42225-04-7

Basic information

• Product Name: 2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE
• Synonyms: BUTTPARK 99\08-43;2-Amino-3-cyano-6-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene;2-Amino-6-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile ,97%;2-amino-6-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile(SALTDATA: FREE);2-amino-6-methyl-4,5,6,7-tetrahydrobenzothiophene-3-carbonitrile;4,5,6,7-Tetrahydrobenzo[b]thiophene-3-carbonitrile, 2-amino-6-methyl-;2-Amino-6-methyl-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitr;2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE
• CAS NO: 42225-04-7
• Molecular Formula: C₁₀H₁₂N₂S
• Molecular Weight: 192.28
• Mol File: 42225-04-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 147℃
• Boiling Point: 392.8 °C at 760 mmHg
• Flash Point: 191.4 °C
• Appearance: /
• Density: 1.22 g/cm³
• Vapor Pressure: 2.23E-06mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE(42225-04-7)
• EPA Substance Registry System: 2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE(42225-04-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 42225-04-7(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C10H12N2S/c1-6-2-3-7-8(5-11)10(12)13-9(7)4-6/h6H,2-4,12H2,1H3/t6-/m1/s1

Upstream product

• 589-92-4 1-methylcyclohexan-4-one 
• 109-77-3 malononitrile 

Downstream Products

• 1243985-34-3 2-(4-chlorophenyl)-7-methyl-5,6,7,8-tetrahydro[b]benzothieno[2,3-d]pyrimidin-4-amine 
• 1243985-35-4 2-(2-chlorophenyl)-7-methyl-5,6,7,8-tetrahydro[b]benzothieno[2,3-d]pyrimidin-4-amine 
• 375355-54-7 C₁₈H₁₇N₃OS₂ 
• 1243985-33-2 2-(4-methoxyphenyl)-7-methyl-5,6,7,8-tetrahydro[b]benzothieno[2,3-d]pyrimidin-4-amine 
• 1243985-32-1 7-methyl-2-(4-methylphenyl)-5,6,7,8-tetrahydro[b]benzothieno[2,3-d]pyrimidin-4-amine 
• 1243985-31-0 7-methyl-2-phenyl-5,6,7,8-tetrahydro[b]benzothieno[2,3-d]pyrimidin-4-amine 

Relevant articles and documents

Novel tetrahydrobenzo[b]thiophen-2-yl)urea derivatives as novel α-glucosidase inhibitors: Synthesis, kinetics study, molecular docking, and in vivo anti-hyperglycemic evaluation

α-Glucosidase inhibitors, which can inhibit the digestion of carbohydrates into glucose, are one of important groups of anti-type 2 diabetic drugs. In the present study, we report our effort on the discovery and optimization of α-glucosidase inhibitors with tetrahydrobenzo[b]thiophen-2-yl)urea core. Screening of an in-house library revealed a moderated α-glucosidase inhibitors, 5a, and then the following structural optimization was performed to obtain more efficient derivatives. Most of these derivatives showed increased inhibitory activity against α-glucosidase than the parental compound 5a (IC50 of 26.71 ± 1.80 μM) and the positive control acarbose (IC50 of 258.53 ± 1.27 μM). Among them, compounds 8r (IC50 = 0.59 ± 0.02 μM) and 8s (IC50 = 0.65 ± 0.03 μM) were the most potent inhibitors, and showed selectivity over α-amylase. The direct binding of both compounds with α-glucosidase was confirmed by fluorescence quenching experiments. Kinetics study revealed that these compounds were non-competitive inhibitors, which was consistent with the molecular docking results that compounds 8r and 8s showed high preference to bind to the allosteric site instead of the active site of α-glucosidase. In addition, compounds 8r and 8s were not toxic (IC50 > 100 μM) towards LO2 and HepG2 cells. Finally, the in vivo anti-hyperglycaemic activity assay results indicated that compounds 8r could significantly decrease the level of plasma glucose and improve glucose tolerance in SD rats treated with sucrose. The present study provided the tetrahydrobenzo[b]thiophen-2-yl)urea chemotype for developing novel α-glucosidase inhibitors against type 2 diabetes.

Structure-Guided Optimization of Inhibitors of Acetyltransferase Eis from Mycobacterium tuberculosis

The enhanced intracellular survival (Eis) protein of Mycobacterium tuberculosis (Mtb) is a versatile acetyltransferase that multiacetylates aminoglycoside antibiotics abolishing their binding to the bacterial ribosome. When overexpressed as a result of promoter mutations, Eis causes drug resistance. In an attempt to overcome the Eis-mediated kanamycin resistance of Mtb, we designed and optimized structurally unique thieno[2,3-d]pyrimidine Eis inhibitors toward effective kanamycin adjuvant combination therapy. We obtained 12 crystal structures of enzyme-inhibitor complexes, which guided our rational structure-based design of 72 thieno[2,3-d]pyrimidine analogues divided into three families. We evaluated the potency of these inhibitors in vitro as well as their ability to restore the activity of kanamycin in a resistant strain of Mtb, in which Eis was upregulated. Furthermore, we evaluated the metabolic stability of 11 compounds in vitro. This study showcases how structural information can guide Eis inhibitor design.

Solvent-free synthesis of 2-aminothiophene-3-carbonitrile derivatives using high-speed vibration milling

The solvent-free synthesis of 2-aminothiophene-3-carbonitrile derivatives by high-speed vibration milling using the inexpensive and environmentally friendly Et2NH as a catalyst was studied. The reaction conditions were optimised and the derivatives were obtained in good yield. This method has advantages in terms of short reaction time and facile conditions.