15854-11-2

Basic information

• Product Name: ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE
• Synonyms: BUTTPARK 99\18-78;CHEMBRDG-BB 3000797;ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE;ETHYL 2-AMINO-4-(4-METHOXYPHENYL)THIOPHENE-3-CARBOXYLATE;3-THIOPHENECARBOXYLIC ACID, 2-AMINO-4-(4-METHOXYPHENYL)-, ETHYL ESTER;AKOS B000797;AKOS BBS-00000791;AKOS MSC-0439
• CAS NO: 15854-11-2
• Molecular Formula: C₁₄H₁₅NO₃S
• Molecular Weight: 277.34
• Mol File: 15854-11-2.mol

Chemical Properties

• Melting Point: 74 °C
• Boiling Point: 424.2 °C at 760 mmHg
• Flash Point: 210.4 °C
• Appearance: /
• Density: 1.233 g/cm³
• Vapor Pressure: 2.1E-07mmHg at 25°C
• Refractive Index: 1.596
• PKA: -0.18±0.10(Predicted)
• CAS DataBase Reference: ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE(15854-11-2)
• EPA Substance Registry System: ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE(15854-11-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 15854-11-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE is used as a key intermediate in the synthesis of various pharmaceutical compounds for its potential role in drug discovery and development. Its unique structural features allow it to be a valuable component in the creation of novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE is utilized as a building block for the assembly of more complex organic molecules. Its functional groups enable it to participate in a range of chemical reactions, facilitating the synthesis of diverse organic compounds.
Used in Material Science:
ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE may also find applications in material science, where its unique properties could contribute to the development of new materials with specific characteristics, such as improved conductivity or stability.
Used in Chemical Research:
As a compound with distinct structural elements, ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE is used in chemical research to explore its reactivity, stability, and potential interactions with other molecules, which can lead to a better understanding of its properties and applications.

InChI:InChI=1/C14H15NO3S/c1-3-18-14(16)12-11(8-19-13(12)15)9-4-6-10(17-2)7-5-9/h4-8H,3,15H2,1-2H3

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 110-91-8 morpholine 
• 17463-82-0 ethyl (Z)-2-cyano-3-(4-methoxyphenyl)-but-2-enoate 
• 13455-80-6 2-cyano-3-(4-methoxy-phenyl)-crotonic acid ethyl ester 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 17537-76-7 5-(4-methoxyphenyl)thieno[2,3-d]pyrimidin-4(3H)-one 
• 851852-96-5 3-(3-fluorophenyl)-2-mercapto-5-(4-methoxyphenyl)-3H-thieno[2,3-d]pyrimidin-4-one 
• 851853-29-7 [3-(3-fluorophenyl)-5-(4-methoxyphenyl)-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-ylsulfanyl]acetic acid ethyl ester 
• 1101067-85-9 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-(4-methoxyphenyl)-thiophene-3-carboxylic acid ethyl ester 
• 17537-76-7 5-(4-methoxy-phenyl)-3H-thieno[2,3-d]pyrimidin-4-one 
• 1616635-96-1 ethyl 2-amino-5-(phenyldiazenyl)-4-(4'-methoxyphenyl)thiophene-3-carboxylate 
• 1616635-97-2 ethyl 2-amino-5-(4-methylphenyldiazenyl)-4-(4'-methoxyphenyl)thiophene-3-carboxylate 
• 1616635-98-3 ethyl 2-amino-5-(4-methoxyphenyldiazenyl)-4-(4'-methoxyphenyl)thiophene-3-carboxylate 
• 1616635-99-4 ethyl 2-amino-5-(4-cyanophenyldiazenyl)-4-(4'-methoxyphenyl)thiophene-3-carboxylate 
• 1616636-00-0 ethyl 2-amino-5-(4-nitrophenyldiazenyl)-4-(4'-methoxyphenyl)thiophene-3-carboxylate 
• 929417-75-4 N-(4-(5-(4-methoxy-phenyl)-7H-thieno[2,3-d]pyrimidin-4-ylamino)-benzenesulfonyl)-acetamide 
• 1018281-39-4 4-piperazin-1-yl-5-(4-methoxy-phenyl)-thieno[2,3-d]pyrimidine 
• 312584-53-5 4-chloro-5-(4-methoxyphenyl)thieno[2,3-d]pyrimidine 
• 935760-50-2 ethyl 5-(4-methoxyphenyl)-4-oxo-3,4-dihydrothieno[2,3-d]-pyrimidine-2-carboxylate 

Relevant articles and documents

Identification of 4-methoxythieno[2,3-d]pyrimidines as FGFR1 inhibitors

Aim. To identify novel FGFR1 inhibitors using virtual screening approach. Methods. We used methods of organic synthesis, molecular docking via the Autodock 4.2.6 program package and in vitro biochemical tests with γ-32P. Results. In vitro experiments showed that 9 of 23 tested compounds possess inhibitory activity against FGFR1 with IC50 values in the range from 0.9 to 5.6 μM. Conclusions. Nine FGFR1 inhibitors were developed. The mode of compounds binding with the ATP-acceptor site was determined using molecular docking methods and the dependence of the compounds’ activity on the substituents R1, R4 and R5 was evaluated.

Design, Synthesis, and Biological Evaluation of 6-Substituted Thieno[3,2- d]pyrimidine Analogues as Dual Epidermal Growth Factor Receptor Kinase and Microtubule Inhibitors

The clinical evidence for the success of tyrosine kinase inhibitors in combination with microtubule-targeting agents prompted us to design and develop single agents that possess both epidermal growth factor receptor (EGFR) kinase and tubulin polymerization inhibitory properties. A series of 6-aryl/heteroaryl-4-(3′,4′,5′-trimethoxyanilino)thieno[3,2-d]pyrimidine derivatives were discovered as novel dual tubulin polymerization and EGFR kinase inhibitors. The 4-(3′,4′,5′-trimethoxyanilino)-6-(p-tolyl)thieno[3,2-d]pyrimidine derivative 6g was the most potent compound of the series as an antiproliferative agent, with half-maximal inhibitory concentration (IC50) values in the single- or double-digit nanomolar range. Compound 6g bound to tubulin in the colchicine site and inhibited tubulin assembly with an IC50 value of 0.71 μM, and 6g inhibited EGFR activity with an IC50 value of 30 nM. Our data suggested that the excellent in vitro and in vivo profile of 6g may be derived from its dual inhibition of tubulin polymerization and EGFR kinase.

Novel 4-oxothienopyrimidinyl propanoic acid derivatives as AMPactivated protein kinase (AMPK) activators

Adenosine 5′-monophosphate (AMP) activated protein kinase (AMPK) is a highly conserved sensor of cellular energy. AMPK has been recognized as a key regulator of mammalian metabolic function and has emerged as an attractive target for the treatment of meta

Part 1: Synthesis and visible absorption spectra of some new monoazo dyes derived from ethyl 2-amino-4-(4′-substitutedphenyl)thiophenes

Series of monoazo dyes from some ethyl 2-amino-4-(4′- substitutedphenyl) thiophenes were prepared and characterized. The structure of the substances was confirmed by FT-IR, 1H NMR and mass spectroscopic techniques. The relationship among the structure of the dyes, their absorption characteristics and the solvatochromic and halochromic behaviors of the dyes were investigated. Introduction of electron-accepting substituent into the diazo moiety results in large bathochromic shifts in all solvents used. The dyes exhibited positive solvatochromism and their solvatochromic properties were discussed in relation to tautomerism.

Synthesis and structure-activity relationships of 2-amino-3-carboxy-4- phenylthiophenes as novel atypical protein kinase C inhibitors

Recent evidence suggests atypical protein kinase C (aPKC) isoforms are required for both TNF- and VEGF-induced breakdown of the blood-retinal barrier (BRB) and endothelial permeability to 70 kDa dextran or albumin. A chemical library screen revealed a series of novel small molecule phenylthiophene based inhibitors of aPKC isoforms that effectively block permeability in cell culture and in vivo. In an effort to further elucidate the structural requirements of this series of inhibitors, we detail in this study a structure-activity relationship (SAR) built on screening hit 1, which expands on our initial pharmacophore model. The biological activity of our analogues was evaluated in models of bona fide aPKC-dependent signaling including NFκB driven-gene transcription as a marker for an inflammatory response and VEGF/TNF-induced vascular endothelial permeability. The EC50 for the most efficacious inhibitors (6, 32) was in the low nanomolar range in these two cellular assays. Our study demonstrates the key structural elements that confer inhibitory activity and highlights the requirement for electron-donating moieties off the C-4 aryl moiety of the 2-amino-3-carboxy-4-phenylthiophene backbone. These studies suggest that this class has potential for further development into small molecule aPKC inhibitors with therapeutic efficacy in a host of diseases involving increased vascular permeability and inflammation.

AXL KINASE INHIBITORS

Axl kinase inhibitory compounds are disclosed, as well as compositions and methods of using the same in the treatment of cancer and other conditions mediated by and/or associated with Axl kinase.

Efficient synthesis of substituted 2-amino-3-carbethoxythiophenes

A microwave-assisted method for the synthesis of a variety of thiophene o-aminoesters (2a-l) has been developed, starting from an appropriate aldehyde, methyl ketone or acetoacetate ester with ethyl cyanoacetate in the presence of elemental sulfur. Copyright Taylor & Francis Group, LLC.

Aryl alkyl ketones in a one-pot Gewald synthesis of 2-aminothiophenes

2-Aminothiophene-3-carboxylates bearing various aryl groups at the 4-position are readily obtained in good to moderate yields by the one-pot Gewald reaction of aryl alkyl ketones with ethyl cyanoacetate and elemental sulfur in the presence of morpholinium acetate and excess morpholine. Georg Thieme Verlag Stuttgart.

SUBSTITUED 3,4-DIHYDROTHIENO [2,3-D] PYRMIDINES AS TISSUE TRANSGLUTAMINASE INHIBITORS

The present invention provides novel compounds and methods useful for treating transglutaminase associated disorders such as celiac spru, Alzheimer's disease and Huntington's disease. Certain compounds of the invention are tissue transglutaminase inhibito

Structure-activity relationship study of novel tissue transglutaminase inhibitors

Thieno[2,3-d]pyrimidin-4-one acylhydrazide derivatives were discovered as moderately potent inhibitors of TGase 2 (tissue transglutaminase) utilizing a fluorescence-based assay that measured TGase 2 catalyzed incorporation of the dansylated Lys derivative