916445-11-9

Basic information

• Product Name: 1-BENZYLSPIRO[INDOLE-3,4''-PIPERIDIN]-2(1H)-ONE
• Synonyms: 1-BENZYLSPIRO[INDOLE-3,4''-PIPERIDIN]-2(1H)-ONE
• CAS NO: 916445-11-9
• Molecular Weight: 0
• Mol File: 916445-11-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-BENZYLSPIRO[INDOLE-3,4''-PIPERIDIN]-2(1H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYLSPIRO[INDOLE-3,4''-PIPERIDIN]-2(1H)-ONE(916445-11-9)
• EPA Substance Registry System: 1-BENZYLSPIRO[INDOLE-3,4''-PIPERIDIN]-2(1H)-ONE(916445-11-9)

Safety Data

• Hazardous Substances Data: 916445-11-9(Hazardous Substances Data)

Usage

Chemical class

Spirooxindole

Explanation

The compound belongs to the spirooxindole class, which is a group of organic compounds containing a spiro junction between an indole and a pyrrolidine or piperidine ring.

Explanation

It is a heterocyclic compound, meaning it contains one or more rings of atoms with at least one ring consisting of non-carbon atoms.

Explanation

The spiro junction in the compound is attached to the piperidine ring, which is a six-membered nitrogen-containing ring.

Explanation

The compound contains an indole moiety, which is a bicyclic aromatic ring system consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Explanation

1-Benzylospiro[indole-3,4''-piperidin]-2(1H)-one has potential pharmacological properties, meaning it may have biological activity and could be used in the development of drugs.

Explanation

The compound has been studied for its potential medicinal use, indicating that it may have therapeutic applications in the treatment of various diseases or conditions.

Explanation

1-Benzylospiro[indole-3,4''-piperidin]-2(1H)-one is of interest as a synthetic intermediate in organic chemistry, meaning it can be used as a building block to create more complex molecules.

Explanation

The unique structure of the compound makes it a valuable target for both chemical synthesis and biological studies, as it may lead to the development of new drugs or provide insights into biological processes.

Heterocyclic compound

Yes

Spiro attachment

To the piperidine ring

Indole moiety

Present

Pharmacological properties

Potential

Medicinal use

Studied for potential

Synthetic intermediate

Of interest in organic chemistry

Unique structure

Valuable target for chemical synthesis and biological studies

Upstream product

• 293744-34-0 tert-butyl 1-benzyl-1,2-dihydro-2-oxospiro[3H-indole-3,4'-piperidine]-1'-carboxylate 
• 252882-60-3 tert-butyl 2-oxo-1,2-dihydro-1'H-spiro[indole-3,4-piperidine]-1'-carboxylate 
• 59-48-3 2-oxoindole 

Relevant articles and documents

1,3,8-triazaspiro[4.5]decane-2,4-diones as efficacious pan-inhibitors of hypoxia-inducible factor prolyl hydroxylase 1-3 (HIF PHD1-3) for the treatment of anemia

The discovery of 1,3,8-triazaspiro[4.5]decane-2,4-diones (spirohydantoins) as a structural class of pan-inhibitors of the prolyl hydroxylase (PHD) family of enzymes for the treatment of anemia is described. The initial hit class, spirooxindoles, was identified through affinity selection mass spectrometry (AS-MS) and optimized for PHD2 inhibition and optimal PK/PD profile (short-acting PHDi inhibitors). 1,3,8-Triazaspiro[4.5]decane-2,4-diones (spirohydantoins) were optimized as an advanced lead class derived from the original spiroindole hit. A new set of general conditions for C-N coupling, developed using a high-throughput experimentation (HTE) technique, enabled a full SAR analysis of the spirohydantoins. This rapid and directed SAR exploration has resulted in the first reported examples of hydantoin derivatives with good PK in preclinical species. Potassium channel off-target activity (hERG) was successfully eliminated through the systematic introduction of acidic functionality to the molecular structure. Undesired upregulation of alanine aminotransferese (ALT) liver enzymes was mitigated and a robust on-/off-target margin was achieved. Spirohydantoins represent a class of highly efficacious, short-acting PHD1-3 inhibitors causing a robust erythropoietin (EPO) upregulation in vivo in multiple preclinical species. This profile deems spirohydantoins as attractive short-acting PHDi inhibitors with the potential for treatment of anemia.