625100-00-7

Basic information

• Product Name: 3-BROMO-5,6,7,8-TETRAHYDRO-1,6-NAPHTHYRIDINE
• Synonyms: 3-BROMO-5,6,7,8-TETRAHYDRO-1,6-NAPHTHYRIDINE;3-bromo-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride;3-BroMo-5,6,7,8-tetrahydro-1,6-naphthyridine hthyridine
• CAS NO: 625100-00-7
• Molecular Formula: C₈H₉BrN₂
• Molecular Weight: 213.07
• Product Categories: CHIRAL CHEMICALS
• Mol File: 625100-00-7.mol

Chemical Properties

• Boiling Point: 283.4 °C at 760 mmHg
• Flash Point: 125.2 °C
• Appearance: /
• Density: 1.503 g/cm³
• Vapor Pressure: 0.00317mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: 2-8°C(protect from light)
• PKA: 7.16±0.20(Predicted)
• CAS DataBase Reference: 3-BROMO-5,6,7,8-TETRAHYDRO-1,6-NAPHTHYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-5,6,7,8-TETRAHYDRO-1,6-NAPHTHYRIDINE(625100-00-7)
• EPA Substance Registry System: 3-BROMO-5,6,7,8-TETRAHYDRO-1,6-NAPHTHYRIDINE(625100-00-7)

Safety Data

• Hazardous Substances Data: 625100-00-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-5,6,7,8-tetrahydro-1,6-naphthyridine is used as a reagent for the preparation of coagulation factor XIa inhibitors. These inhibitors play a crucial role in the development of antithrombotic drugs, which are essential for the prevention and treatment of blood clot-related disorders, such as deep vein thrombosis, pulmonary embolism, and stroke. 3-Bromo-5,6,7,8-tetrahydro-1,6-naphthyridine's unique structure allows for the design of selective and potent inhibitors, making it a valuable asset in the pharmaceutical industry for the development of novel therapeutic agents.

InChI:InChI=1/C8H9BrN2/c9-7-3-6-4-10-2-1-8(6)11-5-7/h3,5,10H,1-2,4H2

Upstream product

• 948306-78-3 C₈H₁₁N₃ 

Downstream Products

• 301666-81-9 3-bromo-7,8-dihydro-1,6-naphthyridin-5(6H)-one 
• 1384873-39-5 (3-((4-fluorophenoxy)methyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)(4-fluorophenyl)methanone 
• 1384873-36-2 (3-((3-fluorophenoxy)methyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)(4-fluorophenyl)methanone 
• 1616293-40-3 (3-(benzyloxy)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)(4-fluorophenyl)methanone 
• 1384873-46-4 cyclopropyl(3-((3-fluorobenzyl)oxy)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone 
• 1469444-72-1 3-(phenylethynyl)-5,6,7,8-tetrahydro-1,6-naphthyridine 
• 1469444-27-6 ethyl 3-(phenylethynyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate 
• 1469444-20-9 2-methyl-1-(3-(phenylethynyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)propan-1-one 
• 80957-68-2 5,6,7,8-tetrahydro-1,6-naphthyridine 
• 1384873-55-5 (4-fluorophenyl)(3-(hydroxymethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone 
• 1384873-51-1 (4-fluorophenyl)(3-vinyl-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone 
• 1384873-32-8 (4-fluorophenyl)(3-(phenoxymethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone 
• 1384873-49-7 (3-bromo-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)(4-fluorophenyl)methanone 
• 1184950-48-8 3-bromo-6-(tert-butoxycarbonyl)-5,6,7,8-tetrahydro-1,6-naphthyridine 

Relevant articles and documents

Design, synthesis, and evaluation of fused heterocyclic analogs of SCH 58261 as adenosine A2A receptor antagonists

SCH 58261 is a reported adenosine A2A receptor antagonist which is active in rat in vivo models of Parkinson's Disease upon ip administration. However, it has poor selectivity versus the A1 receptor and does not demonstrate oral activity. Quinoline analogs have improved upon the selectivity and pharmacokinetics of SCH 58261, but were difficult to handle due to poor aqueous solubility. We report the design and synthesis of fused heterocyclic analogs of SCH 58261 with aqueous solubility as well as improved A2A receptor binding selectivity and pharmacokinetic properties. In particular, the tetrahydronaphthyridine 4s has excellent A2A receptor in vitro binding affinity and selectivity, is active orally in a rat in vivo model of Parkinson's Disease, and has aqueous solubility of 100 μM at physiological pH.