1992
DOI: 10.1021/jm00095a028
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4-Methyl-3-(arylsulfonyl)furoxans: a new class of potent inhibitors of platelet aggregation

Abstract: A series of 4-methyl-3-(arylthio)furoxans were synthesized by oxidation of 1-(arylthio)-2-methylglyoxymes with dinitrogen tetroxide. Reduction with trimethyl phosphite of the furoxan derivatives afforded the corresponding furazans, while oxidation with an equimolar amount of 30% hydrogen peroxide in acetic acid or with an excess of 81% hydrogen peroxide in trifluoroacetic acid afforded the corresponding arylsulfinyl and arylsulfonyl analogues, respectively. All the furoxan and furazan derivatives showed activi… Show more

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Cited by 43 publications
(20 citation statements)
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“…Early reports showing that furoxan derivatives can mimic some of physiological actions of nitric oxide relate to the in vitro antiaggregatory and vasodilating activity of a series of isomer methyl-arylsulfonylfuroxans [7,8]. 4-Methyl-3-phenylsulfonylfuroxan (1), one of the most active products of the series, has been closely examined for its biochemical pharmacology [9].…”
Section: Furoxans As No Donorsmentioning
confidence: 99%
“…Early reports showing that furoxan derivatives can mimic some of physiological actions of nitric oxide relate to the in vitro antiaggregatory and vasodilating activity of a series of isomer methyl-arylsulfonylfuroxans [7,8]. 4-Methyl-3-phenylsulfonylfuroxan (1), one of the most active products of the series, has been closely examined for its biochemical pharmacology [9].…”
Section: Furoxans As No Donorsmentioning
confidence: 99%
“…1 H and 13 C NMR spectra (Experimental) are in keeping with the structural assignments. In particular, in the case of the furoxan isomers they satisfy the rule that both in 1 H and in 13 C NMR spectra, the 3-CH 3 resonance signal is upfield with respect to the one of 4-CH 3 [8,9] and that in the 13 C NMR spectra the resonances of C(1) and C(4) carbons of the 3-Ph group appear upfield with respect to the corresponding resonances of the 4-Ph group [10]. Finally the chemical shift of C3 and C4 carbon atoms of the furoxan ring are in keeping with those observed in aryl-and alkylsulfonyl furoxans [9,11].…”
Section: Resultsmentioning
confidence: 84%
“…This indicates that the vasodilator activity of these specific products is not NO dependent but probably connected with their tissue toxicity. C NMR spectra were recorded on a Bruker Avance 300 at 300 and 75 MHz, respectively, using SiMe 4 as Table 1 Physicochemical parameters and pharmacological activities of furoxan and furazan sulfonic acids (7,8) and related sulfonamides (9)(10)(11)(12)(13)(14)(15)(16) a Potentiometric titrations were performed in water containing methanol as a cosolvent in different ratios depending on the solubility of compounds: pK a values were determined by extrapolation at 0% methanol using the Yasuda-Shedlovsky procedure (experimental). b NMR determination.…”
Section: Resultsmentioning
confidence: 99%
“…Recently,4,2,pyridazine 1,5,6-trioxide (FPTO) was synthesized and shown to stimulate soluble guanylate cyclase in a nitric oxide-independent mechanism (Kots et al, 2000). Because the molecule of FPTO comprises a pyridazine di-N-oxide ring condensed with a furoxan moiety, this drug can also generate nitric oxide and nitric oxide-like species, such as nitroxyl and S-nitrosoglutathione, either spontaneously or thiol-dependently (Calvino et al, 1992;Feelisch et al, 1992;Medana et al, 1994;Ferioli et al, 1995). In addition, it was shown that FPTO is an efficient smooth muscle relaxant and vasodilator in rat aortic rings (Kots et al, 2000).…”
mentioning
confidence: 99%