42784-26-9

Basic information

• Product Name: 1H-Benzimidazole-2-propanamine(9CI)
• Synonyms: 1H-Benzimidazole-2-propanamine(9CI);3-(1H-benzimidazol-2-yl)propanylamine;3-(1H-benzimidazol-2-yl)propan-1-amine(SALTDATA: HCl);1H-BenziMidazole-2-propanaMine;3-(1H-Benzo[d]iMidazol-2-yl)propan-1-aMine;3-(1H-benzo[d]imidazol-2-yl)propan-1-amine HCl
• CAS NO: 42784-26-9
• Molecular Formula: C₁₀H₁₃N₃
• Molecular Weight: 175.23
• Product Categories: BENZIMIDAZOLE;Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 42784-26-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 406.5°Cat760mmHg
• Flash Point: 228.6°C
• Appearance: /
• Density: 1.183g/cm³
• Vapor Pressure: 8.11E-07mmHg at 25°C
• Refractive Index: 1.654
• CAS DataBase Reference: 1H-Benzimidazole-2-propanamine(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole-2-propanamine(9CI)(42784-26-9)
• EPA Substance Registry System: 1H-Benzimidazole-2-propanamine(9CI)(42784-26-9)

Safety Data

• Hazardous Substances Data: 42784-26-9(Hazardous Substances Data)

Usage

Description

1H-Benzimidazole-2-propanamine(9CI) is an organic compound with the molecular formula C10H12N2. It is a derivative of benzimidazole, which is a heterocyclic compound consisting of a benzene ring fused to an imidazole ring. 1H-Benzimidazole-2-propanamine(9CI) is characterized by its amine functional group attached to a propanamine chain, making it a versatile building block for the synthesis of various pharmaceutical compounds.

Uses

1H-Benzimidazole-2-propanamine(9CI) is used as a key intermediate in the synthesis of phenylaminodiheteroarylpyrimidine derivatives and analogs. These derivatives exhibit potent antibacterial properties, making them valuable in the development of new antibiotics to combat drug-resistant bacterial infections.
Used in Pharmaceutical Industry:
1H-Benzimidazole-2-propanamine(9CI) is used as a synthetic building block for the development of novel antibacterial agents. Its unique chemical structure allows for the creation of phenylaminodiheteroarylpyrimidine derivatives with enhanced antibacterial activity against a wide range of bacterial pathogens. This application is particularly important in the face of increasing antibiotic resistance, as it contributes to the discovery of new and effective treatments for bacterial infections.

InChI:InChI=1/C10H13N3/c11-7-3-6-10-12-8-4-1-2-5-9(8)13-10/h1-2,4-5H,3,6-7,11H2,(H,12,13)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 1617531-78-8 benzyl (4-((2-aminophenyl)amino)-4-oxobutyl)carbamate 
• 1617531-94-8 benzyl (3-(1H-benzo[d]imidazol-2-yl)propyl)carbamate 
• 56-12-2 4-amino-n-butyric acid 
• 616-45-5 2-pyrrolidinon 
• 104-15-4 toluene-4-sulfonic acid 

Downstream Products

• 1612183-59-1 4-N-[3-(1H-1,3-benzodiazol-2-yl)propyl]-6-(2,3-dimethylphenyl)pyrimidine-2,4-diamine 
• 79837-04-0 N-{3-[4-(2-amino-2-oxoethyl)phenoxy]-2-hydroxypropyl}-1H-benzimidazole-1-propanamine 

Relevant articles and documents

Impact of N-Alkylamino Substituents on Serotonin Receptor (5-HTR) Affinity and Phosphodiesterase 10A (PDE10A) Inhibition of Isoindole-1,3-dione Derivatives

In this study, a series of compounds derived from 4-methoxy-1H-isoindole-1,3(2H)-dione, potential ligands of phosphodiesterase 10A and serotonin receptors, were investigated as potential antipsychotics. A library of 4-methoxy-1H-isoindole-1,3(2H)-dione derivatives with various amine moieties was synthesized and examined for their phosphodiesterase 10A (PDE10A)-inhibiting properties and their 5-HT1A and 5-HT7 receptor affinities. Based on in vitro studies, the most potent compound, 18 (2-[4-(1H-benzimidazol-2-yl)butyl]-4-methoxy-1H-isoindole-1,3(2H)-dione), was selected and its safety in vitro was evaluated. In order to explain the binding mode of compound 18 in the active site of the PDE10A enzyme and describe the molecular interactions responsible for its inhibition, computer-aided docking studies were performed. The potential antipsychotic properties of compound 18 in a behavioral model of schizophrenia were also investigated.

Efficient synthesis of mibefradil analogues: An insight into in vitro stability

This article describes the synthesis and biological evaluation of a chemical library of mibefradil analogues to investigate the effect of structural modification on in vitro stability. The construction of the dihydrobenzopyran structure in mibefradil derivatives 2 was achieved through two efficient approaches based on a diastereoselective intermolecular Reformatsky reaction and an intramolecular carbonyl-ene cyclization. In particular, the second strategy through the intramolecular carbonyl-ene reaction led to the formation of a key intermediate 3 in a short and highly stereoselective way, which has allowed for practical and convenient preparation of analogues 2. Using this protocol, we could obtain 22 new mibefradil analogues 2, which were biologically tested for in vitro efficacies against T-type calcium channels and metabolic stabilities. Among the synthesized compounds, we found that analogue 2aa containing a dihydrobenzopyran ring and a secondary amine linker showed high % remaining activities of the tested CYP enzymes retaining the excellent T-type calcium channel blocking activity. These findings indicated that the structural modification of 1 was effective for improving in vitro stability, i.e., reducing CYP inhibition and metabolic degradation. the Partner Organisations 2014.