664988-25-4

Basic information

• Product Name: 5-bromo-2-(dibenzylamino)pyridine
• Synonyms: 5-bromo-2-(dibenzylamino)pyridine
• CAS NO: 664988-25-4
• Molecular Formula: C₁₉H₁₇BrN₂
• Molecular Weight: 353
• Mol File: 664988-25-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-bromo-2-(dibenzylamino)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-(dibenzylamino)pyridine(664988-25-4)
• EPA Substance Registry System: 5-bromo-2-(dibenzylamino)pyridine(664988-25-4)

Safety Data

• Hazardous Substances Data: 664988-25-4(Hazardous Substances Data)

Upstream product

• 1072-97-5 5-bromo-2-pyridylamine 
• 100-39-0 benzyl bromide 

Downstream Products

• 444811-18-1 5-bromo-N,N-bis[(4-methoxyphenyl)methyl]pyridin-2-amine 
• 1072-97-5 5-bromo-2-pyridylamine 
• 664988-39-0 1-(6-Dibenzylamino-pyridin-3-yl)-2-((6S,7R)-7-hydroxy-2,2,4,4-tetraisopropyl-[1,3,5,2,4]trioxadisilocan-6-yl)-ethanone 

Relevant articles and documents

Di-aryl guanidinium derivatives: Towards improved α2-Adrenergic affinity and antagonist activity

Compounds with excellent receptor engagement displaying α2-AR antagonist activity are useful not only for therapeutic purposes (e.g. antidepressants), but also to help in the crystallization of this particular GPCR. Therefore, based on our broad experience in the topic, we have prepared eighteen di-aryl (phenyl and/or pyridin-2-yl) mono- or di-substituted guanidines and 2-aminoimidazolines. The in vitro α2-AR binding affinity experiments in human brain tissue showed the advantage of a 2-aminoimidazolinium cation, a di-arylmethylene core, a conformationally locked pyridin-2-yl-guanidine and a di-substituted guanidinium to achieve good α2-AR engagement. After different in vitro [35S]GTPγS binding experiments in human prefrontal cortex tissue, it was possible to identify that compounds 7a, 7b and 7c were α2-AR partial agonist, whereas 8h was a potent α2-AR antagonist. Docking and MD studies with a model of α2A-AR and two crystal structures suggest that antagonism is achieved by compounds carrying a di-substituted guanidine which substituent occupy a pocket adjacent to TM5 without engaging S2005.42 or S2045.46, and a mono-substituted cationic group, which favorably interacts with E942.65.

Conversion of 2-deoxy-D-ribose into 2-amino-5-(2-deoxy-β-D-ribofuranosyl)pyridine, 2′-deoxypseudouridine, and other C-(2′-deoxyribonucleosides)

The synthesis of 2-amino-5-(2-deoxy-β-D-ribofuranosyl)pyridine 2a, 2-amino-5-(2-deoxy-α-D-ribofuranosyl)-pyridine 23, 2-amino-5-(2-deoxy-β-D-ribofuranosyl)-3-methylpyridine 2b, 2-amino-5-(2-deoxy-α-D-ribofuranosyl)-3-methylpyridine 29 and 5-(2-deoxy-β-D-ribofuranosyl)-2,4-dioxopyrimidine [2′-deoxypseudouridine] 30a is described. These C-nucleosides are prepared either from 2-deoxy-3,5-O-(1, 1, 3, 3-tetraisopropyldisiloxan-1,3-diyl)-D-ribofuranose 15 or from 2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-D-ribono-1,4-lactone 16, which are themselves prepared from 2-deoxy-D-ribose 13. The sugar derivatives are first allowed to react with the appropriate 5-lithio-pyridine or 5-lithio-pyrimidine derivatives, which are prepared from 5-bromo-2-(dibenzylamino)pyridine 12a, 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine 12b, 5-bromo-2-dibenzylamino-3-methylpyridine 25 and 5-bromo-2,4-bis(4-methoxybenzyloxy)pyrimidine 33. The products from the reactions between the lithio-derivatives and the lactol 15 are cyclized under Mitsunobu conditions; the products from the reactions between the lithio-derivatives and the lactone 16 are first reduced with L-Selectride before cyclization, also under Mitsunobu conditions, In all cases, the β-anomers of the protected C-nucleosides are the predominant products. Finally, the separation of the α- and β-anomers and the removal of all of the protecting groups are described.