581812-79-5

Basic information

• Product Name: 4-AZEPAN-1-YL-BENZYLAMINE
• Synonyms: 4-AZEPAN-1-YL-BENZYLAMINE;AKOS B033643;1-[4-(azepan-1-yl)phenyl]methanamine
• CAS NO: 581812-79-5
• Molecular Formula: C₁₃H₂₀N₂
• Molecular Weight: 204.31
• Mol File: 581812-79-5.mol

Chemical Properties

• Boiling Point: 358.5±25.0 °C(Predicted)
• Appearance: /
• Density: 1.024±0.06 g/cm3(Predicted)
• PKA: 10.43±0.10(Predicted)
• CAS DataBase Reference: 4-AZEPAN-1-YL-BENZYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AZEPAN-1-YL-BENZYLAMINE(581812-79-5)
• EPA Substance Registry System: 4-AZEPAN-1-YL-BENZYLAMINE(581812-79-5)

Safety Data

• Hazardous Substances Data: 581812-79-5(Hazardous Substances Data)

Upstream product

• 162377-67-5 4-(Hexahydroazepin-1-yl)benzonitrile 
• 111-49-9 hexamethylene imine 
• 1194-02-1 4-fluorobenzonitrile 

Downstream Products

• 946388-37-0 N-(5-(3-(4-(azepan-1-yl)benzyl)ureido)isoquinolin-3-yl)acetamide 
• 581812-64-8 2,2,2-trichloro-N-(isoquinolin-5-yl)acetamide 
• 581812-25-1 N-[4-(1-azepanyl)benzyl]-2-(5-isoquinolinyl)propanamide 
• 1334718-67-0 N-(4-(azepan-1-yl)benzyl)-7-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxamide 

Relevant articles and documents

Lead optimization of a novel series of imidazo[1,2-a]pyridine amides leading to a clinical candidate (Q203) as a multi- and extensively-drug- resistant anti-tuberculosis agent

A critical unmet clinical need to combat the global tuberculosis epidemic is the development of potent agents capable of reducing the time of multi-drug-resistant (MDR) and extensively-drug-resistant (XDR) tuberculosis therapy. In this paper, we report on the optimization of imidazo[1,2-a]pyridine amide (IPA) lead compound 1, which led to the design and synthesis of Q203 (50). We found that the amide linker with IPA core is very important for activity against Mycobacterium tuberculosis H37Rv. Linearity and lipophilicity of the amine part in the IPA series play a critical role in improving in vitro and in vivo efficacy and pharmacokinetic profile. The optimized IPAs 49 and 50 showed not only excellent oral bioavailability (80.2% and 90.7%, respectively) with high exposure of the area under curve (AUC) but also displayed significant colony-forming unit (CFU) reduction (1.52 and 3.13 log10 reduction at 10 mg/kg dosing level, respectively) in mouse lung.

In vitro structure-activity relationship and in vivo characterization of 1-(aryl)-3-(4-(amino)benzyl)urea transient receptor potential vanilloid 1 antagonists

The synthesis and structure-activity relationship of 1-(aryl)-3-(4-(amino) benzyl)urea transient receptor potential vanilloid 1 (TRPV1) antagonists are described. A variety of cyclic amine substituents are well tolerated at the 4-position of the benzyl group on compounds containing either an isoquinoline or indazole heterocyclic core. These compounds are potent antagonists of capsaicin activation of the TRPV1 receptor in vitro. Analogues, such as compound 45, have been identified that have good in vivo activity in animal models of pain. Further optimization of 45 resulted in compound 58 with substantially improved microsome stability and oral bioavailability, as well as in vivo activity.