193537-14-3

Basic information

• Product Name: 2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]PYRIDINE-3,6-DICARBOXYLIC ACID 6-TERT BUTYL ESTER 3-ETHYL ESTER
• Synonyms: Ethyl2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate,N-BOCprotected95%;Ethyl 2-amino-6-Boc-4,7-dihydro-5H-thieno[2,3-c]pyridine-3-carboxylate;6-O-tert-butyl 3-O-ethyl 2-amino-5,7-dihydro-4H-thieno[2,3-c]pyridine-3,6-dicarboxylate;2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]PYRIDINE-3,6-DICARBOXYLIC ACID 6-TERT BUTYL ESTER 3-ETHYL ESTER;6-TERT-BUTYL 3-ETHYL-2-AMINO-4,5-DIHYDRO-THIENO[2,3-C]PYRIDINE-3,6(7H)-DICARBOXYLATE;6-(TERT-BUTYL) 3-ETHYL 2-AMINO-4,7-DIHYDROTHIENO[2,3-C]PYRIDINE-3,6(5H)-DICARBOXYLATE;BUTTPARK 75\08-01;Ethyl 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate, N-BOC protected
• CAS NO: 193537-14-3
• Molecular Formula: C₁₅H₂₂N₂O₄S
• Molecular Weight: 326.41
• EINECS: 251-156-6
• Product Categories: CHIRAL CHEMICALS;Esters;Fused Ring Systems
• Mol File: 193537-14-3.mol
• Article Data: 32

Chemical Properties

• Melting Point: 153 °C
• Boiling Point: 492.504 °C at 760 mmHg
• Flash Point: 251.658 °C
• Appearance: /
• Density: 1.252 g/cm³
• Vapor Pressure: 7.64E-10mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 0.40±0.20(Predicted)
• CAS DataBase Reference: 2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]PYRIDINE-3,6-DICARBOXYLIC ACID 6-TERT BUTYL ESTER 3-ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]PYRIDINE-3,6-DICARBOXYLIC ACID 6-TERT BUTYL ESTER 3-ETHYL ESTER(193537-14-3)
• EPA Substance Registry System: 2-AMINO-4,7-DIHYDRO-5H-THIENO[2,3-C]PYRIDINE-3,6-DICARBOXYLIC ACID 6-TERT BUTYL ESTER 3-ETHYL ESTER(193537-14-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/39
• Hazardous Substances Data: 193537-14-3(Hazardous Substances Data)

Usage

General Description

2-Amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,6-dicarboxylic acid 6-tert butyl ester 3-ethyl ester is a chemical compound with a complex structure that belongs to the class of organic compounds known as thienopyridines. Thienopyridines are compounds containing a thiophene ring fused to a pyridine ring. This specific compound has two ester groups, one tert-butyl ester at the 6-position and one ethyl ester at the 3-position. It also has an amino group at the 2-position. Its properties, usage, and potential applications in specific fields like medicinal chemistry, drug discovery or material science depend on its precise chemical structure and properties, which should be thoroughly studied in dedicated scientific research and assessment.

InChI:InChI=1/C15H22N2O4S/c1-5-20-13(18)11-9-6-7-17(8-10(9)22-12(11)16)14(19)21-15(2,3)4/h5-8,16H2,1-4H3

Upstream product

• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 98977-36-7 3-oxo-piperidine-1-carboxylic acid tert-butyl ester 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 874801-60-2 tert-butytert-butyl-4-oxo-3,4,5,6,7,8-hexahydropyrido[4′,3′:4,5]thieno-[2,3-d]pyrimidine-7-carboxylatel-4-oxo-3,4,5,6,7,8-hexahydropyrido[4′,3′:4,5]thieno-[2,3-d]pyrimidine-7-carboxylate 
• 1416053-09-2 6-tert-butyl-3-ethyl-2-(2-iodobenzamido)-4,5-dihydrothieno[2,3-c]pyridine-3,6(7H)-dicarboxylate 
• 1226548-17-9 tert-butyl (S)-4-((2-hydroxy-1-phenylethyl)amino)-5,8-dihydropyrido[4’,3’:4,5]thieno[2, 3-d]pyrimidine-7(6H)carboxylate 
• 1226548-19-1 (S)-2-phenyl-2-((5,6,7,8-tetrahydropyrido[4’,3’:4,5]thieno[2,3-d]pyrimidin-4-yl)amino)ethan-1-ol 
• 1130155-70-2 tert-butyl 4-[(1R)-1-phenylethyl]amino-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7-carboxylate 
• 1130155-72-4 (R)-N-(1-phenylethyl)-5,6,7,8-tetrahydropyrido[4’,3’:4,5]thieno[2,3-d]pyrimidin-4-amine 

Relevant articles and documents

Synthesis and Evaluation of 2-Aminothiophene Derivatives as Staphylococcus aureus Efflux Pump Inhibitors

2-aminothiophene derivatives (2AT) in which the thiophene ring is fused with a cycloalkyl or a N-acylated piperidine ring by positions 5 and 6 and carrying a 3-carbethoxy group were synthesized and their bacterial growth and enzyme inhibitory effects against efflux proteins of Staphylococcus aureus leading to resistance to fluoroquinolones and erythromycin (ERY) were investigated. Compounds that most effectively decreases the minimum inhibitory concentrations (MICs) of ciprofloxacin (CIP) were assayed for their dose and time effects on the accumulation and efflux of ethidium bromide (EtBr) in the SA-1 strain. None of the compounds displayed antibacterial activity however, three derivatives carrying 2-amino, 2-aminoacetyl and 2-aminotrifluoroacetyl group enhanced the activity of CIP and ERY by 8- and 16-fold, respectively, and were able to restore the sensitivity of resistant strains, acting as typical efflux pump inhibitors (EPIs). The 2-aminoacetyl and 2-aminotrifluoroacetyl derivatives and two other piperidinyl 2-aminotrifluoroacetyl derivatives increased EtBr accumulation in a dose- and time-dependent manner, and one of them was also able to inhibit the EtBr efflux. Taken together, these results represent an important advance in the development of new EPIs, and demonstrate that 2AT represent a good scaffold for developing new antibiotic adjuvants.

Structure based design, synthesis and evaluation of new thienopyrimidine derivatives as anti-bacterial agents

TrmD, tRNA-(N1G37) methyltransferase, a member of SpoU-TrmD (SPOUT) RNA methyltransferase family, is one of the key enzymes responsible for the growth of Staphylococcus aureus, Pseudomonas aeruginosa, Mycobacterium tuberculosis (Mtb) and Mycobacterium abscessus (Mab). A number of TrmD inhibitors including thienopyrimidines and fused thienopyrimidines are reported as potent anti-bacterial and anti-mycobacterial agents. In the current study, a library of ~200 structurally diverse thienopyrimidines were designed and subjected to preliminary in silico studies. 22 of the compounds were selected, synthesized and were evaluated for their inhibitory activities against a panel of pathogens consisting E. coli, S. aureus, K. pneuminiae, A. baumannii and P. aeruginosa and M. tuberculosis (ATCC 27294). Among the tested compounds, 13b, 18a-e were found to inhibit M. tuberculosis (ATCC 27294) with the MIC of 16-32 μg/mL. The compound 18f was found to be selective against S. aureus with the MIC of 4 μg/mL and moderate activity against M. tuberculosis. The selected compounds were further subjected to docking, 3D-QSAR and ADME/T studies to understand the mechanism of action and also their physico chemical profile.

2-Substituted thienotetrahydropyridine derivatives: Allosteric ectonucleotidase inhibitors

The antithrombotic prodrugs ticlopidine and clopidogrel are thienotetrahydro-pyridine derivatives that are metabolized in the liver to produce thiols that irreversibly block adenosine diphosphate (ADP)-activated P2Y12 receptors on thrombocytes. In their native, nonmetabolized form, both drugs were reported to act as inhibitors of ectonucleoside triphosphate diphosphohydrolase-1 (NTPDase1, CD39). CD39 catalyzes the extracellular hydrolysis of nucleoside tri- and diphosphates, mainly adenosine 5?-triphosphate (ATP) and ADP, yielding adenosine monophosphate, which is further hydrolyzed by ecto-5?-nucleotidase (CD73) to produce adenosine. While ATP has proinflammatory effects, adenosine is a potent anti-inflammatory, immunosuppressive agent. Inhibitors of CD39 and CD73 have potential as novel checkpoint inhibitors for the immunotherapy of cancer and infection. In the present study, we investigated 2-substituted thienotetrahydropyridine derivatives, structurally related to ticlopidine, as CD39 inhibitors. Due to their substituent on the 2-position, they will not be metabolically transformed into reactive thiols and can, therefore, be expected to be devoid of P2Y12 receptor-antagonistic activity in vivo. Several of the investigated 2-substituted thienotetrahydropyridine derivatives showed concentration-dependent inhibition of CD39. The most potent derivative, 32, showed similar CD39-inhibitory potency to ticlopidine, both acting as allosteric inhibitors. Compound 32 showed an improved selectivity profile: While ticlopidine blocked several NTPDase isoenzymes, 32 was characterized as a novel dual inhibitor of CD39 and CD73.