William O. Foye

Massachusetts College of Pharmacy and Health Sciences, Concord, Massachusetts, United States

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Publications (119)275.59 Total impact

  • William O. Foye, Winthrop E. Lange
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    ABSTRACT: Semicarbazone hydrochlorides have been prepared of aldehyde analogs of naturally occurring α-amino acids. These compounds were synthesized by a Rosenmund-type reduction of the α-phthalimido acid chlorides, followed by semicarbazone formation and phthaloyl cleavage using hydrazine. Ten per cent palladium-on-charcoal was found more effective for the reduction than the conventional catalyst. Antiviral testing did not reveal any appreciable activity with these compounds.
    Journal of the American Pharmaceutical Association 11/2006; 45(11):742-5. DOI:10.1002/jps.3030451112
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    ABSTRACT: The acute toxicities and antibacterial activities of the various sugar derivatives of bis-(4-aminophenyl)-sulfone have been compared with those of several α-amino acid derivatives. For this purpose, it was necessary to synthesize α-amino acid derivatives and to place the reported toxicity values for the sugar derivatives on a standard basis. It was found that the α-amino acid substituents were less effective in reducing the toxicity of bis-(4-aminophenyl)-sulfone than the sugars, but there was a comparable retention of antitubercular activity with both types of derivatives.
    Journal of the American Pharmaceutical Association 11/2006; 47(11):831-3. DOI:10.1002/jps.3030471120
  • Joseph Pecci, William O. Foye
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    ABSTRACT: Potentiometric titrations were carried out with the title compounds in the presence of various heavy metal cations. Evidence was provided by this method that Cu++, Fe+++, and Al+++ ions were capable of forming stable chelates with these acids. No evidence of chelation was found with Co++, Ni++, Zn++, Mg++, Ca++, or Ag+ ions, although chelates of low stability would not be detected by this procedure. The avidities of these acids for metal ions were recorded as stability constants, and their magnitude indicates that the chelates should be capable of existence in the animal cell.
    Journal of the American Pharmaceutical Association 07/2006; 49(7):411-4. DOI:10.1002/jps.3030490702
  • William O. Foye, Lester Chafetz
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    ABSTRACT: Cyanuric chloride has been condensed with glycine and β-alanine esters to give a series of amino ester derivatives of the s-triazine ring. 2,4,6-Tris-(carbethoxyalkyl) derivatives could not be formed in aqueous media, nor could condensation with urethan be effected. Biological activities of these and other triazines are described.
    Journal of the American Pharmaceutical Association 07/2006; 45(7):461-3. DOI:10.1002/jps.3030450710
  • Edward G. Feldmann, William O. Foye
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    ABSTRACT: D-Glucamine and glycine molecules have been introduced into several nitro and halogenated benzene derivatives in an attempt to reduce the toxic effects to the host of such compounds. A comparison of the acute toxicities of the two types of derivatives showed that the sugar group exerted a definite detoxifying effect, whereas the glycine and giycine ester groups had little effect on toxicity. The antibiotic activities of m-dinitrobenzene, 2,4-dinitroaniline, and p-nitroaniline were wholly removed when the D-glucamine group was present in these molecules, but N-(2-nitro-4,5-dichlorophenyl)-D-glucamine was found to have a relatively broad antibiotic spectrum. The 0-, m-, and p-nitrophenylglycines and their esters revealed a rather limited activity against microorganisms.
    Journal of the American Pharmaceutical Association 07/2006; 48(7):419-22. DOI:10.1002/jps.3030480717
  • Albert E. Buckpitt, William O. Foye
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    ABSTRACT: A number of new substituted amino, chloroamino, and hydroxyamino derivatives of cyanuric chloride have been prepared. Various methods of achieving the condensations were attempted.
    Journal of the American Pharmaceutical Association 07/2006; 41(7):385-7. DOI:10.1002/jps.3030410715
  • William O. Foye, Leo R. Fedor
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    ABSTRACT: N-Substituted derivatives of 1-ethylsulfonylpiperazine have been prepared following the announcement of 1-ethylsulfonyl-4-ethylpiperazine as an antishock agent. Derivatives representing possible oxidation products of the N'-ethyl group were prepared by introducing carboxymethyl and hydroxyethyl groups into 1-ethylsulfonylpiperazine. The latter compound was obtained from 1-benzyloxycarbonylpiperazine, and the benzyloxycarbonyl group was removed by catalytic hydrogenation and by nonhydrolytic cleavage without cleavage of the ethylsulfonyl group.
    Journal of the American Pharmaceutical Association 07/2006; 48(7):412-4. DOI:10.1002/jps.3030480714
  • William O. Foye, Melvin H. Weinswig
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    ABSTRACT: A method has been found whereby aromatically-bound chlorine may be reduced from cyanuric chloride derivatives. This involves catalytic hydrogenolysis with 10 per cent palladium-on-charcoal at atmospheric pressure. A series of mono- and diamino-s-triazines was prepared by this procedure without rupture of the s-triazine or other aromatic rings. Two of the diamino-s-triazines caused decreases of blood glucose in rats but showed no diuretic activity in dogs.
    Journal of the American Pharmaceutical Association 06/2006; 48(6):327-9. DOI:10.1002/jps.3030480609
  • William O. Foye, Matthew Verderame
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    ABSTRACT: Thiol esters of L-cysteine have been prepared from either N-carbobenzyloxy-L-cysteine or N-formyl-L-cysteine by using two-phase reaction mixtures. The carbobenzyloxy groups were removed by nonhydrolytic cleavage with hydrogen bromide. Thio ethers of L-cysteine base were obtained by alkylation in a two-phase reaction and were obtained uncontaminated with N-alkyl products. One compound, the car-boxymethyl thio ether, showed slight antiviral activity.
    Journal of the American Pharmaceutical Association 05/2006; 46(5):273-6. DOI:10.1002/jps.3030460503
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    ABSTRACT: The synthesis of a series of new organo-mercurial diuretics analogous to mersalyl is described. The differences in structure include the presence of other aromatic rings than benzene, and sulfonamide rather than carbonamide linkages. The compounds produced some diuretic activity, but a comparison with commercial compounds is difficult because of solubility problems.
    Journal of the American Pharmaceutical Association 05/2006; 41(5):273-6. DOI:10.1002/jps.3030410516
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    ABSTRACT: Streptomycin has been found to undergo chelation with several metals in aqueous solution. Evidence for chelate formation is provided by a drop in pH during the formation, production of characteristic colors, decreased solubility in water, and absence of metal ions in the solution. The copper chelate, found to be relatively uncontaminated with metal hydroxide, exhibited more prolonged blood levels in guinea pigs than streptomycin sulfate, but also a greater toxicity.
    Journal of the American Pharmaceutical Association 05/2006; 44(5):261-3. DOI:10.1002/jps.3030440503
  • William O. Foye, Ronald N. Duvall
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    ABSTRACT: Cupric and ferrous chelates of p-aminosalicylic acid have been isolated and characterized, and their physical and antitubercular properties compared with those of a previously isolated cupric complex. The cupric chelate showed much higher in vivo antitubercular activity in mice than the cupric complex, and was found to be about thirty times more fat-soluble than the cupric complex. The ferrous chelate was not appreciably active against experimental tuberculosis. The effect of these findings in explaining a possible mechanism of the antitubercular activity of p-aminosalicylic acid is discussed.
    Journal of the American Pharmaceutical Association 04/2006; 47(4):282-5. DOI:10.1002/jps.3030470418
  • William O. Foye, J. George Jeffrey
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    ABSTRACT: A number of o-hydroxyazopyrimidines has been prepared for anticancer testing. These compounds were obtained by direct coupling into the pyrimidine ring, coupling of a diazotized aminopyrimidine into a phenol ring, or coupling of a diazotized aminophenol with acetoacetic ester followed by ring closure with urea or thiourea. Both spectral and chemical evidence suggest that these compounds exist more as quinone hydrazones than as azo compounds. The o-hydroxyazopyrimidines chelated heavy metal ions but did not show appreciable activity against Sarcoma 180.
    Journal of the American Pharmaceutical Association 04/2006; 46(4):224-7. DOI:10.1002/jps.3030460407
  • William O. Foye, Fred B. Block, Winthrop E. Lange
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    ABSTRACT: Metal complexes, which are probably chelates, have been prepared of riboflavin, roboflavin-5′-phosphate, alloxan, and phthaloylhydrazine using divalent copper, cobalt, nickel, iron, and zinc ions. Antitubercular tests in mice showed these chelates to be essentially inactive.
    03/2006; 48(3):183 - 186. DOI:10.1002/jps.3030480313
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    ABSTRACT: A series of eighteen metal chelates and complexes of some a-amino acids, peptides, isonicotinoyl hydrazide, p-aminosalicylic acid, p-acetylaminobenzal thiosemicarbazone, and biotin were screened for antibacterial activity against ten microorganisms. Quantitative tests were carried out on six of these compounds by a modified serial tube dilution method; these compounds were the copper complex and chelate of PASA, cobalt chelates of INH and methionine, and copper chelates of glycyl-DL-alanine and biotin. Evidence indicated that the complexes of methionine and biotin were more active than the metal ions, but the action of the chelates of the antitubercular agents appeared to depend in part on dissociation of the chelates.
    Journal of the American Pharmaceutical Association 03/2006; 49(3):140-3. DOI:10.1002/jps.3030490305
  • William O. Foye, John J. Hefferren
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    ABSTRACT: A method for preparing mono-substituted dithiobiuret derivatives of aldehydes has been developed. Compounds analogous to the aldehyde thiosemicarbazones have been prepared in fair yield and have been shown to exhibit antitubercular activity in vitro.
    Journal of the American Pharmaceutical Association 01/2006; 42(1):31-2. DOI:10.1002/jps.3030420109
  • H F Wang, X D Li, Y M Chen, L B Yuan, William O. Foye
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    ABSTRACT: High doses of 60Co radiation (4.0-8.0 Gy) in mice, rats and rabbits caused increases in rate of platelet aggregation during the first 5 days after irradiation. The inhibitory effects of the extracts of five Chinese drug plants and acetylsalicylic acid on rate of platelet aggregation were observed in both in vitro and in vivo tests, averaging 23-53% in vitro and 46-69% in vivo. Antiradiation tests on mice vs. 7.5-8.0 Gy of gamma-radiation, using the plant extracts and acetylsalicylic acid as protective agents, increased survival rates by 8-50% for the plant extracts and 35% for acetylsalicylic acid.
    Journal of Ethnopharmacology 10/1991; 34(2-3):215-9. DOI:10.1016/0378-8741(91)90040-K · 2.94 Impact Factor
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    ABSTRACT: A series of guanylhydrazones derived from 2- and 4-pyridine and 4-quinoline carboxyaldehydes was synthesized from S-methylisothio-semicarbazide hydroiodide using known procedures. The compounds are analogous to anticancer and antiviral thiosemicarbazones, but several of the guanylhydrazones derived from 4-quinoline carboxaldehyde showed no activity against P388 lymphocytic leukemia in mice. Guanylhydrazones derived from all three heterocyclic aldehydes revealed significant blood pressure lowering effects in the rat, however.
    Journal of Pharmaceutical Sciences 07/1990; 79(6):527-30. DOI:10.1002/jps.2600790615 · 3.01 Impact Factor
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    ABSTRACT: N4-(2-Acetoxyethoxymethyl)-2-acetylpyridine thiosemicarbazone (AATSC) belongs to a series of molecules known to have broad antimicrobial inhibitory activity. These molecules contain the 2-acetoxyethoxy moiety which could conceivably take up a conformation analogous to that of the ribosyl group. Moreover, the thiosemicarbazone moiety, when in the presence of a suitable enzymatic site, could mimic the triazine group, which is found in a number of antifolate drugs. AATSC, which has both bacterial inhibitory activity and water solubility, was accordingly evaluated for its antifolate activity against the bovine liver dihydrofolate reductase. AATSC is shown to be a fully uncompetitive inhibitor of that enzyme. Furthermore, AATSC enhances the activity of methotrexate. Such a potentiation could be useful for therapeutic purposes.
    Biochimica et Biophysica Acta 05/1990; 1034(1):81-5. DOI:10.1016/0304-4165(90)90156-Q · 4.66 Impact Factor
  • Panna Lal Dutta, William O. Foye
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    ABSTRACT: Series of N-substituted diethyl aspartates and N-substituted-3-oxo-1,4-piperazine-2-acetic acid esters were synthesized as potential inhibitors of aspartate transcarbamoylase. The aspartates were obtained by addition of substituted alkyl amines to diethyl maleate, or conversion of the hydroxy ethyl amino adduct to other functions. The 3-oxo-1,4-piperazine-2-acetic acid esters were prepared by addition of ethylene diamine to diethyl maleate, followed by cyclization. Addition of 1,2-diamino-2-methylpropane gave the corresponding 5,5-dimethyl-3-oxo-1,4-piperazine-2-acetic acid ester. N-Acyl derivatives in each series were obtained using the bromoacyl chlorides. A majority of the compounds in each series showed antimicrobial activity against five representative microorganisms, as well as significant activity against aspartate transcarbamoylase. Four of the compounds were found to have significant specificity against several tumor cell lines. A distance of two carbons between N and a reactive function was found to give the best activity for either antimicrobial, antienzyme, or tumor cell specificity activities, in either the open chain aspartates or cyclic piperazines. Little difference in anti-enzyme activity was found between the aspartates and piperazines, but introduction of the planar phenyl substituents lowered inhibitory activity.
    Journal of Pharmaceutical Sciences 05/1990; 79(5):447-52. DOI:10.1002/jps.2600790519 · 3.01 Impact Factor

Publication Stats

461 Citations
275.59 Total Impact Points

Institutions

  • 1958–2006
    • Massachusetts College of Pharmacy and Health Sciences
      • Chemistry
      Concord, Massachusetts, United States
  • 1952–2006
    • University of Wisconsin–Madison
      • School of Pharmacy
      Madison, Wisconsin, United States
  • 1956
    • South Dakota State University
      Brookings, South Dakota, United States