77651-38-8

Basic information

• Product Name: 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE
• Synonyms: CHEMBRDG-BB 3000477;ASISCHEM Z28662;AURORA 4809;4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE, 2-AMINO-5,6-DIHYDRO-;AKOS BBS-00007971;AKOS MSC-0466;AKOS 92560;2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE
• CAS NO: 77651-38-8
• Molecular Formula: C₈H₁₀N₂OS
• Molecular Weight: 182.24
• Product Categories: Thiophene
• Mol File: 77651-38-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 169-171℃
• Boiling Point: 308.2 °C at 760 mmHg
• Flash Point: 140.2 °C
• Appearance: /
• Density: 1.412
• Vapor Pressure: 0.000689mmHg at 25°C
• Refractive Index: 1.702
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 15.70±0.20(Predicted)
• CAS DataBase Reference: 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE(77651-38-8)
• EPA Substance Registry System: 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE(77651-38-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 77651-38-8(Hazardous Substances Data)

Usage

Chemical Properties

Gray solid

InChI:InChI=1/C8H10N2OS/c9-7(11)6-4-2-1-3-5(4)12-8(6)10/h1-3,10H2,(H2,9,11)

Upstream product

• 70291-62-2 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile 
• 120-92-3 cyclopentanone 
• 107-91-5 cyanoacetic acid amide 

Downstream Products

• 299954-05-5 2-(2-chloroacetamido)-5,6-dihydro-4H-cyclopenta[b]thiophen-3-carboxamide 
• 1242054-26-7 2-(2-(4-nitrophenylthio)acetamido)-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxamide 
• 14346-25-9 3,5,6,7-tetrahydro-4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one 
• 91225-70-6 2-(chloromethyl)-3,5,6,7-tetrahydro-4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one 
• 1443930-97-9 2-(3,4-dihydroxyphenyl)-3,5,6,7-tetrahydro-4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one 
• 1609388-83-1 N-(3-carbamoyl-5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)-5-phenyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide 

Relevant articles and documents

Synthesis and characterization of 1,2,4-triazolo[1,5-a]pyrimidine-2-carboxamide-based compounds targeting the PA-PB1 interface of influenza A virus polymerase

Influenza viruses (Flu) are responsible for seasonal epidemics causing high rates of morbidity, which can dramatically increase during severe pandemic outbreaks. Antiviral drugs are an indispensable weapon to treat infected people and reduce the impact on

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.

Exploiting drug-resistant enzymes as tools to identify thienopyrimidinone inhibitors of human immunodeficiency virus reverse transcriptase-associated ribonuclease H

The thienopyrimidinone 5,6-dimethyl-2-(4-nitrophenyl)thieno[2,3-d] pyrimidin-4(3H)-one (DNTP) occupies the interface between the p66 ribonuclease H (RNase H) domain and p51 thumb of human immunodeficiency virus reverse transcriptase (HIV RT), thereby indu