Biomedical subjects
Publications and source records attributed to G Scapini.
The synthesis, diastereomeric separation, assignment to erythro- and threo-configuration by 1HNMR, and optical resolution of 3-(p-trifluoromethyl-phenyl)- and (p-thioanisyl)-2-biphenylyl-3-hydroxypropionic acids are described. The enantiomers were submitted to a preliminary assay to determine antiinflammatory activity.
The optically active diastereometric erythro- and threo-3-thienyl-analogues 6a-d of 3-aryl-2-biphenylyl-3-hydroxy-propionic acids have been prepared. Some stereoisomers of 3-(3-thienyl)derivative 6b showed inhibition around 40% in the carrageenan-induced rat paw edema test.
As a part of wider research project on chiral anti-inflammatory arylacanoic acids, the 3-(o- and m-)-(methyl and methoxy)-phenyl-2-biphenylyl-3-hydroxypropionic acids 3a-d were synthesized and resolved in their optically active erythro and threo stereomers, which were submitted to the carrageenan induced rat paw edema test. With respect to the p-isomers, only the threo p-methoxy substitution enhances the anti-inflammatory activity. Some conclusions on structure-activity relationship are discussed.
The authors synthesized the title compounds as analogues of previously prepared potential antiphlogistic agents. Starting from appropriate carbonyl compound and alpha-metallated phenylacetic acid the diastereomeric racemate pairs were obtained; they were separated, attributed to erythro/threo-configuration by NMR and finally resolved. The potassium salts of the enantiomers were tested for analgesic and antiinflammatory activity, as well as for acute toxicity. Their action in the carrageenan test has been found to be stereoselective, but relatively poor or of briefly lastening.
The optically active stereomers of some 3-(fluoro-, chloro-, bromophenyl)-2-biphenylyl-3-hydroxypropionic acids were prepared and tested for antiinflammatory activity. Surprisingly, the four bromo-isomers were the most active ones, particularly in the threo configuration.
The in vitro antimicrobial activity of the title polymers is described. Iodoethylation leads to a sensible improvement of activity only when the amino groups present in the main backbone of the polymers are connected by a long aliphatic chain.
As part of a wider research project on structure-activity relationships of chiral arylalkanoic acids, stereomeric aryl- biphenylyl-hydroxypropionic acids 3a-d have been prepared and their antiinflammatory activity evaluated. Diastereomeric racemic erythro- and threo-acids have been synthesized by reaction of alpha-lithiated biphenylyl-acetic acid salts with the appropriate aldehyde. They were separated, and after attribution of their relative configuration by 1H-NMR analysis, resolved. The antiinflammatory activities of the enantiomeric potassium salts were determined by the carrageenan test.
The reaction between o-hydroxybutyrophenone and tris(2-chloroethyl)amine gave two analogues (II, V) of the well-known local anesthetic ketocaine (I). Compounds II and V showed interesting antitumor activity in mice implanted with Ehrlich ascites tumor cells (% T/C = 149 at 5 mg/kg and 171 at 50 mg/kg, respectively). Further studies on the pharmacological behavior of these new compounds are in progress.
The preparation of some homologues of 2-(4-cyclohexylphenyl)-3-hydroxypropionic acid, the separation of the diastereomeric race-mates, their attribution to erythro and threo series, and the optical resolution of the enantiomers are described. The optical antipodes were screened for acute toxicity, as well as for antiinflammatory and analgesic activity.
The synthesis of some homologues of 2-(4-biphenylyl)-3-hydroxypropionic acid, the separation of related diastereoisomers, their attribution to erythro and threo series, and resolution of the optical antipodes are described. The antiinflammatory activity--initially tested by carrageenin assay--proves generally influenced by steric configuration and is interesting for the isohexanoic derivative.
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The synthesis and chemical behaviour of pyrimidothiazine derivatives with a carboxyl group in position 7 [compounds (II) and (III)] or in position 6 [compounds (IV) and (V)] are described. It has been shown that these products, analogous with the isosteric benzothiazines, have the 5H-pyrimidothiazine structure. Compounds (II), (III) and (IV) show immunological activity, inhibiting passive cutaneous anaphyllaxis in the rat.
Some 1-(5'-nitrofurfuryl)-5-halouracils were synthetized and tested in vitro for antimicrobial activity. N.M.R. spectra of the compounds proved 1-substitution on uracil.
The synthesis, diastereoisomeric separation, attribution to erythro and threo series, and resolution of the enantiomers of 2-(4-biphenylyl)-3-oxybutyric acid are described. The four isomers were tested for anti-inflammatory activity: the preliminary results are interesting, particular those for the (--) erythro enantiomer.
The N.M.R. spectra of 1H-benz[e]indene-1,3(2H)-dione (I), 1H-benz[e]indene-2,3-dihydro-1-one (II), 7-methyl-3H-benz[e]indene-1,2-dihydro-3-one (III) and of their oximes, phenylhydrazones and 4-methylthiosemicarbazones show the preferential substitution at 3 position for monoderivatives of (I). This is very interesting in correlation with the structure-activity relationship of derivatives of (I) and (II), some of which have shown in vitro antiviral action in previous research.
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