169332-15-4

Basic information

• Product Name: 1-[4-( Triisopropylsilyl)oxylp henyl]- 2-(4-hydroxy-4-pheny1piperidino)-1-propanone
• Synonyms: 1-[4-( Triisopropylsilyl)oxylp henyl]- 2-(4-hydroxy-4-pheny1piperidino)-1-propanone
• CAS NO: 169332-15-4
• Molecular Formula: C₂₉H₄₃NO₃Si
• Molecular Weight: 481.74212
• Mol File: 169332-15-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-[4-( Triisopropylsilyl)oxylp henyl]- 2-(4-hydroxy-4-pheny1piperidino)-1-propanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-( Triisopropylsilyl)oxylp henyl]- 2-(4-hydroxy-4-pheny1piperidino)-1-propanone(169332-15-4)
• EPA Substance Registry System: 1-[4-( Triisopropylsilyl)oxylp henyl]- 2-(4-hydroxy-4-pheny1piperidino)-1-propanone(169332-15-4)

Safety Data

• Hazardous Substances Data: 169332-15-4(Hazardous Substances Data)

Usage

Chemical structure

A complex organic molecule with a piperidino group, a phenyl group, and a silyl group.

Classification

A ketone derivative.

Potential applications

Medicinal chemistry and drug synthesis.

Biological activity

The presence of hydroxy and piperidino groups suggests potential biological activity.

Pharmaceutical development

Could be utilized in the development of pharmaceuticals.

Triisopropylsilyl group

Often used as a protecting group in organic synthesis to prevent unwanted reactions.

Synthetic pathway

The presence of the triisopropylsilyl group may indicate a specific synthetic pathway or functionalization strategy.

Versatility

Has potential as a versatile building block in the synthesis of biologically active compounds and pharmaceuticals.

Upstream product

• 70-70-2 4-hydroxypropiophenone 
• 134136-88-2 1-(4-{[tris(1-methylethyl)silyl]oxy}phenyl)propan-1-one 
• 13154-24-0 triisopropylsilyl chloride 
• 40807-61-2 4-hydroxy-4-phenylpiperidin 
• 134136-66-6 4-(triisopropylsilyloxy)-alpha-bromopropiophenone 

Downstream Products

• 186906-86-5 1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanone 
• 134234-12-1 (+/-)-Traxoprodil 
• 134234-12-1 Traxoprodil 
• 134234-12-1 (+)-(1S,2S)-1-(4-hydroxy-phenyl)-2-(4-hydroxy-4-phenylpiperidino-1-yl)-1-propanol 

Relevant articles and documents

2-PIPERIDINO-1-ALKANOL DERIVATIVES AS NEUROPROTECTIVE AGENTS

A method of blocking N-methyl-D-aspartic acid (NMDA) receptor sites in a mammal in need thereof with an effective NMDA blocking (neuroprotective and antiischemic) amount of 2-piperidino-1-alkanol derivatives and 2-azabicyclo-1-alkanol derivatives and analogs and pharmaceutically acceptable salts thereof; methods of using these compounds in the treatment of stroke, spinal cord trauma, traumatic brain injury, multiinfarct dementia, CNS degenerative diseases such as Alzheimer's disease, senile dementia of the Alzheimer's type, Huntington's disease, Parkinson's disease, epilepsy, amyotrophic lateral sclerosis, pain, AIDS dementia, psychotic conditions, drug addictions, migraine, hypoglycemia, anxiolytic conditions, urinary incontinence and an ischemic event arising from CNS surgery, open heart surgery or any procedure during which the function of the cardiovascular system is compromised.

(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.

Nortropyl-1-alkanol derivatives as antiischemic agents

2-(8-Azabicyclo[3.2.1]oct-8-yl)alkanols of the formula STR1 wherein Q is S or CH=CH; X is H, OH or another aromatic substituent; R is hydrogen, alkyl, alkenyl or alkynyl; Y and Y1 are taken together and are arylmethylene or aralkylmethylene (or a corresponding epoxy derivative) or Y and Y1 are taken separately and Y is hydrogen or OH, and Y1 is aryl, aralkyl, arylthio, or aryloxy; and structurally related 2-(piperidino)alkanols; pharmaceutical compositions thereof; methods of treating CNS disorders therewith; and intermediates useful in the preparation of said compounds.