251449-67-9

Basic information

• Product Name: 1-BOC-3-(2-METHYLPHENYL)-3-HYDROXYPIPERIDINE
• Synonyms: 1-BOC-3-(2-METHYLPHENYL)-3-HYDROXYPIPERIDINE
• CAS NO: 251449-67-9
• Molecular Formula: C₁₇H₂₅NO₃
• Molecular Weight: 291.388
• Mol File: 251449-67-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-BOC-3-(2-METHYLPHENYL)-3-HYDROXYPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BOC-3-(2-METHYLPHENYL)-3-HYDROXYPIPERIDINE(251449-67-9)
• EPA Substance Registry System: 1-BOC-3-(2-METHYLPHENYL)-3-HYDROXYPIPERIDINE(251449-67-9)

Safety Data

• Hazardous Substances Data: 251449-67-9(Hazardous Substances Data)

Upstream product

• 95-46-5 2-methylphenyl bromide 
• 98977-36-7 3-oxo-piperidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 213923-84-3 2-chloro-4-(5-(2-methylphenyl)-1,2,3,6-tetrahydropyridino)-6-methylpyrimidine 

Relevant articles and documents

Chemical modification of aryl-1,2,3,6-tetrahydropyridinopyrimidine derivative to discover corticotropin-releasing factor1 receptor antagonists: Aryl-1,2,3,6-tetrahydropyridino-purine, -3H-1,2,3-triazolo[4,5-d]pyrimidine, -purin-8-one, and -7H-pyrrolo[2,3-d]pyrimidine derivatives

Structure-affinity relationships (SARs) of non-peptide CRF1 antagonists suggest that such antagonists can be constructed of three units: a hydrophobic unit (Up-Area), a proton accepting unit (Central-Area), and an aromatic unit (Down-Area). Recently, various non-peptide corticotropin-releasing factor1 (CRF1) receptor antagonists obtained by modification of the Central-Area have been reported. In contrast, we modified the Up-Area and presented 4- or 5-aryl-1,2,3,6-tetrahydropyridinopyrimidine derivatives including potent CRF receptor ligands 1a-c, and proposed that the 4- or 5-aryl-1,2,3,6-tetrahydropyridino moiety might be useful as a substituent in the Up-Area. Our interest shifted to the chemical modification in which the pyrimidine ring of 1a-c was replaced by other heterocycles, purine ring of 2, 3H-1,2,3-triazolo[4,5-d]pyrimidine ring of 3, purin-8-one ring of 4 and 7H-pyrrolo[2,3-d]pyrimidine ring of 5. Among them, 5-aryl-1,2,3,6-tetrahydropyridinopurine compound 6j (CRA0186) had the highest affinity for CRF1 receptors (IC50=20 nM). We report here the synthesis and SARs of derivatives 6-9.

Synthesis and structure-affinity relationships of 4-(5-Aryl-1,2,3,6-tetrahydropyridino)pyrimidine derivatives as corticotropin-releasing factor1 receptor antagonists

Recently, various non-peptide corticotropin-releasing factor1 (CRF1) receptor antagonists have been reported. Structure-affinity relationships (SARs) of non-peptide CRF1 antagonists suggest that such antagonists can be constructed of three units: a hydrophobic unit (Up-Area), a proton accepting unit (Central-Area), and an aromatic unit (Down-Area). We previously presented 4-aryl-1,2,3,6-tetrahydropyridinopyrimidine derivatives including potent CRF receptor ligands 1a and 1b and proposed that the 4-aryl-1,2,3,6-tetrahydropyridino moiety might be useful as a substituent in the Up-Area. Our interest shifted to 5-aryl-1,2,3,6-tetrahydropyridinopyrimidine derivatives 2, among which compound 2m (CRA0165) had highest affinity for CRF1 receptors (IC50=11 nM). We report here the design, synthesis and SARs of derivatives 2.