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Biomedical subjects

W O Foye

Publications and source records attributed to W O Foye.

At least 37 records · Page 2Linked to original sources
PubMed1983

Synthesis and antileukemic activity of 2-(2-methylthio-2-aminovinyl)-1-methylquinolinium iodides.

Reaction of 2-bis(2-methylthio)vinyl-1-methylquinolinium iodide with several heterocyclic aliphatic amines at 30-70 degrees resulted in replacement of one methylthio group to give the title compounds. Reaction with pyrrolidine gave an unidentified product lacking sulfur. Antileukemic screening against P-388 lymphocytic leukemia showed positive activity only with the 6-methyl-morpholino derivative, whereas the 6-unsubstituted morpholino derivative was inactive. This result is in contrast to previous testing results with the 2-bis(2-methylthio)vinyl compounds where both 6-substituted and 6-unsubstituted derivatives showed activity.

Animals↗
PubMed1982

DNA-binding specificity and RNA polymerase inhibitory activity of bis(aminoalkyl)anthraquinones and bis(methylthio)vinylquinolinium iodides.

The determination of DNA-binding specificities for a series of bis(methylthio)vinylquinolinium iodides and two bis (aminoalkyl)-anthraquinones was accomplished by spectral analysis, equilibrium dialysis, elevation of melting temperature, and inhibition of DNA function as a template for Escherichia coli RNA-polymerase transcription activity in vitro. Studies of complex formation were carried out by comparison of difference spectra of the compounds in the presence of native double-stranded DNA and separated-strand DNA. Base specificity of the interaction between DNA and the compounds was demonstrated for both series, particularly for the anthraquinones, for the guanine-cytosine base pair. Comparison of the difference spectra of the compounds in the presence of DNA with varied base-pair ratios showed a strong preference of the anthraquinones for the guanine-cytosine base pair, but the quinolinium compounds showed no preference. The linear-binding isotherm for the quinolinium compounds indicated one type of binding site, while two types of binding sites were apparent for the anthraquinones. Since only one anthraquinone was active in leukemia tests, factors other than DNA binding must account for the activity of the antileukemic derivative.

Animals↗
PubMed1982

Local anesthetics: 2-N,N-dialkylaminoacyl-2'-methyl (or 2',6'-dimethyl)-4'-butylaminoanilides.

A series of tetracaine analogs based on the lidocaine structure, having a 2'-methyl-(or 2',6'-dimethyl)-4-butylaminoanilide moiety with alpha substitution on the dialkylaminoacyl function, has been synthesized. Local anesthetic activity was found with the N-butyl derivatives in both the 2'-methyl and 2',6'-dimethyl series using both the method of rabbit cornea loss of reflex and spinal anesthesia in sheep. Duration of activity of the compounds was greater than that of lidocaine, but less than that of tetracaine, with comparable dosage levels.

Anesthesia, Spinal↗
PubMed1982

Synthesis of omega-(4-aminophenylsulfonamido)alkyl disulfides and thiosulfates and their activity against dihydropteroate synthetase from sulfanilamide-resistant Neisseria gonorrhoeae.

A series of omega-(4-aminophenylsulfonamido)alkyl disulfides and omega-(4-aminophenylsulfonamido)alkanethiosulfates was synthesized from the reaction of p-acetamidobenzenesulfanilyl chloride and either the aminoalkyl disulfide dihydrobromide or the aminoalkyl bromide hydrobromide followed by sodium thiosulfate. Several of the compounds showed inhibitory activity against dihydropteroate synthetase isolated from a sulfanilamide-resistant strain of Neisseria gonorrhoeae of the same order of activity as that of sulfanilamide. An increase in the hydrophobic nature of the sulfanilamide structure did not increase inhibitory activity against this enzyme.

Chemical Phenomena↗
PubMed1981

Inhibition of mucopolysaccharide sulfation.

A method of measuring the inhibition of sulfation in mucopolysaccharides employed the coupled enzyme system of Wortman. This procedure utilized the phenol and mucopolysaccharide sulfotransferases of beef cornea extract. Compounds tested against this system included amino acids, salicylates, 2-mercaptoethylamine and a derivative, heterocyclic ethanethiosulfuric acids, arylsulfonamidoethanethiosulfates, and several other compounds. In general, the salicylates and thiosulfates were inhibitory, with sodiumm 2-(4-acetamidobenzenesulfonamido)-ethanethiosulfate being the most inhibitory and 2-mercaptoethylguanidine trithiocarbonic acid the second most inhibitory. Salicylamide and allopurinol, which have been employed in kidney stone therapy, were inhibitors. Kidney stones have a mucopolysaccharide sulfate matrix, which is involved in their growth.

Animals↗
PubMed1981

Synthesis of N-glycosylthioureas, N-glycosylrhodanines, and N-glycosyl-2-aminothiazoles and their antimicrobial activity.

A method for obtaining N-beta-D-glucopyranosylthioureas was found in the aminolysis of N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-5-aralkylidenerhodan ines. Aminolysis of the triacetylated or tribenzoylated ribosylrhodanines generally did not give ribosylthioureas but resulted in glycosidic cleavage, although N-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)thioureas were obtained using morpholine and hydroxylamine. Ring closure of N-beta-D-glucopyranosylthiourea with ethyl bromopyruvate gave ethyl 2-(N-beta-D-glucopyranosyl)aminothiazole-4-carboxylate, and ammonolysis led to the corresponding 4-carboxamide. Antimicrobial screening against five microorganisms showed that N-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)rhodanine and the glucosylaminothiazole-4-carboxylate had the broadest spectrum of inhibitory activity, although the thioureas usually showed inhibition of some organisms.

Anti-Infective Agents↗
PubMed1980

Antiradiation compounds XVII: binding ability of radiation-protective N-heterocyclic aminoethyl disulfides and thiosulfates to DNA.

Binding parameters for a series of N-heterocyclic aminoethyl disulfides and thiosulfates to DNA were determined at different ionic strengths and pH values. None of the thiosulfates showed any binding ability, but the disulfides revealed DNA binding abilities that were suppressed both by increased ionic strength and hydrogen-ion concentration. No correlation between DNA binding ability and radiation protective activity in mice was evident.

Binding Sites↗
PubMed1980

Antileukemic activity of 2-bis(2-methylthio)vinyl-1-methylquinolinium iodides.

Reaction of 1-methylquinolinium-2-dithioacetic acid zwitterions with excess methyl iodide in dimethylformamide gave the corresponding bis(2-methylthio)vinyl derivatives. These compounds were more soluble in both aqueous and organic media than the dithioacetic acid zwitterions but showed comparable antileukemic activity in mice. Reaction with morpholine converted a bis(2-methylthio)vinyl derivative almost quantitatively to the 2-mono(methylthio)-2-morpholino derivative. Leukemia cell culture studies of the 6-methyl derivative showed no effect on cell cycle processes.

Animals↗
PubMed1979

Metal-binding abilities of radioprotective aminoalkyl disulfides and thiosulfates.

Mental-binding stability constants for several heterocyclic aminoalkyl disulfides and thiosulfates with Ni(II) and Al(III) were determined. The data obtained indicated that both classes of compounds were acting as bidentate chelating agents and that the heterocyclic rings apparently prevented tridentate behavior of the disulfides because of steric hindrance. The magnitude of the constants indicated that metal complexes of these compounds could exist in a cellular environment, but no correlation with radiation-protective activity was apparent.

Aluminum↗
PubMed1979

6-substituted 1-methylquinolinium-2-dithioacetic acid zwitterions: antileukemia activity.

Condensation of the anhydro bases derived from 6-substituted 1-methylquinaldinium iodides with carbon disulfide provided the 2-dithioacetic acid zwitterions. Since 1.6-dimethylquinolinium-2-dithioacetic acid zwitterion previously showed appreciable activity against P-388 lymphocytic leukemia in mice, a series of analogs with other 6-substituents was synthesized to assess the importance of substitution in this position. Both electron-donating and electron-attracting 6-substituents gave compounds with antileukemia activity. The 6-unsubstituted analog had only marginal activity.

Animals↗
PubMed1979

Heterocyclic analogs of amphetamine: Thioureas, dithiocarbamates, and negatively substituted amides.

A series of heterocyclic analogs of amphetamine was synthesized. The heterocycles employed included the 2-furyl, 2-thienyl, 3-methyl-2-thienyl, 3-pyridyl, and 6-methyl-2-pyridyl rings. The aliphatic amine group was converted to the N-methylthiourea, dithiocarbamate, methanesulfonyl, trifluoromethanesulfonyl, and trifluoracetyl functions since similar conversions of the beta-phenethylamine structure had shown blood pressure-lowering effects and some loss of behavioral effects. p-Chlorophenyl and 1-naphthyl analogs were also converted to these derivatives. Behavioral and other biological effects, including antiarthritic, passive cutaneous anaphylactic, and antimicrobial, were observed. The 3-methyl-2-thienyl analog of amphetamine significantly increased papillary muscle contractile force without producing arhythmias.

Amides↗
PubMed1979

Mercaptoalkylamine coordination compounds of platinum(II) and palladium(II) and their anticancer activity.

A series of coordination compounds of platinum(II) and palladium(II) with several amino- and heterocyclic aminoalkyl mercaptans was synthesized, and their structures were determined by IR absorption and elemental analyses. Because of the tendency of the mercapto group to undergo oxidation on reaction with metals, as observed with copper(II), the complexes were obtained by use of the aminoalkylthiosulfates, which decomposed to the thiol in either acid or alkaline solution. Furthermore, palladium-sulfide complex formation by reaction with an aminoalkyltrithiocarbonate made it possible to distinguish between metal-sulfur and metal-nitrogen bonds in the 650--400-cm-1 region. Anticancer screening against L-1210 lymphoid leukemia in mice did not reveal positive activity among the compounds tested.

Animals↗
PubMed1978

Pyridinium- and quinolinium-2-dithioacetic acid zwitterions: antiradiation and anticancer activities.

Pyridinium-, quinolinium-, and one pyrimidinium-2-dithioacetic acid zwitterions were prepared by condensation of the N-methyl heterocyclic anhydro bases with carbon disulfide. Reaction of the 2-methylpyridine methiodide anhydro base with carbon disulfide resulted in replacement of the 2-methyl group to give the 1-methylpyridinium-2-dithioacetic acid zwitterion. The 1,6-dimethylquinolinium-2-dithioacetic acid zwitterion showed appreciable anticancer activity against P-388 lymphocytic leukemia in mice, but the other zwitterions tested showed no activity. No antiradiation activity was found for 1-methyl-pyridinium-2-dithioacetic acid zwitterion.

Acetates↗
PubMed1977

Sulfur-containing derivatives of amphetamine: thioureas, methanesulfonamides, and trifluoromethanesulfonamides.

N-Methylthiourea, methanesulfonamide, and trifluoromethanesulfonamide derivatives of amphetamine, 4-nitroamphetamine, and 4-aminoamphetamine were synthesized. The N-methylthiourea derivative of amphetamine, as well as the triethylammonium salt of the dithiocarbamate, produced significant depressor effects in normotensive dogs. N,N'-Bis(methanesulfonyl)-1-methyl-2-(4-aminophenyl)ethylamine and N-trifluoromethanesulofonyl-1-methyl-2-phenylethylamine, but not N-methanesulfonyl-1-methyl-2-phenylethylamine and N-trifluoroacetyl-1-methyl-2-(4-trifluoromethanesulfonamido-phenyl))ethylamine, showed significant antiobesity effects in rats.

Amphetamines↗
PubMed1977

N-Glucopyranosyl-5-aralkylidenerhodanines: synthesis and antibacterial and antiviral activities.

A series N-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-5-aralkylidenerhodanines was synthesized, and the acetyl groups were removed to give N-beta-D-glucopyranosyl-5-aralkylidenerhodanies without cleavage of the rhodanine ring by means of acid hydrolysis. Alkaline hydrolysis with ammonia in methanol resulted in cleavage to N-glucosylthiourea, providing evidence for N-glycoside formation. A number of the rhodanine derivatives, especially those with nitro or chloro groups in the aromatic ring, showed antibacterial activity. N-beta-D-Glucopyranosyl-5-(4-nitrobenzylidene) rhodanine showed antiviral activity by inhibition of viral RNA synthesis. Some effect on blood sugar levels also was observed with several rhodanines.

Animals↗
PubMed1976

Synthesis and biological evaluation of tetrakis(acetylsalicylato)-mu-dicopper(II).

The synthesis of a copper-aspirin chelate, previously reported to be a more active anti-inflammatory agent than aspirin itself, is given. Reaction of potassium acetylsalicylate with cupric sulfate gave a stable copper complex, which analysis and molecular weight determination showed to be a 4:2 chelate structure. Oil-water partition measurements showed the complex to be 10-fold more oil soluble than aspirin. Biological evaluation in rats showed the copper complex of aspirin to be approximately equal to aspirin in reducing carrageenan-induced inflammation, but it was 1.7 times more active than aspirin in reducing the primary lesion of adjuvant arthritis. Whereas aspirin produced a 50% or greater incidence of GI erosions at doses of 100-300 mg/kg in rats, the copper complex caused no erosions in doses up to 1200 mg/kg.

Aluminum↗
PubMed1976

Antiradiation compounds XVI: N-heterocyclic aminoethyl disulfides and aminoethanethiosulfuric acids.

A series of N-heterocyclic and N-heterocyclic alkyl derivatives of bis(2-aminoethyl) disulfide and aminoethanethiosulfuric acid was synthesized as potential antiradiation and anticancer agents. The compounds were prepared by the reactions of the heterocyclic halides with bis(2-aminoethyl) disulfide and aminoethanethiosulfuric acid. A dithio acid derivative, 3,3-dimercapto-2-cyanoacryloylpyrrolidide, was also prepared. Several compounds, including the dithio acid derivative, provided good radiation protection to mice. None of the compounds screened showed appreciable anticancer activities in two leukemia systems.

Animals↗