173281-01-1

Usage

General Description

2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]THIOPYRAN-3-CARBOXYLIC ACID ETHYL ESTER is a chemical compound with the molecular formula C11H13NO4S2. It is an ethyl ester derivative of thieno[2,3-c]thiopyran-3-carboxylic acid, containing an amino group and a carboxylic acid group. 2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]THIOPYRAN-3-CARBOXYLIC ACID ETHYL ESTER has potential biological and pharmacological activities and has been studied for its potential applications in the pharmaceutical industry. It may possess anti-inflammatory, antioxidant, and neuroprotective properties, and its chemical structure makes it a valuable candidate for further research and development in drug discovery and medicinal chemistry.

Upstream product

• 1072-72-6 Tetrahydrothiopyran-4-one 
• 105-56-6 ethyl 2-cyanoacetate 
• 10292-84-9 ethyl 2-cyano-2-(2H-thiopyran-4(3H,5H,6H)-ylidene)acetate 
• 4131-74-2 Dimethyl 3,3'-thiodipropionate 
• 4160-61-6 3-methoxycarbonyltetrahydropyran-4-one 

Downstream Products

• 1180526-91-3 ethyl 2-[(triphenylphosphanylidene)amino]-4,7-dihydro-5H-thieno[2,3-c]thiopyran-3-carboxylate 

Relevant academic research and scientific papers

New Hetero-Annelation Reactions Using N-[bis-(Methylthio)-methylene]-amino and Related Reagents

Reaction of acyclic (R1-3) and cyclic (R4-5) BMMA (=N-[bis-(methylthio)-methylene]-amino) reagents with Gewald-type thiophene derivatives (2, 3) led to annelation of pyrimidine moieties. Thus, linear thiazolo- or thiazino- and pyrrolo-, pyrido- or azepino-fused thiopyrano[4′,3′:4,5]thieno-[2,3-d]pyrimidines (5 and 6) as well as the angular imidazo-fused thiopyrano[4′,3′:4,5]thieno-[2,3-d]pyrimidine 8 were easily obtained from one-pot reactions in good yields.

Synthesis of New Fused Heterocycles by Annelation of Thiopyranothienopyrimidines

Appropriately substituted thienothiopyrans (2, 3, 5, 6, 10, 11) were converted into 1,5,6,8-tetrahydro-2H-thiopyranothienopyrimidin-4(3H)-ones (4, 7, 12).These in turn were used as key intermediates for annelations of thiazolo and 1,3-thiazino moieties to yield the tetracyclic target structures 7, 8, 9, and 13, derived from two novel heterocyclic ring systems. - Keywords: Fused S,N-heterocycles; Thienothiopyrans; 1,5,6,8-Tetrahydro-2H-thiopyranothienopyrimidin-4(3H)-ones; Thiazolothiopyranothienopyrimidin-5-ones; 2H,6H,8H-Thiopyranothienopyrimidothiazin-6-one.

Efficient three-component Gewald reactions under Et3N/H 2O conditions

In a medium consisting of triethylamine and water, methylene ketones undergo room temperature Gewald reactions with elemental sulfur and ethyl cyanoacetate (or malononitrile) to yield 2 aminothiophene derivatives efficiently within short time periods. Because of the high polarity of the medium, products precipitate in the reaction mixtures spontaneously. This makes isolation of the products easy by simple filtration and avoids cumbersome chromatographic separations. Mechanistic studies suggest that the reactions proceed via a Knoevenagel condensation pathway(equation presented). 2013

Aqueous DABCO, an efficient medium for rapid organocatalyzed Knoevenagel condensation and the Gewald reaction

In the presence of water and 1,4-diazabicyclo[2.2.2]octane, several aldehydes and cyclic ketones underwent efficient Knoevenagel condensation with malononitrile and ethyl cyanoacetate to produce the respective α.β-unsaturated systems within fairly short time periods. As a result, high yields of conjugated products were easily obtained. Products could be engaged in a Gewald reaction, either stepwise or in situ, to produce efficiently their respective 2-aminothiophenes within 4-7 h. TUeBITAK.

THIENOPYRIMIDINE INHIBITORS OF ATYPICAL PROTEIN KINASE C

The present invention provides a compound of formula (I) or a salt thereof, wherein R1, R2, R3, R4, R5, R6, A, G, M, Q and X are as defined herein. A compound of formula (I) and its salts h

NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS

The present application relates to cannabinoid receptor ligands containing compounds of formula (I) wherein A, R1, R2, and R3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

Efficient synthesis and fungicidal activities of 3,5,6,8-tetrahydro-4h- thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-ones

The carbodiimides 4, obtained from reactions of iminophosphorane 3 with aromatic isocyanates, reacted with amines, phenols, or ROH to give 2-substituted 3,5,6,8-tetrahydro-4H-thiopyrano[4′,3′ :4,5]thieno [2,3-d]pyrimidin-4-ones 6 in the presence of a catalytic amount of sodium alkoxide or solid potassium carbonate in satisfactory yields. Compounds 6 exhibited fungicidal activity. For example, compounds 6e, 6m, and 6s showed 70% inhibition activities against Dothiorella gregaria in 100 mg/L.

Synthesis and SAR of thiophene containing kinesin spindle protein (KSP) inhibitors

We have identified and synthesized a series of thiophene containing inhibitors of kinesin spindle protein. SAR studies led to the synthesis of 33, which was co-crystallized with KSP and determined to bind to an allosteric pocket previously described for o

ANTHELMINTIC AND INSECTICIDAL THIOPHENE DERIVATIVES

Novel anthelmintic compositions containing thiophene derivatives as active ingredients are disclosed.

Discovery and SAR of a novel selective and orally bioavailable nonpeptide classical competitive inhibitor class of protein-tyrosine phosphatase 1B

Reversible phosphorylation and dephosphorylation of key proteins on tyrosine residues are important parts of intracellular signaling triggered by hormones and other agents. Recent knock-out studies in mice have identified PTP1B as a potential target for t