133-08-4Relevant articles and documents
Structure-retention relationship in a series of chiral 1,4-disubstituted piperazine derivatives on carbohydrate chiral stationary phases
Chilmonczyk, Zdzislaw,Sienicki, Lukasz,Lozowicka, Bozena,Lisowska-Kuzmicz, Malgorzata,Jonczyk, Anna,Aboul-Enein, Hassan Y.
, p. 439 - 443 (2005)
New racemic 1,4-disubstituted piperazines chemically named ethyl 2-[(4-pyrimidin-2yl-piperazine-1yl)carbonyl]C3-C5-alkanoates 1-7 were synthesized. The compounds were resolved into enantiomers on cellulose tris(4-methylbenzoate) and amylose tris(3,5-dimethylphenylcarbamate) stationary phases using hexane/propan-2-ol mobile phases. The optimum separation conditions for the compounds were obtained on cellulose tris(4-methylbenzoate) with 5% of 2-propanol in hexane. The relationship between structural and chromatographic parameters is discussed.
Co-Catalytic Effects in Phase-Transfer Catalyzed Reactions
Szabo, G. T.,Aranyosi, K.,Csiba, M.,Toke, L.
, p. 565 - 566 (1987)
The phase-transfer catalyzed alkylation reaction of diethyl malonate with butyl bromide using solid potassium carbonate as base could not be accelerated above a limiting reaction rate by increasing the concentration of the onium salt catalyst.The rate limit could be exceeded by using crown ether in addition to an onium salt.Polyethylene glycols exhibit a similar effect.These results were used to improve the yields in a series of related alkylation reactions.
Alkylation of malonic and acetoacetic esters in an ionic liquid
Kryshtal, Galina V.,Zhdankina, Galina M.,Zlotin, Sergei G.
, p. 57 - 58 (2002)
1-Butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]) has been used as a recyclable medium in the alkylation of malonic and acetoacetic esters with alkyl, benzyl and prenyl halides.
Xanthenylacetic Acid Derivatives Effectively Target Lysophosphatidic Acid Receptor 6 to Inhibit Hepatocellular Carcinoma Cell Growth
Gnocchi, Davide,Cavalluzzi, Maria M.,Mangiatordi, Giuseppe F.,Rizzi, Rosanna,Tortorella, Cosimo,Spennacchio, Mauro,Lentini, Giovanni,Altomare, Angela,Sabbà, Carlo,Mazzocca, Antonio
, p. 2121 - 2129 (2021)
Despite the increasing incidence of hepatocellular carcinoma (HCC) worldwide, current pharmacological treatments are still unsatisfactory. We have previously shown that lysophosphatidic acid receptor 6 (LPAR6) supports HCC growth and that 9-xanthenylacetic acid (XAA) acts as an LPAR6 antagonist inhibiting HCC growth without toxicity. Here, we synthesized four novel XAA derivatives, (±)-2-(9H-xanthen-9-yl)propanoic acid (compound 4 – MC9), (±)-2-(9H-xanthen-9-yl)butanoic acid (compound 5 – MC6), (±)-2-(9H-xanthen-9-yl)hexanoic acid (compound 7 – MC11), and (±)-2-(9H-xanthen-9-yl)octanoic acid (compound 8 – MC12, sodium salt) by introducing alkyl groups of increasing length at the acetic α-carbon atom. Two of these compounds were characterized by X-ray powder diffraction and quantum mechanical calculations, while molecular docking simulations suggested their enantioselectivity for LPAR6. Biological data showed anti-HCC activity for all XAA derivatives, with the maximum effect observed for MC11. Our findings support the view that increasing the length of the alkyl group improves the inhibitory action of XAA and that enantioselectivity can be exploited for designing novel and more effective XAA-based LPAR6 antagonists.
Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)
Condon, Sylvie,Le Gall, Erwan,Pichon, Christophe,Presset, Marc,Xavier, Tania
supporting information, p. 2085 - 2094 (2021/09/02)
The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.
Synthesis of protected α-amino acids: Via decarboxylation amination from malonate derivatives
Dai, Qipu,Fu, Hui,Hu, Changwen,Li, Peihe,Li, Xiaoying,Wang, Zheng
, p. 4439 - 4446 (2020/10/20)
A general and efficient strategy for the synthesis of protected α-amino acids is reported. The method uses malonate derivatives as the starting materials and Cs2CO3 as a base at 60 degrees, giving α-amino acid derivatives in moderate yields by releasing CO2. This methodology shows broad substrate scope (primary and secondary acids), excellent functional group tolerance and high efficiency to give the desired products under mild reaction conditions. It also allows the construction of β and γ-amino acids and other unnatural products.
