324769-03-1

Basic information

• Product Name: (3S,5R)-1-benzyl-3,5-diMethylpiperidin-4-one
• Synonyms: (3S,5R)-1-benzyl-3,5-diMethylpiperidin-4-one
• CAS NO: 324769-03-1
• Molecular Formula: C₁₄H₁₉NO
• Molecular Weight: 217.31
• Mol File: 324769-03-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (3S,5R)-1-benzyl-3,5-diMethylpiperidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5R)-1-benzyl-3,5-diMethylpiperidin-4-one(324769-03-1)
• EPA Substance Registry System: (3S,5R)-1-benzyl-3,5-diMethylpiperidin-4-one(324769-03-1)

Safety Data

• Hazardous Substances Data: 324769-03-1(Hazardous Substances Data)

Usage

General Description

(3S,5R)-1-benzyl-3,5-diMethylpiperidin-4-one is a chemical compound with a piperidinone structure, featuring a benzyl group attached to the nitrogen atom. The compound has a 3S,5R stereochemistry, indicating the specific arrangement of substituent groups around the piperidine ring. This molecule is a chiral compound, meaning it has non-superimposable mirror images (enantiomers). It is commonly used as an intermediate in the synthesis of various pharmaceuticals and organic compounds, and its unique structure makes it valuable in medicinal research and drug development. Additionally, its piperidinone framework confers potential biological activity, making it an interesting target for studies in pharmacology and medicinal chemistry.

Upstream product

• 862283-46-3 3,5-dimethyl 1-benzyl-3,5-dimethyl-4-oxopiperidine-3,5-dicarboxylate 

Downstream Products

• 945922-04-3 (3R,4s,5S)-1-benzyl-3,5-dimethylpiperidin-4-ol 
• 862284-53-5 (3R,4s,5S)-1-benzyl-3,5-dimethyl-4-pyridin-2-ylpiperidin-4-ol 
• 862284-11-5 (3R,4s,5S)-1-benzyl-3,5-dimethyl-4-pyridin-3-ylpiperidin-4-ol 
• 862284-05-7 (3R,4s,5S)-1-benzyl-4-(4-methoxyphenyl)-3,5-dimethylpiperidin-4-ol 
• 862283-37-2 (3R,4s,5S)-1-benzyl-4-cyclohexyl-3,5-dimethylpiperidin-4-ol 
• 1221821-84-6 tert-butyl (3R,5S)-3,5-dimethyl-4-oxopiperidine-1-carboxylate 
• 862284-26-2 (3R,4s,5S)-1-benzyl-4-cyclopropyl-3,5-dimethylpiperidin-4-ol 
• 862283-91-8 (3R,4s,5S)-1-benzyl-4-(4-fluorophenyl)-3,5-dimethylpiperidin-4-ol 

Relevant articles and documents

Discovery of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans

The relevance of the melanocortin system to sexual activity is well established, and nonselective peptide agonists of the melanocortin receptors have shown evidence of efficacy in human sexual dysfunction. The role of the MC4 receptor subtype has received particular scrutiny, but the sufficiency of its selective activation in potentiating sexual response has remained uncertain owing to conflicting data from studies in preclinical species. We describe here the discovery of a novel series of small-molecule MC4 receptor agonists derived from library hit 2. The addition of methyl substituents at C3 and C5 of the 4-phenylpiperidin-4-ol ring was found to be markedly potency-enhancing, enabling the combination of low nanomolar potencies with full rule-of-five compliance. In general, the series shows only micromolar activity at other melanocortin receptors. Our preferred compound 40a provided significant systemic exposure in humans on both sublingual and oral administration and was safe and well tolerated up to the maximum tested dose. In a pilot clinical study of male erectile dysfunction, the highest dose of 40a tested (200 mg) provided a similar level of efficacy to sildenafil.

CHEMOKINE RECEPTOR ANTAGONISTS

A compound of formula (I) or a pharmaceutically acceptable salt or prodrug ester thereof, wherein the variants R, R9, Z, X, Q and Y are defined in the specification.