W J Pannekoek

Publications (2)6.11 Total impact

• Article: Synthesis of oximes, aziridines, and allyl alcohols derived from substituted 1-phenyl-1-nonen-3-ones as potential cytotoxic and antitumor agents.

  J R Dimmock, P J Smith, L M Noble, W J Pannekoek
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  ABSTRACT: A number of nuclear-substituted 1-phenyl-1-nonen-3-one oximes were synthesized. Reduction of several of these compounds with lithium aluminum hydride yielded the corresponding 1-phenyl-2,3-epiminononanes, shown by 100-MHz NMR spectroscopy to be the cis-geometrical isomers. When several ring-substituted 4-dimethylaminomethyl-1-phenyl-1-nonen-3-ones were treated with hydroxylamine hydrochloride under forcing conditions, the product isolated was the corresponding oxime. Reaction under mild conditions led only to the isolation of the Michael addition product of the oxime in low yield. Reduction of some nuclear-substituted 4-dimethylaminomethyl-1-phenyl-1-nonen-3-ones with sodium borohydride led to the formation of the corresponding allyl alcohols, and the products were shown by 1H- and 13C-NMR spectroscopy to be the threo-isomers or, alternatively, a mixture of erythro- and threo-isomers. Reaction of phosphoric acid with one of the substituted allyl alcohols led to a diolefin, shown by NMR spectroscopy to be a mixture of (E, E)- and (E, Z)-isomers in a ratio of 65:35.
  Journal of Pharmaceutical Sciences 12/1978; 67(11):1536-9. · 3.06 Impact Factor
• Article: Synthesis of diastereoisomeric 4-dimethylamino-3-phenyl-2-butanols and related esters for antimicrobial evaluation.

  J R Dimmock, D K Kowal, W A Turner, P J Smith, L M Noble, W J Pannekoek
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  ABSTRACT: 4-Dimethylamino-3-phenyl-2-butanone was reduced to the corresponding diastereoisomeric alcohols, which were separated by fractional crystallization of the corresponding hydrochloride salts. The configuration of the diastereoisomeric alcohols was determined by PMR spectroscopy. The assignments were confirmed by a consideration of the mass spectral data obtained for the two alcohols. Acylation of the alcohols gave the corresponding esters. Antimicrobial evaluation of the compounds prepared showed that 4-dimethylamino-3-phenyl-2-butanone had a promising level of antifungal activity while the other derivatives showed either a low level of potency or were inactive.
  Journal of Pharmaceutical Sciences 04/1978; 67(3):401-4. · 3.06 Impact Factor