74720-33-5

Usage

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Ir-Catalyzed Double Asymmetric Hydrogenation of 3,6-Dialkylidene-2,5-diketopiperazines for Enantioselective Synthesis of Cyclic Dipeptides

An Ir/spiro[4,4]-1,6-nonadiene-based phosphine-oxazoline ligand (SpinPHOX) complex-catalyzed double asymmetric hydrogenation of 3,6-dialkylidene-1,4-dimethylpiperazine-2,5-diones has been developed, providing efficient and practical access to a wide varie

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.

Solution-phase combinatorial synthesis and evaluation of piperazine-2,5- dione derivatives

An efficient one-pot synthesis of a 61-membered combinatorial chemistry library of piperazine-2,5-diones was accomplished. Results of combinatorial synthesis, purification, analysis, and biological evaluation are described.

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

Potassium Fluoride on Alumina: Condensation of 1,4-Diacetylpiperazine-2,5-dione with Aldehydes. Dry Condensation under Microwave Irradiation. Synthesis of Albonursin and Analogues

1,4-Diacetylpiperazine-2,5-dione (1) was condensated with aldehydes (2) with KF on alumina without solvent under microwaves or in at room temperature in the presence of DMF.The reaction was stereoselective and some natural products (4a-c) like albonursin (4c) were synthesized.

Pyrazine Chemistry. II. Reduction of 3,6-Dibenzylidenepiperazine-2,5-diones

A reinvestigation of the reduction of 3,6-dibenzylidenepiperazine-2,5-dione (1) with zinc and acetic acid established that this reaction gave (Z)-6-benzyl-3-benzylidenepiperazine-2,5-dione (10).When a mixture of acetic acid and hydrochloric acid was used

α,β-Unsaturated Carboxylic Acid Derivatives. Part 18. Syntheses of Geometric Isomers of 3,6-Dibenzylidene- and 3-p-Anisylidene-6-benzylidene-2,5-piperazinediones

Naturally occuring 3,6-dibenzylidene- and 3-p-anisylidene-6-benzylidene-2,5-piperazinediones and their geometric isomers were synthesized by the condensation of 1-acetyl or 1,4-diacetyl derivative of (E)- and (Z)-benzylidene- or p-anisylidene-2,5-piperazinediones with an appropriate aldehyde.The configuration of these compounds were assigned on the basis of the spectroscopic analyses, and those of natural products were determined to be (3Z,6Z).