43182-10-1

Usage

Chemical Properties

WHITE TO ALMOST WHITE FINE CRYSTALLINE POWDER

InChI:InChI=1/C14H13N3/c15-14-16-12-8-4-5-9-13(12)17(14)10-11-6-2-1-3-7-11/h1-9H,10H2,(H2,15,16)

Upstream product

• 119392-78-8 O-benzoyl-2-benzylaminobenzamide oxime 
• 934-32-7 1H-benzimidazol-2-amine 
• 74-88-4 methyl iodide 
• 71-43-2 benzene 
• 100-39-0 benzyl bromide 
• 162938-41-2 1,3-dihydrobenzimidazol-2-imine 
• 95-54-5 1,2-diamino-benzene 
• 100-44-7 benzyl chloride 
• 119392-79-9 O-acetyl-2-benzylaminobenzamide oxime 

Downstream Products

• 109635-41-8 N-(1-Benzyl-1H-benzoimidazol-2-yl)-2-chloro-nicotinamide 
• 109635-50-9 7-Benzyl-7H-1,6,7,11b-tetraaza-benzo[c]fluoren-5-one 
• 144836-27-1 [1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-(1-benzyl-1H-benzoimidazol-2-yl)-amine 
• 144836-23-7 (1-Benzyl-1H-benzoimidazol-2-yl)-[1-(3,4,5-trimethoxy-phenyl)-meth-(E)-ylidene]-amine 
• 120625-22-1 N-(1-Benzyl-1H-benzoimidazol-2-yl)-4-methyl-benzamide 
• 120625-23-2 N-(1-Benzyl-1H-benzoimidazol-2-yl)-4-methoxy-benzamide 
• 144836-19-1 4-{[(E)-1-Benzyl-1H-benzoimidazol-2-ylimino]-methyl}-2-methoxy-phenol 
• 139979-78-5 N-(1-Benzyl-1H-benzoimidazol-2-yl)-benzamidine 
• 139954-25-9 N-(1-Benzyl-1H-benzoimidazol-2-yl)-4-methyl-benzamidine 
• 139954-26-0 N-(1-Benzyl-1H-benzoimidazol-2-yl)-4-methoxy-benzamidine 
• 139954-28-2 N-(1-Benzyl-1H-benzoimidazol-2-yl)-4-chloro-benzamidine 
• 139954-27-1 N-(1-Benzyl-1H-benzoimidazol-2-yl)-2-chloro-benzamidine 
• 139954-29-3 N-(1-Benzyl-1H-benzoimidazol-2-yl)-3-chloro-benzamidine 
• 134937-75-0 2-(3-Benzyl-2-imino-2,3-dihydro-benzoimidazol-1-yl)-N-(2,6-dichloro-phenyl)-acetamide 

Relevant academic research and scientific papers

Characterization of 2-amino-1-benzylbenzimidazole and its metabolites using tandem mass spectrometry

We have investigated the in vitro hamster hepatic microsomal metabolism of the amino-azaheterocycle, 2-amino-1-benzylbenzimidazole (ABB). Three major metabolites were isolated and structurally characterized, using a combination of off-line HPLC, in conjunction with both electron ionization and fast atom bombardment ionization tandem mass spectrometry. ABB was shown to be debenzylated to afford 2-aminobenzimidazole (AB), as well as N- and C-oxidized to give 1-benzyl-N2-hydroxyaminobenzimidazole (BHB) and 2-amino-1-benzyl-hydroxybenzimidazole, respectively. The possible reasons for formation of the exocyclic hydroxylamine BHB are discussed. Furthermore, ABB is proposed as a suitable model compound for investigating parameters that control formation of toxic hydroxylamines derived from amino-azaheterocycles.

A novel 2-aminobenzimidazole-based compound Jzu 17 exhibits anti-angiogenesis effects by targeting VEGFR-2 signalling

Background and Purpose: Recent development in drug discovery have shown benzimidazole to be an important pharmacophore,. Benzimidazole derivatives exhibit broad-spectrum pharmacological properties including anti-microbial, anti-diabetic and anti-tumour activity. However, whether benzimidazole derivatives are effective in suppressing angiogenesis and its underlying mechanisms remain incompletely understood. In this study, we aim to characterize the anti-angiogenic mechanisms of a novel 2-aminobenzimidazole-based compound, Jzu 17, in an effort to develop novel angiogenesis inhibitor. Experimental Approach: Effects of Jzu 17 on endothelial cell proliferation, migration, invasion, and activation of signalling molecules induced by VEGF-A, were analysed by immunoblotting, MTT, BrdU, migration, and invasion assays. We performed tube formation assay, aorta ring sprouting assay, matrigel plug assay, and a mouse model of metastasis to evaluate ex vivo and in vivo anti-angiogenic effects of Jzu 17. Key Results: Jzu 17 inhibited VEGF-A-induced cell proliferation, migration, invasion, and endothelial tube formation of HUVECs. Jzu 17 suppressed VEGF-A-induced microvessel sprouting ex vivo and attenuated VEGF-A- or tumour cell-induced neovascularization in vivo. Jzu 17 also reduced B16F10 melanoma lung metastasis. In addition, Jzu 17 inhibited the phosphorylation of VEGFR-2 and its downstream signalling molecules in VEGF-A-stimulated HUVECs. Results from computer modelling further showed that Jzu 17 binds to VEGFR-2 with high affinity. Conclusions and Implications: Jzu 17 may inhibit endothelial remodelling and suppress angiogenesis through targeting VEGF-A-VEGFR-2 signalling. These results also suggest Jzu 17 as a potential lead compound and warrant the clinical development of similar agents in the treatment of cancer and angiogenesis-related diseases.

TOLL-LIKE RECEPTOR AGONISTS

Compounds described herein can be used for therapeutic purposes. The compounds can be TLR agonists, such as TLR7 or TLR8 agonists. The compounds can be included in pharmaceutical compositions and used for therapies were being a TLR agonist is useful. The pharmaceutical compositions can include any ingredients, such as carries, diluents, excipients, fillers or the like that are common in pharmaceutical compositions. The compounds can be those illustrated or described herein as well as derivatives thereof, prodrugs thereof, salts thereof, or stereoisomers thereof, or having any chirality at any chiral center, or tautomer, polymorph, solvate, or combinations thereof. As such, the compounds can be used as adjuvants in vaccines, as well as for other therapeutic purposes described herein.

Human toll-like receptor 8-selective agonistic activities in 1-alkyl-1 h -benzimidazol-2-amines

Toll-like receptor (TLR)-8 agonists strongly induce the production of T helper 1-polarizing cytokines and may therefore serve as promising candidate vaccine adjuvants, especially for the very young and the elderly. Earlier structure-based ligand design led to the identification of 3-pentyl-quinoline-2-amine as a novel, human TLR8-specific agonist. Comprehensive structure-activity relationships in ring-contracted 1-alkyl-1H-benzimidazol-2-amines were undertaken, and the best-in-class compound, 4-methyl-1-pentyl-1H-benzo[d]imidazol-2-amine, was found to be a pure TLR8 agonist, evoking strong proinflammatory cytokine and Type II interferon responses in human PBMCs, with no attendant CD69 upregulation in natural lymphocytic subsets. The 1-alkyl-1H-benzimidazol-2-amines represent a novel, alternate chemotype with pure TLR8-agonistic activities and will likely prove useful not only in understanding TLR8 signaling but also perhaps as a candidate vaccine adjuvant.

Small-molecule agonists for type-2 orexin receptor

Methods and compositions for agonizing a type-2 orexin receptor (OX2R) in a cell determined to be in need thereof, including the general method of (a) administering to a subject a cyclic guanidinyl OX2R agonist and (b) detecting a resultant enhanced wakefulness or increased resistance to diet-induced accumulation of body fat, or abbreviated recovery from general anesthesia or jet lag.

Synthesis, in vitro antiplatelet activity and molecular modelling studies of 10-substituted 2-(1-piperazinyl)pyrimido[1,2-a]benzimidazol-4(10H)-ones

The multistep preparation of the new 10-substituted 2-(1-piperazinyl) pyrimido[1,2-a]benzimidazol-4(10H)-ones 6a-o, and of the two isomers 10-ethyl-2-(diethylamino)pyrimido[1,2-a]benzimidazol-4(10H)-one 6p and 10-ethyl-4-(diethylamino)pyrimido[1,2-a]benzimidazol-2(10H)-one 13, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca 2+ ionophore A23187 were here described. Nine out of fifteen 2-(1-piperazinyl)derivatives (6g-o) showed good inhibitory properties towards all the platelet aggregation agonists used. Moreover, a molecular modelling study has been performed on two of the best compounds of this series (6i and 6o) to confirm in silico their interactions with the catalytic site of human platelet PDE3, using the X-ray data of the PDE3B isoform in complex with an inhibitor.

Synthesis of phenyl 1-benzyl-1H-benzo [d] imidazol-2-ylcarbamates

1H-Benzo [d] imidazol-2-amine reacts with benzyl halides to give 1-benzyl-1Hbenzo [d] imidazol-2-amines (3a-k). These compounds were treated with phenylchloro formate to yield phenyl 1-benzyl-1H-benzo [d] imidazol-2-ylcarbamates (5a-k). They have been screened for their antibacterial activity.

COMPOUNDS FOR TREATING CANCER

Compounds of general formula (I): wherein R1, R2, R3, R4, R5, R6, X and Y are as defined herein are inhibitors of Bcl-2 and are useful for treating diseases characterised by abnormal cell growth and/or dysregulated apoptosis.

PROLYL HYDROXYLASE INHIBITORS

The invention described herein relates to certain bicyclic heteroaromatic N-substituted glycine derivatives of formula (I) which are antagonists of HIF prolyl hydroxylases and are useful for treating diseases benefiting from the inhibition of these enzymes, anemia being one example.

Synthesis and?QSAR studies of?novel 1-substituted-2-aminobenzimidazoles derivatives

A series of novel 1-substituted-2-aminobenzimidazole derivatives were synthesized. The structures of the synthesized compounds were confirmed by 1H-NMR spectra and by elemental analysis. Acute toxicities of these compounds were detected on mice via toxicity (logLD50). QSAR analysis of these chemicals was studied on the relationship between acute toxicity and the octanol/water partition coefficient (LogP). The products were identified by the results of elemental analysis and 1H-NMR spectra. The toxicity (logLD50) of 2-aminobenzimidazole 1-substituents were correlated well with the partition coefficient LogP, r = 0.9243. The bioactivity (toxicity) of 2-aminobenzimidazoles can be predicted by the molecular structural parameter such as LogP.