Synthesis and antimicrobial activity of aromatic dicarboxaldehydes.
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Biomedical subjects
Publications and source records attributed to L Garuti.
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A short series of di-functionalized benzodifurans and phenanthrolines were synthesized for in vitro antimicrobial activity. Dicarboxaldehydes, chiefly those with a phenanthroline supporting moiety, proved to be most effective, showing significant fungal growth inhibition.
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A short series of N-monosubstituted (aryl, aminoacyl, dipeptidyl)-2-(2-aminothiazol-4-yl)-(Z) -2-methoxyiminoacetamides was synthesized and tested for antimicrobial activity. A few members showed a somewhat interesting inhibitory action against Cryptococcus neoformans (MIC = 150 micrograms/ml).
A series of 1,2,3,4-tetrahydroquinolines and of 1,2,3,4-tetrahydroisoquinolines were synthesised and evaluated for analgesic activity by both hot-plate and acetic acid writhing methods in rats. Te most potent compound was 2-methyl-1,2,3,4-tetrahydro-5-quinolinol (IV i) which was shown to be 1/8 and 1/50 as active as morphine according to the employed assay. The analgesic activity was shown to be associated to a not selective action on the CNS.
Some benzyloxyimio compounds, related to oxiconazole and having a 1H-indole or 1H-benzimidazole moiety, have been synthesized and tested in vitro for their antimycotic activity against Candida tropicalis and C. albicans. The most active was showed to be 0-(2,4-dichlorobenzyl)-1-benzyl-5-nitro-1H-benzimidazole-2-carboxaldehyd e oxime (MIC: 25 micrograms/ml against both microorganisms). A structural feature important for the biological activity of the series appears to be presence of a benzimidazole nucleus substituted by an electron withdrawing group.
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1-(Naphtho[1,2-b]furan-2-yl)-2-(isopropylamino)ethanol (II) and 1-(naphtho[2,3-b]furan-2-yl)-2-(isopropylamino)ethanol (III) show low beta-adrenergic blocking activity and unlike the naphtho [2,1-b]furan derivatives (1,2) do not appear to give rise to metabolites with high beta-adrenoceptor inhibitory properties. The inclusion of the --OCH2-- moiety in an aromatic nucleus larger than the benzofuran system (bufuralol, Ro 3-3528) caused loss of the biological activity.
Some derivatives of N'-(5-nitro-2-furoyl)-N2-(3-chloro-1H-indenyl-2-methylene)hydrazine (I) were synthesized and screened for in vitro antimicrobial activity. None was more active than the parent compound and the greater hydrophilic character was associated with loss of inhibitory activity against gram-negative bacteria.
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Some 1-(naphtho[2,1-b]furan-2-yl)-2-(t-butylamino)ethanols were synthesized for possible beta-adrenergic receptor blockade. The compounds may be considered to be derived from naphthyloxypropanolamines, the side chain of which is partially included in a furan ring. The pharmacological profile of 1-(naphtho[2,1-b]furan-2-yl)-2-(t-butylamine)ethanol (I b) is quite similar to that of propranolol without cardiac depressant properties.
Some bis-amidinohydrazones of N-heterocyclic aromatic dialdehydes were synthesised and tested in vitro against the MP mutant of the herpes simplex virus type 1 [HSV - I (MP)]. Of the compounds tested, only those with and indole substrate showed some measure of biological activity.