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KMID : 1059519850290060651
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Journal of the Korean Chemical Society
1985 Volume.29 No. 6 p.651 ~ p.655
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Synthesis of Nucleophilic Adducts of Thiols (Ⅷ). Addition of L-Glutathione to β,β-Diethoxycarbonylstyrene Derivatives
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Kim Tae-Rin
Choi Sung-Yongn
Shin Joon-Seob
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Abstract
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A series of S-(2,2-diethoxycarbonyl-1-phenylethyl)-L-glutathione derivatives (11a-e) were synthesized from the reaction of β,β-diethoxycarbonylstyrene with L-glutathione in 9 : 1 aqueous methanol. Thus, S-(2,2-diethoxycarbonyl-1-phenylethyl)-L-glutathione (11a), S-2,2-diethoxycarbonyl-1-(3',4'-methylenedioxy)phenylethyl-L-glutathione (11b), S-2,2-diethoxycarbonyl-1-(3',4',5'-trimethoxy)phenylethyl-L-glutathione (11c), S-2,2-diethoxycarbonyl-1-(4'-hydroxy)phenylethyl-L-glutathione (11d), S-2,2-diethoxycarbonyl-1-(4'-methoxy)phenylethyl-L-glutathione (11e) were obtained in good yields. The structure of the adducts was characterized by analytical and spectral data. The effects of pH and solvents upon the yields were also briefly examined. In the range of pH from 4.0 to 8.0, the aqueous methanol were found to be the best solvent for the addition reaction and the antibacterial activities of the adducts to Gram(+) bacteria were found to be weak.
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