. Can. J . Chem. 63, 3317 (1985). The initial oxidation stages of lactic acid by acid permanganate were investigated. The rate of the induction period was slow and then gradually increased. The kinetics of oxidation were second order, first order with respect to both lactic acid and Mn(VI1). The reaction was acid catalyzed. Addition of Mn(I1) ions largely increased the rate of the initial stages and decreased the rate of the following stages. The oxidation rate was decreased by the addition of F-or P,o:-ions. The Arrhenius equation was valid for the reaction between 16.5 and 34°C. Activation parameters were evaluated and a mechanism consistent with the results obtained was proposed.
Several C-10 substituted cannabidiol (CBD) derivatives and novel oxepin derivatives of delta 9-tetrahydrocannabinol (delta 9-THC) were synthesized and evaluated for biological activity in mice and dogs. Treatment of 10-bromocannabidiol diacetate (3) with various amines in Me2SO gave the corresponding 10-aminocannabidiol derivatives 4-6. Similarly, treatment of 3 with NaN3 gave the azido compound 7, which with LiA1H4 afforded the 10-aminocannabidiol 9. However, reduction of 7 with CrCl2 formed the amide 8, which on further reduction with LiA1H4 gave the N-ethyl analogue 10. Coupling of 9 with 11 in the presence of dicyclohexylcarbodiimide formed 12, which was then deprotected with HCl to give the analogue 13. The oxepin analogue 14a was synthesized from 3 by treatment with Na2CO3 in CH3OH/H2O at room temperature. The dimethylheptyl analogue 14b was similarly prepared. Incorporation of N-ethyl (10), N-methyl-N-propargyl (6), and morpholino (4) groups in CBD at position 10 resulted in analogues that were more potent than CBD in producing hypoactivity in mice. These analogues had relatively little effect on rectal temperature. Selected substitutions at C-10 also resulted in analogues that were partially effective in blocking delta 9-THC antinociceptive activity. This blockade was observed particularly in compound 10, which also showed unusually toxic properties. Incorporation of a seven-membered oxepin in the delta 9-THC structure eliminated cannabinoid activity although substitution of the pentyl side chain with a 1,2-dimethylheptyl in the oxepin 14b resulted in CNS depression in mice.
A new series of 2‐aryl(alkyl)oxazoloquinolines (IV) were prepared by the reaction of 7‐amino‐8‐hydroxyquinoline with aromatic (or aliphatic) aldehydes in the presence of piperidine as a catalyst. Interaction of 2‐methyloxazolo[4,5‐h]quinoIine with aromatic aldehydes in the presence of piperidine as a catalyst gave 2‐stilbyloxazolo [4,5‐h]quinolines. The structural configuration of the prepared compounds was determined by elemental and spectral analysis.
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