31891-06-2

Usage

Uses

Used in Organic Chemical Synthesis:
Ethyl 2-aminothiophene-3-carboxylate is used as an intermediate in the organic chemical synthesis industry. It is utilized for the production of a wide range of compounds due to its unique chemical properties, which make it a valuable component in the synthesis process.

InChI:InChI=1/C7H9NO2S/c1-2-10-7(9)5-3-4-11-6(5)8/h3-4H,2,8H2,1H3

Upstream product

• 40018-26-6 1,4-dithiane-2,5-diol 
• 105-56-6 ethyl 2-cyanoacetate 
• 67-56-1 methanol 
• 56387-08-7 2-aminothiophene-3-carboxylic acid 

Downstream Products

• 158461-05-3 1-(4-bromo-2-fluorobenzyl)-3-(3-ethoxycarbonyl-thiophen-2-yl)urea 
• 103979-54-0 1H,2H,4H-thieno[2,3-d][1,3]oxazine-2,4-dione 
• 654667-25-1 4-chloro-6-(3-trifluoromethyl-phenyl)-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 106667-62-3 C₁₄H₁₃N₃O₅S 
• 1384579-52-5 ethyl 2-(phenylethynyl)thiophene-3-carboxylate 
• 1384579-71-8 7-iodo-6-phenyl-4H-thieno[3,2-c]pyran-4-one 
• 920433-35-8 ethyl-2-(2-iodobenzamido)thiophene-3-carboxylate 
• 888412-99-5 ethyl 2-([1,1'-biphenyl]-4-ylcarboxamido)thiophene-3-carboxylate 
• 1585969-81-8 2-([1,1'-biphenyl]-4-yl-carboxamido)thiophene-3-carboxylic acid 
• 468096-22-2 2-mercapto-3-(4-methylphenyl)thieno[2,3-d]pyrimidin-4(3H)-one 

Relevant academic research and scientific papers

α,α′-N-boc-substituted Bi- and terthiophenes: Fluorescent precursors for functional materials

Fluorescent α,α′-diamide substituted bi- and terthiophene derivatives were prepared by Stille and Suzuki couplings. Their one-pot deprotection and coupling with 2-thiophene carboxaldehyde led to stable conjugated azomethines. These exhibited electrochromic properties, and they were used to fabricate a working electrochromic device.

Design, Synthesis, and Structure-Activity Relationship of N-Aryl- N′-(thiophen-2-yl)thiourea Derivatives as Novel and Specific Human TLR1/2 Agonists for Potential Cancer Immunotherapy

The previous virtual screening of ten million compounds yielded two novel nonlipopeptide-like chemotypes as TLR2 agonists. Herein, we present the chemical optimization of our initial hit, 1-phenyl-3-(thiophen-2-yl)urea, which resulted in the identification of SMU-C80 (EC50 = 31.02 ± 1.01 nM) as a TLR2-specific agonist with a 370-fold improvement in bioactivity. Mechanistic studies revealed that SMU-C80, through TLR1/2, recruits the adaptor protein MyD88 and triggers the NF-κB pathway to release cytokines such as TNF-α and IL-1β from human, but not murine, cells. To the best of our knowledge, it is the first species-specific TLR1/2 agonist reported until now. Moreover, SMU-C80 increased the percentage of T, B, and NK cells ex vivo and activated the immune cells, which suppressed cancer cell growth in vitro. In summary, we obtained a highly efficient and specific human TLR1/2 agonist that acts through the MyD88 and NF-κB pathway, facilitating cytokine release and the simultaneous activation of immune cells that in turn affects the apoptosis of cancer cells.

Synthesis of thienopyridinones via hydrazide-alkyne cyclization

A novel and efficient method for the synthesis of thieno[3,2-c]pyridinones have been developed. The synthetic strategy relies on the synthesis of halothiophene esters utilized as substrates for subsequent Sonogashira cross-coupling reactions. Hydrazinolysis of corresponding esters and following hydrazide-alkyne ring closure transformations resulted in target thienopyridinones in good yields. It is also shown that pure hydrazine monohydrate is required to facilitate the hydrazide formations.

Subtle modifications to a thieno[2,3-d]pyrimidine scaffold yield negative allosteric modulators and agonists of the dopamine D2 receptor

We recently described a structurally novel series of negative allosteric modulators (NAMs) of the dopamine D2 receptor (D2R) based on thieno[2,3-d]pyrimidine 1, showing it can be structurally simplified to reveal low molecular weight, fragment-like NAMs that retain robust negative cooperativity, such as 3. Herein, we report the synthesis and functional profiling of analogues of 3, placing specific emphasis on examining secondary and tertiary amino substituents at the 4-position, combined with a range of substituents at the 5/6-positions (e.g. aromatic/aliphatic carbocycles). We identify analogues with diverse pharmacology at the D2R including NAMs with sub-μM affinity (9h) and, surprisingly, low efficacy partial agonists (9d and 9i).

A Thieno[2,3- d]pyrimidine Scaffold Is a Novel Negative Allosteric Modulator of the Dopamine D2 Receptor

Recently, a novel negative allosteric modulator (NAM) of the D2-like dopamine receptors 1 was identified through virtual ligand screening. This ligand comprises a thieno[2,3-d]pyrimidine scaffold that does not feature in known dopaminergic ligands. Herein, we provide pharmacological validation of an allosteric mode of action for 1, revealing that it is a NAM of dopamine efficacy and identify the structural determinants of this allostery. We find that key structural moieties are important for functional affinity and negative cooperativity, while functionalization of the thienopyrimidine at the 5- and 6-positions results in analogues with divergent cooperativity profiles. Successive compound iterations have yielded analogues exhibiting a 10-fold improvement in functional affinity, as well as enhanced negative cooperativity with dopamine affinity and efficacy. Furthermore, our study reveals a fragment-like core that maintains low μM affinity and robust negative cooperativity with markedly improved ligand efficiency.

Computer-aided identification, synthesis and evaluation of substituted thienopyrimidines as novel inhibitors of HCV replication

A structure-based virtual screening technique was applied to the study of the HCV NS3 helicase, with the aim to find novel inhibitors of the HCV replication. A library of ～450000 commercially available compounds was analysed in silico and 21 structures were selected for biological evaluation in the HCV replicon assay. One hit characterized by a substituted thieno-pyrimidine scaffold was found to inhibit the viral replication with an EC50value in the sub-micromolar range and a good selectivity index. Different series of novel thieno-pyrimidine derivatives were designed and synthesised; several new structures showed antiviral activity in the low or sub-micromolar range.

Thiazole formation through a modified Gewald reaction

The synthesis of thiazoles and thiophenes starting from nitriles, via a modified Gewald reaction has been studied for a number of different substrates. 1,4-Dithiane-2,5-diol was used as the aldehyde precursor to give either 2-substituted thiazoles or 2-substituted aminothiophenes depending on the substitution of the α-carbon to the cyano group.

Benzamidobenzoic acids as potent PqsD inhibitors for the treatment of Pseudomonas aeruginosa infections

Targeting PqsD is a promising novel approach to disrupt bacterial cell-to-cell-communication in Pseudomonas aeruginosa. In search of selective PqsD inhibitors, two series of benzamidobenzoic acids - one published as RNAP inhibitors and the other as PqsD inhibitors - were investigated for inhibitory activity toward the respective other enzyme. Additionally, novel derivatives were synthesized and biologically evaluated. By this means, the structural features needed for benzamidobenzoic acids to be potent and, most notably, selective PqsD inhibitors were identified. The most interesting compound of this study was the 3-Cl substituted compound 5 which strongly inhibits PqsD (IC 50 6.2 μM) while exhibiting no inhibition of RNAP.

Ligand-free Pd-catalyzed C-N cross-coupling/cyclization strategy: An unprecedented access to 1-thienyl pyrroloquinoxalines for the new approach towards apoptosis

The link between PDE4 and apoptosis prompted us to design and synthesize for the first time a series of novel 1-thienyl pyrroloquinoxalines as potential PDE4 inhibitors/apoptotic agents. A ligand-free Pd-catalyzed C-N cross-coupling/cyclization strategy h

An efficient synthesis of 2-aminothiophenes via the gewald reaction catalyzed by an N-methylpiperazine-functionalized polyacrylonitrile fiber

A new N-methylpiperazine-functionalized polyacrylonitrile fiber has been developed to catalyze the Gewald reaction between 2,5-dihydroxy-1,4-dithiane and activated nitriles to afford 3-substituted 2-aminothiophenes in good to excellent yields (65-91%). Low catalyst loading (8.0 mol%), simple procedure, high yields, excellent recyclability, and reusability (up to 10 times with minimal loss of catalytic activity) are attractive features of this fiber catalyst. Georg Thieme Verlag Stuttgart · New York.