136117-70-9

Basic information

• Product Name: IMidazo[1,2-a]pyridine-8-carbonitrile
• Synonyms: IMidazo[1,2-a]pyridine-8-carbonitrile
• CAS NO: 136117-70-9
• Molecular Formula: C₈H₅N₃
• Molecular Weight: 143.1454
• Mol File: 136117-70-9.mol

Chemical Properties

• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.56±0.50(Predicted)
• CAS DataBase Reference: IMidazo[1,2-a]pyridine-8-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: IMidazo[1,2-a]pyridine-8-carbonitrile(136117-70-9)
• EPA Substance Registry System: IMidazo[1,2-a]pyridine-8-carbonitrile(136117-70-9)

Safety Data

• Hazardous Substances Data: 136117-70-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Imidazo[1,2-a]pyridine-8-carbonitrile is utilized as a key intermediate in the synthesis of pharmaceuticals for its versatile reactivity and potential biological activity. Its unique structure allows for the development of new drugs and bioactive compounds, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Synthesis:
In the agrochemical industry, Imidazo[1,2-a]pyridine-8-carbonitrile is employed as a building block in the creation of new agrochemicals. Its reactivity and potential biological activity make it a valuable component in the development of innovative and effective products for agricultural applications.
Used as a Research Reagent in Organic Chemistry:
Imidazo[1,2-a]pyridine-8-carbonitrile serves as a research reagent in organic chemistry laboratories. Its unique structure and reactivity make it a valuable tool for various synthetic purposes, aiding in the exploration and understanding of chemical reactions and the development of novel synthetic methodologies.

Upstream product

• 24517-64-4 2-amino-3-pyridinecarbonitrile 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 107-20-0 2-chloroethanal 

Downstream Products

• 885276-26-6 3-iodoimidazo[1,2-a]pyridine-8-carbonitrile 
• 933721-91-6 imidazo[1,2-a]pyridin-8-ylmethanamine 
• 133427-07-3 methyl 8-imidazo<1,2-a>pyridinecarboxylate 
• 136117-74-3 8-imidazo<1,2-a>pyridinecarboxaldehyde 

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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.