503149-20-0

Basic information

• Product Name: 1-benzyloxycarbonyl-4-(1-phenyl-1H-tetrazol-5-yl)piperidine
• Synonyms: 1-benzyloxycarbonyl-4-(1-phenyl-1H-tetrazol-5-yl)piperidine
• CAS NO: 503149-20-0
• Molecular Weight: 363.419
• Mol File: 503149-20-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-benzyloxycarbonyl-4-(1-phenyl-1H-tetrazol-5-yl)piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyloxycarbonyl-4-(1-phenyl-1H-tetrazol-5-yl)piperidine(503149-20-0)
• EPA Substance Registry System: 1-benzyloxycarbonyl-4-(1-phenyl-1H-tetrazol-5-yl)piperidine(503149-20-0)

Safety Data

• Hazardous Substances Data: 503149-20-0(Hazardous Substances Data)

Usage

Chemical structure

A piperidine derivative containing a tetrazole group and a benzyloxycarbonyl protecting group.

Potential applications

Pharmaceutical applications, drug discovery and development, medicinal chemistry.

Biological activity

The tetrazole group may confer potential biological activity.

Functional group protection

The benzyloxycarbonyl group is often used to protect reactive functional groups in organic synthesis.

Further research

Additional research and experimentation are necessary to fully understand the potential uses and effects of this compound.

Upstream product

• 4648-54-8 trimethylsilylazide 
• 10315-00-1 1-benzyloxycarbonylisonipecotic acid anilide 
• 10314-98-4 1-benzyloxycarbonylpiperidine-4-carboxylic acid 

Downstream Products

• 503149-26-6 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(1-phenyl-1H-tetrazol-5-yl)piperidino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine 
• 503149-23-3 4-(1-phenyl-1H-tetrazol-5-yl)piperidine 

Relevant articles and documents

Discovery and preclinical profile of teneligliptin (3-[(2S,4S)-4-[4-(3- methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl] thiazolidine): A highly potent, selective, long-lasting and orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

Dipeptidyl peptidase IV (DPP-4) inhibition is suitable mechanism for once daily oral dosing regimen because of its low risk of hypoglycemia. We explored linked bicyclic heteroarylpiperazines substituted at the γ-position of the proline structure in the course of the investigation of l-prolylthiazolidines. The efforts led to the discovery of a highly potent, selective, long-lasting and orally active DPP-4 inhibitor, 3-[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5- yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl]thiazolidine (8g), which has a unique structure characterized by five consecutive rings. An X-ray co-crystal structure of 8g in DPP-4 demonstrated that the key interaction between the phenyl ring on the pyrazole and the S2 extensive subsite of DPP-4 not only boosted potency, but also increased selectivity. Compound 8g, at 0.03 mg/kg or higher doses, significantly inhibited the increase of plasma glucose levels after an oral glucose load in Zucker fatty rats. Compound 8g (teneligliptin) has been approved for the treatment of type 2 diabetes in Japan.