carbonylamino, C0-C3alkylenecarbocyclyl and C0-C3 alkyleneheterocyclyl;R5 is hydrogen, C1-C6alkyl, C1-C6alkoxyC1-C6alkyl or C3-C7cycloalkyl;R6 is hydrogen, C1-C6alkyl, C1-C6alkoxy, C0-C3alkylenecarbocyclyl, C0-C3alkylene-heterocyclyl, hydroxy, bromo, chloro or fluoro have utility in the treatment or prophylaxis of flaviviral infections such as HCV

Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350

SAR analysis performed with a limited set of cyclopentane-containing macrocycles led to the identification of N-[17-[2-(4-isopropylthiazole-2-yl)-7-methoxy-8-methylquinolin-4-yloxy]- 13-methyl-2,14-dioxo-3,13-diazatricyclo [13.3.0.04,6]octadec-7-ene-4-carbonyl](cyclopropyl)sulfonamid e (TMC435350, 32c) as a potent inhibitor of HCV NS3/4A protease (Ki = 0.36 nM) and viral replication (replicon EC50 = 7.8 nM). TMC435350 also displayed low in vitro clearance and high permeability, which were confirmed by in vivo pharmacokinetic studies. TMC435350 is currently being evaluated in the clinics.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers thereof, wherein X is N, CH and where X bears a double bond it is C; R1 is -OR5, -NH-SO2R6; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, or C3-7cycloalkyl; R4 is isoquinolinyl optionally substituted with one, two or three substituents each independently selected from C1-6alkyl, C1-6alkoxy, hydroxy, halo, polyhalo- C1-6alkyl, polyhaloC1-6alkoxy, amino, mono- or diC1-6alkylamino, mono- or DiC1-6alkylaminocarbonyl, C1-6alkylcarbonyl-amino, aryl, and Het; n is 3, 4, 5, or 6; each dashed line (represented by ) represents an optional double bond; R5 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R6 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; each aryl is phenyl optionally substituted with one, two or three substituents; and each Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms each independently selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.