74720-33-5

Basic information

• Product Name: piperafizine B
• Synonyms: piperafizine B
• CAS NO: 74720-33-5
• Molecular Formula: C₁₈H₁₄N₂O₂
• Molecular Weight: 290.321
• Mol File: 74720-33-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 646.2°C at 760 mmHg
• Flash Point: 258.2°C
• Appearance: /
• Density: 1.278g/cm³
• Vapor Pressure: 1.37E-16mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: piperafizine B(CAS DataBase Reference)
• NIST Chemistry Reference: piperafizine B(74720-33-5)
• EPA Substance Registry System: piperafizine B(74720-33-5)

Safety Data

• Hazardous Substances Data: 74720-33-5(Hazardous Substances Data)

Usage

Description

Piperafizine B, with the chemical abstracts service number (CAS#) 74720-33-5, is a unique compound known for its distinct properties and applications in various fields. It is characterized by its ability to contribute to the stereoselective synthesis of certain complex molecules, making it a valuable asset in the realm of chemical research and development.

Uses

Used in Pharmaceutical and Chemical Research:
Piperafizine B is utilized as a reagent in the stereoselective preparation of diketopiperazine bisepoxides. This application is particularly significant in the pharmaceutical industry, where the synthesis of such complex molecules can lead to the development of novel drugs with improved efficacy and selectivity. The stereoselective nature of its use ensures that the desired molecular configurations are achieved, which is crucial for the biological activity and safety of the resulting compounds.

InChI:InChI=1/C18H14N2O2/c21-17-15(11-13-7-3-1-4-8-13)19-18(22)16(20-17)12-14-9-5-2-6-10-14/h1-12H,(H,19,22)(H,20,21)/b15-11-,16-12-

Upstream product

• 100-52-7 benzaldehyde 
• 30166-29-1 1-acetyl-3-[(Z)-benzylidene]-2,5-piperazinedione 
• 68662-68-0 1,4-diacetyl-(Z)-3-benzylidene-2,5-piperazinedione 
• 3027-05-2 N,N'-diacetylpiperazin-2,5-dione 
• 19459-03-1 (Z)-3-phenylmethylenepiperazine-2,5-dione 

Downstream Products

• 94514-45-1 1,4-dimethyl-(Z)-3-(Z)-6-dibenzylidene-2,5-piperazinedione 
• 40739-77-3 (+/-)-(Z)-6-benzyl-3-benzylidenepiperazine-2,5-dione 
• 2308-61-4 (+/-)-cis-3,6-dibenzylpiperazine-2,5-dione 
• 15136-18-2 (+/-)-trans-3,6-dibenzylpiperazine-2,5-dione 
• 13795-55-6 (+/-)-cis-3,6-dibenzyl-1,4-dimethylpiperazine-2,5-dione 
• 133008-21-6 (S,Z)-3-benzyl-6-benzylidene-1,4-dimethylpiperazine-2,5-dione 
• 61125-52-8 (+/-)-cis-3,6-dibenzyl-1,4-dimethylpiperazine-2,5-dione 
• 81536-08-5 (2S,5S)-1,4-dimethyl-2,5-bis(phenylmethyl)piperazine 

Relevant articles and documents

Enantioselective Synthesis of Chiral Substituted 2,4-Diketoimidazolidines and 2,5-Diketopiperazines via Asymmetric Hydrogenation

An enantioselective hydrogenation of 5-alkylidene-2,4-diketoimidazolidines (hydantoins) and 3-alkylidene-2,5-ketopiperazines catalyzed by the Rh/f-spiroPhos complex under mild conditions has been developed, which provides an efficient approach to the highly enantioselective synthesis of chiral hydantoins and 2,5-ketopiperazine derivatives with high enantioselectivities up to 99.9% ee.

Discovery of a class of diketopiperazines as antiprion compounds

Prion diseases are fatal neurodegenerative and infectious disorders for which effective pharmacological tools are not yet available. This unmet challenge and the recently proposed interplay between prion diseases and Alzheimer's have led to a more urgent demand for new antiprion agents. Herein, we report the identification of a novel bifunctional diketopiperazine (DKP) derivative 1d, which exhibits activity in the low micromolar range against prion replication in ScGT1 cells, while showing low cytotoxicity. Supported by properly addressed molecular modeling studies, we hypothesized that a planar conformation is the major determinant for activity in this class of compounds. Moreover, studies aimed at assessing the mechanism-of-action at the molecular level showed that 1d might interact directly with recombinant prion protein (recPrP) to prevent its conversion to the pathogenic misfolded prion protein (PrPSc)-like form. This investigation suggests that DKP based antiprion compounds can serve as a promising lead scaffold in developing new drugs to combat prion diseases.

Pharmaceutical compounds

Diketopiperazines of the formula: STR1 where each of R1 to R10, which may be the same or different, is independently selected from the group consisting of hydrogen, C1 -C6 alkyl unsubstituted or substituted by o