444811-18-1

Basic information

• Product Name: 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine
• Synonyms: 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine
• CAS NO: 444811-18-1
• Molecular Formula: C₂₁H₂₁BrN₂O₂
• Molecular Weight: 413.30764
• Mol File: 444811-18-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine(444811-18-1)
• EPA Substance Registry System: 5-bromo-2-[bis(4-methoxybenzyl)amino]pyridine(444811-18-1)

Safety Data

• Hazardous Substances Data: 444811-18-1(Hazardous Substances Data)

Upstream product

• 1072-97-5 5-bromo-2-pyridylamine 
• 824-94-2 p-methoxybenzyl chloride 
• 664988-25-4 2-[(N,N-dibenzyl)amino]-5-bromopyridine 

Downstream Products

• 1072-97-5 5-bromo-2-pyridylamine 
• 1319054-97-1 C₂₅H₃₀N₂O₃ 
• 1319054-98-2 C₂₅H₂₈N₂O₃ 
• 1319054-99-3 C₂₅H₃₀N₂O₂ 
• 246219-79-4 2-(6-amino-pyridin-3-yl)-2-methyl-propionic acid methyl ester 
• 385449-77-4 2-(6-amino-pyridin-3-yl)-2-methyl-propionic acid 

Relevant articles and documents

HETEROCYCLIC COMPOUNDS AS PRMT5 INHIBITORS

The compounds of Formula I, Formula Ia, and Formula Ib are described herein along with their analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts, pharmaceutical compositions, metabolites, and prodrugs thereof. These compounds inhibit PRMT5 and are useful as therpeautic or ameliorating agent for diseases that are involved in cellular growth such as malignant tumors, schizophrenia, Alzheimer's disease, Parkinson's disease and the like.

Fragment-based identification of amides derived from trans-2-(pyridin-3-yl) cyclopropanecarboxylic acid as potent inhibitors of human nicotinamide phosphoribosyltransferase (NAMPT)

Potent, trans-2-(pyridin-3-yl)cyclopropanecarboxamide-containing inhibitors of the human nicotinamide phosphoribosyltransferase (NAMPT) enzyme were identified using fragment-based screening and structure-based design techniques. Multiple crystal structures were obtained of initial fragment leads, and this structural information was utilized to improve the biochemical and cell-based potency of the associated molecules. Many of the optimized compounds exhibited nanomolar antiproliferative activities against human tumor lines in in vitro cell culture experiments. In a key example, a fragment lead (13, KD = 51 μM) was elaborated into a potent NAMPT inhibitor (39, NAMPT IC 50 = 0.0051 μM, A2780 cell culture IC50 = 0.000 49 μM) which demonstrated encouraging in vivo efficacy in an HT-1080 mouse xenograft tumor model.

CYCLOPROPYL AMIDE DERIVATIVES

The present invention relates to certain cyclopropyl amide compounds, pharmaceutical compositions comprising such compounds, and methods of treating cancer, including leukemias and solid tumors, inflammatory diseases, osteoporosis, atherosclerosis, irritable bowel syndrome, and other diseases and medical conditions, with such compounds and pharmaceutical compositions. The present invention also relates to certain cyclopropyl amide compounds for use in inhibiting nicotinamide phosphoribosyltransferase ("NAMPT").

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.