5269-44-3

Basic information

• Product Name: diethyl 5-{3-[4-(3-chlorophenyl)piperazin-1-yl]-2,5-dioxopyrrolidin-1-yl}benzene-1,3-dicarboxylate
• CAS NO: 5269-44-3
• Molecular Formula: C₁₂H₁₉NO₂Si
• Molecular Weight: 513.97
• Mol File: 5269-44-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 717.5°C at 760 mmHg
• Flash Point: 387.7°C
• Density: 1.338g/cm³
• Vapor Pressure: 1.95E-20mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: diethyl 5-{3-[4-(3-chlorophenyl)piperazin-1-yl]-2,5-dioxopyrrolidin-1-yl}benzene-1,3-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl 5-{3-[4-(3-chlorophenyl)piperazin-1-yl]-2,5-dioxopyrrolidin-1-yl}benzene-1,3-dicarboxylate(5269-44-3)
• EPA Substance Registry System: diethyl 5-{3-[4-(3-chlorophenyl)piperazin-1-yl]-2,5-dioxopyrrolidin-1-yl}benzene-1,3-dicarboxylate(5269-44-3)

Safety Data

• Hazardous Substances Data: 5269-44-3(Hazardous Substances Data)

Upstream product

• 63-91-2 L-phenylalanine 
• 10416-59-8 N,O-Bis(trimethylsilyl)acetamide 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 75-77-4 chloro-trimethyl-silane 

Downstream Products

• 195244-96-3 N-(9-phenylfluoren-9-yl)-L-phenylalanine 
• 129943-49-3 (S)-3-Methyl-2-[(S)-3-phenyl-2-((E)-3-pyridin-3-yl-allyloxycarbonylamino)-propionylamino]-butyric acid tert-butyl ester 
• 35661-40-6 N-Fmoc L-Phe 
• 129943-38-0 (S)-3-Phenyl-2-((E)-3-pyridin-3-yl-allyloxycarbonylamino)-propionic acid 
• 47672-25-3 N-trityl-L-phenylalanine 

Relevant articles and documents

Solid phase synthesis of 1-aminohydantoin libraries

The solid support synthesis of a series of I-aminohydantoins based on a diverse set of hydrazino amino acid, aldehydes, and amines is described. The method involves the construction of resin attached hydrazino acid precursors, followed by subsequent derivatization, and then cyclizative cleavage off the resin. Overall yields vary per example between 15 and 60%, and the samples are suitable for biological evaluations without further purification.

Mild, Rapid, and Chemoselective Procedure for the Introduction of the 9-Phenyl-9-fluorenyl Protecting Group into Amines, Acids, Alcohols, Sulfonamides, Amides, and Thiols

The 9-phenyl-9-fluorenyl (PhF) group has been used as an Nα protecting group of amino acids and their derivatives mainly as a result of its ability to prevent racemization. However, installing this group using the standard protocol, which employs 9-bromo-9-phenylfluorene/K3PO4/Pb(NO3)2, often takes days and yields can be variable. Here, we demonstrate that the PhF group can be introduced into the amino group of Weinreb's amides and methyl esters of amino acids, as well as into alcohols and carboxylic acids, rapidly and in excellent yields, using 9-chloro-9-phenylfluorene (PhFCl)/N-methylmorpholine (NMM)/AgNO3. Nα-PhF-protected amino acids can be prepared from unprotected α-amino acids, rapidly and often in near quantitative yields, by treatment with N,O-bis(trimethylsilyl)acetamide (BSA) and then PhFCl/NMM/AgNO3. Primary alcohols can be protected with the PhF group in the presence of secondary alcohols in moderate yield. Using PhFCl/AgNO3, a primary alcohol can be protected in good yield in the presence of a primary ammonium salt or a carboxylic acid. Primary sulfonamides and amides can be protected in moderate to good yields using phenylfluorenyl alcohol (PhFOH)/BF3·OEt2/K3PO4, while thiols can be protected in good to excellent yield using PhFOH/BF3·OEt2 even in the presence of a carboxylic acid or primary ammonium group.

Alpha-helical mimetics

Benzoyl urea derivatives that are alpha helical peptides mimetics that mimic BH3-only proteins, compositions containing them, their conjugation to cell-targeting-moieties, and their use in the regulation of cell death are disclosed. The benzoyl urea derivatives are capable of binding to and neutralizing pro-survival Bcl-2 proteins. Use of benzoyl urea derivatives in the treatment and/or prophylaxis of diseases or conditions associated with deregulation of cell death are also described.