92932-02-0

Basic information

• Product Name: 2-AMino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid tert-butyl ester
• Synonyms: 2-AMino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid tert-butyl ester
• CAS NO: 92932-02-0
• Molecular Formula: C₁₃H₁₉NO₂S
• Molecular Weight: 253.36046
• Mol File: 92932-02-0.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-AMino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid tert-butyl ester(92932-02-0)
• EPA Substance Registry System: 2-AMino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid tert-butyl ester(92932-02-0)

Safety Data

• Hazardous Substances Data: 92932-02-0(Hazardous Substances Data)

Usage

Chemical Class

Carboxylic acid tert-butyl ester

Structural Components

Benzo[b]thiophene ring
Amino group
Carboxylic acid functional group
Tert-butyl ester group

Functional Groups

Amino group: Provides reactivity and potential for forming various chemical bonds.
Carboxylic acid functional group: Contributes to acidity and chemical reactivity.
Tert-butyl ester group: Imparts stability and protection to the carboxylic acid functionality.

Pharmacological Properties

Interesting pharmacological properties: Suggests potential therapeutic effects or biological activity.

Applications

Pharmaceutical industry: Potential applications in drug synthesis.
Synthesis of various drugs and related compounds: Indicates versatility in drug development.

Value as Building Block

Valuable building block for the development of new pharmaceutical products: Highlights its importance in drug discovery and synthesis.
Valuable building block for the development of new agrochemical products: Suggests potential applications in agriculture and crop protection.

Overall Importance

Significant potential in pharmaceutical and agrochemical industries: Indicates broad utility and relevance in diverse fields of chemistry and industry.

Upstream product

• 1116-98-9 cyanoacetic acid tert-butyl ester 
• 110-82-7 cyclohexane 
• 108-94-1 cyclohexanone 

Downstream Products

• 1452776-89-4 2-(benzylsulfanyl)-3-(methylsulfonyl)-5,6,7,8-tetrahydrobenzo-[4,5]thieno[2,3-d]pyrimidin-4(3H)-one 
• 1452776-88-3 3-(4-methylbenzenesulfonyl)-2-(benzylsulfanyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]-pyrimidin-4(3H)-one 
• 1452776-86-1 4-((2-(methylsulfanyl)-4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno-[2,3-d]pyrimidin-3(4H)-yl)sulfonyl)benzonitrile 
• 1452776-85-0 3-(4-methylbenzenesulfonyl)-2-(methylsulfanyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one 
• 1452849-80-7 (Z)-2-((methylsulfonamido)(benzylsulfanyl)methyleneamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid 
• 1452849-79-4 (Z)-2-((4-methylbenzenesulfonamido)(benzylsulfanyl)-methyleneamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid 
• 1452849-77-2 (Z)-2-((4-cyanobenzenesulfonamido)(methylsulfanyl)-methyleneamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid 
• 1452849-76-1 (Z)-2-((4-methylbenzenesulfonamido)(methylsulfanyl)-methyleneamino)-4,5,6,7-tetra-hydrobenzo[b]thiophene-3-carboxylic acid 
• 1452849-75-0 (Z)-tert-butyl 2-((methylsulfonamido)(benzylsulfanyl)-methyleneamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 1452849-74-9 (Z)-tert-butyl 2-((4-methylbenzenesulfonamido)(benzylsulfanyl)-methyleneamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 1452849-72-7 (Z)-tert-butyl 2-((4-cyanobenzenesulfonamido)(methylsulfanyl)-methyleneamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 1452849-71-6 (Z)-tert-butyl 2-((4-methylbenzenesulfonamido)(methylsulfanyl)-methyleneamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 1452776-83-8 tert-butyl 2-(3-(4-cyanobenzenesulfonyl)thioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 1452776-82-7 tert-butyl 2-(3-(4-methylbenzenesulfonyl)thioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 

Relevant articles and documents

Design, synthesis, in vitro antiproliferative activity evaluation of 2-alkanoylamidothiophene-3-carboxamide derivatives

A series of 2-alkanoylamidothiophene-3-carboxamide derivatives were synthesized based on the hit compound 1. The anti-proliferative activity of all the compounds in vitro against MGC-803 (stomach) and HCT-116 (colon) cancer cell lines using SRB assays were tested. Several compounds showed improved anti-proliferative activity against MGC-803 and HCT-116. SAR study revealed that chlorine substituent in the 2-acetylamino part was important for anti-proliferative activity. 5a, 11b, 11c and 11d were the most potent compounds against MGC-803 (IC50s = 2.32-2.95 μM), and 5a and 11c also showed good anti-proliferative activity against HCT-116 cells (IC50s = 3.41-3.75 μM). In addition, the anti-proliferative activity of 11b and 11d could be attributed to the apoptosis in HCT116 cells via caspase 3 activation, confirmed by flow cytometry assay and western blot analysis. Meanwhile, 11b and 11d decreased the mitochondrial membrane potential (MMP) in HCT116 cells.

Discovery, structure-activity relationship study and biological evaluation of 2-thioureidothiophene-3-carboxylates as a novel class of C-X-C chemokine receptor 2 (CXCR2) antagonists

The C-X-C motif ligand 8 and C-X-C chemokine receptor 2 (CXCL8-CXCR2) axis is involved in pathogenesis of various diseases including inflammation and cancers. Various CXCR2 antagonists are under development for several diseases. Our previous high-throughput cell-based assay specific for CXCR2 has identified a pyrimidine-based compound CX797 acting on CXCR2 down-stream signaling. A lead optimization campaign through scaffold-hopping strategy led to a series of 2-thioureidothiophene-3-carboxylates (TUTP) as novel CXCR2 antagonists. Structure-activity relationship study of TUTPs led to the identification of compound 52 that significantly inhibited CXCR2-mediated β-arrestin recruitment signaling (IC50 = 1.1±0.01 μM) with negligible effect on CXCL8-mediated cAMP signaling and calcium flux. Similar to the known CXCR2 antagonist SB265610, compound 52 inhibited CXCL8-CXCR2 induced phosphorylation of ERK1/2. TUTP compounds also inhibited CXCL8-mediated cell migration and showed synergy with doxorubicin in ovarian cancer cells, thereby supporting TUTPs as promising compounds for cancer treatment.

An NMDAR positive and negative allosteric modulator series share a binding site and are interconverted by methyl groups

N-methyl-D-aspartate receptors (NMDARs) are an important receptor in the brain and have been implicated in multiple neurological disorders. Many non-selective NMDAR-targeting drugs are poorly tolerated, leading to efforts to target NMDAR subtyp