1026235-61-9

Basic information

• Product Name: 2-[4-(4-Fluoro-phenyl)-4-hydroxy-piperidin-1-yl]-1-(4-triisopropylsilanyloxy-phenyl)-propan-1-one
• CAS NO: 1026235-61-9
• Molecular Weight: 499.741
• Mol File: 1026235-61-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-[4-(4-Fluoro-phenyl)-4-hydroxy-piperidin-1-yl]-1-(4-triisopropylsilanyloxy-phenyl)-propan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[4-(4-Fluoro-phenyl)-4-hydroxy-piperidin-1-yl]-1-(4-triisopropylsilanyloxy-phenyl)-propan-1-one(1026235-61-9)
• EPA Substance Registry System: 2-[4-(4-Fluoro-phenyl)-4-hydroxy-piperidin-1-yl]-1-(4-triisopropylsilanyloxy-phenyl)-propan-1-one(1026235-61-9)

Safety Data

• Hazardous Substances Data: 1026235-61-9(Hazardous Substances Data)

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 70-70-2 4-hydroxypropiophenone 
• 134136-88-2 1-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)propan-1-one 
• 3888-65-1 4-(4-fluorophenyl)piperidin-4-ol 
• 134136-66-6 4-(triisopropylsilyloxy)-alpha-bromopropiophenone 

Relevant articles and documents

(1S,2S)-1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol: A potent new neuroprotectant which blocks N-methyl-D-aspartate responses

(1S,2S)-1-(4-Hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol (20, CP-101,606) has been identified as a potent and selective N-methyl-D- aspartate (NMDA) antagonist through a structure activity relation (SAR) program based on ifenprodil, a known antihypertensive agent with NMDA antagonist activity. Sites on the threo-ifenprodil skeleton explored in this report include the pendent methyl group (H, methyl, and ethyl nearly equipotent; propyl much weaker), the spacer group connecting the C-4 phenyl group to the piperidine ring (an alternating potency pattern with 0 and 2 carbon atoms yielding the greatest potency), and simple phenyl substitution (little effect). While potent NMDA antagonists were obtained with a two atom spacer, this arrangement also increased α1 adrenergic affinity. Introduction of a hydroxyl group into the C-4 position on the piperidine ring resulted in substantial reduction in α1 adrenergic affinity. The combination of these observations was instrumental in the discovery of 20. This compound potently protects cultured hippocampal neurons from glutamate toxicity (IC50 = 10 nM) while possessing little of the undesired α1 adrenergic affinity (IC50 ~ 20 μM) of ifenprodil. Furthermore, 20 appears to lack the psychomotor stimulant effects of nonselective competitive and channel-blocking NMDA antagonists. Thus, 20 shows great promise as a neuroprotective agent and may lack the side effects of compounds currently in clinical trials.