946135-52-0

Basic information

• Product Name: 1'-(TERT-BUTOXYCARBONYL)-2-OXOSPIRO[INDOLINE-3,4'-PIPERIDINE]-5-CARBOXYLIC ACID
• Synonyms: 1'-(TERT-BUTOXYCARBONYL)-2-OXOSPIRO[INDOLINE-3,4'-PIPERIDINE]-5-CARBOXYLIC ACID;-2-oxospiro[indoline-3,4'-piperidine]-5-carboxylic acid
• CAS NO: 946135-52-0
• Molecular Formula: C18H22N2O5
• Molecular Weight: 346.37768
• Mol File: 946135-52-0.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1'-(TERT-BUTOXYCARBONYL)-2-OXOSPIRO[INDOLINE-3,4'-PIPERIDINE]-5-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1'-(TERT-BUTOXYCARBONYL)-2-OXOSPIRO[INDOLINE-3,4'-PIPERIDINE]-5-CARBOXYLIC ACID(946135-52-0)
• EPA Substance Registry System: 1'-(TERT-BUTOXYCARBONYL)-2-OXOSPIRO[INDOLINE-3,4'-PIPERIDINE]-5-CARBOXYLIC ACID(946135-52-0)

Safety Data

• Hazardous Substances Data: 946135-52-0(Hazardous Substances Data)

Usage

General Description

1'-(tert-butoxycarbonyl)-2-oxospiro[indoline-3,4'-piperidine]-5-carboxylic acid is a chemical compound with potential applications in pharmaceutical and medicinal chemistry. It is a spiropiperidine derivative with a tert-butoxycarbonyl protecting group and a carboxylic acid functional group. 1'-(TERT-BUTOXYCARBONYL)-2-OXOSPIRO[INDOLINE-3,4'-PIPERIDINE]-5-CARBOXYLIC ACID may find use as a building block in the synthesis of various biologically active molecules, particularly those targeting the central nervous system. Additionally, it may have potential as a drug candidate for the treatment of neurological disorders or psychiatric conditions. Its structure and properties make it a versatile starting material for further chemical modifications and drug design efforts. Overall, this compound has the potential to contribute to the development of new drugs and therapeutic agents.

Upstream product

• 94-09-7 p-aminoethylbenzoate 
• 118753-70-1 N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine 
• 102359-00-2 2-oxoindoline-5-carboxylic acid 
• 61394-56-7 ethyl 3-(methylthio)-2-oxindoline-5-carboxylate 
• 61394-49-8 ethyl 2-oxindoline-5-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 946135-53-1 ethyl 1'-methyl-2-oxospiro[indoline-3,4'-piperidine]-5-carboxylate 
• 946135-56-4 C₂₁H₂₀N₂O₇Cl₆ 
• 946135-54-2 1'-tert-butyl 5-ethyl-2-oxospiro[indoline-3,4'-piperidine]-1',5-dicarboxylate 

Downstream Products

• 1185754-11-3 (E)-1-methyl-5-(4-methylpiperazine-1-carbonyl)-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidin]-2-one 
• 1185754-10-2 (E)-N-(2-hydroxyethyl)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxamide 
• 1185754-09-9 (E)-1-methyl-2-oxo-1'-(3-(2-(trifiuoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxamide 
• 1185754-07-7 (E)-N,N,1-trimethyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxamide 
• 1184728-92-4 (E)-methyl 2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-pi-peridine]-5-carboxylate 
• 1185754-05-5 (E)-methyl 1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-pi-peridine]-5-carboxylate 
• 1185754-06-6 (E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carboxylic acid 
• 1185754-14-6 (E)-1-methyl-2-oxo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)spiro[indoline-3,4'-piperidine]-5-carbonitrile 

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.