227029-23-4

Basic information

• Product Name: 8-benzyl-1-(4-chlorophenyl)-1,3,8-triazaspiro[4.5]dec-2-en-4-one
• Synonyms: 8-benzyl-1-(4-chlorophenyl)-1,3,8-triazaspiro[4.5]dec-2-en-4-one
• CAS NO: 227029-23-4
• Molecular Weight: 353.851
• Mol File: 227029-23-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 8-benzyl-1-(4-chlorophenyl)-1,3,8-triazaspiro[4.5]dec-2-en-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8-benzyl-1-(4-chlorophenyl)-1,3,8-triazaspiro[4.5]dec-2-en-4-one(227029-23-4)
• EPA Substance Registry System: 8-benzyl-1-(4-chlorophenyl)-1,3,8-triazaspiro[4.5]dec-2-en-4-one(227029-23-4)

Safety Data

• Hazardous Substances Data: 227029-23-4(Hazardous Substances Data)

Upstream product

• 1045-51-8 1-benzyl-4-(4-chloro-phenylamino)-piperidine-4-carboxylic acid amide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 106-47-8 4-chloro-aniline 
• 972-20-3 1-benzyl-4-(4-chloro-phenylamino)-piperidine-4-carbonitrile 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 976-96-5 8-benzyl-1-(4-chlorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one 

Relevant articles and documents

1,3,8-TRIAZASPIRO COMPOUNDS AND THEIR USE AS MEDICAMENTS FOR THE TREATMENT OF REPERFUSION INJURY

The present invention relates to a 1,3,8-triazaspiro compound of Formula (I), wherein A is -CH2, -SO2 -, -NH-CO-, -NH-CS- or -CO-; the dashed line represents a single or double bond; R1 is a substituent selected from (C1-C3) alkyl, phenyl, thienyl and cyclohexyl, said substituent being optionally substituted by halogen or (C1 -C3) alkyl; and R2 is a substituent selected from H, (C1-C3) alkyl, (C1-C3) alkoxy, -CF3 and halogen; and wherein, when the dashed line is a double bond, A is -CH2 - and R1 is phenyl, or a pharmaceutically acceptable salt thereof for use in the treatment of reperfusion injury diseases. The 1,3,8-triazaspiro compound of the invention is a selective inhibitor of the C subunit of the F1/Fo-ATP synthase complex and a modulator of the mitochondrial permeability transition pore activity in mammalian cells and tissues, in the treatment of reperfusion injury diseases.

Design, synthesis, and biological evaluation of halogenated N-(2-(4-Oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)ethyl)benzamides: Discovery of an isoform-selective small molecule phospholipase D2 inhibitor

Phospholipase D (PLD) catalyzes the conversion of phosphatidylcholine to the lipid second messenger phosphatidic acid. Two mammalian isoforms of PLD have been identified, PLD1 and PLD2, which share 53% sequence identity and are subject to different regulatory mechanisms. Inhibition of PLD enzymatic activity leads to increased cancer cell apoptosis, decreased cancer cell invasion, and decreased metastasis of cancer cells; therefore, the development of isoform-specific, PLD inhibitors is a novel approach for the treatment of cancer. Previously, we developed potent dual PLD1/PLD2, PLD1-specific (>1700-fold selective), and moderately PLD2-preferring (>10-fold preferring) inhibitors. Here, we describe a matrix library strategy that afforded the most potent (PLD2 IC50 = 20 nM) and selective (75-fold selective versus PLD1) PLD2 inhibitor to date, N-(2-(1-(3-fluorophenyl)-4-oxo-1, 3,8-triazaspiro[4.5]decan-8-yl)ethyl)-2-naphthamide (22a), with an acceptable DMPK profile. Thus, these new isoform-selective PLD inhibitors will enable researchers to dissect the signaling roles and therapeutic potential of individual PLD isoforms to an unprecedented degree.