212631-61-3 Usage
Description
N-(CYCLOPROPYLMETHOXY)-3,4,5-TRIFLUORO-2-[(4-IODO-2-METHYLPHENYL)AMINO]-BENZAMIDE is a complex organic compound characterized by its unique molecular structure, which includes a cyclopropromethoxy group, a trifluoro-substituted benzene ring, and an iodinated phenyl group. N-(CYCLOPROPYLMETHOXY)-3,4,5-TRIFLUORO-2-[(4-IODO-2-METHYLPHENYL)AMINO]-BENZAMIDE is known for its potent biological activities and is often utilized in various pharmaceutical applications due to its ability to selectively inhibit specific protein targets.
Uses
Used in Pharmaceutical Industry:
N-(CYCLOPROPYLMETHOXY)-3,4,5-TRIFLUORO-2-[(4-IODO-2-METHYLPHENYL)AMINO]-BENZAMIDE is used as a potent inhibitor for [specific protein target] due to its high selectivity and cell permeability. N-(CYCLOPROPYLMETHOXY)-3,4,5-TRIFLUORO-2-[(4-IODO-2-METHYLPHENYL)AMINO]-BENZAMIDE has demonstrated the ability to reduce the phosphorylation of [specific protein] and inhibit the growth of certain cell lines in vitro, making it a promising candidate for the development of targeted therapies against various diseases.
Used in Research Applications:
In the field of biological research, N-(CYCLOPROPYLMETHOXY)-3,4,5-TRIFLUORO-2-[(4-IODO-2-METHYLPHENYL)AMINO]-BENZAMIDE serves as a valuable tool for studying the role of [specific protein target] in cellular processes and disease progression. By selectively inhibiting this protein, researchers can gain insights into its function and potential therapeutic applications in the treatment of various conditions.
Used in Drug Development:
N-(CYCLOPROPYLMETHOXY)-3,4,5-TRIFLUORO-2-[(4-IODO-2-METHYLPHENYL)AMINO]-BENZAMIDE is also utilized in the development of new drugs targeting [specific protein target]. Its high potency and selectivity make it an attractive starting point for the design and optimization of novel therapeutic agents with improved pharmacological properties and reduced side effects.
Biological Activity
Potent inhibitor of MEK1/2. Inhibits isolated enzyme at a concentration of 8 nM and inhibits MEK activity in synovial fibroblasts at concentrations of 30-100 nM. Highly selective for MEK; IC 50 values are > 1, > 4, > 4 and > 10 μ M for ERK, c-Src, cdks and PI 3-kinase γ respectively. Antihyperalgesic; blocks static allodynia in the streptozocin model of neuropathic pain following i.t. administration.
in vitro
pd 198306 inhibits the isolated mek at a concentration of 8 nm and inhibits mek activity in synovial fibroblasts at 30–100 nm, depending on the species. pd 198306 is highly selective for mek and has a ic50 of >4 um for c-src, >1 um for erk, >4 um for cyclin-dependent kinases and >10 um for phosphatidylinositol 3-kinase [1].
in vivo
rabbits treated with pd 198306 showd a significant dose-dependent reduction in the level of phospho-erk-1/2 and a lower level of mmp-1. pd 198306 can partially decrease the development of some of the structural changes in experimental rabbit model of osteoarthritis [1]. pd 198306 dose-dependently blocked static allodynia in both the streptozocin and the chronic constriction injury models of neuropathic pain. these antihyperalgesic effects correlated with a reduction in the elevated levels of active erk1 and 2 in lumbar spinal cord [2].
IC 50
8 nm for mek [1]
references
[1] pelletier jp, fernandes jc, brunet j, moldovan f, schrier d, flory c, martel-pelletier j. in vivo selective inhibition of mitogen-activated protein kinase kinase 1/2 in rabbit experimental osteoarthritis is associated with a reduction in the development of structural changes. arthritis rheum. 2003 jun;48(6):1582-93.[2] ciruela a, dixon ak, bramwell s, gonzalez mi, pinnock rd, lee k. identification of mek1 as a novel target for the treatment of neuropathic pain. br j pharmacol. 2003 mar;138(5):751-6.
Check Digit Verification of cas no
The CAS Registry Mumber 212631-61-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,1,2,6,3 and 1 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 212631-61:
(8*2)+(7*1)+(6*2)+(5*6)+(4*3)+(3*1)+(2*6)+(1*1)=93
93 % 10 = 3
So 212631-61-3 is a valid CAS Registry Number.
InChI:InChI=1/C18H16F3IN2O2/c1-9-6-11(22)4-5-14(9)23-17-12(7-13(19)15(20)16(17)21)18(25)24-26-8-10-2-3-10/h4-7,10,23H,2-3,8H2,1H3,(H,24,25)
212631-61-3Relevant articles and documents
The discovery of the benzhydroxamate MEK inhibitors CI-1040 and PD 0325901
Barrett, Stephen D.,Bridges, Alexander J.,Dudley, David T.,Saltiel, Alan R.,Fergus, James H.,Flamme, Cathlin M.,Delaney, Amy M.,Kaufman, Michael,LePage, Sophie,Leopold, Wilbur R.,Przybranowski, Sally A.,Sebolt-Leopold, Judith,Van Becelaere, Keri,Doherty, Annette M.,Kennedy, Robert M.,Marston, Dan,Howard Jr., W. Allen,Smith, Yvonne,Warmus, Joseph S.,Tecle, Haile
supporting information; experimental part, p. 6501 - 6504 (2009/10/01)
A novel series of benzhydroxamate esters derived from their precursor anthranilic acids have been prepared and have been identified as potent MEK inhibitors. 2-(2-Chloro-4-iodo-phenylamino)-N-cyclopropylmethoxy-3,4-difluoro-benzam ide, CI-1040, was the first MEK inhibitor to demonstrate in vivo activity in preclinical animal models and subsequently became the first MEK inhibitor to enter clinical trial. CI-1040 suffered however from poor exposure due to its poor solubility and rapid clearance, and as a result, development of the compound was terminated. Optimization of the diphenylamine core and modification of the hydroxamate side chain for cell potency, solubility, and exposure with oral delivery resulted in the discovery of the clinical candidate N-(2,3-dihydroxy-propoxy)-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-b enzamide PD 0325901.
4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as MEK inhibitors
-
, (2008/06/13)
Phenylamino benzhydroxamic acid derivatives of formula (I) where R1, R2, R3, R4, R5, and R6 are hydrogen or substituent groups such as alkyl, and where R7 is hydrogen or an organic radical, are potent inhibitors of MEK and, as such, are effective in treat
