40106-12-5

Basic information

• Product Name: 2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBOXAMIDE
• Synonyms: NSC727447;2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiophene-3-carboxamide
• CAS NO: 40106-12-5
• Molecular Formula: C₁₀H₁₄N₂OS
• Molecular Weight: 210.3
• Mol File: 40106-12-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 347.5°Cat760mmHg
• Flash Point: 163.9°C
• Appearance: /
• Density: 1.278g/cm³
• Vapor Pressure: 5.38E-05mmHg at 25°C
• Refractive Index: 1.639
• Storage Temp.: room temp
• Solubility: DMSO: >10mg/mL
• CAS DataBase Reference: 2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBOXAMIDE(40106-12-5)
• EPA Substance Registry System: 2-AMINO-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBOXAMIDE(40106-12-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 40106-12-5(Hazardous Substances Data)

Usage

General Description

2-Amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide is a chemical compound that belongs to the class of organic compounds known as tetrahydrothiophenes. These are organosulfur compounds that contain a saturated, five-member ring with one sulfur atom and four carbon atoms. As an organic compound, it has the molecular formula C8H12N2OS. Details about its physical characteristics, bioavailability, toxicity, and specific applications are not extensively documented publicly, and it may require further study to comprehensively understand its practical uses and potential risks in different applications. It's crucial to handle this and similar compounds with proper safety measures in accordance with chemical guidelines.

InChI:InChI=1/C10H14N2OS/c11-9(13)8-6-4-2-1-3-5-7(6)14-10(8)12/h1-5,12H2,(H2,11,13)

Upstream product

• 107-91-5 cyanoacetic acid amide 
• 502-42-1 cycloheptanone 
• 23917-22-8 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carbonitrile 

Downstream Products

• 95211-47-5 1,2-dihydro-3-methyl-1-oxo-cyclohepta(b)thieno[2,3-d]pyrimidine 
• 40106-31-8 6,7,8,96,7,8,9-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4(3H)-one-tetrahydro-5H-cyclohepta[4,5]thieno[2,3-d]pyrimidin-4(3H)-one 
• 63667-94-7 2-phenyl-1,2,3,5,6,7,8,9-octahydro-cyclohepta[4,5]thieno[2,3-d][1,3,2]diazaborinin-4-one 

Relevant articles and documents

Synthesis and cytotoxic activity of some new heterocycles incorporating cyclohepta[b]thiophene-3-carboxamide derivatives

A series of 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxamide-heterocyclic hybrids were synthesized, characterized and their cytotoxic potencies were assessed on four human cell lines. Cyanoacetamide derivative (5) was used as the key synthetic intermediate for the synthesis many derivatives in this study, derivatives 9, 11, 12 were formed by coupled compound 5 with different aryl/heteryl diazonium chlorides, Gewald reaction and Knoevenagel condensation were used for synthesis derivatives 13, 14, 16 by treated cyanoacetamide (5) with different reagents. In another route, compound 5 treated with phenyl isothiocyanate give thiocarbamoyl derivative (7) which used as intermediate underwent oxidative cyclization with different moieties to offer the corresponding thiazoles and thiophene 18, 19, 20, 21, respectively. in vitro cytotoxic activity of prepared compounds were tested against four human tumor cell lines. The result revealed that compound 11a displayed promising cytotoxic activity against HepG2, HCT-116, MCF-7, and PC3 cancer cell lines comparing to the positive control (Doxorubicin).

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.

Structure–activity relationships for inhibitors of Pseudomonas aeruginosa exoenzyme S ADP-ribosyltransferase activity

During infection, the Gram-negative opportunistic pathogen Pseudomonas aeruginosa employs its type III secretion system to translocate the toxin exoenzyme S (ExoS) into the eukaryotic host cell cytoplasm. ExoS is an essential in vivo virulence factor that enables P. aeruginosa to avoid phagocytosis and eventually kill the host cell. ExoS elicits its pathogenicity mainly via ADP-ribosyltransferase (ADPRT) activity. We recently identified a new class of ExoS ADPRT inhibitors with in vitro IC50 of around 20 μM in an enzymatic assay using a recombinant ExoS ADPRT domain. Herein, we report structure–activity relationships of this compound class by comparing a total of 51 compounds based on a thieno [2,3-d]pyrimidin-4(3H)-one and 4-oxo-3,4-dihydroquinazoline scaffolds. Improved inhibitors with in vitro IC50 values of 6 μM were identified. Importantly, we demonstrated that the most potent inhibitors block ADPRT activity of native full-length ExoS secreted by viable P. aeruginosa with an IC50 value of 1.3 μM in an enzymatic assay. This compound class holds promise as starting point for development of novel antibacterial agents.