31968-60-2

Upstream product

• 85-44-9 phthalic anhydride 

Downstream Products

• 5776-78-3 6-[6-(6-amino-hexanoylamino)-hexanoylamino]-hexanoic acid 
• 63330-01-8 6-phthalimido-hexanoic acid anilide 
• 357271-57-9 (R)-4-(1-methylethyl)-3-(1-oxo-5-phthalimidohexanoyl)-5,5-diphenyloxazolidin-2-one 
• 948317-85-9 monophenyl [6-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-1-hydroxy-1-(hydroxy-phenoxy-phosphoryl)hexyl]phosphonate 
• 1435263-58-3 C₃₃H₃₇N₃O₃ 
• 164979-93-5 (S)-N-propyl-N-[(6-amino-1-oxo)hexyl]-5,6-di(phenylmethoxy)-1,2,3,4-tetrahydro-2-naphthylamine 
• 59472-16-1 6-amino-N-phenyl-hexanamide hydrochloric acid salt 
• 2014-58-6 6-(6-aminohexanamido)hexanoic acid 
• 86451-34-5 N-(6-Aminohexyl)-N-benzyl-N'-methylmethylenediamine 
• 86451-33-4 Methyl N-(6-aminohexanoyl)-N-benzylaminomethylcarbamate 
• 86451-32-3 N-Benzyl-N-aminocarbonylmethyl-6-aminohexanamide 
• 97125-05-8 6-(3,4-dihydroisoquinolin-2(1H)-yl)hexan-1-amine 
• 97124-84-0 6-(2,3-Dihydro-indol-1-yl)-hexylamine 
• 81960-05-6 6-(piperidine-1-yl)hexan-1-amine 

Relevant academic research and scientific papers

Assembling of medium/long chain-based β-arylated unnatural amino acid derivatives via the Pd(II)-catalyzed sp3 β-C-H arylation and a short route for rolipram-type derivatives

In this paper, we report the assembling of libraries of β-arylated short/medium/long chain-based non-α-amino acid (aminoalkanoic acid) derivatives via the Pd(II)-catalyzed, bidentate directing group 8-aminoquinoline-aided sp3 β-C-H activation/arylation method. Short/medium chain-based unnatural amino acid derivatives containing an aryl group at the β-position are promising small molecules with therapeutic properties. Thus, it is necessary to enrich the libraries of short/medium/long chain-based unnatural amino acid derivatives containing an aryl group at the β-position. Considering the importance of β-arylated short/medium/long chain-based non-α-amino acid derivatives, an inclusive attention was paid to explore the Pd(II)-catalyzed sp3 β-C-H arylation of short/medium/long chain-based non-α-amino acids. Representative synthetic transformations including a short route for the assembling of rolipram and related compounds and 3-arylated GABA derivatives such as, baclofen, phenibut and tolibut were shown using selected β-C-H arylated non-α-amino acid derivatives.

ω-Phthalimidoalkyl Aryl Ureas as Potent and Selective Inhibitors of Cholesterol Esterase

Cholesterol esterase (CEase), a serine hydrolase thought to be involved in atherogenesis and thus coronary heart disease, is considered as a target for inhibitor development. We investigated recombinant human and murine CEases with a new fluorometric assay in a structure–activity relationship study of a small library of ω-phthalimidoalkyl aryl ureas. The urea motif with an attached 3,5-bis(trifluoromethyl)phenyl group and the aromatic character of the ω-phthalimide residue were most important for inhibitory activity. In addition, an alkyl chain composed of three or four methylene groups, connecting the urea and phthalimide moieties, was found to be an optimal spacer for inhibitors. The so-optimized compounds 2 [1-(3,5-bis(trifluoromethyl)phenyl)-3-(3-(1,3-dioxoisoindolin-2-yl)propyl)urea] and 21 [1-(3,5-bis(trifluoromethyl)phenyl)-3-(4-(1,3-dioxoisoindolin-2-yl)butyl)urea] exhibited dissociation constants (Ki) of 1–19 μm on the two CEases and showed either a competitive (2 on the human enzyme and 21 on the murine enzyme) or a noncompetitive mode of inhibition. Two related serine hydrolases—monoacylglycerol lipase and fatty acid amide hydrolase—were inhibited by ω-phthalimidoalkyl aryl ureas to a lesser extent.

Stereoselective synthesis of β-alkylated α-amino acids via palladium-catalyzed alkylation of unactivated methylene C(sp3)-H Bonds with Primary Alkyl Halides

We report a new set of reactions based on the Pd-catalyzed alkylation of methylene C(sp3)-H bonds of aliphatic quinolyl carboxamides with α-haloacetate and methyl iodide and applications in the stereoselective synthesis of various β-alkylated α-amino acids. These reactions represent the first generally applicable method for the catalytic alkylation of unconstrained and unactivated methylene C-H bonds with high synthetic relevance. When applied with simple isotope-enriched reagents, they also provide a convenient and powerful means to site-selectively incorporate isotopes into the carbon scaffolds of amino acid compounds.

Syntheses of phosphonic esters of alendronate, pamidronate and neridronate

Several synthetic pathways for obtaining phosphonic esters of the amino bisphosphonic acids (NBPs) pamidronate, alendronate and neridronate were investigated. The general guideline was to react N-protected amino acids activated as phthalimide esters or as acyl chlorides. Succinimide esters were found less reactive and quickly abandoned. γ-Lactam formation arises when starting from Boc- or Cbz-protected amino acids. The phthalimide N-protecting group allowed access to alkyl or aryl mono-, di- (symmetric or not) and triesters of these three NBPs in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.