292644-33-8

Basic information

• Product Name: 2-(3-AMino-4-Methylphenyl)-1H-Benzo[d]iMidazole
• Synonyms: 2-(3-AMino-4-Methylphenyl)-1H-Benzo[d]iMidazole;5-(1H-benzo[d]iMidazol-2-yl)-2-MethylbenzenaMine
• CAS NO: 292644-33-8
• Molecular Formula: C₁₄H₁₃N₃
• Molecular Weight: 223.27312
• Mol File: 292644-33-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 478.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.247±0.06 g/cm3(Predicted)
• PKA: 11.43±0.10(Predicted)
• CAS DataBase Reference: 2-(3-AMino-4-Methylphenyl)-1H-Benzo[d]iMidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-AMino-4-Methylphenyl)-1H-Benzo[d]iMidazole(292644-33-8)
• EPA Substance Registry System: 2-(3-AMino-4-Methylphenyl)-1H-Benzo[d]iMidazole(292644-33-8)

Safety Data

• Hazardous Substances Data: 292644-33-8(Hazardous Substances Data)

Usage

InChI:InChI=1S/C14H13N3/c1-9-6-7-10(8-11(9)15)14-16-12-4-2-3-5-13(12)17-14/h2-8H,15H2,1H3,(H,16,17)

Upstream product

• 31680-07-6 4-methyl-3-nitrobenzaldehyde 
• 95-54-5 1,2-diamino-benzene 
• 7681-38-1 sodium hydrogen sulfate 
• 100726-38-3 2-(4-methyl-3-nitro-phenyl)-1H-benzimidazole 

Downstream Products

• 1126408-37-4 N-(5-(1H-benzo[d]imidazol-2-yl)-2-methylphenyl)-4-(pyridin-2-ylmethoxy)benzamide 

Relevant articles and documents

Synthesis and structure-activity relationship of non-peptidic antagonists of neuropilin-1 receptor

Neuropilins (NRPs) are VEGF-A165 co-receptors over-expressed in tumor cells, and considered as targets in angiogenic-related pathologies. We previously identified compound 1, the first non-peptidic antagonist of the VEGF-A165/NRP binding, which exhibits in vivo anti-angiogenic and anti-tumor activities. We report here the synthesis and biological evaluations of new antagonists structurally-related to compound 1. Among these molecules, 4a, 4c and 4d show cytotoxic effects on HUVEC and MDA-MB-31 cells, and antagonize VEGF-A165/NRP-1 binding. This study confirmed our key structure-activity relationships hypothesis and paved the way to compound 1 'hit to lead' optimization.

Pharmaceutical compositions comprising Neuropilin inhibitors, and their use for the prevention and/or treatment of angiogenic disorders and cancers

The present invention relates to a pharmaceutical composition comprising a compound of general formula (I), wherein - Z1 is S or O, preferably S; - -Z2- is -NRa-, wherein Ra is H, OH, alkyl, alkoxy, aryle, alkenyl, alkynyl, amine, preferably Ra is H; -N=; O; S; -CRb=, wherein Rb is H, OH, alkyl, alkoxy, aryle, alkenyl, alkynyl, amine, NO2, Cl, Br, I, F, preferably H; -CHRc-, wherein Rc is H, OH, alkyl, alkoxy, aryle, alkenyl, alkynyl, amine, NO2, Cl, Br, I, F, or -CH2-; preferably -Z2- is -NH- or -N=; - each of R1 and R2 is independently H, OH, alkyl, alkoxy, aryle, alkenyl, alkynyl, amine, NO2, Cl, Br, I, F; preferably R1 and R2 together and with N and Z2 form an heterocycle eventually substituted, more preferably a substituted azocine, 3H-indole, indazole, 2-imidazoline, 2-pyrazoline, benzthiazole, purine, pyrimidine, pyridine, pyridazine, pyrazine, pyrazole, thiazole, isothiazole, oxazole, isoxazole, quinoline, isoquinoline, quinoxaline, quinazoline, 1-8-naphthyridine, perimidine, [1,10]-phenantroline, phthalazine, pteridine, triazole, triazine, furazan, 6H-1,2,5-thiadiazine, 1,3,4-thiadiazole, tetrazole, or a substituted imidazole and even more preferably a benzimidazole; - R5 is H, OH, C1-4 alkyl, C1-4 alkoxy, C1-4 alkenyl, C1-4 alkynyl, amine, preferably R5 is NH2, NO2, Cl, F, Br, I; more preferably R5 is H or CH3; even more preferably R5 is CH3; - each of R8 and R9 is independently, H, OH, alkyl, alkoxy, aryle, alkenyl, alkynyl, amine, NO2, Cl, Br, I, F; preferably R8 and R9 together form a cycle comprising 5 or 6 atoms, preferably an heterocycle comprising 5 or 6 atoms, more preferably a 1,3-dioxacyclopentene or a 1,4-dioxane; and - each of R3, R4, R6, R7, R10 and R11 is independently, H, OH, C1-4 alkyl, C1-4 alkoxy, C1-4 alkenyl, C1-4 alkynyl, amine, NO2, F, Cl, Br, I; preferably H, CH3, OCH3, OH, NH2, NO2, Cl, F, Br, I; more preferably is H or CH3; even more preferably is H, or esters or salts thereof; in association with at least one pharmaceutically acceptable vehicle; and to the use thereof for inhibiting the Neuropilin pathways in the treatment of cancer and of angiogenic diseases.