264623-57-6

Basic information

• Product Name: 6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID
• Synonyms: 6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID;Pyrido[3,4-b]pyrazine-6,7(5H)-dicarboxylic acid, 7,8-dihydro-, 6-(1,1-diMethylethyl) ester;7,8-Dihydropyrido[3,4-b]pyrazine-6,7(5H)-dicarboxylic acid 6-(tert-butyl) ester;7,8-Dihydro-5H-pyrido[3,4-b]pyrazine-6,7-dicarboxylic acid 6-tert-butyl ester;6-[(tert-butoxy)carbonyl]-5H,6H,7H,8H-pyrido[3,4-b]pyrazine-7-carboxylic acid;6-tert-Butoxycarbonyl-7,8-dihydro-5H-pyrido[3,4-b]pyrazine-7-carboxylic acid
• CAS NO: 264623-57-6
• Molecular Formula: C₁₃H₁₇N₃O₄
• Molecular Weight: 279.29178
• Mol File: 264623-57-6.mol

Chemical Properties

• Boiling Point: 446.6°C at 760 mmHg
• Flash Point: 223.9°C
• Appearance: /
• Density: 1.309
• Vapor Pressure: 9.29E-09mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID(264623-57-6)
• EPA Substance Registry System: 6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID(264623-57-6)

Safety Data

• Hazardous Substances Data: 264623-57-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID is used as a synthetic intermediate for the development of new pharmaceutical compounds, leveraging its unique molecular structure to create novel drugs with potential therapeutic benefits.
Used in Agrochemical Industry:
In the agrochemical sector, 6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID is utilized as a building block in the synthesis of agrochemicals, contributing to the creation of innovative products for crop protection and enhancement of agricultural yields.
Used in Organic Chemistry Research:
6-(TERT-BUTOXYCARBONYL)-5,6,7,8-TETRAHYDROPYRIDO[3,4-B]PYRAZINE-7-CARBOXYLIC ACID is employed as a research compound in organic chemistry, facilitating the exploration of new reaction pathways and the discovery of its reactivity with various other substances, thereby expanding the understanding of its potential applications in diverse fields.

InChI:InChI=1/C13H17N3O4/c1-13(2,3)20-12(19)16-7-9-8(14-4-5-15-9)6-10(16)11(17)18/h4-5,10H,6-7H2,1-3H3,(H,17,18)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 264623-82-7 ethyl 6-acetyl-7-ethoxycarbonyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylate 
• 264623-56-5 (+/-)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxylic acid hydrochloride 
• 51043-75-5 2,3-bis(chloromethyl)pyrazine 
• 5910-89-4 2,3-dimethylpyrazine 
• 764635-62-3 5,6,7,8-tetrahydro-pyrido[3,4-b]pyrazine-7-carboxylic acid 

Downstream Products

• 264624-08-0 (+/-)-N-benzyloxy-6-tert-butoxycarbonyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-7-carboxamide 

Relevant articles and documents

Synthesis and Evaluation of Novel Tetrahydronaphthyridine CXCR4 Antagonists with Improved Drug-like Profiles

Our first-generation CXCR4 antagonist TIQ15 was rationally modified to improve drug-like properties. Introducing a nitrogen atom into the aromatic portion of the tetrahydroisoquinoline ring led to several heterocyclic variants including the 5,6,7,8-tetrahydro-1,6-naphthyridine series, greatly reducing the inhibition of the CYP 2D6 enzyme. Compound 12a demonstrated the best overall properties after profiling a series of isomeric tetrahydronaphthyridine analogues in a battery of biochemical assays including CXCR4 antagonism, CYP 2D6 inhibition, metabolic stability, and permeability. The butyl amine side chain of 12a was substituted with various lipophilic groups to improve the permeability. These efforts culminated in the discovery of compound 30 as a potent CXCR4 antagonist (IC50 = 24 nM) with diminished CYP 2D6 activity, improved PAMPA permeability (309 nm/s), potent inhibition of human immunodeficiency virus entry (IC50 = 7 nM), a cleaner off-target in vitro safety profile, lower human ether a-go-go-related gene channel activity, and higher oral bioavailability in mice (% FPO = 27) compared to AMD11070 and TIQ15.

Synthesis and structure-activity relationships of 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-based hydroxamic acids as HB-EGF shedding inhibitors

HB-EGF Shedding inhibitors have been expected to become effective medicines for skin diseases caused by the proliferation of keratinocytes. In order to discover novel HB-EGF shedding inhibitors and clarify their structure-activity relationships, 5,6,7,8-tetrahydronaphthylidine-based hydroxamic acid and 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-based hydroxamic acids have been synthesized. Among the synthesized compounds, the ethoxyethoxy derivative 3o and the methoxypropoxy derivative 3p exhibited much more potent HB-EGF shedding inhibitory activity than CGS 27023A. The structural modification of 5,6,7,8-tetrahydropyrido[3,4-b]pyrazine-based hydroxamic acids enabled us to establish the following structure-activity relationships; the existences of the hydroxamic acid, the sulfonamide, and the phenyl moieties are crucial for a potent HB-EGF shedding inhibitory activity, and the stereochemistry of the alpha carbon of hydroxamic acid is also important. In addition, from the comparison of their HB-EGF shedding inhibitory activities with their MMPs inhibitory activities, we found that the S1′ pocket of the responsible enzyme for HB-EGF shedding is deep unlike that of MMP-1.

Keratinocyte growth inhibitors and hydroxamic acid derivatives

This invention relates to a keratinocyte-proliferation inhibitor comprising as active ingredient a compound having an activity of inhibiting the solubilization of heparin-binding EGF-like growth factor bound to cell membranes and a compound of the formula (I); or pharmaceutically acceptable salt thereof, wherein R1, R2, R3 are hydrogen atom or alkyl and X is substituted benzene or the like.