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45. Synthesis of 6 alpha-methyldigitoxigenin 3-acetate.

Author

Valcavi U, Corsi B, Innocenti S, and Martelli P

Subjects
Animals, Cats, Chemistry, Pharmaceutical, Digitoxigenin pharmacology, Guinea Pigs, Cardanolides analogs & derivatives, Digitoxigenin analogs & derivatives, Heart drug effects
Published
1975

46. Mass spectrometric identification of urinary and plasma metabolites of 9-hydroxy-19,20-bis-nor-prostanoic acid (rosaprostol).

Author

Benfenati E, Fanelli R, Chiabrando C, Valcavi U, Bosone E, and Farina P

Subjects
Animals, Female, Humans, Mass Spectrometry, Rats, Anti-Ulcer Agents metabolism, Fatty Acids metabolism, Prostaglandins, Synthetic metabolism, Prostanoic Acids metabolism
Abstract

9-Hydroxy-19,20-bis-nor-prostanoic acid (Rosaprostol) is an antiulcer compound with antisecretory and cytoprotective action. We studied the metabolites of Rosaprostol found in human plasma and in human and rat urine. Sixteen different metabolites were tentatively identified on the basis of their mass spectra. Two presumed metabolites were synthesized. To clarify the identities of some of them, deuterated Rosaprostol was administered to rats and mass spectra of the deuterated and protonated metabolites were examined. Rosaprostol is metabolized following three metabolic pathways leading, combined, to oxidized compounds with a lower number of carbons than the parent drug.

Published
1988
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47. Synthesis and in vitro antibacterial activity of a new series of monobactam derivatives.

Author

Valcavi U, Aveta R, Brandt A, Corsi GB, Bosone E, Farina P, and Guazzi G

Subjects
Anti-Bacterial Agents pharmacology, Chemical Phenomena, Chemistry, Microbial Sensitivity Tests, Monobactams pharmacology, Anti-Bacterial Agents chemical synthesis, Bacteria drug effects, Monobactams chemical synthesis
Abstract

Using as a model monobactams with a substituted alpha-oxyimino moiety in the side chain (aztreonam), a series of 2-(2-aminothiazol-4-yl)-2-hydrazono-acetamido monobactam (II a, f) were prepared by condensation of the hydrazones (I a, e) (Z form) with tetrabutylammonium 3-amino-4-methyl-2-oxo-1-azetidin-sulphonate. Isomerization occurred during this synthesis and gave the E form of all compounds. Monobactams (II a, f) showed no significant in vitro antibacterial activity when compared with aztreonam and with some cephalosporins bearing the same E-hydrazono side chain.

Published
1988

48. Gastric antisecretory, antiulcer and cytoprotective properties of 9-hydroxy-19,20-bis-nor-prostanoic acid in experimental animals.

Author

Valcavi U, Caponi R, Brambilla A, Palmira M, Minoja F, Bernini F, Musanti R, and Fumagalli R

Subjects
Animals, Cell Survival drug effects, Digestive System drug effects, Guinea Pigs, Histamine Antagonists, In Vitro Techniques, Male, Muscle Contraction drug effects, Muscle, Smooth drug effects, Pentagastrin antagonists & inhibitors, Rats, Rats, Inbred Strains, Anti-Ulcer Agents, Fatty Acids pharmacology, Gastric Juice metabolism, Prostanoic Acids pharmacology
Abstract

9-Hydroxy-19,20-bis-nor-prostanoic acid (IBI-C83) was evaluated on gastric acid secretion and gastric lesions induced in laboratory animals by a variety of experimental conditions: compound IBI-C83 is proved effective in decreasing basal, histamine- and pentagastrin-stimulated total acid output in rats and in pentagastrin perfused dogs. The concentration of N-acetylneuraminic acid in the gastric fluid, a marker of mucus secretion, is enhanced in rats by IBI-C83. This drug prevents gastric damage induced by non-steroidal antiinflammatory compounds such as acetylsalicylic acid, indometacin and phenylbutazone, gastric ulcers following pylorus ligation, and facilitates healing of the gastric ulcers evoked by subserosal injection of acetic acid. A prominent feature of IBI-C83 is its capacity to protect the rat from gastric damage elicited by necrotizing agents such as absolute ethanol, hydrochloric acid and hypertonic saline. This property, called "cytoprotection" and common to naturally occuring prostaglandins, is independent on the antisecretory activity of IBI-C83 and is not shared, at least in the reported experimental models, by the H2-receptor antagonist cimetidine. In spite of the prostaglandin-like properties displayed in its cytoprotective activity, compound IBI-C83 does not affect cardiovascular functions, gastrointestinal transit and uterine motility.

Published
1982

50. Synthesis and antiviral activities of 2-substituted azino-3-(D-arabinofuranosyl)-5-carboxymethylene-thiazolidine-4-ones.

Author

Rusjakovski B, Kobe J, Brdar B, Japelj M, and Valcavi U

Subjects
Arabinonucleosides pharmacology, Chemical Phenomena, Chemistry, Cytopathogenic Effect, Viral drug effects, Thiazoles pharmacology, Viral Plaque Assay, Antiviral Agents chemical synthesis, Arabinonucleosides chemical synthesis, Thiazoles chemical synthesis
Abstract

2-(1-Isopropylidene)azino-3-beta and 3-alpha-D-arabinofuranosyl-5-methoxycarbonylmethylenethiazolidine-4-ones (III) and (IV) have been synthesized by condensation of benzylated alpha-chloro-D-arabinofuranose (V) with o-(trimethylsilyl)-2-(1-isopropilidene)azino-5-methoxycarbonylmethylen- thiazolidine-4-one (VI) in the presence of SnCl4 or molecular sieves. Condensation of benzoylated alpha, beta-bromo-D-arabinose (VII) with (VI) led exclusively to the alpha anomer (VIII). 2-(1-Isopropylidene)azino-3-alpha-D-arabinofuranosyl-5-carbamoylmethylene- thiazolidine-4-one (IX) has been synthesized from (IV) (R, R1, R2 = CH3). 1H-N.M.R. and 13C-N.M.R. data confirmed the structures of (III) and (IV) (R, R1, R2 = CH3 and R, R1 = CH3, R2 = Ph). Antiviral activities were tested on monolayer cultures of KB-cells. Whereas previously tested beta-D-ribofuranosyl derivatives had moderate activity, alpha and/or beta-D-arabinofuranosyl derivatives are totally inactive against herpes simplex and poliovirus.

Published
1982

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