101820-69-3

Basic information

• Product Name: IMidazo[1,2-a]pyridine-3-aceticacid,ethylester
• Synonyms: IMidazo[1,2-a]pyridine-3-aceticacid,ethylester;ETHYL IMIDAZO[1,2-A]PYRIDIN-3-YL-ACETATE;Minodronic Acid interMediate;ethyl 2-(iMidazo[1,2-a]pyridin-3-yl)acetate;Minodronic acid InterMediate A;2-(iMidazo[1,2-a]pyridin-3-yl)acetic acid ethyl ester;Midazo[1,2-a]pyridine-3-aceticacid,ethylester;Ethyl imidazo[1,2-a]pyridine-3-acetate
• CAS NO: 101820-69-3
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.22518
• EINECS: 1592732-453-0
• Mol File: 101820-69-3.mol

Chemical Properties

• Appearance: /
• Density: 1.19±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.27±0.50(Predicted)
• CAS DataBase Reference: IMidazo[1,2-a]pyridine-3-aceticacid,ethylester(CAS DataBase Reference)
• NIST Chemistry Reference: IMidazo[1,2-a]pyridine-3-aceticacid,ethylester(101820-69-3)
• EPA Substance Registry System: IMidazo[1,2-a]pyridine-3-aceticacid,ethylester(101820-69-3)

Safety Data

• Hazardous Substances Data: 101820-69-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
IMidazo[1,2-a]pyridine-3-acetic acid, ethyl ester is used as a key building block for the synthesis of biologically active molecules, which are crucial for the development of new drugs. Its unique structure allows it to be a versatile component in medicinal chemistry, contributing to the creation of potential drug candidates with novel mechanisms of action.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, IMidazo[1,2-a]pyridine-3-acetic acid, ethyl ester is utilized as a subject of study to explore its potential applications and properties. Researchers investigate its interactions with biological targets and its capacity to modulate various biological pathways, which can lead to the discovery of new therapeutic agents.
Used in Drug Synthesis:
IMidazo[1,2-a]pyridine-3-acetic acid, ethyl ester is employed as a synthetic intermediate in the preparation of pharmaceutical compounds. Its reactivity and structural features make it a valuable component in the synthesis of complex molecules with potential therapeutic applications.
Used in Drug Design:
As a heterocyclic compound with a unique combination of rings, IMidazo[1,2-a]pyridine-3-acetic acid, ethyl ester is used in drug design to create novel chemical entities with specific pharmacological properties. Its incorporation into drug molecules can enhance their affinity for target proteins, improve their pharmacokinetic profiles, and potentially lead to more effective treatments for various diseases.

Upstream product

• 504-29-0 2-aminopyridine 
• 2960-66-9 4-oxo-but-2-enoic acid ethyl ester 
• 19255-60-8 (E)-4,4-dimethoxy-but-2-enoic acid ethyl ester 
• 2568-30-1 2-chloromethyl-1,3-dioxolane 
• 75-05-8 acetonitrile 
• 13176-46-0 4-bromoethyl acetoacetate 
• 623-73-4 diazoacetic acid ethyl ester 
• 274-76-0 imidazo[1,2-a]pyridine 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 117459-95-7 N-(prop-2-yn-1-yl)pyridin-2-amine 
• 59006-06-3 ethyl 3,4-dibromobutanoate 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 19255-60-8 4,4-dimethoxy-but-2-enoic acid ethyl ester 

Downstream Products

• 17745-04-9 imidazo<1,2-a>pyridin-3-acetic acid 
• 603288-22-8 LY2090314 
• 603281-60-3 LY2090314 
• 21801-86-5 2-(imidazo-[1,2-a]pyridin-3-yl)acetamide 

Relevant articles and documents

Synthesis of Luminescent Fused Imidazole Bicyclic Acetic Esters by a Multicomponent Palladium Iodide-Catalyzed Oxidative Alkoxycarbonylation Approach

A new multicomponent catalytic approach to important fused imidazole bicyclic acetic esters, whose core is present in many biologically active principles, is presented. It is based on the sequential cyclization-alkoxycarbonylation-isomerization of readily available N-heterocyclic propargylamine derivatives, carried out under oxidative conditions using a simple catalytic system consisting of PdI2 (1 mol%) in conjunction with KI (1 equiv.), in the presence of AcONa as additive (1 equiv.) at 100 °C under 20 bar of a 4 : 1 mixture CO-air. Under the optimized conditions, several N-(prop-2-yn-1-yl)pyridin-2-amines were smoothly converted into alkyl 2-(imidazo[1,2-a]pyridin-3-yl)acetates in fair yields (51–77 %). The method was also applied to the conversion of N-(prop-2-yn-1-yl)pyrimidin-2-amine into 2-(imidazo[1,2-a]pyrimidin-3-yl)acetate and of N-(prop-2-yn-1-yl)pyrazin-2-amine into 2-(imidazo[1,2-a]pyrazin-3-yl)acetate. Some of the newly synthesized bicyclic derivatives have shown promising luminescence properties.

Practical and scalable preparation of Minodronic acid and Zolpidem from 2-chloroimidazole[1,2-a]pyridines

Practical and scalable procedures for Minodronic acid and Zolpidem are developed with short reaction sequences from 2-aminopyridines and maleic anhydride, respectively. The new procedures avoid column chromatography for the purification in all synthetic steps. Key aspects of this development involve reductive hydrodechlorination and Suzuki coupling reaction of 2-chloroimidazole[1,2-a]pyridines, and their application towards synthesis of the two drugs is also addressed.

The development of potent and selective bisarylmaleimide GSK3 inhibitors

Many 3-aryl-4-(1,2,3,4-tetrahydro[1,4]diazepino[6,7,1-hi]indol-7-yl) maleimides exhibit potent GSK3 inhibitory activity (50), although few show significant selectivity (>100 ×) versus CDK2, CDK4, or PKCβII. However, combining 3-(imidazo[1,2-a]pyridin-3-yl), 3-(pyrazolo[1,5-a]pyridin-3-yl) or aza-analogs with a 4-(2-acyl-(1,2,3,4- tetrahydro[1,4]diazepino[6,7,1-hi]indol -7-yl)) group on the maleimide resulted in very potent inhibitors of GSK3 (≤5 nM) with >160 to >10,000-fold selectivity versus CDK2/4 and PKCβII. These compounds also inhibited tau phosphorylation in cells and were effective in lowering plasma glucose in a rat model of type 2 diabetes (ZDF rat).

Substituted 3-imidazo[1,2-a]pyridin-3-yl-4-(1,2,3,4-tetrahydro-[1,4] diazepino-[6,7,1-hi]indol-7-yl)pyrrole-2,5-diones as highly selective and potent inhibitors of glycogen synthase kinase-3

Glycogen synthase kinase-3 (GSK3) is involved in signaling from the insulin receptor. Inhibitors of GSK3 are expected to effect lowering of plasma glucose similar to insulin, making GSK3 an attractive target for the treatment of type 2 diabetes. Herein we report the discovery of a series of potent and selective GSK3 inhibitors. Compounds 7-12 show oral activity in an in vivo model of type II diabetes, and 9 and 12 have desirable PK properties.

Structure-based discovery of potent and selective small-molecule inhibitors targeting signal transducer and activator of transcription 3 (STAT3)

STAT3 has been validated as an attractive anticancer target due to its important roles in cancer initiation and progression. However, discovery of potent and selective STAT3 small-molecule inhibitors with druglike properties is still challenging. In this study, two series of substituted 2-phenylquinolines and 2-arylimidazo[1,2-a]pyridines were designed through structure-based drug discovery approach by condensing the privileged structures of STX-119 and SH4-54. Our study has resulted in the discovery of a number of highly potent and selective STAT3 inhibitors, exemplified by compound 39 with the privileged structure of 2-phenylimidazo[1,2-a]pyridine, which selectively inhibits phosphorylation of STAT3 and suppresses subsequent signaling pathway. Moreover, 39 inhibits cell growth, migration and invasion of human triple negative breast cancer (TNBC) cells lines. Consistently, it achieves significant and dose-dependent tumor growth inhibition in both cell line-derived and patient-derived xenograft tumor models in mice. These results clearly indicate that 39 is a highly potent and selective STAT3 inhibitor.

Method for preparing minodronic acid intermediate 2-(imidazo[1,2-alpha]pyridine-3-yl) acetate compound

The invention belongs to the technical field of pharmacy, relates to a preparation method of a drug intermediate, and specifically relates to a method for preparing an anti-osteoporosis drug minodronic acid intermediate 2-(imidazo[1,2-alpha]pyridine-3-yl) acetate compound. According to the preparation method, a 2-(2-halogenated imidazo[1,2-alpha]pyridine-3-yl) acetate compound is used as a raw material, and the 2-(imidazo[1,2-alpha]pyridine-3-yl) acetate compound is prepared through a one-step reduction reaction. The preparation method disclosed by the invention has the advantages of high yield, low by-products, convenient operation, low cost and easiness in large-scale production, and can be directly used for industrial preparation of minodronic acid.

METHODS FOR HAIR FOLLICLE STEM CELL PROLIFERATION

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