42784-26-9

Usage

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

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

Downstream Products

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

Relevant academic research and scientific papers

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.

4-Isopropylchroman-3-ol derivatives

The present invention relates to a novel 4-isopropylchroman-3-ol compound, a pharmaceutical composition comprising the novel compound as an effective component, and to an intermediate compound useful for synthesizing the compound. When administered to a patient with a drug causing toxicity, the novel 4-isopropylchroman-3-ol compound exhibits efficacy of reducing toxicity of the drug by reducing antagonism regarding a T-type calcium channel and/or activity of cytochrome P450 isozyme.

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.

Process for preparing a 2(ω-aminoalkyl)-1,3-heterocyclic compounds

2-(ω-AMINOALKYL)-1,3-HETEROCYCLIC COMPOUNDS ARE PREPARED BY REACTING A COMPOUND SELECTED FROM THE GROUP OF A DIAMINE, AN AMINOHYDROXY AND AN AMINOTHIOL COMPOUND, SAID COMPOUND HAVING THE FORMULA: EQU1 wherein EQU2 A is a bivalent chain of 2 or 3 carbon atoms, which can also be part of a bivalent, optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical, and X is oxygen, sulphur or the group EQU3 wherein R7 is as defined herein with a lactam having the formula EQU4 WHEREIN B is selected from the group of a single bond, oxygen, sulphur, the group EQU5 wherein R6 is as defined herein, and arylene, R1, r2, r3 and R4, which may be the same or different, are selected from the group of hydrogen, halogen, nitro and optionally substituted aliphatic, cycloaliphatic, araliphatic and aromatic, R5, r6 and R7, which may be the same or different, are selected from the group of hydrogen and optionally substituted aliphatic, cycloaliphatic, araliphatic and aromatic, and n and m, which may be the same or different, are intergers of from 1 to 14, with the proviso that the sum of n and m does not exceed 15, At a temperature of from 100° to 300°C in the presence of at least a catalytic quantity of an acid and/or an acid catalyst.