Synthesis and physiological activity of alpha-and beta-campholenic thioesters
1996
Nomura, M. (Kinki Univ., Higashiosaka, Osaka (Japan)) | Asakura, M. | Fujihara, Y.
Alpha- and beta-Campholenic nitriles 3a and 3b were prepared by various methods and converted to campholenic acids 4a and 4b by hydrolysis. The acids were condensed with ethylthiol, n-propylthiol, isoprophylthiol, n-buthylthiol and sec-buthylthiol to obtain thioester compounds 5a-9b in 17-56% yields in three steps, the first being the imidation of d-camphor 1. The ten terpene derivatives obtained were tested for antimicrobial activity and growth-regulating activity in plants. For antimicrobial activity on Bacillus subtilis, Escherichia coli, and Staphylococcus aureus, S-propyl-2-(2,2,3-trimethylcyclopenta-3-en-1-yl)-thioacetate 6a (at 50 ppm) derived from 3a, inhibited the growth of E. coli
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