136117-72-1

Basic information

• Product Name: 6-BROMO-2-CHLOROMETHYL-IMIDAZO[1,2-A]PYRIDINE
• Synonyms: 6-BROMO-2-CHLOROMETHYL-IMIDAZO[1,2-A]PYRIDINE;6-broMo-2-(chloroMethyl)H-iMidazo[1,2-a]pyridine
• CAS NO: 136117-72-1
• Molecular Formula: C₈H₆BrClN₂
• Molecular Weight: 245.5
• Product Categories: Methyl Halides;Fused Ring Systems;Methyl Halides
• Mol File: 136117-72-1.mol

Chemical Properties

• Appearance: /
• Density: 1.73g/cm³
• Refractive Index: 1.679
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-BROMO-2-CHLOROMETHYL-IMIDAZO[1,2-A]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2-CHLOROMETHYL-IMIDAZO[1,2-A]PYRIDINE(136117-72-1)
• EPA Substance Registry System: 6-BROMO-2-CHLOROMETHYL-IMIDAZO[1,2-A]PYRIDINE(136117-72-1)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• WGK Germany: 3
• Hazardous Substances Data: 136117-72-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
6-BROMO-2-CHLOROMETHYL-IMIDAZO[1,2-A]PYRIDINE is used as a key intermediate in the synthesis of various therapeutic agents and bioactive compounds. Its unique structure and functional groups enable the creation of diverse drug candidates with potential applications in treating various diseases.
Used in Antimicrobial and Antifungal Agents:
6-BROMO-2-CHLOROMETHYL-IMIDAZO[1,2-A]PYRIDINE is used as an active pharmaceutical ingredient for the development of new drugs with potent antimicrobial and antifungal activities. Its ability to target and inhibit the growth of harmful microorganisms makes it a valuable tool in combating infectious diseases.
Used in Cancer Treatment Research:
6-BROMO-2-CHLOROMETHYL-IMIDAZO[1,2-A]PYRIDINE is used as a potential therapeutic agent in the treatment of cancer. Its biological activities and chemical properties are being studied for their potential to target and inhibit the growth of cancer cells, offering new avenues for cancer treatment.
Used in Medicinal Chemistry:
6-BROMO-2-CHLOROMETHYL-IMIDAZO[1,2-A]PYRIDINE is used as a versatile chemical building block in medicinal chemistry. Its unique structure and functional groups allow for the design and synthesis of novel compounds with potential therapeutic applications, contributing to the advancement of drug discovery and development.

InChI:InChI=1/C8H6BrClN2/c9-6-1-2-8-11-7(3-10)5-12(8)4-6/h1-2,4-5H,3H2

Upstream product

• 1072-97-5 5-bromo-2-pyridylamine 
• 534-07-6 1,3-Dichloroacetone 
• 110-71-4 1,2-dimethoxyethane 
• 136117-71-0 6-bromo-2-hydroxymethylimidazo<1,2-a>pyridine 
• 67625-37-0 ethyl 6-bromoimidazo<1,2-a>pyridine-2-carboxylate 

Downstream Products

• 913530-53-7 6-bromo-2-[(4-chlorophenylsulfonyl)methyl]-3-nitroimidazo[1,2-a]pyridine 
• 877071-33-5 6-bromo-3-nitro-2-(tosylmethyl)imidazo[1,2-a]pyridine 
• 1092355-02-6 2-(4-fluorobenzyl)-6-(4-methoxyphenyl)imidazo[1,2-a]pyridine 
• 1092355-01-5 2-benzyl-6-(thien-3-yl)imidazo[1,2-a]pyridine 
• 1092354-99-8 6-phenyl-2-(thien-3-ylmethyl)imidazo[1,2-a]pyridine 
• 182181-01-7 6-Bromo-2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]methyl]-imidazo[1,2-a]pyridine 

Relevant articles and documents

Targeting the human parasite Leishmania donovani: Discovery of a new promising anti-infectious pharmacophore in 3-nitroimidazo[1,2-a]pyridine series

We report herein the discovery of antileishmanial molecules based on the imidazo[1,2-a]pyridine ring. In vitro screenings of imidazopyridines belonging to our chemical library, toward the promastigotes stage of Leishmania donovani, J774A.1 murine and HepG2 human cells, permitted to identify three selective hit-compounds (12, 20 and 28). New derivatives were then synthesized to allow structure-activity and -toxicity relationships analyses, enabling to characterize a lead-compound (44) displaying both a high potency (IC 50 = 1.8 μM) and a good selectivity index, in comparison with three antileishmanial reference drug-compounds (amphotericin B, miltefosine and pentamidine). Moreover, lead-compound 44 also exhibits good in vitro activity against the intracellular amastigote stage of L. donovani. Thus, the 6-halo-3-nitro-2-(phenylsulfonylmethyl)imidazo[1,2-a]pyridine scaffold appears as a new promising selective antileishmanial pharmacophore, especially when substituted at position 8 by a bromine atom.

6-[123I]Iodo-2-[[4-(2-methoxyphenyl) piperazin-1-yl]methyl] imidazo[1,2-a]pyridine as potential SPECT agent for imaging dopamine D 4 receptor: Synthesis and in vivo evaluation in a nonhuman primate

The dopamine O4 receptor subtype has drawn considerable attention due to its potential implication in schizophrenia and erectile dysfunction. 6-[123I]Iodo-2-[[4-(2-methoxyphenyl)piperazin-1-yl] methyl]imidazo[1,2-a]pyridine [123

2-[(4-Phenylpiperazin-1-yl)methyl]imidazo(di)azines as selective D 4-ligands. Induction of penile erection by 2-[4-(2-methoxyphenyl) piperazin-1-ylmethyl]imidazo[1,2-a]pyridine (PIP3EA), a potent and selective D4 partial agonist

A series of novel 2-[(4-phenylpiperazin-1-yl)methyl]imidazoazines and aza-analogues were prepared and screened at selected dopamine, serotonin, and adrenergic receptor subtypes. 2-Substituted imidazopyridines and pyridazines presented high affinities and

Heterocyclic compounds, their production and use

Heterocyclic compounds represented by the general formula (I) wherein R stands for an optionally substituted aromatic heterocyclic group; X stands for oxygen atom, an optionally oxidated sulfur atom, —C(═O)— or —CH(OH)—; Y stands for CH or N; m denotes an integer of 0 to 10: n denotes an integer of 1 to 5: cyclic group ?stands for an optionally substituted aromatic azole group; and ring A is optionally further substituted, or salts thereof. The compound (I) possesses action of inhibiting tyrosine kinase and useful as antitumor agents.

IMIDAZO[1,2-A]PYRIDINES FOR THE TREATMENT OF CNS AND CARDIAC DISEASES

The present invention relates to imidazo[1,2-a]pyridine compounds of formula (1) STR1 which are dopamine D-4 antagonists and useful as anti-psychotic agents.

Imidazo[1,2-a]pyridines. Synthesis and inotropic activity of new 5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinone derivatives

A series of 1,2-dihydro-5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinones was synthesized and evaluated for positive inotropic activity. 1,2-Dihydro-5-imidazo[1,2-a]pyridin-6-yl-6-methyl-2-oxo-3- pyridinecarbonitrile (11a) hydrochloride monohydrate (E-1020) was found to be a potent and selective inhibitor of phosphodiesterase III and a long-acting, potent, orally active positive inotropic agent. Additional imidazo[1,2-a]pyridin-2-yl (3a), -3-yl (16), -7-yl (20) and -8-yl (24a) compounds were also prepared. Altering the pyridine substitution from the 2-position to the 6-position produced a 2-fold increase in the i.v. cardiotonic potency (ED50) from 52 to 23 μg/kg, while substitution at the 3-, 7- or 8-position reduced potency. In the 2-positional isomers, introduction of halogen groups enhanced the activity and 3-chloro-1,2-dihydro-5-(6-fluoroimidazo[1,2-a]pyridin-2-yl)-6-methyl-2(1H)- pyridinone (3a) was the most potent (i.v. ED50 11 μg/kg) in this seris. E-1020 is presently under development for the treatment of congestive heart failure.