19369-53-0

Basic information

• Product Name: 2-AMINO-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 12-AMINO-6-METHYLTHIOPHENE-3-CARBOXYLATE;methyl 2-amino-5-methylthiophene-3-carboxylate(SALTDATA: FREE);3-Thiophenecarboxylic acid, 2-aMino-5-Methyl-, Methyl ester;2-Amino-3-(methoxycarbonyl)-5-methylthiophene;2-amino-5-methyl-3-thiophenecarboxylic acid methyl ester
• CAS NO: 19369-53-0
• Molecular Formula: C₇H₉NO₂S
• Molecular Weight: 171.22
• Mol File: 19369-53-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 278.2 °C at 760 mmHg
• Flash Point: 122 °C
• Appearance: /
• Density: 1.264 g/cm³
• Vapor Pressure: 0.00434mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: 2-8°C(protect from light)
• PKA: 0.42±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER(19369-53-0)
• EPA Substance Registry System: 2-AMINO-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER(19369-53-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 19369-53-0(Hazardous Substances Data)

Usage

Uses

Methyl 2-Amino-5-methylthiophene-3-carboxylate is used as a starting reagent in the synthesis of Thieno[2,3-b]Pyridinones and 4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine derivatives, compounds that act as cytoprotectants and inhibitors of the N-Methyl-D-aspartate (NMDA) receptor.

InChI:InChI=1/C7H9NO2S/c1-4-3-5(6(8)11-4)7(9)10-2/h3H,8H2,1-2H3

Upstream product

• 123-38-6 propionaldehyde 
• 105-34-0 methyl 2-cyanoacetate 

Downstream Products

• 72242-31-0 5-methyl-2-(2-nitro-anilino)-thiophene-3-carboxylic acid methyl ester 
• 108831-66-9 6-Methylthieno<2,3-d>pyrimid-4-one 
• 67171-50-0 methyl 2-acetamido-5-methylthiophene-3-carboxylate 

Relevant articles and documents

Structure-activity relationship of tumor-selective 5-substituted 2-amino-3-carboxymethylthiophene derivatives

Methyl-2-amino-5-[2-(4-methoxyphenethyl)]thiophene-3-carboxylate (8c) is the prototype of a well-defined class of tumorselective agents. Compound 8c preferentially inhibited the proliferation of a number of tumor cell lines including many human T-lymphoma/leukemia cells, but also several prostate, renal, central nervous system and liver tumor cell types. Instead, a broad variety of other tumor cell lines including B-lymphomas and HeLa cells were not affected. The tumor selectivity (TS; selectivity index or preferential suppression of CEM lymphoma (IC50=0.90 mm) versus HeLa tumor cell carcinoma (IC50=39 mm)) amounted up to ～43 for 8c. At higher concentrations, the compound proved cytotoxic rather than cytostatic. The antiproliferative potency and selectivity of 8c could be preserved by replacing the ethyl linker between the 2-amino- 3-carboxymethylthiophene and the substituted aryl by a thioalkyl but not by an oxyalkyl nor an aminoalkyl. Among >50 novel 8c derivatives, the 5-(4-ethyl- and 4-isopropylarylmethylthio) thiophene analogues, methyl-2-amino-5-((4-ethylphenylthio) methyl)thiophene-3-carboxylate (13m) and methyl-2- amino-5-((4-isopropylphenylthio)methyl)thiophene-3-carboxylate (13n), were more potent (IC50 : 0.3-0.4 mm) and selective (TS: 100-144) anti-T-lymphoma/leukemia agents than the prototype compound.

Design, Synthesis, and SAR Studies of Heteroarylpyrimidines and Heteroaryltriazines as CB2R Ligands

Herein we describe the design and synthesis of a new series of heteroarylpyrimidine/heteroaryltriazine derivatives on the basis of quinazoline-2,4(1H,3H)-diones as CB2R-selective ligands using a bioisosterism strategy. An acetamide group was explored to displace the enamine linker of the lead compound for the purpose of stereoisomerism elimination and hydrophilicity increase. As a result, some of the synthesized compounds showed high bioactivity and selectivity for CB2R in calcium mobilization assays, and four displayed CB2R agonist activity, with EC50 values below 30 nm. The compound exhibiting the highest agonist activity toward CB2R (EC50=7.53±3.15 nm) had a selectivity over CB1R of more than 1328-fold. Moreover, structure–activity relationship (SAR) studies indicated that the substituents on the nucleus play key roles in the functionality of a ligand, with one such example demonstrating CB2R antagonist activity. Additionally, molecular docking simulations were conducted with the aim of better understanding of these new derivatives in relation to the structural requirements for agonists/antagonists binding to CB2R.

Heteroarylpyrimindinedione derivative and use thereof

The invention provides a heteroarylpyrimindinedione derivative and use thereof. The heteroarylpyrimindinedione derivative comprises a compound with a structure shown as general formula I, and a pharmaceutically acceptable salt or hydrate thereof. The derivative is obtained by chemical synthesis, and pharmacological experiments prove that the active ligand with cannabinoid type II receptor CB2 can be used for preparation of drugs for prevention and mitigation of CB2 receptor-mediated diseases, and the drug is cannabinoid CB2 receptor agonist's agonist, partial agonist, inverse agonist or antagonist. And the general structural formula I is shown as the specification.