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101. Spectroscopic studies of the reaction between bovine serum amine oxidase (copper-containing) and some hydrazides and hydrazines

Author

Morpurgo, L, Befani, O, Sabatini, S, Mondovì, B, Artico, M, Corelli, F, Massa, S, Stefancich, G, and Avigliano, L

Abstract

The carbonyl cofactor of bovine serum amine oxidase, recently identified as pyrroloquinoline quinone [Ameyama, Hayashi, Matsushita, Shinagawa & Adachi (1984) Agric. Biol. Chem. 48, 561-565; Lobenstein-Verbeek, Jongejan, Frank & Duine (1984) FEBS Lett. 170, 305-309], reacts stoichiometrically and irreversibly with hydrazides of phenylacetic acid and of benzoic acid. With the phenylacetic hydrazides a reversible intermediate step was detected by competition with substrate, carbonylic reagents or phenylhydrazine, a typical inhibitor of the enzyme. All hydrazides form an intense broad band with maximum absorbance in a narrow wavelength range (350-360 nm), irrespective of the acyl group, suggesting that the transition is located on the organic cofactor. A different situation is found with some phenylhydrazines, where extended conjugation can occur between the cofactor and the phenyl pi-electron system via the azo group, as shown by the lower energy and higher intensity of the transition. In this case the transition is sensitive to substituents in the phenyl ring. The c.d. spectrum of the adducts is influenced by the type of hydrazide (derived from phenylacetic acid or benzoic acid), by pH and by NN-diethyldithiocarbamate binding to copper, probably as a result of shifts of equilibria between hydrazone-azo tautomers.

Published
1988
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104. Synthesis of C-Alkylcalix[4]arenes. 5. Design, Synthesis, Computational Studies, and Homodimerization of Polymethylene-Bridged Resorc[4]arenes

Author

Botta, B., Monache, G. D., De Cristina Rosa, M. , Seri, C. , Benedetti, Botta, M., Corelli, F., Masignani, V., Tafi, A., Gacs Baitz, E. , Santini, A. , Misiti, IACOVINO, Rosa, Botta, B., Monache, G. D., De Cristina, Rosa, M., Seri, C., Benedetti, Iacovino, Rosa, Botta, M., Corelli, F., Masignani, V., Tafi, A., Gacs, Baitz, E., Santini, and A., Misiti

Subjects
Molecular dynamics, chemistry.chemical_compound, Crystallography, Design synthesis, chemistry, Molecular model, Dimer, Organic Chemistry, Calixarene, Supramolecular chemistry, Molecule, Derivative (chemistry)
Abstract

Treatment of tetraalcohol 1 with glutaroyl (2a, n = 3), adipoyl (2b, n = 4), and pimeloyl (2c, n = 5) dichlorides in the presence of Et 3N gave the corresponding double-spanned calix[4]resorcarenes 3a-c, in which the insertion of two polymethylene bridges led to the formation of a cavity-shaped architecture resembling a basket. NMR, X-ray, and molecular dynamic studies showed that one of the two equivalent flattened-cones, which constituted the original cone conformation of 1, had been frozen in the basket derivative. In the solid state the calixarene 3b exists as a supramolecular dimer, in which one of the handles is inserted in the concave cavity of an adjacent molecule. A molecular modeling study revealed that the minimum absolute free energy was associated to the unsymmetrical type of dimer named AB-AC.

105. [Heterocyclic systems. V. Synthesis and CNS activity of derivatives of 6H-pyrrolo (1,2-a) (1,4)-benzodiazepine]

Author

Corelli F, Massa S, Gc, Pantaleoni, Palumbo G, and Donatella FANINI

Subjects
Benzodiazepines, Chemistry, Mice, Behavior, Animal, Chemical Phenomena, Muscle Relaxants, Central, Animals, Central Nervous System Depressants, Anticonvulsants, Mice, Inbred Strains, Pyrroles, Motor Activity, Postural Balance
Abstract

The synthesis of new derivatives of 6H-pyrrolo[1,2-a] [1,4]benzodiazepine is described. These compounds were tested for activity on the C.N.S. by several screening tests on mice.

Published
1984

112. [Heterocyclic systems. IV. Synthesis and CNS activity of derivatives of 4H,6H-pyrrolo[1,2-a][4,1]-benzoxazepine]

Author

Massa S, Corelli F, Gc, Pantaleoni, and Giancarlo Palumbo

Subjects
Male, Mice, Oxazepines, Psychotropic Drugs, Behavior, Animal, Animals, Anticonvulsants, Female, Receptors, Cell Surface, Azepines, Motor Activity, Receptors, GABA-A, Psychomotor Performance
Abstract

The synthesis of derivatives of 4H,6H-pyrrolo[1,2-a][4,1]-benzoxazepine is described. These compounds were tested for activity on type (I) and (II) benzodiazepine receptors by several screening tests on mice.

Published
1983

114. [Non-steroidal anti-inflammatory agents. IV. Synthesis and pharmacologic activity of aroylthiopheneacetic acids with a pyrrole group]

Author

Massa S, Stefancich G, Artico M, Corelli F, Gc, Pantaleoni, Palumbo G, Donatella FANINI, and Giorgi R

Subjects
Chemistry, Chemical Phenomena, Anti-Inflammatory Agents, Non-Steroidal, Animals, Pyrroles, Rats, Inbred Strains, Thiophenes, Rats
Abstract

The synthesis of new antiinflammatory aroylthiopheneacetic acids bearing a pyrrole moiety is described. These compounds can be regarded as analogues of thiaprofen and related isosteres. The antiinflammatory activity of the new pyrryl derivatives has been evaluated in comparison with indomethacin, tolmetin and the unknown 5-(2-chlorobenzoyl)thiophene-2-acetic acid. Among tested derivatives the compounds containing the pyrrole ring were devoid of analgesic-antiinflammatory activities.

Published
1986

120. Synthesis, neuropsychopharmacological effects and analgesic-antiinflammatory activities of pyrrole analogues of lefetamine

Author

Massa, S., Stefancich, G., Artico, M., Corelli, F., Silvestri, R., Pantaleoni, G. C., Fanini, D., Giancarlo Palumbo, and Giorgi, R.

Subjects
Male, Chemical Phenomena, Muscle Relaxants, Central, Anti-Inflammatory Agents, Non-Steroidal, Rats, Inbred Strains, Motor Activity, Rats, Chemistry, Mice, Phenethylamines, Exploratory Behavior, Reaction Time, Animals, Anticonvulsants, Female, Psychomotor Performance
Abstract

The synthesis of pyrrole analogues of the analgesic drug lefetamine is reported. These derivatives bear the 1-phenyl-2-(1H-pyrrol-1-yl)ethylamino moiety. Compounds were evaluated for analgesic activities in mice by the hot plate and Randall-Selitto tests. Antiinflammatory activity was tested by the carrageenan-induced rat paw edema method. General neuropsychopharmacological effects were also screened. The most interesting compound, N,N-dimethyl-1-phenyl-2-(1H-pyrrol-1-yl)ethylamine, showed an analgesic effect comparable to that of lefetamine, but devoid of the neurotoxicity of this drug.

Published
1989

124. [Non-steroidal anti-inflammatory agents. III. Synthesis and analgesic-anti-inflammatory activity of 4-(pyrrol-1-yl)phenylacetamides and 4-(pyrrol-1-yl)phenethylamines]

Author

Stefancich G, Artico M, Corelli F, Massa S, Gc, Pantaleoni, Palumbo G, Donatella FANINI, and Giorgi G

Subjects
Chemistry, Mice, Chemical Phenomena, Acetamides, Anti-Inflammatory Agents, Non-Steroidal, Phenethylamines, Animals, Edema, Pyrroles, Rats, Inbred Strains, Carrageenan, Rats
Abstract

Preparation of some 4-(pyrrol-1-yl)phenylacetamides and 4-(pyrrol-1-yl)phenylethylamines starting from 4-(pyrrol-1-yl)phenylacetic acid is reported. The new compounds were tested as analgesic-antiinflammatory agents. Data from pharmacological screening indicate 1-[4-(pyrrol-1-yl)phenylethyl]piperidine as the most active substance.

Published
1984

130. [Nonsteroidal anti-inflammatory agents. V. Synthesis of 1-aryl-5-(1-pyrryl)-pyrazolyl-4-acetic acids with potential anti-inflammatory action]

Author

Corelli F, Massa S, Stefancich G, Silvestri R, Artico M, Gc, Pantaleoni, Giancarlo Palumbo, Fanini D, and Giorgi R

Subjects
Male, Mice, Anti-Inflammatory Agents, Non-Steroidal, Animals, Pyrazoles, Rats, Inbred Strains, Acetates, Rats
Abstract

The synthesis of 1-aryl-5-(1-pyrryl)pyrazoles bearing at position 4 an acetic or alpha-propionic chain is described. The new compounds can be structurally related to lonazolac and its analogues with analgesic-antiinflammatory activities. When tested pharmacologically in comparison with tolmetin and indomethacin none of the above derivatives showed any appreciable activity.

133. [New psychotropic agents. 2. Synthesis and pharmacologic activity of derivatives of 5H-pyrrolo[1,2-b][1,2,5]benzotriazepines]

Author

Stefancich G, Artico M, Corelli F, Massa S, Gc, Pantaleoni, Palumbo G, Donatella FANINI, and Giorgi R

Subjects
Male, Chemistry, Mice, Psychotropic Drugs, Chemical Phenomena, Animals, Anticonvulsants, Female, Pyrroles, Benzazepines, Motor Activity
Abstract

Bischler-Napieralski intramolecular cyclization of N-(2-aroylaminophenyl)-N-methyl-1H-pyrrol-1-amines and reaction of arylaldehydes on N-(2-aminophenyl)-N-methyl-1H-pyrrol-1-amine furnished 11-aryl-5-methyl-5H-pyrrolo[1,2-b][1,2,5]benzotriazepines and 11-aryl-10,11-dihydro-5-methyl-5H-pyrrolo[1,2-b][1,2,5]benzotriazepin es respectively. The latter reaction required in some cases the use of p-toluenesulphonic acid as a catalyst. The new tricyclic derivatives described were tested for pharmacological evaluation of their psychotropic activity.

138. [Heterocyclic systems. III. Synthesis and CNS activity of derivatives of pyrrole(2,1-c) (1,4)benzodiazocine]

Author

Massa S, Corelli F, De Martino G, Gc, Pantaleoni, Fanini D, and Giancarlo Palumbo

Subjects
Central Nervous System, Mice, Behavior, Animal, Animals, Anticonvulsants, Pyrroles, Azocines
Abstract

5,11-Dioxo-1,2,3,5,6,11,12,12a-octahydropyrrolo [2,1-c] [1,4]benzodiazepine and the corresponding 2-hydroxyderivative were prepared by the intramolecular cyclization of 1-(2-aminophenylacetyl)pyrrolidin-2-carboxylic acid and 1-(2-aminophenylacetyl)-4-hydroxypyrrolidin-2-carboxylic acid; some of the tricyclic compounds were tested for neuropsychopharmacological effects.

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