872530-68-2

Basic information

• Product Name: tert-butyl 2-amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate
• Synonyms: tert-butyl 2-amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate
• CAS NO: 872530-68-2
• Molecular Weight: 344.478
• Mol File: 872530-68-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: tert-butyl 2-amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2-amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate(872530-68-2)
• EPA Substance Registry System: tert-butyl 2-amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate(872530-68-2)

Safety Data

• Hazardous Substances Data: 872530-68-2(Hazardous Substances Data)

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 1116-98-9 cyanoacetic acid tert-butyl ester 

Downstream Products

• 1209007-28-2 tert-butyl 2-(acetylamino)-6-benzyl-3a,4,5,6,7,7a-hexahydrothieno[2,3-c]pyridine-3-carboxylate 
• 872530-89-7 tert-butyl 6-benzyl-2-(3-trichloroacetylureido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate 
• 872530-70-6 tert-butyl 6-benzyl-4,5,6,7-tetrahydro-2-(3-isopropylureido)thieno[2,3-c]pyridine-3-carboxylate 
• 872530-81-9 tert-butyl 6-benzyl-4,5,6,7-tetrahydro-2-(3-phenylthioureido)thieno[2,3-c]pyridine-3-carboxylate 
• 872531-15-2 tert-butyl 6-benzyl-2-[(4-benzyl-1-piperazinylcarbonyl)amino]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate 
• 872531-10-7 tert-butyl 6-benzyl-2-[3-(3,4-dimethoxybenzyl)-3-methylureido]-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate 
• 872531-13-0 tert-butyl 6-benzyl-4,5,6,7-tetrahydro-2-[(4-morpholinylcarbonyl)amino]thieno[2,3-c]pyridine-3-carboxylate 
• 872531-07-2 tert-butyl 6-benzyl-2-(3-benzyl-3-methylureido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate 
• 872531-05-0 tert-butyl 6-benzyl-2-(3,3-diethylureido)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate 
• 872530-92-2 tert-butyl 6-benzyl-4,5,6,7-tetrahydro-2-ureidothieno[2,3-c]pyridine-3-carboxylate 

Relevant articles and documents

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.

Discovery of novel (4-piperidinyl)-piperazines as potent and orally active acetyl-CoA carboxylase 1/2 non-selective inhibitors: F-Boc and triF-Boc groups are acid-stable bioisosteres for the Boc group

Novel (4-piperidinyl)-piperazine derivatives were synthesized and evaluated as ACC1/2 non-selective inhibitors. Optimization of the substituents on the nitrogen of the piperidine ring led to the identification of the fluorine substituted tert-butoxycarbonyl group. Advanced analog, 1,1,1-trifluoro-2- methylpropan-2-yl 4-{4-[(2-amino-6-methyl-1-benzothiophen-3-yl)carbonyl] piperazin-1-yl}piperidine-1-carboxylate (12c) showed potent inhibitory activities in enzyme-assay and cell-based assays. Compound 12c also exhibited reduction of hepatic de novo fatty acid synthesis in rats after oral administration.