Optical resolution of 1-(1-naphthyl)ethylamine by its dicarboxylic acid derivatives: Structural features of the oxalic acid derivative diastereomeric salt pair

Chirality ◽  
2009 ◽  
Vol 21 (3) ◽  
pp. 331-338 ◽  
Author(s):  
Laura Bereczki ◽  
Petra Bombicz ◽  
József Bálint ◽  
Gabriella Egri ◽  
József Schindler ◽  
...  
Keyword(s):  
Oxalic Acid ◽  
Dicarboxylic Acid ◽  
Acid Derivative ◽  
Optical Resolution ◽  
Structural Features

INDUCED ASYMMETRY AND OPTICAL RESOLUTION OF 2-PHENYLPYRIDINE DERIVATIVES

1938 ◽  
Vol 16b (4) ◽  
pp. 109-113 ◽  
Author(s):  
J. G. Breckenridge ◽  
O. C. Smith
Keyword(s):  
Dicarboxylic Acid ◽  
Acid Derivative ◽  
Opposite Direction ◽  
Optical Rotation ◽  
Dimethyl Ester ◽  
Optical Resolution ◽  
Cinchona Alkaloids ◽  
Diphenic Acid

It was shown in 1927 that quinine, when combined with a diphenic acid derivative, gave a salt with an optical rotation in the opposite direction to that of the free alkaloid ("Kuhn's effect"). The present authors have prepared the salts of four of the cinchona alkaloids with 2-phenylpyridine-2′:3-dicarboxylic acid, and find similar results. In addition, a partial optical resolution of a derivative of this acid has been effected, the dextro-form of the methiodide of the dimethyl ester having been isolated.

STUDIES ON THE BIOSYNTHESIS OF PYOCYANINE

1962 ◽  
Vol 8 (1) ◽  
pp. 49-56 ◽  
Author(s):  
J. M. Ingram ◽  
A. C. Blackwood
Keyword(s):  
Amino Acids ◽  
Pseudomonas Aeruginosa ◽  
Oxalic Acid ◽  
Dicarboxylic Acid ◽  
Sodium Formate ◽  
Complete Medium ◽  
Tetracarboxylic Acid ◽  
Dipotassium Salt

The biosynthesis of pyocyanine, the blue phenazine pigment produced by Pseudomonas aeruginosa, was studied by the addition of radioactive substrates to a culture growing on a complete medium. The distribution of labelled carbon from radioactive substrates in the pyocyanine was examined by degrading the pigment to 1-hydroxyphenazine, quinoxaline dicarboxylic acid, quinoxaline, and pyrazine tetracarboxylic acid dipotassium salt, and thus 7 of the 13 carbons were assayed separately or in pairs.Glycerol-1,3-C14 is the principal donor of radioactivity to the pyocyanine carbon, but not all the carbon atoms tested were labeled. Alanine-U-C14 contributed carbon to pyocyanine also, but not to all carbons, and at a much lower level of efficiency than glycerol. However, with leucine-U-C14, all carbon atoms tested were labeled to a slight extent. These amino acids, when labeled specifically, and glutamate-U-C14, oxalic acid-C14, and sodium formate-C14 did not contribute significantly to pyocyanine carbon.The distribution of radioactivity from glycerol in the pyocyanine molecule suggests the pigment is formed from glycerol or a product closely related to it by the condensation of two carbon units or the condensation of four and two carbon units.

Succinic, fumaric, adipic and oxalic acid cocrystals of promethazine hydrochloride

2019 ◽  
Vol 75 (2) ◽  
pp. 107-119 ◽  
Author(s):  
Gheorghe Borodi ◽  
Alexandru Turza ◽  
Oana Onija ◽  
Attila Bende
Keyword(s):  
Oxalic Acid ◽  
Dicarboxylic Acid ◽  
Density Functional ◽  
Water Solubility ◽  
Lattice Parameter ◽  
Acetonitrile Solution ◽  
Stoichiometric Ratio ◽  
Scanning Calorimetry ◽  
Equilibrium Configurations ◽  
Promethazine Hydrochloride

Novel cocrystals of promethazine hydrochloride [PTZ-Cl; systematic name: N,N-dimethyl-1-(10H-phenothiazin-10-yl)propan-2-aminium chloride] with succinic acid (PTZ-Cl-succinic, C17H21N2S+·Cl−·0.5C4H6O4), fumaric acid (PTZ-Cl-fumaric, C17H21N2S+·Cl−·0.5C4H4O4) and adipic acid (PTZ-Cl-adipic, C17H21N2S+·Cl−·0.5C6H10O4) were prepared by solvent drop grinding and slow evaporation from acetonitrile solution, along with two oxalic acid cocrystals which were prepared in tetrahydrofuran (the oxalic acid hemisolvate, PTZ-Cl-oxalic, C17H21N2S+·Cl−·0.5C2H2O4) and nitromethane (the hydrogen oxalate salt, PTZ-oxalic, C17H21N2S+·C2HO4 −). The crystal structures obtained by crystallization from tetrahydrofuran and acetonitrile include the Cl− ion in the lattice structures, while the Cl− ion is missing from the crystal structure obtained by crystallization from nitromethane (PTZ-oxalic). In order to explain the formation of the two types of supramolecular configurations with oxalic acid, the intermolecular interaction energies were calculated in the presence of the two solvents and the equilibrium configurations were determined using density functional theory (DFT). The cocrystals were studied by X-ray diffraction, IR spectroscopy and differential scanning calorimetry. Additionally, a stability test under special conditions and water solubility were also investigated. PTZ-Cl-succinic, PTZ-Cl-fumaric and PTZ-Cl-adipic crystallized having similar lattice parameter values, and showed a 2:1 PTZ-Cl to dicarboxylic acid stoichiometry. PTZ-Cl-oxalic crystallized in a 2:1 stoichiometric ratio, while the structure lacking the Cl atom belongs has a 1:1 stoichiometry. All the obtained crystals exhibit hydrogen bonds of the type PTZ...Cl...(dicarboxylic acid)...Cl...PTZ, except for PTZ-oxalic, which forms bifurcated bonds between the hydrogen oxalate and promethazinium ions, along with an infinite hydrogen-bonded chain between the hydrogen oxalate anions.

Studies on Pd(1,4-bis(2-hydroxyethyl)piperazine)-dicarboxylic acid complexes as models for carboplatin with structural features enhancing the interaction with DNA

2019 ◽  
Vol 72 (12) ◽  
pp. 2035-2049
Author(s):  
Mohamed R. Shehata ◽  
Mohamed M. Shoukry ◽  
Mahmoud A. Mabrouk ◽  
Anna Kozakiewicz ◽  
Rudi van Eldik
Keyword(s):  
Dicarboxylic Acid ◽  
Structural Features ◽  
Hydroxyethyl Piperazine

scholarly journals Optical Resolution of 2,2′,6,6′-Tetrafluorobiphenyl-3,3′-dicarboxylic Acid

1982 ◽  
Vol 55 (12) ◽  
pp. 3828-3830 ◽  
Author(s):  
Noriko Hasaka ◽  
Masayoshi Okigawa ◽  
Isao Kouno ◽  
Nobusuke Kawano
Keyword(s):  
Dicarboxylic Acid ◽  
Optical Resolution

scholarly journals Convenient Optical Resolution of Axially Chiral 1,1′-Binaphthyl-2,2′-dicarboxylic Acid

1988 ◽  
Vol 61 (3) ◽  
pp. 1032-1034 ◽  
Author(s):  
Shigeyoshi Kanoh ◽  
Yukihiko Hongoh ◽  
Masatoshi Motoi ◽  
Hiroshi Suda
Keyword(s):  
Dicarboxylic Acid ◽  
Optical Resolution ◽  
Axially Chiral

scholarly journals A new facile synthesis of dimethyl 4-(2-(2,6-bis(methoxycarbonyl)pyridin-4-yl)vinyl) pyridine-2,6-dicarboxylate

2010 ◽  
Vol 29 (2) ◽  
pp. 165
Author(s):  
Guoliang Gu ◽  
Ming Lu
Keyword(s):  
Dicarboxylic Acid ◽  
Acid Derivative ◽  
Title Compound ◽  
Molar Ratio ◽  
Facile Synthesis ◽  
Nitrogen Bases ◽  
Pyridine Dicarboxylic Acid ◽  
Vinyl Pyridine

A new facile synthesis of pyridine dicarboxylic acid derivative, dimethyl 4-(2-(2,6-bis(methoxycarbonyl)pyridin-4-yl)vinyl)pyridine-2,6-dicarboxylate (DVDPA), from dimethyl 4-(chloromethyl)pyridine-2,6-dicarboxylate (CMDPA) in presence of nitrogen bases has been described. The influences of different base/CMDPA molar ratio and different nitrogen bases were also investigated. The result has shown that the yield could reach 81 % when triethylamine was used and the molar ratio of base/CMDPA was 2.4. The overall yield of title compound via the three-step synthesis starting from dimethyl 4-(hydroxylmethyl)pyridine-2,6-dicarboxylate (HMDPA) was improved to 69 %.

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