195987-41-8 Usage
Description
(4R)-4-benzyl-2-(3H-imidazol-4-ylmethyl)-5-thiophen-2-ylsulfonyl-2,5-diazabicyclo[5.4.0]undeca-8,10,12-triene-9-carbonitrile is a complex organic compound characterized by its unique molecular structure. It is a derivative of diazabicyclo compounds with a benzyl and imidazol-4-ylmethyl group attached to the 4R position. Additionally, it features a thiophen-2-ylsulfonyl group and a carbonitrile functional group. This molecule is known for its potential applications in various fields due to its specific chemical properties and interactions.
Uses
Used in Pharmaceutical Industry:
(4R)-4-benzyl-2-(3H-imidazol-4-ylmethyl)-5-thiophen-2-ylsulfonyl-2,5-diazabicyclo[5.4.0]undeca-8,10,12-triene-9-carbonitrile is used as a potent and selective inhibitor of farnesyltransferase for the treatment of chronic myeloid leukemia stem/progenitor cells, including CD34+38cells. It induces mitochondrial apoptosis through the activation of protein kinase Cβ, which is crucial in targeting cancer cells and halting their growth.
Used in Cancer Research:
(4R)-4-benzyl-2-(3H-imidazol-4-ylmethyl)-5-thiophen-2-ylsulfonyl-2,5-diazabicyclo[5.4.0]undeca-8,10,12-triene-9-carbonitrile is utilized in cancer research as a potent inhibitor of farnesyltransferase (FTase), which plays a significant role in the growth of various cancer cells expressing wild-type Ras and mutant K-Ras. It has demonstrated the ability to inhibit the growth of MEK2, A2780, PC3, HCT116, MIP, RC-165, and MIA PaCa-2 cancer cells, making it a valuable tool in the development of targeted cancer therapies.
Used in Drug Development:
(4R)-4-benzyl-2-(3H-imidazol-4-ylmethyl)-5-thiophen-2-ylsulfonyl-2,5-diazabicyclo[5.4.0]undeca-8,10,12-triene-9-carbonitrile is employed in drug development for its ability to induce apoptosis in HCT116 cells in a concentration-dependent manner. Its in vivo curative properties in an HCT116 mouse xenograft model and its capacity to reduce tumor growth in Calu-1, HT-29, EJ-1, and MIA PaCa-2 mouse xenograft models make it a promising candidate for further pharmaceutical development.
Chemical Properties:
(4R)-4-benzyl-2-(3H-imidazol-4-ylmethyl)-5-thiophen-2-ylsulfonyl-2,5-diazabicyclo[5.4.0]undeca-8,10,12-triene-9-carbonitrile is a pale yellow solid, which indicates its stability and potential for formulation in various pharmaceutical applications.
Check Digit Verification of cas no
The CAS Registry Mumber 195987-41-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,5,9,8 and 7 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 195987-41:
(8*1)+(7*9)+(6*5)+(5*9)+(4*8)+(3*7)+(2*4)+(1*1)=208
208 % 10 = 8
So 195987-41-8 is a valid CAS Registry Number.
InChI:InChI=1/C25H23N5O2S2/c26-13-20-8-9-24-21(11-20)15-30(34(31,32)25-7-4-10-33-25)23(12-19-5-2-1-3-6-19)17-29(24)16-22-14-27-18-28-22/h1-11,14,18,23H,12,15-17H2,(H,27,28)/t23-/m1/s1
195987-41-8Relevant articles and documents
Novel triethylsilane mediated reductive N-alkylation of amines: Improved synthesis of 1-(4-imidazolyl)methyl-4-sulfonylbenzodiazepines, new farnesyltransferase inhibitors
Chen, Bang-Chi,Sundeen, Joseph E.,Guo, Peng,Bednarz, Mark S.,Zhao, Rulin
, p. 1245 - 1246 (2001)
An improved synthesis of 1-(imidazolyl)methyl-4-sulfonylbenzodiazapines, new farnesyltransferase inhibitors, was achieved using a novel reductive N-alkylation method. The new method involves reaction of a secondary amine with analdehyde using triethylsilane in the presence of trifluoroacetic acid, giving a tertiary amine in 90-95% isolated yields.
Discovery of (R)-7-cyano-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-3-(phenylmethyl)-4- (2-thienysulfonyl)-1H-1,4-benzodiazepine (BMS-214662), a farnesyltransferase inhibitor with potent preclinical antitumor activity
Hunt,Ding,Batorsky,Bednarz,Bhide,Cho,Chong,Chao,Gullo-Brown,Guo,Soong Hoon Kim,Lee,Leftheris,Miller,Mitt,Patel,Penhallow,Ricca,Rose,Schmidt,Slusarchyk,Vite,Manne
, p. 3587 - 3595 (2007/10/03)
Continuing structure-activity studies were performed on the 2,3,4,5-tetrahydro-1-(imidazol-4-ylalkyl)-1,4-benzodiazepine farnesyltransferase (FT) inhibitors. These studies demonstrated that a 3(R)-phenylmethyl group, a hydrophilic 7-cyano group, and a 4-s
