253175-91-6

Basic information

• Product Name: 1-Piperazinecarboxylic acid, 4-(phenylacetyl)-, 1,1-dimethylethyl ester
• CAS NO: 253175-91-6
• Molecular Formula: C17H24N2O3
• Molecular Weight: 304.389
• Mol File: 253175-91-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-Piperazinecarboxylic acid, 4-(phenylacetyl)-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Piperazinecarboxylic acid, 4-(phenylacetyl)-, 1,1-dimethylethyl ester(253175-91-6)
• EPA Substance Registry System: 1-Piperazinecarboxylic acid, 4-(phenylacetyl)-, 1,1-dimethylethyl ester(253175-91-6)

Safety Data

• Hazardous Substances Data: 253175-91-6(Hazardous Substances Data)

Upstream product

• 103-82-2 phenylacetic acid 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 536-74-3 phenylacetylene 
• 5042-34-2 N-(4-acetamidophenylsulfonyl)-2-phenylacetamide 

Downstream Products

• 1622867-05-3 C₂₆H₂₄N₄O₃S 
• 502644-42-0 2-chloro-6-ethyl-4-[4-(phenylacetyl)piperazin-1-yl]thieno[2,3-d]pyrimidine 
• 1599431-89-6 (E)-3-(4-methoxyphenyl)-1-(4-(2-phenylacetyl)piperazin-1-yl)prop-2-en-1-one 
• 1599431-88-5 (E)-1-(4-(2-phenylacetyl)piperazin-1-yl)-3-(p-tolyl)prop-2-en-1-one 
• 1599431-87-4 (E)-3-(4-bromophenyl)-1-(4-(2-phenylacetyl)piperazin-1-yl)prop-2-en-1-one 
• 1599432-09-3 2-(3,4-dimethylphenoxy)-1-(4-(2-phenylacetyl)piperazin-1-yl)ethanone 
• 1599431-86-3 2-(4-bromophenoxy)-1-(4-(2-phenylacetyl)piperazin-1-yl)ethanone 
• 461415-11-2 2-(4-chlorophenoxy)-1-(4-(2-phenylacetyl)piperazin-1-yl)ethanone 
• 1018574-27-0 2-chloro-1-(4-(2-phenylacetyl)piperazin-1-yl)ethanone 
• 1599431-91-0 (E)-3-(3-fluoro-4-methylphenyl)-1-(4-(2-phenylacetyl)piperazin-1-yl)prop-2-en-1-one 
• 1599431-90-9 (E)-3-(3,4-dichlorophenyl)-1-(4-(2-phenylacetyl)piperazin-1-yl)prop-2-en-1-one 
• 88372-33-2 2-phenyl-1-(piperazin-1-yl)ethanone 

Relevant articles and documents

Structure-Activity Relationships of Potent, Targeted Covalent Inhibitors That Abolish Both the Transamidation and GTP Binding Activities of Human Tissue Transglutaminase

Human tissue transglutaminase (hTG2) is a multifunctional enzyme. It is primarily known for its calcium-dependent transamidation activity that leads to formation of an isopeptide bond between glutamine and lysine residues found on the surface of proteins, but it is also a GTP binding protein. Overexpression and unregulated hTG2 activity have been associated with numerous human diseases, including cancer stem cell survival and metastatic phenotype. Herein, we present a series of targeted covalent inhibitors (TCIs) based on our previously reported Cbz-Lys scaffold. From this structure-activity relationship (SAR) study, novel irreversible inhibitors were identified that block the transamidation activity of hTG2 and allosterically abolish its GTP binding ability with a high degree of selectivity and efficiency (kinact/KI > 105 M-1 min-1). One optimized inhibitor (VA4) was also shown to inhibit epidermal cancer stem cell invasion with an EC50 of 3.9 μM, representing a significant improvement over our previously reported "hit" NC9.

B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether

The use of B(OCH2CF3)3 for mediating direct amidation reactions of a wide range of pharmaceutically relevant carboxylic acids and amines is described, including numerous heterocycle-containing examples. An initial screen of solvents for the direct amidation reaction suggested that cyclopentyl methyl ether, a solvent with a very good safety profile suitable for use over a wide temperature range, was an excellent replacement for the previously used solvent acetonitrile. Under these conditions amides could be prepared from 18 of the 21 carboxylic acids and 18 of the 21 amines examined. Further optimisation of one of the low yielding amidation reactions (36% yield) via a design of experiments approach enabled an 84% yield of the amide to be obtained.

Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides

(Chemical Equation Presented) A direct, simple, and efficient route from terminal alkynes to amides is achieved by their copper(I)-catalyzed reaction with sulfonyl azides (see scheme). The reaction proceeds with the in situ generation of copper(I) acetylides and represents a one-step formal oxidative hydration of a triple bond.