1313730-14-1

1313730-14-1 structure

Name: CCR2 antagonist 4 hydrochloride
Chemical Name: N-(2-{[(3R)-1-(4-Chlorobenzyl)-3-pyrrolidinyl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide hydrochloride (1:1)
CAS Number: 1313730-14-1
Molecular Formula: C₂₁H₂₂Cl₂F₃N₃O₂
Molecular Weight: 476.319
Catalog: Signaling Pathways GPCR/G Protein CCR
Create Date: 2018-06-09 17:16:42
Modify Date: 2024-01-10 17:35:04
CCR2 antagonist 4 hydrochloride (Teijin compound 1 hydrochloride) is a potent and specific CCR2 antagonist, with IC50s of 180 nM for CCR2b. CCR2 antagonist 4 hydrochloride potently inhibits MCP-1-induced chemotaxis with an IC50 of 24 nM[1].

Name	N-(2-{[(3R)-1-(4-Chlorobenzyl)-3-pyrrolidinyl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide hydrochloride (1:1)
Synonyms	Benzamide, N-[2-[[(3R)-1-[(4-chlorophenyl)methyl]-3-pyrrolidinyl]amino]-2-oxoethyl]-3-(trifluoromethyl)-, hydrochloride (1:1) N-(2-{[(3R)-1-(4-Chlorobenzyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide hydrochloride (1:1) N-(2-{[(3R)-1-(4-Chlorobenzyl)-3-pyrrolidinyl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide hydrochloride (1:1)

Description	CCR2 antagonist 4 hydrochloride (Teijin compound 1 hydrochloride) is a potent and specific CCR2 antagonist, with IC50s of 180 nM for CCR2b. CCR2 antagonist 4 hydrochloride potently inhibits MCP-1-induced chemotaxis with an IC50 of 24 nM[1].
Related Catalog	Signaling Pathways >> GPCR/G Protein >> CCR Signaling Pathways >> Immunology/Inflammation >> CCR Research Areas >> Inflammation/Immunology
Target	CCR2b:180 nM (IC50)
In Vitro	Ile263 and Thr292 in CCR2 contribute significantly to binding of CCR2 antagonist 4 in CCR2. Residue Glu291 in TM7, a highly conserved residue in many CC chemokine receptors, contributes substantially to binding of the protonated CCR2 antagonist 4 hydrochloride, and CCL2. His121 on TM3 and Ile263 on TM6 also strongly interact with CCR2 antagonist 4 hydrochloride[2].
In Vivo	In ApoE-deficient mice, Vp-TSL targets specifically aortic plaque endothelial VCAM-1 and CCR2 antagonist 4 hydrochloride reduces the mouse monocyte/macrophage cell line (RAW 264.7) adhesion/ infiltration into the aorta[3].
References	[1]. Moree WJ, et al. Potent antagonists of the CCR2b receptor. Part 3: SAR of the (R)-3-aminopyrrolidine series. Bioorg Med Chem Lett. 2008 Mar 15;18(6):1869-73. [2]. Hall SE, et al. Elucidation of binding sites of dual antagonists in the human chemokine receptors CCR2 and CCR5. Mol Pharmacol. 2009 Jun;75(6):1325-36. [3]. Calin M, et al. VCAM-1 directed target-sensitive liposomes carrying CCR2 antagonists bind to activated endothelium and reduce adhesion and transmigration of monocytes. Eur J Pharm Biopharm. 2015 Jan;89:18-29.

Molecular Formula	C₂₁H₂₂Cl₂F₃N₃O₂
Molecular Weight	476.319
Exact Mass	475.104126

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