lithium in dry Et20 under Nj at -70°. After 2 hr the mixture was warmed to room temp and hydrolyzed (H20). The resulting a-(2-pyridyl) 6-methyl-2-trifluoromethyl-4-quinolyl ketone was reerystd from EtOH (30%) mp 155°( lit.8 mp 153°). The results of these experiments are shown in Table II.As might have been expected the reaction between 4-quinolyllithiums and pipecolenic acid which has two active hydrogens and would form a dianion with two proximate negative charges, Field, et al.failed to give the piperidyl ketone; in the case of the 6-Me derivative the corresponding parent quinoline was obtained in 55% yield.The reaction of 4-cyano-6,8-dimethyl-2-trifluoromethylquinoline (13s) with 2-PyLi in Et20 at -70°for 4 hr under N2 and purification by column chromatography on silica gel (CHC13) gave 50%c of 2-pyridyl 6,8-dimethyl-2-trifluoromethyl-4-quinolyl ketone, mp 94°( lit.8 mp 98°).
Dithiocarbamates and thiuram disulfides have long been noted for antifungal activity against human pathogens.1 2 More specifically, potassium N,N-dimethyldithiocarbamate inhibited Histoplasma capsulaban at <10 Mg/ml in vitro, and some trithiopercarbamates, IVIDNCfSlSSR3, at 1-5 ag/ml.3 Thioacetic and thiopropionic acid also inhibited H. capsulatum (10-20 yug/ml).4 5Latentiation of thioacetic and other thio acids as the carbonyl disulfides, R^CfO)-SSR2, produced compds having in vitro activity at conens ranging upward from 8 ag/ml, suggesting that R2S moieties without functional groups were not particularly promising for latentiation.6 Since the moiety S(CH2)r S02Na gave quite good results when used to latentiate a radioprotective thiol, 2-acetamidoethanethiol,6 this moiety seemed a worthwhile one to try with dithiocarbamates and a thio acid.Compds 2-5 (Table I) were prepared by oxodisulfide cleavage,6 in which the appropriate thiolate reacts with 1,2-dithiane 1,1-dioxide (1), as shown by eq 1; these reactions thus extend oxodisulfide cleavage to include thio and dithiocarbamic acid salts. RC(X)SNa + (CH,)4S0,S RC(X)SS(CH2)4SO,Na
The spectra of photoelectrons from elements in D-peniciiiamine and related compounds were measured. Binding energies and photoelectron widths recorded were for N, 0, C, K, S, and Zn electron energy levels. In D-peniciiiamine and other a-amlno acids, the nitrogen was found to exist as a zwitterion with a N(1s) blndlng energy >401 eV. in the sodium salt of D-penicillamine and the potassium salt of giycine the nitrogen was found to exist as a free amine with a N(1s) binding energy <400 eV. in the zinc penicillamine complex, a mixture of the free amine and zwitterion was observed. This zinc complex structure Is discussed in terms of surface bonding. Zlnc blndlng energy data are also dlscussed.
Organic Disulfides and Related Substances. 32 corresponding carboxamide. This was unsuccessful; the only product, isolated in low yield, was 17: mp 130-131°; mass spectrum (70 eV) m/e (rel intensity) 273 (100), 159 (71), 114 (15), 81 (25).
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