158980-21-3

Basic information

• Product Name: Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate
• Synonyms: ETHYL 6-AMINO-IMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLATE;6-AMINOIMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER;Imidazo[1,2-a]pyridine-2-carboxylic acid, 6-amino-, ethyl ester (9CI);6-AMINOIMIDAZO[1,2-A]PYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER, 95+%;Ethyl 6-aMinoiMidazo[1,2-a]pyridin-2-carboxylate;Imidazo[1,2-a]pyridine-2-carboxylic acid, 6-amino-, ethyl ester
• CAS NO: 158980-21-3
• Molecular Formula: C₁₀H₁₁N₃O₂
• Molecular Weight: 205.21
• EINECS: 201-215-5
• Product Categories: AMINOACID;Heterocycle-Pyridine series
• Mol File: 158980-21-3.mol

Chemical Properties

• Appearance: /
• Density: 1.35 g/cm³
• Refractive Index: 1.637
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.98±0.50(Predicted)
• CAS DataBase Reference: Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate(158980-21-3)
• EPA Substance Registry System: Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate(158980-21-3)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 158980-21-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drug molecules with biological activity. Its unique molecular structure allows for the creation of compounds with potential therapeutic effects.
Used in Agrochemical Synthesis:
In the agrochemical industry, Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate is utilized as a precursor in the production of agrochemicals, contributing to the development of new compounds with pesticidal or herbicidal properties.
Used in Medicinal Chemistry Research:
Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate serves as a valuable building block in medicinal chemistry research, where it is employed for the synthesis of biologically active compounds. Its molecular structure provides a foundation for the exploration of novel therapeutic agents.
Used in Chemical and Pharmaceutical Industry R&D:
In research and development within the chemical and pharmaceutical industries, Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate is used to explore its potential in creating new chemical entities and improving existing ones, driving innovation in drug discovery and chemical synthesis.

InChI:InChI=1/C10H11N3O2/c1-2-15-10(14)8-6-13-5-7(11)3-4-9(13)12-8/h3-6H,2,11H2,1H3

Upstream product

• 38923-08-9 ethyl 6-nitroimidazo<1,2-a>pyridine-2-carboxylate 
• 70-23-5 ethyl Bromopyruvate 
• 4214-76-0 5-nitro-pyridin-2-ylamine 

Downstream Products

• 1345681-72-2 (S)-N-(2-(1-(chloromethyl)-5-hydroxy-9-methyl-2,3-dihydro-1H-benzo[e]indole-3-carbonyl)-imidazo[1,2-a]pyridin-6-yl)-4-(methoxymethoxy)benzamide 
• 1403333-28-7 (S)-N-(1-(3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-6-(3,3-dimethylureido)imidazo[1,2-a]pyridine-2-carboxamide 
• 845827-07-8 ethyl 6-({[4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl]carbonyl}-amino)imidazo[1,2-a]pyridine-2-carboxylate 
• 1048367-56-1 ethyl 6-(4'-tert-butylbiphenyl-2-ylcarboxamido)imidazo[1,2-α]pyridine-2-carboxylate 

Relevant articles and documents

Design and Synthesis of Imidazo[1,2-a]pyridines with Carboxamide Group Substitution and In silico Evaluation of their Interaction with a LuxR-type Quorum Sensing Receptor

Quorum sensing, an important process of bacterial communication, is involved in the development of complex behavior and expression of virulence factors that become important due to its key role in infection process. In this manuscript, docking studies wer

HETEROCYCLIC COMPOUNDS AS PRMT5 INHIBITORS

The compounds of Formula I, Formula Ia, and Formula Ib are described herein along with their analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites, and prodrugs thereof. These compounds inhibit PRMT5 and are useful as therpeautic or ameliorating agent for diseases that are involved in cellular growth such as malignant tumors, schizophrenia, Alzheimer's disease, Parkinson's disease and the like.

SUBSTITUTED OXOPYRIDINE DERIVATIVES

The invention relates to substituted oxopyridine derivatives and to processes for their preparation, and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular cardiovascular disorders, preferably thrombotic or thromboembolic disorders, and oedemas, and also ophthalmic disorders.

Design, synthesis, and evaluation of linker-duocarmycin payloads: Toward selection of HER2-targeting antibody-drug conjugate SYD985

Antibody-drug conjugates (ADCs) that are currently on the market or in clinical trials are predominantly based on two drug classes: auristatins and maytansinoids. Both are tubulin binders and block the cell in its progression through mitosis. We set out to develop a new class of linker-drugs based on duocarmycins, potent DNA-alkylating agents that are composed of a DNA-alkylating and a DNA-binding moiety and that bind into the minor groove of DNA. Linker-drugs were evaluated as ADCs by conjugation to the anti-HER2 antibody trastuzumab via reduced interchain disulfides. Duocarmycin 3b, bearing an imidazo[1,2-a]pyridine-based DNA-binding unit, was selected as the drug moiety, notably because of its rapid degradation in plasma. The drug was incorporated into the linker-drugs in its inactive prodrug form, seco-duocarmycin 3a. Linker attachment to the hydroxyl group in the DNA-alkylating moiety was favored over linking to the DNA-binding moiety, as the first approach gave more consistent results for in vitro cytotoxicity and generated ADCs with excellent human plasma stability. Linker-drug 2 was eventually selected based on the properties of the corresponding trastuzumab conjugate, SYD983, which had an average drug-to-antibody ratio (DAR) of about 2. SYD983 showed subnanomolar potencies against multiple human cancer cell lines, was highly efficacious in a BT-474 xenograft model, and had a long half-life in cynomolgus monkeys, in line with high stability in monkey and human plasma. Studies comparing ADCs with a different average DAR showed that a higher average DAR leads to increased efficacy but also to somewhat less favorable physicochemical and toxicological properties. Fractionation of SYD983 with hydrophobic interaction chromatography resulted in SYD985, consisting of about 95% DAR2 and DAR4 species in an approximate 2:1 ratio and having an average DAR of about 2.8. SYD985 combines several favorable properties from the unfractionated ADCs with an improved homogeneity. It was selected for further development and recently entered clinical Phase I evaluation.

IMPROVED PROCESS FOR MAKING DUOCARMYCIN PRODRUGS

The present invention relates to a process comprising converting a compound of formula (I) into a compound of formula (II) by reaction with an organolithium reagent, which compound can be further converted into duocarmycin analogues consisting of a DNA- alkylating and a DNA-binding part, and still further into corresponding antibody-drug conjugates.

NOVEL CC-1065 ANALOGS AND THEIR CONJUGATES

This invention relates to novel analogs of the DNA-alkylating agent CC-1065 and to their conjugates. Furthermore this invention concerns intermediates for the preparation of said agents and conjugates. The conjugates are designed to release their (multiple) payload after one or more activation steps and/or at a rate and time span controlled by the conjugate in order to selectively deliver and/or controllably release one or more of said DNA alkylating agents. The agents, conjugates, and intermediates can be used to treat an illness that is characterized by undesired (cell) proliferation. As an example, the agents and the conjugates of this invention may be used to treat a tumor.

Discovery of imidazo[1,2-a]pyridines as potent MCH1R antagonists

A series of imidazo[1,2-a]pyridine derivatives was identified and evaluated for MCH1R binding and antagonistic activity. Introduction of a methyl substituent at the 3-position of imidazo[1,2-a]pyridine provided compounds with a significant improvement in MCH1R affinity. Representative compounds in this series exhibited good potency and brain exposure in rats.

GUT MICROSOMAL TRIGLYCERIDE TRANSPORT PROTEIN INHIBITORS

Compounds represented by formula (I): are inhibitors of gut microsomal triglyceride transfer protein. Such compounds are useful in treating diseases or conditions such as diabetes and obesity, along with patients are risk for developing such diseases or conditions.

COMPARED REACTIVITY OF 3-, 5-, 6-, AND 8-AMINOIMIDAZOPYRIDINES IN COMBES REACTION: ACCESS TO IMIDAZONAPHTHYRIDINES AND DIPYRIDOIMIDAZOLE

The synthesis of imidazonaphthyridines and dipyridoimidazole by treatment of aminoimidazopyridines following the Combes procedure is described.