85716-87-6

Basic information

• Product Name: ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE
• Synonyms: AKOS B019362;2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-BENZO[B]THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER;ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE;ART-CHEM-BB B019362;2-isothiocyanato-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester;ethyl 2-isothiocyanato-4,5,6,7-tetrahydrobenzothiophene-3-carboxylate;IVK/1270156;ZINC00161819
• CAS NO: 85716-87-6
• Molecular Formula: C₁₂H₁₃NO₂S₂
• Molecular Weight: 267.37
• Mol File: 85716-87-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 45 °C
• Boiling Point: 178 °C
• Flash Point: 222.9°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 4.1E-08mmHg at 25°C
• Refractive Index: 1.652
• CAS DataBase Reference: ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE(85716-87-6)
• EPA Substance Registry System: ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE(85716-87-6)

Safety Data

• Hazard Codes: Xi
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39:Wear suitabl
• HazardClass: IRRITANT
• Hazardous Substances Data: 85716-87-6(Hazardous Substances Data)

Usage

General Description

ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE is a chemical compound that belongs to the class of isothiocyanates and is commonly used in organic synthesis. It is a yellowish liquid with a strong odor that is soluble in organic solvents. ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE is known for its potential biological activities, including its antimicrobial, antifungal, and anticancer properties. It is also used in the production of pharmaceuticals and as a reagent in chemical reactions.ETHYL 2-ISOTHIOCYANATO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXYLATE should be handled with care and stored in a cool, dry place away from direct sunlight and sources of ignition.

InChI:InChI=1/C12H13NO2S2/c1-2-15-12(14)10-8-5-3-4-6-9(8)17-11(10)13-7-16/h2-6H2,1H3

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 108-94-1 cyclohexanone 
• 4506-71-2 ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 75-15-0 carbon disulfide 
• 90543-03-6 4,5,6,7-Tetrahydro-2-(triphenylphosphoranylidenamino)benzothiophen-3-carbonsaeure-ethylester 
• 463-71-8 thiophosgene 

Downstream Products

• 109315-56-2 2-[3-(3-Ethoxycarbonyl-4-phenyl-thiophen-2-yl)-thioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 105544-62-5 N-(3-carboethoxy-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)-N-thiourea 
• 151094-90-5 2,3,5,6,7,8-hexahydro-3-amino-2-thioxo<1>benzothieno<2,3-d>pyrimidin-4(1H)-one 
• 207743-82-6 2-(3-Cyclohexyl-3-methyl-thioureido)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 42076-12-0 N¹-(3-carbethoxy-4,5,6,7-tetrahydrobenzothien-2-yl)-N²-phenylthiourea 
• 65234-02-8 3-(4-Methoxy-phenyl)-2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 59898-68-9 3-benzyl-2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 746653-50-9 3-{[1-(4-Fluoro-phenyl)-meth-(E)-ylidene]-amino}-2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 342779-35-5 3-(4-difluoromethoxy-phenyl)-2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 380342-22-3 3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 325996-39-2 2-[2-(4-bromo-phenyl)-2-oxo-ethylsulfanyl]-3-phenyl-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 312585-66-3 2-[2-(4-chloro-phenyl)-2-oxo-ethylsulfanyl]-3-(4-methoxy-phenyl)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 

Relevant articles and documents

Synthesis of urea analogues bearing N-alkyl-N’-(thiophen-2-yl) scaffold and evaluation of their innate immune response to toll-like receptors

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Discovery of a novel 5-HT3 antagonist/5-HT1A agonist 3-amino-5,6,7,8-tetrahydro-2-{4-[4-(quinolin-2-yl)piperazin-1-yl]butyl} quinazolin-4(3 H)-one (TZB-30878) as an orally bioavailable agent for irritable bowel syndrome

We have prepared a series of quinazolinone derivatives linked with piperazinylquinoline for the treatment of irritable bowel syndrome (IBS). Using pharmacophore analysis, we designed and synthesized compounds which bind to both serotonin receptor subtype 1A (5-HT1A) and subtype 3 (5-HT 3). Quinazolinone derivatives with a sulfur atom in the linker showed high affinity in in vitro assays, but low in vivo activity. Focusing on the linker to improve the pharmacokinetic profile, the sulfur atom in the linker was replaced with a methylene group. Further optimization led to the discovery of compound 17m (TZB-30878) (J. Pharmacol. Exp. Ther. 2007, 322, 1315 -1323, Patent WO2005082887 (A1), 2005), a novel 5-HT1A agonist/5-HT3 antagonist in the 3-aminoquinazolinone series. In in vivo functional assays, 17m dose dependently inhibited the Bezold-Jarisch reflex and induced 5-HT 1A-mediated behaviors, and in an IBS animal model, 17m significantly inhibited stress-induced defecation. Pretreatment by WAY-100635 (5-HT 1A antagonist) significantly attenuated but did not abolish the inhibitory effects of 17m. These results suggested that 17m exerted inhibitory effects via both 5-HT1A agonistic and 5-HT3 antagonistic activities and that 17m would be useful as a therapeutic agent for IBS.