329068-27-1

Basic information

• Product Name: 2-AMINO-N-PHENYL-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBOXAMIDE
• Synonyms: 2-AMINO-N-PHENYL-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBOXAMIDE;2-amino-N-phenyl-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiophene-3-carboxamide;Oprea1_713403;SBB001167;ZINC00130306
• CAS NO: 329068-27-1
• Molecular Formula: C16H18N2OS
• Molecular Weight: 286.4
• Mol File: 329068-27-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-AMINO-N-PHENYL-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-N-PHENYL-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBOXAMIDE(329068-27-1)
• EPA Substance Registry System: 2-AMINO-N-PHENYL-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[B]THIOPHENE-3-CARBOXAMIDE(329068-27-1)

Safety Data

• Hazardous Substances Data: 329068-27-1(Hazardous Substances Data)

Upstream product

• 621-03-4 cyanoacetanilide 
• 62-53-3 aniline 
• 502-42-1 cycloheptanone 

Relevant articles and documents

Exploring the cycloheptathiophene-3-carboxamide scaffold to disrupt the interactions of the influenza polymerase subunits and obtain potent anti-influenza activity

With the aim to identify small molecules able to disrupt PA-PB1 subunits interaction of influenza virus (flu) RNA-dependent RNA polymerase, and based on previous structural and computational information, in this paper we have designed and synthesized a new series of cycloheptathiophene-3-carboxamide (cHTC) derivatives. Their biological evaluation led to highlight important structural insights along with new interesting compounds, such as the 2-hydroxybenzamido derivatives 29, 31, and 32, and the 4-aminophenyl derivative 54, which inhibited viral growth in the low micromolar range (EC50 = 0.18–1.2 μM) at no toxic concentrations (CC50 > 250 μM). This study permitted to obtain among the most potent anti-flu compounds within the PA-PB1 interaction inhibitors, confirming the cHTC scaffold as particularly suitable to achieve innovative anti-flu agents.

Substituted 2-Acylaminocycloalkylthiophene-3-carboxylic Acid Arylamides as Inhibitors of the Calcium-Activated Chloride Channel Transmembrane Protein 16A (TMEM16A)

Transmembrane protein 16A (TMEM16A), also called anoctamin 1 (ANO1), is a calcium-activated chloride channel expressed widely mammalian cells, including epithelia, vascular smooth muscle tissue, electrically excitable cells, and some tumors. TMEM16A inhibitors have been proposed for treatment of disorders of epithelial fluid and mucus secretion, hypertension, asthma, and possibly cancer. Herein we report, by screening, the discovery of 2-acylaminocycloalkylthiophene-3-carboxylic acid arylamides (AACTs) as inhibitors of TMEM16A and analysis of 48 synthesized analogs (10ab-10bw) of the original AACT compound (10aa). Structure-activity studies indicated the importance of benzene substituted as 2- or 4-methyl, or 4-fluoro, and defined the significance of thiophene substituents and size of the cycloalkylthiophene core. The most potent compound (10bm), which contains an unusual bromodifluoroacetamide at the thiophene 2-position, had IC50 of ～30 nM, ～3.6-fold more potent than the most potent previously reported TMEM16A inhibitor 4 (Ani9), and >10-fold improved metabolic stability. Direct and reversible inhibition of TMEM16A by 10bm was demonstrated by patch-clamp analysis. AACTs may be useful as pharmacological tools to study TMEM16A function and as potential drug development candidates.