716358-35-9

Basic information

• Product Name: 1-Piperidinecarboxylic acid, 4-(2-oxoethyl)-4-phenyl-, 1,1-dimethylethyl ester
• CAS NO: 716358-35-9
• Molecular Formula: C18H25NO3
• Molecular Weight: 303.401
• Mol File: 716358-35-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-Piperidinecarboxylic acid, 4-(2-oxoethyl)-4-phenyl-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperidinecarboxylic acid, 4-(2-oxoethyl)-4-phenyl-, 1,1-dimethylethyl ester(716358-35-9)
• EPA Substance Registry System: 1-Piperidinecarboxylic acid, 4-(2-oxoethyl)-4-phenyl-, 1,1-dimethylethyl ester(716358-35-9)

Safety Data

• Hazardous Substances Data: 716358-35-9(Hazardous Substances Data)

Usage

Molecular structure

A compound containing a piperidine ring, a phenyl group, an ester group, and an amino acid moiety.

+ Appearance

White solid

+ Solubility

Insoluble in water, soluble in organic solvents such as ethanol, methanol, and acetonitrile.

+ Stability

Stable under normal temperatures and pressures.

+ Reactivity

Can react with other compounds in peptide synthesis.

+ Building block

Used in the construction of complex peptide molecules.

+ Protecting group

Used as a protecting group in peptide synthesis.

+ Pharmaceutical synthesis

Used as a starting material in the synthesis of various pharmaceuticals and biologically active compounds.

+ Research tool

Valuable tool in medicinal and biochemical research.

+ Ester group

The 1,1-dimethylethyl ester moiety provides stability to the compound.

+ Amino acid moiety

The carboxylic acid group and the amino group are present in the compound, which is typical of an amino acid.

+ Phenyl group

A benzene ring attached to the piperidine ring through an ethyl group.

+ Piperidine ring

A six-membered nitrogen-containing aromatic ring.

+ Molecular weight

313.4

+ Melting point

85-88°C

+ Boiling point

Not applicable as it is a solid at boiling point of water.

Upstream product

• 716360-34-8 C₁₈H₂₇NO₃ 
• 716358-34-8 tert-butyl 4-[(E/Z)-2-methoxyethenyl]-4phenylpiperidine-1-carboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 108-86-1 bromobenzene 
• 644982-19-4 4-(1-cyano-1-ethoxycarbonyl-methyl)-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 917220-87-2 4-(carboxy-cyano-methyl)-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 
• 193537-11-0 tert-butyl 4-(1-cyano-2-ethoxy-2-oxoethylidene)-4-piperidine-1-carboxylate 
• 878130-36-0 4-cyanomethyl-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 716353-48-9 C₃₃H₄₄N₄O₂ 
• 1071993-40-2 C₃₂H₄₄N₄O₃ 
• 717101-63-8 C₃₃H₄₄N₄O₂ 
• 717101-72-9 C₃₃H₄₄N₄O 
• 716353-96-7 C₃₅H₃₇N₃O₃ 
• 716344-75-1 C₃₅H₄₀ClN₅O₃S 

Relevant articles and documents

Novel 4,4-disubstituted piperidine-based C-C chemokine receptor-5 inhibitors with high potency against human immunodeficiency virus-1 and an improved human ether-a-go-go related gene (hERG) profile

We recently described (J. Med. Chem. 2008, 51, 6538-6546) a novel class of CCR5 antagonists with strong anti-HIV potency. Herein, we detail SAR converting leads 1 and 2 to druglike molecules. The pivotal structural motif enabling this transition was the secondary sulfonamide substituent. Further finetuning of the substituent pattern in the sulfonamide paved the way to enhancing potency and bioavailability and minimizing hERG inhibition, resulting in discovery of clinical compound 122 (GSK163929).

Discovery of bioavailable 4,4-disubstituted piperidines as potent ligands of the chemokine receptor 5 and inhibitors of the human immunodeficiency virus-1

We describe robust chemical approaches toward putative CCR5 scaffolds designed in our laboratories. Evaluation of analogues in the 125I-[MIP-1β] binding and Ba-L-HOS antiviral assays resulted in the discovery of 64 and 68 in the 4,4-disubstitited piperidine class H, both potent CCR5 ligands (pIC50 = 8.30 and 9.00, respectively) and HIV-1 inhibitors (pIC50 = 7.80 and 7.84, respectively, in Ba-L-HOS assay). In addition, 64 and 68 were bioavailable in rodents, establishing them as lead molecules for further optimization toward CCR5 clinical candidates.

CCR5 ANTAGONISTS AS THERAPEUTIC AGENTS

The present invention relates to compounds of formula (I) or pharmaceutically acceptable derivatives thereof, useful in the treatment or prophylaxis of CCR5-related diseases and disorders, for example, in the inhibition of HIV replication, the prevention or treatment of an HIV infection, and in the treatment of the resulting acquired immune deficiency syndrome (AIDS).