Prostaglandins (PG's) are a very important class of naturally occurring physiologically active substances, which have been the subject of continuous attention by biologists, pharmacists and chemists since their discovery in the 1930s. Pharmacological studies have shown that prostaglandins exhibit an extremely broad spectrum of activity such as on the smooth muscles of various organs, their mediating role in the central and peripheral nervous systems, in inflammatory processes, and their hormone-like and antihormonal activities. Due to the diversified biological activity and rapid metabolism of the natural prostaglandins, a lot of effort has been done to synthesize prostaglandin analogs. Particularly interesting are the prostaglandin analogs containing heteroatoms in the cyclopentane ring which have received a great deal of attention in relation to their potential biological properties and diversified biological activity.This article is dedicated to Prof. Sune K. Bergstrom (in memoriam) for his milestone contributions to prostaglandin research.
Nesse trabalho é relatada a síntese de uma série de ácidos N-aril antranílicos inéditos, com bons a excelentes rendimentos, empregando irradiação de microondas como fonte de aquecimento para promover a reação de acoplamento de Ullmann entre ácidos antranílicos e brometos de arila contendo grupos substituintes doadores ou aceptores de elétrons.In this paper we report the synthesis of a series of novel N-aryl anthranilic acids, with good to excellent yields, employing microwaves as heat source to promote the Ullmann coupling between anthranilic acids and aryl bromides possessing electron donating or withdrawing groups.
Due to the high symmetry and low polarity of the cyclopropane (C 3 H 6), cyclobutane (C 4 H 8), prismane (C 6 H 6), and cubane (C 8 H 8), it is widely known that these structures unlikely act as proton receptors to form intermolecular interactions with monoprotic acids, such as the hydrogen fluoride. Although the C 3 H 6 ÁÁÁHF, C 4 H 8 ÁÁÁHF, C 6 H 6 ÁÁÁHF, and C 8 H 8 ÁÁÁHF are weakly bound complexes, in this current work, all of them were definitively certified on the basis of a theoretical analysis. In according with the structural parameters and spectroscopy modes appraised through the density-functional theory calculations, the more accentuated perturbations are manifested in the hydrogen fluoride. The new hydrogen bond forms framed as pseudo-πÁÁÁH and CÁÁÁH were unveiled through the calculations of the quantum theory of atoms in molecules and natural bond orbital. In this context, the knowledge about the nature of these hydrogen bonds is necessary, wherein it used the symmetry-adapted perturbation theory for computing the contributions of the electrostatic, polarization, exchange, dispersion, and charge transfer terms. Lastly, the practical behavior of these hydrocarbons under the condition to form intermolecular interactions was examined by taking into account the solvent effect with calculations of the polarizable continuum model.
Organic chemistry Z 0200 Synthesis and Biological Activity of Prostaglandin Analogues Containing Heteroatoms in the Cyclopentane Ring -[92 refs.]. -(BIAGGIO, F. C.; RUFINO, A. R.; ZAIM, M. H.; ZAIM, C. Y. H.; BUENO, M. A.; RODRIGUES, A.; Curr. Org. Chem. 9 (2005) 5, 419-457; Fac. Eng. Quim., 12608 Sao Paulo, Brazil; Eng.) -Lindner 46-262
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