111042-89-8

Basic information

• Product Name: METHYL 3-AMINOTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE
• Synonyms: AKOS 93608;METHYL 3-AMINOTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE;METHYL 3-AMINOTHIOPHENO[2,3-B]PYRIDINE-2-CARBOXYLATE;Thieno[2,3-b]pyridine-2-carboxylic acid, 3-amino-, methyl ester (9CI);3-aminothieno[2,3-b]pyridine-2-carboxylic acid methyl ester;2-(Methoxycarbonyl)thieno[2,3-b]pyridin-3-amine;3-AMino-thieno[2,3-b]pyridin-2-carboxylic acid Methyl ester;3-AMino-2-carboMethoxythieno[2,3-b]pyridine
• CAS NO: 111042-89-8
• Molecular Formula: C9H8N2O2S
• Molecular Weight: 208.24
• Product Categories: AMINOACID
• Mol File: 111042-89-8.mol

Chemical Properties

• Melting Point: 198-200°C
• Boiling Point: 377.6°C at 760 mmHg
• Flash Point: 182.1°C
• Appearance: /
• Density: 1.422g/cm³
• Vapor Pressure: 6.69E-06mmHg at 25°C
• Refractive Index: 1.699
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 4.96±0.40(Predicted)
• CAS DataBase Reference: METHYL 3-AMINOTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-AMINOTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE(111042-89-8)
• EPA Substance Registry System: METHYL 3-AMINOTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE(111042-89-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 111042-89-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 3-AMINOTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE is used as a building block for the synthesis of various pharmaceuticals due to its unique chemical structure and potential biological activities, which contribute to the development of new therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL 3-AMINOTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE is employed as a component in the creation of agrochemicals, leveraging its chemical properties to enhance crop protection and management.
Used in Research and Development:
METHYL 3-AMINOTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE is used as a research tool for exploring new drug candidates and chemical reactions, providing insights into the compound's therapeutic potential and facilitating advancements in medicinal chemistry.
Used in the Treatment of Neurological Diseases:
METHYL 3-AMINOTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE is utilized in the development of treatments for neurological disorders, capitalizing on its potential biological activities to target and alleviate symptoms associated with such conditions.
Used in the Treatment of Cardiovascular Diseases:
METHYL 3-AMINOTHIENO[2,3-B]PYRIDINE-2-CARBOXYLATE is applied in the research and potential treatment of cardiovascular diseases, aiming to improve patient outcomes through its incorporation into novel therapeutic strategies.

InChI:InChI=1/C9H8N2O2S/c1-13-9(12)7-6(10)5-3-2-4-11-8(5)14-7/h2-4H,10H2,1H3

Upstream product

• 6602-54-6 2-chloro-3-pyridinecarbonitrile 
• 2365-48-2 Methyl thioglycolate 
• 55557-52-3 2-chloro-3-cyanopyrazine 
• 123972-89-4 ethoxyrhiocarbonylsulfanylacetic acid methyl ester 

Downstream Products

• 26579-54-4 3-aminothieno[2,3-b]pyridine 
• 890095-19-9 3-aminothieno[2,3-b]pyridine-2-carboxylic acid hydrazide 
• 1299492-66-2 3-aminothieno[2,3-b]pyridine-2-carboxylic acid naphthalen-1-yl-methylene hydrazide 
• 1299492-70-8 3-aminothieno[2,3-b]pyridine-2-carboxylic acid (3-methyl-3H-imidazol-4-yl-methylene) hydrazide 
• 1427420-71-0 C₁₈H₁₈N₂O₅S 

Relevant articles and documents

One-pot approach to construct benzo[4,5]thieno[3,2-b]indoles, pyrido[3′,2’:4,5]thieno[3,2-b]indoles and pyrazino[2′,3’:4,5]thieno[3,2-b]indoles based on the Fischer indole synthesis

During this study, series of benzo[4,5]thieno[3,2-b]indoles, pyrido[3′,2’:4,5]thieno[3,2-b]indoles and pyrazino[2′,3’:4,5]thieno[3,2-b]indoles were efficiently synthesized from benzo- and pyrido- or pyrazino-fused 3-aminothiophene-2-carboxylates, respectively, using one-pot two-step strategy based on the Fischer indolization reaction. The essence of this synthetic approach is acid-promoted reaction of the 3-aminothiophene intermediates, in situ generated from the corresponding ring-fused 3-aminothiophene-2-carboxylates, with arylhydrazines to give arylhydrazones of thiophen-3(2H)-ones, followed by their indolization to afford thieno[3,2-b]indole-cored molecules.

Xanthates as Thiol Surrogates for Nucleophilic Substitution with Aryl Halides

We herein report an unprecedented xanthate-based protocol for the preparation of aryl-alkyl thioethers. Heating xanthates with aryl halides and namely cesium carbonate in methanol provides the target thioethers in generally good yields within short reaction times. This method allows one to avoid contact with odorous thiols and also to introduce substituents of which the corresponding thiols are virtually unavailable or inconvenient in use.

Polysubstituted thieno[2,3-b]pyridine derivatives, and preparation method and application thereof

The invention discloses polysubstituted thieno[2,3-b]pyridine derivatives, and a preparation method and an application thereof. The structural formula of the derivatives are represented by formula I shown in the description. A compound for inhibiting a urea transporter is screened by using an erythrocyte model. Experimental results show that the compounds (represented by formula I-1) can inhibit the permeation of a urea transporter UT-B mediated erythrocyte membrane to urea, and the effect of the compounds has a dose-dependent relationship; the compounds represented by the formula I-1 have nocytotoxic effect on MDCK cells within an effective dose range, so the effect of the compounds represented by the formula I-1 on inhibiting cell permeation urea is irrelevant to the cytotoxicity of thecompounds; the inhibition effect of the compounds represented by the formula I-1 on the urea transporter UT-B is gradually enhanced; the inhibiting effect of the compounds represented by the formulaI-1 on the UT-B is reversible; and in-vivo test results show that the compounds represented by the formula I-1 can significantly increase the urination volume of rats, reduce the concentration of ureain rat urine and reduce the osmotic pressure, so that the compounds represented by the formula I-1 generate a urea selective diuresis effect in vivo.

Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors

Microwave irradiation of 2-halobenzonitriles and methyl thioglycolate in the presence of triethylamine in DMSO at 130°C provides rapid access to 3-aminobenzo[b]thiophenes in 58-96% yield. This transformation has been applied in the synthesis of the thieno

Synthesis and structure-activity relationship studies of 2-(1,3,4-oxadiazole-2(3H)-thione)-3-amino-5-arylthieno[2,3-b]pyridines as inhibitors of DRAK2

In recent years, DAPK-related apoptosis-inducing protein kinase 2 (DRAK2) has emerged as a promising target for the treatment of a variety of autoimmune diseases and for the prevention of graft rejection after organ transplantation. However, medicinal chemistry optimization campaigns for the discovery of novel small-molecule inhibitors of DRAK2 have not yet been published. Screening of a proprietary compound library led to the discovery of a benzothiophene analogue that displays an affinity constant (Kd) value of 0.25 μM. Variation of the core scaffold and of the substitution pattern afforded a series of 5-arylthieno[2,3-b]pyridines with strong binding affinity (Kd=0.008 μM for the most potent representative). These compounds also show promising activity in a functional biochemical DRAK2 enzyme assay, with an IC50 value of 0.029 μM for the most potent congener. Selectivity profiling of the most potent compounds revealed that they lack selectivity within the DAPK family of kinases. However, one of the less potent analogues is a selective ligand for DRAK2 and can be used as starting point for the synthesis of selective and potent DRAK2 inhibitors.

Synthesis and Structure-Activity Relationship Studies of 2-(1,3,4-Oxadiazole-2(3H)-thione)-3-amino-5-arylthieno[2,3-b]pyridines as Inhibitors of DRAK2

In recent years, DAPK-related apoptosis-inducing protein kinase 2 (DRAK2) has emerged as a promising target for the treatment of a variety of autoimmune diseases and for the prevention of graft rejection after organ transplantation. However, medicinal chemistry optimization campaigns for the discovery of novel small-molecule inhibitors of DRAK2 have not yet been published. Screening of a proprietary compound library led to the discovery of a benzothiophene analogue that displays an affinity constant (Kd) value of 0.25 μM. Variation of the core scaffold and of the substitution pattern afforded a series of 5-arylthieno[2,3-b]pyridines with strong binding affinity (Kd=0.008 μM for the most potent representative). These compounds also show promising activity in a functional biochemical DRAK2 enzyme assay, with an IC50 value of 0.029 μM for the most potent congener. Selectivity profiling of the most potent compounds revealed that they lack selectivity within the DAPK family of kinases. However, one of the less potent analogues is a selective ligand for DRAK2 and can be used as starting point for the synthesis of selective and potent DRAK2 inhibitors.

Synthesis and biological evaluation of 2-(alkoxycarbonyl)-3-anilinobenzo[b] thiophenes and thieno[2,3-b]pyridines as new potent anticancer agents

Two new series of inhibitors of tubulin polymerization based on the 2-(alkoxycarbonyl)-3-(3′,4′,5′-trimethoxyanilino)benzo[b] thiophene and thieno[2,3-b]pyridine molecular skeletons were synthesized and evaluated for antiproliferative activity on a panel

BENZOFURAN AND BENZOTHIOPHENE DERIVATIVES SUBSTITUTED WITH AMIDE, PROCESS FOR THE PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME

The present invention relates to a novel benzofuran or benzothiophene derivative substituted with amide. The inventive benzofuran or benzothiophene derivative substituted with amide effectively inhibits ischemic cell death, and thus, can be advantageously

Nucleophilic Displacements in Pyridine Rings

The reactions of halopyridines containing an electron withdrawing group (-CN, -CO2R, -COMe, -NO2) with sulphur nucleophiles is reported.