39588-26-6

Usage

Uses

Used in Pharmaceutical Industry:
Imidazo[1,2-a]pyridin-2-amine is used as a key intermediate in the synthesis of various drugs for its ability to interact with specific biological targets. It is particularly valuable in the development of anti-cancer, anti-inflammatory, and anti-infective medications, where its unique structure contributes to the efficacy of these treatments.
Used in Agrochemical Industry:
In the agrochemical sector, Imidazo[1,2-a]pyridin-2-amine serves as a building block for the creation of compounds with pesticidal properties, leveraging its interaction with biological targets to control or eliminate pests.
Used in Material Science:
Imidazo[1,2-a]pyridin-2-amine is used as a component in the development of specialized polymers and coatings. Its unique chemical structure allows for the engineering of materials with specific properties, such as enhanced durability or resistance to environmental factors.
Safety Considerations:
Given the potential hazardous properties of Imidazo[1,2-a]pyridin-2-amine, it is crucial to follow proper safety protocols during its handling, storage, and use. This includes the use of appropriate personal protective equipment, adherence to material safety data sheets, and proper disposal methods to minimize risks to human health and the environment.

Upstream product

• 38922-76-8 N-imidazo[1,2-a]pyridin-2-yl-acetamide 
• 856856-72-9 2-[2-{(p-toluenesulfonyl)imino}pyridin-1-yl]acetamide 
• 504-29-0 2-aminopyridine 
• 144-83-2 sulphapyridine 
• 52776-76-8 N-(2-pyridyl)-p-toluenesulfonamide 
• 421595-80-4 imidazo[1,2-a]pyridine-2-carbonyl azide 

Downstream Products

• 421596-02-3 4-ethyl-3-methyl-dipyrido[1,2-a;2',3'-d]imidazole 
• 1369586-30-0 C₁₆H₁₆N₄O 
• 1369586-34-4 C₁₆H₁₆N₄O 
• 1369586-42-4 C₁₈H₂₀N₄O₂ 
• 1369586-22-0 (2S,4S)-4-benzyl-2-(4-nitrophenyl)-1,2,3,4-tetrahydro-5H-pyrido-[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one 
• 1369586-26-4 (2R,4S)-4-benzyl-2-(4-nitrophenyl)-1,2,3,4-tetrahydro-5H-pyrido-[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one 
• 1369585-03-4 (4S)-4-benzyl-2-(4-nitrophenyl)-3,4-dihydro-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one 
• 1369585-11-4 (4S)-4-benzyl-2-phenyl-3,4-dihydro-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one 
• 1369585-14-7 (4S)-4-benzyl-2-(4-methylphenyl)-3,4-dihydro-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one 
• 1369585-17-0 (4S)-4-benzyl-2-(3-methylphenyl)-3,4-dihydro-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one 
• 1369585-21-6 (4S)-4-benzyl-2-(2-methylphenyl)-3,4-dihydro-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one 
• 1369585-26-1 (4S)-4-benzyl-2-(4-methoxyphenyl)-3,4-dihydro-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one 
• 1369585-30-7 (4S)-4-benzyl-2-isobutyl-3,4-dihydro-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one 
• 1369585-34-1 (4S)-4-benzyl-2-(3-pyridinyl)-3,4-dihydro-5H-pyrido[1',2':1,2]imidazo[4,5-d][1,3]diazepin-5-one 

Relevant academic research and scientific papers

Imidazopyridine-fused [1,3]diazepinones: modulations of positions 2 to 4 and their impacts on the anti-melanoma activity

A series of 19 novel pyrido-imidazodiazepinones, with modulations of positions 2, 3 and 4 of the diazepine ring were synthesised and screened for their in vitro cytotoxic activities against two melanoma cell lines (A375 and MDA-MB-435) and for their poten

Imidazopyridine-fused [1,3]-diazepinones part 2: Structure-activity relationships and antiproliferative activity against melanoma cells

We recently described a pyrido-imidazodiazepinone derivative which could be a promising hit compound for the development of new drugs acting against melanoma cells. In this study, a series of 28 novel pyrido-imidazodiazepinones were synthesized and screen

Pyrido-imidazodiazepinones as a new class of reversible inhibitors of human kallikrein 7

The human tissue kallikrein-7 (KLK7) is a chymotryptic serine protease member of tissue kallikrein family. KLK7 is involved in skin homeostasis and inflammation. Excess of KLK7 activity is also associated with tumor metastasis processes, especially in ovarian carcinomas, prostatic and pancreatic cancers. Development of Kallikrein 7 inhibitors is thus of great interest in oncology but also for treating skin diseases. Most of the developed synthetic inhibitors present several drawbacks such as poor selectivity and unsuitable physico-chemical properties for in vivo use. Recently, we described a practical sequence for the synthesis of imidazopyridine-fused [1,3]-diazepines. Here, we report the identification of pyrido-imidazodiazepinone core as a new potential scaffold to develop selective and competitive inhibitors of kallikrein-related peptidase 7. Structure-activity relationships (SAR), inhibition mechanisms and selectivity as well as cytotoxicity against selected cancer cell lines were investigated.

Imidazopyridine-fused [1,3]-diazepinones: Synthesis and antiproliferative activity

A series of 15 pyrido-imidazo-1,3-diazepin-5-ones and pyrido-1,3-diazepine- 2,5-diones were synthesized and their anticancer activities were evaluated. Among tested compounds on a cell lines panel, compound 6a presents the best growth inhibition activity on 21 cell lines with a cytotoxic effect on MDA-MB-435 melanoma cells. This compound led to deep cell morphological changes and revealed to be an inhibitor of the Hepatocyte progenitor kinase-like kinase (HGK), which is known to be implicated in the migration, adhesion and invasion of various tumor cells.

An efficient synthesis of pyrido-imidazodiazepinediones

We herein report the synthesis of a series of 12 optically pure 3,4-dihydro-1H-pyrido-[1′,2′:1,2]-imidazo[ 4,5-d][1,3]diazepine-2,5- diones, which form a new family of azaheterocycle-fused [1,3]diazepines. The key step of the synthesis consists in a selec

Selective C-acylation of 2-aminoimidazo[1,2- a ]pyridine: Application to the synthesis of imidazopyridine-fused [1,3]diazepinones

A series of 20 optically pure 3,4-dihydro-5H-pyrido[1′,2′:1,2] imidazo[4,5-d][1,3]diazepin-5-ones which form a new family of azaheterocycle-fused [1,3]diazepines were synthesized in four steps with 17-66% overall yields. The key step consists of a selecti

Aminoimidazo[1,2-a]pyridines: Regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines

In order to study the regioselectivity of thermal cyclocondensation, aminoimidazo[1,2-a]pyridines (AIP) 5a-e were prepared, further converted into iminophosphoranes 7a-e, and ultimately converted regioselectively in angular annulated imidazonaphthyridines (IN) 8a, 10a, 11a, 12a or linear annulated dipyridoimidazole (DPI) 17a. From 2-substituted derivative 23, the peri annulated product 24a was obtained. The starting amines 5a-f reacted with aldehydes to yield regioselectively IN 8a-c, 10a-c, 11a-c, 12a,b, DPI 16a-e, 17a-d and TIBO like structures (±)-13 and 24a-c, as proved by X-ray analysis. The 1,2- or 1,4-addition between amines and α,β-unsaturated aldehydes concerning the pyridine and imidazole moieties is discussed in the light of these results.