14080-51-4

Usage

Uses

Used in Organic Synthesis:
2-Amino-thiophene-3-carboxylic acid amide is used as a key intermediate for the synthesis of a variety of organic compounds. Its unique structure allows for the creation of diverse chemical entities, facilitating the development of novel molecules with potential applications across different industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-Amino-thiophene-3-carboxylic acid amide is utilized as a building block for the development of new drugs. Its biological activities and chemical properties make it a promising candidate for the creation of therapeutic agents targeting various diseases and conditions.
Used in Agrochemical Production:
2-Amino-thiophene-3-carboxylic acid amide is employed as a chemical intermediate in the production of agrochemicals. Its role in the synthesis of these compounds contributes to the development of effective products for agricultural applications, such as pesticides and herbicides.
Used in Dye Manufacturing:
2-AMINO-THIOPHENE-3-CARBOXYLIC ACID AMIDE is also used in the manufacturing of dyes, where its chemical structure contributes to the color-producing properties of the final product. Its versatility in synthesis allows for the creation of a wide range of dyes with different color characteristics, suitable for various applications.
Used in Pharmaceutical Industry for Drug Development:
2-Amino-thiophene-3-carboxylic acid amide holds potential in the pharmaceutical industry for the development of new drugs due to its biological activities. Its presence in the synthesis of drug candidates can lead to the discovery of innovative therapeutics with improved efficacy and safety profiles.

InChI:InChI=1/C5H6N2OS/c6-4(8)3-1-2-9-5(3)7/h1-2H,7H2,(H2,6,8)

Upstream product

• 6851-93-0 thioacetaldehyde 
• 107-91-5 cyanoacetic acid amide 
• 40018-26-6 1,4-dithiane-2,5-diol 
• 75-07-0 acetaldehyde 

Downstream Products

• 21582-51-4 2-methylthieno[2,3-d]pyrimidin-4(3H)-one 
• 18740-38-0 1H-thieno[2,3-d]pyrimidine-2,4-dione 
• 117516-97-9 2-thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-one 
• 773140-09-3 2-(2-fluoro-benzoylamino)-thiophene-3-carboxylic acid amide 
• 14080-50-3 thieno[2,3-d]pyrimidin-4(3H)one 
• 775301-62-7 2-(2-(2-chlorophenyl)acetamido)thiophene-3-carboxamide 
• 923442-15-3 2-(2-(4-ethoxyphenyl)acetamido)thiophene-3-carboxamide 
• 771503-50-5 2-(2-(3,4-dimethoxyphenyl)acetamido)thiophene-3-carboxamide 
• 756849-36-2 2-(2-(biphenyl-4-yl)acetamido)thiophene-3-carboxamide 
• 870698-01-4 2-(2-(4-(2-(trifluoromethyl)phenylsulfonyl)piperazin-1-yl)acetamido)thiophene-3-carboxamide 
• 1246072-89-8 2-(2-(benzo[b]thiophen-3-yl)acetamido)thiophene-3-carboxamide 
• 1308685-84-8 2-(2-(2-phenylthiazol-4-yl)acetamido)thiophene-3-carboxamide 
• 1308685-78-0 2-cinnamamidothiophene-3-carboxamide 
• 1308685-98-4 2-(2-(4-cyanophenyl)acetamido)thiophene-3-carboxamide 

Relevant academic research and scientific papers

A novel series of positive modulators of the AMPA receptor: Discovery and structure based hit-to-lead studies

Starting from an HTS derived hit 1, application of biostructural data facilitated rapid optimization to lead 22, a novel AMPA receptor modulator. This is the first demonstration of how structure based drug design can be exploited in an optimization program for a glutamate receptor.

Anti-glioma effects of 2-aminothiophene-3-carboxamide derivatives, ANO1 channel blockers

Anoctamin1 (ANO1), a calcium-activated chloride ion channel (CaCC), is associated with various physiological functions including cancer progression and metastasis/invasion. ANO1 has been considered as a promising target for cancer therapeutics as ANO1 is over-expressed in a variety of cancers including glioblastoma (GBM) and inhibition of ANO1 has been reported to suppress cell proliferation, migration and invasion in GBM. GBM is one of the most common and aggressive cancers with poor prognosis with median survival for 15 months. Lack of effective treatment options against GBM emphasizes urgent necessity of effective GBM therapeutics. In an effort to discover potent and selective ANO1 inhibitors capable of inhibiting GBM cells, we have designed and synthesized a series of new 2-aminothiophene-3-carboxamide derivatives and performed SAR studies using both fluorescent cellular membrane potential assay and whole-cell patch-clamp recording. We observed that among these substances, 9c and 10q strongly suppress ANO1 channel activities and possess remarkable selectivity over ANO2. Unique structural feature of 10q, a cyclopentane-fused thiophene-3-carboxamide derivative, is the presence of benzoylthiourea functionality which dramatically contributes to activity. Both 9c and 10q suppress more strongly proliferation of GBM cells than four reference compounds including 3, Ani-9 and are also capable of inhibiting much more strongly colony formation than reference compounds in both 2D colony formation assay and 3D soft agar assay using U251 glioma cells. In addition, 9c and 10q suppress far more strongly migration/invasion of GBM cells than reference compounds. We, for the first time, found that the combination of ANO1 inhibitor (9c or 3) and temozolomide (TMZ) brings about remarkable synergistic effects in suppressing proliferation of GBM cells. Our study may provide an insight into designing selective and potent ANO1 inhibitors aiming at GBM treatment.

Concise synthesis of tpca-1 and related thiophene-carboxamides by cross coupling

A synthesis of 5-substituted 2-[(aminocarbonyl)amino]-3-thiophene-carboxamides is described. The coupling reaction of 2-ureidothiophene-3-carboxamide and various aryl compounds allows the concise approach of promising candidates for IKK-2 inhibitor, such as TPCA-1.

SUBSTITUTED 2- AMIDOQUINAZOL-4-ONES AS MATRIX METALLOPROTEINASE-13 INHIBITORS

The present invention provides a novel amide derivative having a matrix metalloproteinase inhibitory activity, and useful as a pharmaceutical agent, which is a compound represented by the formula (I) wherein ring A is an optionally substituted, nitrogen containing heterocycle, ring B is an optionally substituted monocyclic homocycle or an optionally substituted monocyclic heterocycle, Z is N or NR1 (R1 is a hydrogen atom or an optionally substituted hydrocarbon group), is a single bond or a double bond, R2 is a hydrogen atom or an optionally substituted hydrocarbon group, X is an optionally substituted spacer having 1 to 6 atoms, ring C is (1) an optionally substituted homocycle or (2) an optionally substituted heterocycle other than a ring represented by (II) (X′ is S, O, SO, or CH2), and at least one of ring B and ring C has substituent(s), provided that N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]2 hydroxypropyl}5,6 dimethyl 4 oxo 1,4 dihydrothieno[2,3-d]pyrimidine-2-carboxamide is excluded, or a salt thereof.

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.

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.

THIENOPYRIDINE AND THIENOPYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are thienopyridine and thienopyrimidine compounds of formula (I) for treatment of JAK kinase mediated diseases, including JAK2 kinase-, JAK3 kinase- or TYK2 kinase-mediated diseases. Also provided are pharmaceutical compositions comprising

Discovery of (+)-N-(3-aminopropyl)-N-[1-(5-benzyl-3-methyl-4-oxo-[1,2] thiazolo[5,4- d ]pyrimidin-6-yl)-2-methylpropyl]-4-methylbenzamide (AZD4877), a kinesin spindle protein inhibitor and potential anticancer agent

Structure-activity relationship analysis identified (+)-N-(3-aminopropyl)- N-[1-(5-benzyl-3-methyl-4-oxo-[1,2]thiazolo[5,4-d]pyrimidin-6-yl) -2-methylpropyl]-4-methylbenzamide (AZD4877), from a series of novel kinesin spindle protein (KSP) inhibitors, as exhibiting both excellent biochemical potency and pharmaceutical properties suitable for clinical development. The selected compound arrested cells in mitosis leading to the formation of the monopolar spindle phenotype characteristic of KSP inhibition and induction of cellular death. A favorable pharmacokinetic profile and notable in vivo efficacy supported the selection of this compound as a clinical candidate for the treatment of cancer.

ANTI-CANCER DRUGS AND USES RELATING THERETO FOR METASTATIC MALIGNANT MELANOMA AND OTHER CANCERS

The present invention discloses triazene analogs of the general formula (I) and formula (II), their tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, and pharmaceutically acceptable salts thereof for the metastatic malignant melanoma and other cancers including but not limited to lymphomas, sarcomas, carcinomas, and gliomas. The invention further discloses a process for the preparation of the above said triazene analogs of formula (I) and formula (II), and their pharmaceutically acceptable compositions.

ANTI-CANCER DRUGS AND USES RELATING THERETO FOR METASTATIC MALIGNANT MELANOMA AND OTHER CANCERS

The present invention discloses triazene analogs of the general formula (I) and formula (II), their tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, and pharmaceutically acceptable salts thereof for the metastatic malignant melanoma and other cancers including but not limited to lymphomas, sarcomas, carcinomas, and gliomas. The invention further discloses a process for the preparation of the above said triazene analogs of formula (I) and formula (II), and their pharmaceutically acceptable compositions.