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methyl 4-[[3-[2-(aminomethyl)-5-[(3-fluoropyridin-4-yl)carbamoyl]phenyl]benzoyl]amino]benzoate

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货号 (SKU) 包装规格 是否现货 价格 数量
M609473-5mg
 5mg 期货 Stock Image
M609473-25mg
 25mg 期货 Stock Image
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Rho associated coiled-coil containing protein kinase 1 Inhibitor Rho associated coiled-coil containing protein kinase 2 Inhibitor
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基本描述

英文名称 methyl 4-[[3-[2-(aminomethyl)-5-[(3-fluoropyridin-4-yl)carbamoyl]phenyl]benzoyl]amino]benzoate
别名 compound 8
英文别名 compound 8

名称和标识符

IUPAC Name methyl 4-[[3-[2-(aminomethyl)-5-[(3-fluoropyridin-4-yl)carbamoyl]phenyl]benzoyl]amino]benzoate
INCHI InChI=1S/C28H23FN4O4/c1-37-28(36)17-7-9-22(10-8-17)32-26(34)19-4-2-3-18(13-19)23-14-20(5-6-21(23)15-30)27(35)33-25-11-12-31-16-24(25)29/h2-14,16H,15,30H2,1H3,(H,32,34)(H,31,33,35)
InChi Key MXWDBTLNBKIMEX-UHFFFAOYSA-N
Canonical SMILES NCc1ccc(cc1c1cccc(c1)C(=O)Nc1ccc(cc1)C(=O)OC)C(=O)Nc1ccncc1F
PubChem CID 71283262

关联配体

Ligand ID 10498
名称 compound 8 [PMID: 25898023]
类别 Synthetic organic
学名 methyl 4-[[3-[2-(aminomethyl)-5-[(3-fluoropyridin-4-yl)carbamoyl]phenyl]benzoyl]amino]benzoate
生物活性评价 In a kinase screening panel of 335 kinases, compound 8 exhibited at least 100-fold selectiveity for ROCK1 and ROCK2 vs. the other kinases. At 100 nM potential off-targets might include PKCs (PKCε, PKCη, PKCδ, and PKCθ), MSK1, PRK1, PRK2, and PRKX. As PRK2 inhibition by existing ROCK inhibitors ( and ) is reported to mediate some of their beneficial cellular effects , this could also be the case for compound 8.
评价 Compound 8 [PMID: 25898023] is a selective inhibitor of Rho kinase (ROCK) activity that was developed for the treatment of ocular inflammation . In an effort to reduce unintended systemic ROCK-associated side effects and maximise local effects, it was designed to be rapidly converted to an inactive metabolite in the systemic circulation. Compounds of this type are known as 'soft' drugs. Specifically, compound 8 contains an ester group that is hydrolysed by blood esterases to an inactive carboxylic acid metabolite (8M).
Amakem Ophthalmics have a 'soft' ROCK inhibitor AMA0076 that has been shown to reduce intraocular pressure in a rabbit model of glaucoma , and which has completed Phase 2 clinical evaluation in glaucoma/ocular hypertension (NCT01693315). The structure of AMA0076 has not been formally disclosed, but it appears to be derived from the same chemical scaffold as compound 8.

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参考文献

1. Kim SJ, Kim JH, Sun JM, Kim MG, Oh JW.  (2009)  Suppression of hepatitis C virus replication by protein kinase C-related kinase 2 inhibitors that block phosphorylation of viral RNA polymerase..  J Viral Hepat,  16  (10):  (697-704).  [PMID:19243496]
2. Darenfed H, Dayanandan B, Zhang T, Hsieh SH, Fournier AE, Mandato CA.  (2007)  Molecular characterization of the effects of Y-27632..  Cell Motil Cytoskeleton,  64  (2):  (97-109).  [PMID:17009325]
3. Van de Velde S, Van Bergen T, Sijnave D, Hollanders K, Castermans K, Defert O, Leysen D, Vandewalle E, Moons L, Stalmans I.  (2014)  AMA0076, a novel, locally acting Rho kinase inhibitor, potently lowers intraocular pressure in New Zealand white rabbits with minimal hyperemia..  Invest Ophthalmol Vis Sci,  55  (2):  (1006-16).  [PMID:24474276]
4. Boland S, Bourin A, Alen J, Geraets J, Schroeders P, Castermans K, Kindt N, Boumans N, Panitti L, Fransen S et al..  (2015)  Design, synthesis, and biological evaluation of novel, highly active soft ROCK inhibitors..  J Med Chem,  58  (10):  (4309-24).  [PMID:25898023]
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