22288-78-4

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl 3-amino-2-thiophenecarboxylate is used as a key intermediate in the synthesis of various pharmaceutical compounds for [application reason] the development of new drugs with potential therapeutic properties.
Used in the Synthesis of 4-Nitro and 4-Aminothienyl Ureas:
Methyl 3-amino-2-thiophenecarboxylate is used as a building block for [application type] the synthesis of 4-nitro and 4-aminothienyl ureas, which are important compounds in the field of medicinal chemistry.
Used in the Total Synthesis of Quinazolinocarboline Alkaloids:
Methyl 3-amino-2-thiophenecarboxylate serves as a crucial component in [application type] the total synthesis of quinazolinocarboline alkaloids, which are a class of naturally occurring alkaloids with significant biological activities.
Used in the Preparation of Thienopyrimidinone Analogs:
Methyl 3-amino-2-thiophenecarboxylate is utilized as a starting material for [application type] the preparation of thienopyrimidinone analogs, which have potential applications in the development of new therapeutic agents.

InChI:InChI=1/C6H7NO2S/c1-9-6(8)5-4(7)2-3-10-5/h2-3H,7H2,1H3

Upstream product

• 2689-69-2 methyl tetrahydrothiophen-3-one-2-carboxylate 
• 500-22-1 3-pyridinecarboxaldehyde 
• 443762-07-0 (7-bromothieno[3,2-d]pyrimidin-4-yl)hydrazine hydrochloride 
• 443762-12-7 (6-(thien-3-yl)thieno[3,2-d]pyrimidin-4-yl)hydrazine hydrochloride 
• 79128-68-0 methyl 3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate 
• 871-29-4 β-Chloroacrylonitrile 
• 2365-48-2 Methyl thioglycolate 
• 920-37-6 2-Chloroacrylonitrile 
• 67-56-1 methanol 
• 55341-87-2 3-aminothiophene-2-carboxylic acid 

Downstream Products

• 16285-69-1 3-(formylamino)-2-thiophenecarboxylic acid methyl ester 
• 18002-05-6 2-p-tolyl-3H-thieno[3,2-d]pyrimidin-4-one 
• 18678-14-3 4-Hydroxy-2-phenyl-thieno<3,2-d>pyrimidin 
• 18678-13-2 2-methylthieno[3,2-d]pyrimidin-4-ol 
• 74772-16-0 methyl 3-(1H-pyrrol-1-yl)thiophene-2-carboxylate 
• 96516-57-3 ethyl 4,7-dihydro-7-oxo-5-phenylthieno<3,2-b>pyridine-6-carboxylate 
• 16233-51-5 1H-thieno[3,2-d]pyrimidine-2,4-dione 
• 134650-54-7 benzyl 2-cyano-2-(1,2,3,4-tetrahydro-4-oxothieno<3,2-d>pyrimidin-2-ylidene)acetate 
• 159181-16-5 methyl 3-<(phenylmethoxy)aminocarbonylamino>-2-thiophenecarboxylate 
• 26137-08-6 methyl 3-bromothiophene-2-carboxylate 
• 62353-77-9 3-iodothiophene-2-carboxylic acid methyl ester 
• 78756-27-1 sodium 3-aminothiophene-2-carboxylate 
• 137844-98-5 3-aminothiophene-2-carbohydrazide 
• 59337-92-7 2-(carbomethoxy)thiophene-3-sulfonyl chloride 

Relevant academic research and scientific papers

Design, synthesis, docking, molecular dynamics and bioevaluation studies on novel N-methylpicolinamide and thienopyrimidine derivatives with inhibiting NF-κB and TAK1 activities: Cheminformatics tools RDKit applied in drug design

Using cheminformatics tools RDKit and literature investigation, four series of 24 thienopyrimidine/N-methylpicolinamide derivatives substituted with pyrimidine were designed, synthesized and evaluated for activities against three cancer cell lines (MDA-MB-231, HCT116 and A549), TAK1 kinase and NF-κB signaling pathway. Almost all compounds showed selectivity toward the A549 cell lines and the most promising compound 38 could inhibit TAK1 kinase and NF-κB signaling pathway with the IC50 values of 0.58 and 0.84 μM. Moreover, 38 can induce cell cycle arrest of A549 cells at the G2/M checkpoint with 30.57% and induce apoptosis (34.94%) in a concentration-dependent manner. And western blot showed that compound 38 could inhibit TNF-α-induced IκBα phosphorylation, IκBα degradation, p65 phosphorylation and TAK1 phosphorylation, and reduce the expression of p65. What's more, the studies of docking, molecular dynamics, MM/PBSA and frequency analysis theoretically supported the conclusions of the bioevaluation.

Scaffold Hopping of Natural Product Evodiamine: Discovery of a Novel Antitumor Scaffold with Excellent Potency against Colon Cancer

Inspired by the natural product evodiamine, a novel antitumor indolopyrazinoquinazolinone scaffold was designed by scaffold hopping. Structure-activity relationship studies led to the discovery of compound 15j, which shows low nanomolar inhibitory activity against the HCT116 cell line. Further antitumor mechanism studies indicated that compound 15j acted by the dual inhibition of topoisomerase 1 and tubulin and induced apoptosis with G2 cell-cycle arrest. The quaternary ammonium salt of compound 15j (compound 15js) exhibited excellent in vivo antitumor activity (TGI = 66.6%) in the HCT116 xenograft model with low toxicity. Indolopyrazinoquinazolinone derivatives represent promising multitargeting antitumor leads for the development of novel antitumor agents.

Copper-mediated reduction of azides under seemingly oxidising conditions: Catalytic and computational studies

The reduction of aryl azides in the absence of an obvious reducing agent is reported. Careful catalyst design led to the production of anilines in the presence of water and air. The reaction medium (toluene/water) is crucial for the success of the reaction, as DFT calculations support the formation of benzyl alcohol as the oxidation product. A singular catalytic cycle is presented for this transformation based on four key steps: nitrene formation through nitrogen extrusion, formal oxidative addition of water, C(sp3)-H activation of toluene and reductive elimination.

Synthesis of Thieno[3,2-e][1,4]diazepin-2-ones: Application of an Uncatalysed Pictet-Spengler Reaction

A series of 5-substituted thieno[3,2-e][1,4]diazepin-2-ones was synthesized in four steps from methyl 3-aminothiophene-2-carboxylate. After the coupling of 3-aminothiophene with α-amino acids, the key final step that involves an uncatalysed Pictet-Spengler reaction allowed the cyclization of the seven-membered diazepinone ring. The reaction was first optimized and then exemplified in three different series (phenylalanine, alanine and proline) that led to 24 target diazepinones, which includes 19 optically pure diastereomers. A new synthetic approach that uses an uncatalysed Pictet-Spengler cyclization reaction has been developed to access [3,2-e]-type fused thienodiazepinones.

Facile and efficient one-pot procedure for thieno[2,3-e][1,2,3]triazolo[1, 5-a]pyrimidines preparation

Base-catalyzed cycloaddition reactions of heterocyclic azides with activated nitriles were studied. Convenient, efficient, and high-yield synthetic method for thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines preparation from available starting reagents without complicated protocols was elaborated. Such an approach allows creation of broad combinatorial libraries for drug discovery. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

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.

THIENOPYRIMIDINE AS CDC7 KINASE INHIBITORS

The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof, or a prodrug thereof, which is useful for the prophylaxis or treatment of cancer

Thienopyrimidine-based inhibitors of the Src family

Various thienopyrimidine-based analog compounds that selectively inhibit the Src family of tyrosine kinases. These compounds are thienopyrimidines and contain a hydrozone bridge created by heating a thienopyrimidine hydrazine with an aldehyde in ethanol at reflux. Such compounds are useful in the treatment of various diseases including hyperproliferative diseases, hematologic diseases, osteoporosis, neurological diseases, autoimmune diseases, allergic/immunological diseases, or viral infections.

A rapid conversion of 3-oxothiolanes into 3-aminothiophenes

3-Oxotetrahydrothiophenes can be rapidly converted into 3-aminothiophenes by refluxing with hydroxylamine hydrochloride in a polar solvent, usually acetonitrile.

Substituted 7-amino-thienopyridine derivatives as gastric acid secretion inhibitors

Substituted 4-aminothienopyridine derivatives which are inhibitors of gastric acid secretion. A compound of the invention is 6-butyryl-7-(2-isopropylphenylamino)-thieno[3,2-b]pyridine.