82437-65-8

Basic information

• Product Name: methyl 3-amino-4-(4-methoxyphenyl)-2-thiophenecarboxylate
• Synonyms: methyl 3-amino-4-(4-methoxyphenyl)-2-thiophenecarboxylate
• CAS NO: 82437-65-8
• Molecular Weight: 263.317
• Mol File: 82437-65-8.mol

Chemical Properties

• CAS DataBase Reference: methyl 3-amino-4-(4-methoxyphenyl)-2-thiophenecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-amino-4-(4-methoxyphenyl)-2-thiophenecarboxylate(82437-65-8)
• EPA Substance Registry System: methyl 3-amino-4-(4-methoxyphenyl)-2-thiophenecarboxylate(82437-65-8)

Safety Data

• Hazardous Substances Data: 82437-65-8(Hazardous Substances Data)

Upstream product

• 161833-42-7 3-amino-4-bromo-2-thiophenecarboxylic acid methyl ester 
• 5720-07-0 4-methoxyphenylboronic acid 
• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 53283-60-6 α-Hydroxymethyl-4-methoxy-phenylacetonitril 
• 35070-82-7 2-(4-methoxyphenyl)-3-oxopropanenitrile 
• 105-13-5 4-Methoxybenzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 
• 104-47-2 p-methoxybenzylnitrile 
• 2365-48-2 Methyl thioglycolate 

Downstream Products

• 156274-09-8 methyl 3-(1-pyrrolyl)-4-para-methoxyphenyl-2-thiophenecarboxylate 
• 649757-61-9 3-Amino-4-(4-methoxy-phenyl)-thiophene-2-carboxylic acid 
• 82437-73-8 4-(4-Methoxy-phenyl)-thiophene-2-carboxylic acid methyl ester 
• 178062-61-8 3-(3-Chloro-2,2-dimethyl-propionylamino)-4-(4-methoxy-phenyl)-thiophene-2-carboxylic acid methyl ester 
• 82437-75-0 3-(4-methoxy-phenyl)-thiophene 
• 82437-70-5 4-(4-Methoxy-phenyl)-thiophen-3-ylamine 
• 82437-74-9 4-(4-methoxyphenyl)thiophene-2-carboxylic acid 
• 1621967-76-7 7-(4-methoxyphenyl)-3-(4-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one 
• 1111737-77-9 methyl 3-bromo-4-(4-methoxyphenyl)thiophene-2-carboxylate 
• 1026810-40-1 Acetic acid 2-[7-(4-methoxy-phenyl)-2,4-dioxo-3,4-dihydro-2H-thieno[3,2-d]pyrimidin-1-ylmethoxy]-ethyl ester 

Relevant articles and documents

Novel Solid-phase and solution-phase synthetic methods for trisubstituted Thieno[3,2-d]pyrimidine derivatives

The coupling of 7-aryl-3,4-dihydro-4-oxothieno[3,2-d]pyrimidine-2-carboxylic acid with a primary alkylamineloaded acid-sensitive methoxy benzaldehyde (AMEBA) resin, a benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (BOP)-mediated amination reaction, and cleavage from the solid support yielded N-alkyl-4-(alkylamino)-7-arylthieno[3,2-d]pyrimidine-2-carboxamide derivatives. The progress of the reactions on solid phase was monitored through attenuated total reflectance-FTIR spectroscopy and was compared with representative solution-phase surrogates. Additionally, N-acylation (acid chloride, InF3 , CH3 CN, room temperature) and cyclization (DBN, 1,4-dioxane, 80 ° C) of a 3-amino-4-(4-t-butoxycarbonylphenyl) thiophene-2-carboxamide intermediate under previously unreported conditions provided 2-substituted thieno[3,2-d]pyrimidin-4(3H)-one derivatives, which were subsequently converted to 2-substituted 4-alkylamino-7-[4-(alkylaminocarbonyl)phenyl]thieno[3,2-d]pyrimidine derivatives through a reaction sequence consisting of a BOP-mediated amination reaction, t-butyl deprotection, and amide formation.

Synthesis and biological evaluation of N3-alkyl-thienopyrimidin-4-ones as mGluR1 antagonists

Metabotropic glutamate receptor subtype 1 (mGluR1) is a potential target for the treatment of neuropathic pain, and there has been much effort to discover mGluR1 antagonists. In this study, a series of N3-alkyl-thienopyrimidin-4-ones were prepared by introducing various alkyl and aryl groups to the N3- and 7-positions of the thienopyrimidin-4-one core structure, respectively, and their inhibitory activities against mGluR1 were biologically evaluated. Structure-activity relationship study revealed that the trans-4-methylcyclohexyl, cycloheptyl, and cyclooctyl groups at N3-position, and 2-fluorophenyl group at 7-position were most effective in potentiating the inhibitory activity of the thienopyrimidin-4-one derivatives against mGluR1. Among the synthesized compounds, 3-cyclooctyl-7-phenylthienopyrimidin-4-one and 3-cycloheptyl-7-(2-fluorophenyl)thienopyrimidin-4-one exhibited the most potent inhibitory activities with IC50 values of 115 and 107 nM, respectively.

Novel thienopyrimidinones as mGluR1 antagonists

There has been much attention to discover mGluR1 antagonists for treating various central nervous system diseases such as seizures and neuropathic pain. Thienopyrimidinone derivatives were designed, synthesized, and biologically evaluated against mGluR1. Among the synthesized compounds, 3-(4-methoxyphenyl)- 7-(o-tolyl)thienopyrimidin-4-one 30 exhibited the most potent inhibitory activity with an IC50 value of 45 nM and good selectivity over mGluR5. Also, the selective mGluR1 antagonist 30 showed marginal hERG channel activity (IC50 = 9.87 μM), good profiles to CYP isozymes, and a good pharmacokinetic profile. Overall, the compound 30 was identified as a selective mGluR1 antagonist with a good pharmacokinetic profile, which is probably devoid of cardiac side effect and drug-drug interactions. Therefore, the compound 30 can be expected to be broadly used as mGluR1 antagonistic chemical probe in in vitro and in vivo study for investigating CNS diseases.

Phase transfer catalysis assisted thorpe reaction for the synthesis of 3-aminothiophene-2-carboxylates

Thorpe cyclization constructing synthetically important methyl or ethyl 3-amino-4-arylthiophene-2-carboxylates has been studied using eco friendly phase transfer catalysis technique. 3-Amino-4-arylthiophene-2-carboxylates have been synthesized from 3-hydr

Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents

Structure-activity relationship studies of a new series of tripentones (thieno[2,3-b]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2,3-b]pyrrolizin-8-one 20 (leukemia L1210, IC50 = 15 nM) was shown to be a potent inhibitor of tubulin polymerization.

Synthesis of thieno[3,2-d]pyrimidine-2,4-diones cyclic and acyclic nucleosides as potential anti HIV agents

Synthesis of cyclic and acyclic nucleosides was achieved by alkylation of 7-methyl or arylthieno[3,2-d]pyrimidine-2,4-diones following the Vorbruggen and Niedballa's method [1]. After a possible deprotection, potential anti HIV agents were obtained.

Synthese d'amino-3 thiophenes a partir d'aryl- et d'hetaryl-acetonitrile (1)

Applying Fiesselman's condensation to α-hydroxymethylene nitriles the authors describe a synthesis of substituted aminothiophenes.