Biomedical subjects
Publications and source records attributed to L Pecori Vettori.
The synthesis of some 3-(1,3,4-thiadiazol-2-yl)pyrazolo[1,5-a]-pyrimidine derivatives is performed by reacting 2-(3-amino-1,2-dihydro-5-oxo-5H-pyrazol-4-il)-1,3,4- thiadiazoles with 2,4-pentanedione, ethyl 3-oxobutyrate and diethyl ethoxymethylenemalonate. The antimicrobial activity of the synthesized compounds is reported.
2-Amino-4-phenylpyrrolyl-3-carbonitrile (I) was reacted with ethyl formylacetate sodium salt affording 1,4-dihydro-4-oxo-7-phenylpyrolo[1,2-a]pyrimidin-8-carbonitrile (II), which was alkylated with EtI to give (III), which in turn was hydrolyzed to (IV). Treatment of both (III) and (IV) with 99% H3PO4 at approximately 200 degrees gave 1,4-dihydro-1-ethyl-7-phenylpyrrolo-[1,2-a]pyrimidin-4-one (V) whose structure was ascertained by an unequivocal synthesis starting from (I) and diethyl ethoxymethylenmalonate. Compound (V) was prepared in order to test its pharmacological properties in comparison with 4,7-dihydro-4-ethyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-one, which showed an antiinflammatory activity comparable to that of phenylbutazone and indomethacine, and which was found devoid of ulcerogenic properties.
4,7-Dihydro-4-ethyl-2-phenylpyrazolo-[1,5-a]pyrimidin-7-one (FPP028) is the prototype of a class of pyrazolo[1,5-a]pirimidine derivatives that has been shown to possess marked antiinflammatory and analgesic properties; 1,4-dihydro-1-ethyl-7-phenylpyrrolo[1,2-a]pyrimidin-4-one (FPP129) is a new compound belonging to a series of pyrrolo[1,2-a]pirimidine derivatives that has been synthetized in an attempt to reduce certain toxic effects observed with FPP028. To evaluate these two compounds more fully, in the present study we determined the LD50 of FPP129 in mice and assessed its activity in different experimental inflammation models. Ulcerogenic properties of FPP129 were evaluated by the test of stress-induced ulcer in rats. We also studied the in vitro and ex vivo effects of both FPP028 and FPP129 in a series of platelet-aggregation experiments using either arachidonate or collagen as aggregating agents. In the carraggeenan-induced paw edema, FPP129 exerted a marked anti-inflammatory activity with an ED50 of 22.2 mg/kg. FPP129 inhibited also the edema induced by concanavalin-A or Paf-acether. The in vitro anti-aggregatory activity of FPP028 was shown to be much less than that of indomethacin, thus confirming the hypothesis that the compound is a very weak inhibitor of cyclooxygenase. Ex vivo, both FPP028 and FPP129 were shown to exert no antiaggregatory effect in rabbits after administration of doses equal to the ED50. No ulcerogenic activity was found with FPP129, this result being consistent with previous observations on FPP028. Our data show tha FPP028 and FPP129 do not share a typical mechanism of action (cyclooxygenase inhibition) found with the majority of nonsteroidal antiinflammatory drugs. Nonetheless, the antiinflammatory properties of these compounds, together with their lack of ulcerogenic activity, indicate that both FPP028 and FPP129 are potentially interesting for future therapeutic use.
The synthesis of some 2-[5-amino-1-methyl-3-oxo-4-pyrazolynyl]-1,3,4-thiadiazole derivatives is accomplished by reacting 5-amino-1-methyl-3-oxopryrazolynyl-4-dithiocarbohydrazide with carboxylic acid derivatives. The structure of the compounds obtained is verified by means of 1H and 13C-N.M.R. spectra. Antimicrobial and antifungal activity of some of the described compounds was tested in a preliminary screening.
2-Phenylpryrazolo [1,5-a]pyrimidine (I) 4,7-dihydro-2-phenylpyrazolo [1,5-a]pyrimidin-7-one (II) and 4,5-dihydro-2-phenylpyrazolo [1,5-a]pyrimidin-5-one (III) are prepared. Because of the interesting antipyretic, hypothermizing and anti-inflammatory properties of some of their derivatives, the above mentioned compounds are used as reference compounds in a Q.S.A.R. study still in progress. Methylation of (II) and (III) with (CH3)2SO4 and CH2N2 gives methylderivatives whose structure is determined by spectroscopic means.
The paper reports the pharmacological activity in vitro and in vivo of a series of pyrazolo[1,5-a]pyrimidine derivatives. Some of these compounds have proved to be active in decreasing the body temperature. They are also very active inhibitors of the guinea-pig lung prostaglandin-sintetase.
Structures of condensation products between 3-phenyl-5-aminopyrazole and ethyl ethoxymethylenacetoacetate and ethyl acetonoxalate are demonstrated, namely ethyl 2-phenyl-7-methylpyrazolo[1,5-a]pyrimidin-6-carboxylate and ethyl 2-phenyl-7-methylpyrazolo[1,5-a]pyrimidin-5-carboxylate. Studies on antipyretic and hypothermizing activity of the acid derived from the latter and of other compounds are reported.
The synthesis of ethyl 2-phenyl-7-alkyl (or 7-phenyl)pyrazolo[1,5-a]pyrimidine-5-carboxylate and ethyl 2-phenyl-7-alkyl (or 7-phenyl)pyrazolo[1.5-a]pyrimidine-6-carboxylate are reported. Decarboxylation of the acids, obtained by hydrolysis of the above esters, yields the same compounds. N.M.R. data on the reduction products of the ethyl 6-carboxylate confirm all the assigned structures.
In the course of researches on pyrazolo[1,5-a]pyrimidine compounds, methylation reactions with (CH3)2SO4 and CH2N2 are studied. Methylderivatives structure is assigned by means of a spectroscopic investigation. A relationship between the kind of reagent and the methyl group position is stressed.
The synthesis of 1,2,4,6-tetrahydro-2-methyl-3-hydroxypyrazolo [3,4-d] [1,3]thiazine-4,6-dithione is described. By spectroscopic methods the anphionic structure of this and other related compounds is demonstrated. In addition, the action of alkylating reagents upon pyrazolo-[3,4-d] [1,3]thiazine-4,6-dithionic compounds is examined and described. The biological activity of the new synthesized compounds is reported.
Compounds of the 7H-furo-[3,2-g]-1-benzopyran system are prepared by condensation of kellinone with malonic acid derivatives. The 4,9-dimethoxy-5-methyl-7-H-furo-[3,2g]-1-benzopyran-7-one-6-carboxylic acid chloride reacts with aliphatic and heterocyclic amines and with aliphatic aminoalcohols giving amides that could have pharmacological interest.
The reaction between 1,2-diphenyl-4-bis-(methylthio)methylenepyrazolidin-3,5-dione with serine and cysteine and their derivatives is described. The structure of the resulting compounds is assigned spectrophotometrically.
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