312917-14-9 Usage
Description
N-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]thienyl-2-yl)-1-naphthalenecarboxamide, also known as JNK inhibitor IX, is a compound that specifically inhibits JNK2 and JNK3 by binding to their ATP binding domain. It has minimal or no activity against JNK1, p38α, and a panel of 30 other kinases. This inhibitor has been shown to induce prometaphase arrest-dependent apoptotic cell death in human Jurkat T cells.
Uses
Used in Pharmaceutical Industry:
N-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]thienyl-2-yl)-1-naphthalenecarboxamide is used as a JNK inhibitor for the development of therapeutic agents targeting JNK2 and JNK3. Its specificity in inhibiting these kinases makes it a valuable tool in the research and treatment of various diseases and conditions where JNK2 and JNK3 play a significant role.
Used in Research Applications:
In the field of cell biology and molecular biology, N-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]thienyl-2-yl)-1-naphthalenecarboxamide is used as a research tool to study the role of JNK2 and JNK3 in cellular processes, such as cell death and survival, inflammation, and stress responses. Its ability to induce prometaphase arrest-dependent apoptotic cell death in human Jurkat T cells makes it a useful compound for investigating the mechanisms underlying these processes.
Used in Drug Development:
N-(3-Cyano-4,5,6,7-tetrahydrobenzo[b]thienyl-2-yl)-1-naphthalenecarboxamide is used as a lead compound in the development of new drugs targeting JNK2 and JNK3 for the treatment of diseases where these kinases are implicated, such as cancer, neurodegenerative disorders, and inflammatory conditions. Its specificity and potency in inhibiting JNK2 and JNK3 make it a promising starting point for the design and synthesis of more potent and selective inhibitors.
References
1) Angell?et al. (2007),?N-(3-Cyano-4,5,6,7-tetrahydro-1-benzothien-2-yl)amides as potent, selective, inhibitors of JNK2 and JNK3; Med. Chem. Lett.,?17?1296
2) Jang?et al.?(2014),?Inhibition of JNK2 and JNK3 by JNK inhibitor IX induces prometaphase arrest-dependent apoptotic cell death in human Jurkat T cells?; Biochem. Biophys. Res. Commun.,?452?845
Check Digit Verification of cas no
The CAS Registry Mumber 312917-14-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,1,2,9,1 and 7 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 312917-14:
(8*3)+(7*1)+(6*2)+(5*9)+(4*1)+(3*7)+(2*1)+(1*4)=119
119 % 10 = 9
So 312917-14-9 is a valid CAS Registry Number.
InChI:InChI=1/C20H16N2OS/c21-12-17-15-9-3-4-11-18(15)24-20(17)22-19(23)16-10-5-7-13-6-1-2-8-14(13)16/h1-2,5-8,10H,3-4,9,11H2,(H,22,23)
312917-14-9Relevant articles and documents
N-(3-Cyano-4,5,6,7-tetrahydro-1-benzothien-2-yl)amides as potent, selective, inhibitors of JNK2 and JNK3
Angell, Richard M.,Atkinson, Francis L.,Brown, Murray J.,Chuang, Tsu Tshen,Christopher, John A.,Cichy-Knight, Maria,Dunn, Allison K.,Hightower, Kendra E.,Malkakorpi, Susanna,Musgrave, James R.,Neu, Margarete,Rowland, Paul,Shea, Robyn L.,Smith, Jeffery L.,Somers, Donald O.,Thomas, Sonia A.,Thompson, Gladstone,Wang, Ruolan
, p. 1296 - 1301 (2007/10/03)
The identification and exploration of a novel, potent and selective series of N-(3-cyano-4,5,6,7-tetrahydro-1-benzothien-2-yl)amide inhibitors of JNK2 and JNK3 kinases is described. Compounds 5a and 11a were identified as potent inhibitors of JNK3 (pIC50 6.7 and 6.6, respectively), with essentially equal potency against JNK2 (pIC50 6.5). Selectivity within the mitogen-activated protein kinase (MAPK) family, against JNK1, p38α and ERK2, was observed for the series. X-ray crystallography of 5e and 8a in JNK3 revealed a unique binding mode, with the 3-cyano substituent forming an H-bond acceptor interaction with the hinge region of the ATP-binding site.
