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

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

Uses

Used in Pharmaceutical Industry:
(1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate is used as a potential pharmaceutical agent for its unique structure and functional groups, which may offer novel therapeutic properties and mechanisms of action.
Used in Agrochemical Industry:
In the agrochemical industry, (1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate may be utilized as a novel active ingredient in the development of pesticides or herbicides, leveraging its complex structure and functional groups to target specific pests or weeds effectively.
Used in Materials Science:
(1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate may find applications in materials science, where its unique structure and functional groups could be employed to create new materials with specific properties, such as improved strength, flexibility, or chemical resistance.
Further research and analysis are required to fully understand the potential uses and properties of (1R,2S)-ethyl 1-((1R,2R,4S)-2-(hex-5-en-1-yl(Methyl)carbaMoyl)-4-hydroxycyclopentanecarboxaMido)-2-vinylcyclopropanecarboxylate, as its complex structure and multiple functional groups may offer a wide range of applications across various industries.

Upstream product

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

Downstream Products

• 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 
• 862175-03-9 1-{[4-(4-bromo-benzensulphonyloxy-2-(hex-5-enyl-methyl-carbamoyl)-cyclopentanecarbonyl)]-amino}2-vinyl-cyclopropanecarboxylic acid ethyl ester 

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.

HCV INHIBITING MACROCYCLIC PHOSPHONATES AND AMIDOPHOSPHATES

Inhibitors of HCV replication of Formula (I) the /V-oxides, salts, and stcreochcmically isomeric forms thereof; pharmaceutical compositions containing compounds (1) and processes for preparin compounds (I). The side chain R2 is an amidophosphate or a phosphonate group and X, R1, R3, E and n are as defined in the application.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of Formula (I) and the salts and stereoisomers thereof, wherein each dashed line (represented by - - - - -) represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1 -6alkyl, C3 -7cycloalkyl; n is 3, 4, 5, or 6; R4 is C1-6alkyl or C3-7cycloalkyl; R5 is hydrogen, halo, C1-6alkyl, hydroxy, C1 -6alkoxy, polyhaloC1 -6alkyl; R6 is hydrogen, C1-6alkoxy, mono- or diC1 -6alkylamino; or R5 and R6 may form a 5- or 6-membered unsaturated or partially unsaturated ring, optionally co mprising one or two selected from O, N and S; R7 is hydrogen; C3-7cycloalkyl optionally subst ituted with C1-6alkyl; or C1-6alkyl optionally subst ituted with C3 -7cycloalkyl; R8 is C3-7cycloalkyl optionally subst ituted with C1 -6alkyl; C1 -6alkyl optionally substituted with C3-7cycloalkyl; or -NR8aR8b; R8a and R8b are C1-6alkyl, or both may form a 5- or 6-membered saturated heterocyclic ring; pharmaceut ical compositions containing compounds (I) and processes for preparing compounds (I).

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.

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Inhibitors of HCV replication of formula (I), and the N-oxides, salts, and stereoisomers thereof, wherein each dashed line represents an optional double bond; X is Ν, CH and where X bears a double bond it is C; R1a and R1b are hydrogen, C3-7cycloalkyl, aryl, Het, C1-6alkoxy, C1-6alkyl optionally substituted with halo, C1-6alkoxy, cyano, polyhaloC11-6alkoxy, C3-7cycloalkyl, aryl, or with Het; or R1a and R1b together with the nitrogen to which they are attached form a 4 to 6 membered heterocyclic ring which may be optionally substituted; L is a direct bond, -O- , -O-C1-4alkanediyl-, -O-CO-, -O-C(=O)-ΝR5a - or -O -C(=O)-NR5a-C1-4alkanediyl-; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl, amino, mono- or diC1-6alkylamino; R4 is aryl or a saturated, a partially unsaturated or completely unsaturated 5 or 6 membered monocyclic or 9 to 12 membered bicyclic heterocyclic ring system wherein said ring system contains one nitrogen, and optionally one to three additional heteroatoms selected from O, S and N, and wherein the remaining ring members are carbon atoms; wherein said ring system may be optionally substituted; n is 3, 4, 5, or 6; p is 1 or 2; aryl is phenyl, naphthyl, indanyl, or 1,2,3,4-tetrahydronaphthyl, each of which may be optionally substituted with one, two or three substituents; and Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from N, O and S , being optionally condensed with a benzene ring, and wherein Het may be optionally substituted with one, two or three substituents; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I).

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, and stereoisomers, wherein each dashed line represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR7, -NH-SO2R8; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, C3-7cycloalkyl; R4 is aryl or Het; n is 3, 4, 5, or 6; R5 is halo, C1-6alkyl, hydroxy, C1-6alkoxy, phenyl, or Het; R6 is C1-6alkoxy, or dimethylamino; R7 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R8 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl optionally substituted with one, two or three substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms 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.