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
• Article Data: 12

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

General Description

ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE is a chemical compound with the molecular formula C14H15NO3S. It is a Thiophene-based compound containing an amino group, a methoxyphenyl group, and an ethyl ester group. ETHYL 2-AMINO-4-(4-METHOXYPHENYL)-3-THIOPHENECARBOXYLATE is often used as a building block in organic synthesis and pharmaceutical research. It has potential applications in the development of new drugs and materials due to its unique structure and properties. However, it is important to handle this compound with care as it may have hazardous properties if not handled properly.

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

Downstream Products

• 17537-76-7 5-(4-methoxyphenyl)thieno[2,3-d]pyrimidin-4(3H)-one 
• 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 
• 935759-63-0 5-(4-methoxyphenyl)-4-oxo-N-{3-[2-(1H-1,2,4-triazol-3-yloxy)ethoxy]benzyl}-3,4-dihydro-thieno[2,3-d]pyrimidine-2-carboxamide 
• 1639810-22-2 C₁₆H₁₄N₂O₄S 
• 1432511-22-2 benzyl 2-{[(tert-butoxy)carbonyl]amino}-4-(4-methoxyphenyl)thiophene-3-carboxylate 

Relevant articles and documents

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.

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.