4333-65-7Relevant academic research and scientific papers
Structure-activity relationships (SAR) and structure-kinetic relationships (SKR) of sulphone-based CRTh2 antagonists
Buil, Maria Antonia,Calbet, Marta,Castillo, Marcos,Castro, Jordi,Esteve, Cristina,Ferrer, Manel,Forns, Pilar,González, Jacob,López, Sara,Roberts, Richard S.,Sevilla, Sara,Vidal, Bernat,Vidal, Laura,Vilaseca, Pere
, p. 102 - 133 (2016/03/04)
Monocyclic and bicyclic ring systems were investigated as the "core" section of a series of diphenylsulphone-containing acetic acid CRTh2 receptor antagonists. A range of potencies were observed and single-digit nanomolar potencies were obtained in both the monocyclic and bicyclic cores. Residence times for the monocyclic compounds were very short. Some of the bicyclic cores displayed better residence times. A methyl group in the northern part of the core, between the head and tail was a necessary requirement for the beginnings of long residence times. Variations of the tail substitution maximised potencies and residence times.
Intra- and intermolecular C(sp2)-H...O hydrogen bonds in a series of isobenzofuranone derivatives: Manifestation and energetics
Niebel, Claude,Lokshin, Vladimir,Sigalov, Mark,Krief, Pnina,Khodorkovsky, Vladimir
supporting information; experimental part, p. 3689 - 3699 (2009/05/07)
Derivatives 2-6 were prepared as models for studying intra- and intermolecular C(sp2)-H...O hydrogen bonding. Their X-ray structures confirm the presence of intramolecular hydrogen bonds in derivatives of the a series: the corresponding C...O distances vary between 2.91 and 2.97 A. The corresponding 13C-1H coupling constants are increased by about 7.5 Hz, and the 1H chemical shifts in CDCl3 are 9.1-10.7 ppm. No intramolecular hydrogen bonds can form in derivatives of the isomeric b series. In this series, the chemical shifts of the corresponding aromatic protons exhibit strong solvent dependency; in particular, they are as sensitive as the proton in chloroform to the presence of DMSO. The vinylic protons activated by the electron-accepting COOR groups behave similarly. Quantum mechanical calculations in the gas phase and in DMSO reproduce the experimental observations. Energies of the intramolecular hydrogen bonds evaluated by two independent approaches vary between 3.7 and 4.4 kcal mol-1 in the gas phase and still amount to at least 2.5 kcal mol-1 in 2a in DMSO. These estimates are practically independent of the computational method (HF, MP2, and DFT B3LYP were employed for derivatives 2). We conclude that the behavior of both activated aromatic and vinylic C(sp2)-H atoms in the studied derivatives is qualitatively and quantitatively similar to the behavior of the C(sp 3)-H atom in chloroform. The existence of hydrogen bonds involving these atoms can easily be detected by NMR spectroscopy. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Method for producing alkyl 3-phthalidylideneacetate
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, (2008/06/13)
A method for producing an alkyl 3-phthalidylideneacetate has the step of treating phthalic anhydride with a monoalkyl malonate or a salt thereof having the following formula: wherein M represents a hydrogen atom, K, Na, Li, or NH4, and R represents a lower alkyl group having 1 to 5 carbon atoms. By using the above method, the desired alkyl 3-phthalidylideneacetate can be obtained at a high yield.
