Synthesis of .alpha.-methylene-.gamma.-butyrolactones: a structure-activity relationship study of their allergenic power
- 1 September 1980
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 23 (9), 1031-1038
- https://doi.org/10.1021/jm00183a013
Abstract
.alpha.-Methylene-.gamma.-butyrolactones (35) were prepared and their allergenic properties tested on the skin of guinea pigs experimentally sensitized to alantolactone, isoalantolactone and .alpha.-methylene-.gamma.-butyrolactone. The first 2 groups of animals cross-react to lactones containing 9-18 C atoms but not to smaller .alpha.-methylene-.gamma.-butyrolactones. Animals sensitized to .alpha.-methylene-.gamma.-butyrolactone react only with .alpha.-methylene-.gamma.-butyrolactones containing 6 and 7 C atoms. These results are discussed in relation to the allergic contact dermatitis mechanism.This publication has 4 references indexed in Scilit:
- Dynamic NMR study of 3-methylene-1-oxaspiro[4.5]decan-2-one and single-crystal x-ray diffraction analysis of cis-8-tert-butyl-3-methylene-1-oxaspiro[4.5]decan-2-oneThe Journal of Organic Chemistry, 1978
- Allergic contact dermatitis due to sesquiterpene lactones.British Journal of Dermatology, 1978
- Synthesis of and allergic contact dermatitis to bicyclo-[2,2,1]-heptyl-α-methylene-γ-butyrolactones derived from norbornene and campheneCanadian Journal of Biochemistry, 1978
- Cysteine scavengers. 2. Synthetic .alpha.-methylenebutyrolactones as potential tumor inhibitorsJournal of Medicinal Chemistry, 1974