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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 29, Number 6
JKCSEZ 29(6)
December 20, 1985 

Synthesis of Nucleophilic Adducts of Thiols (Ⅷ). Addition of L-Glutathione to β,β-Diethoxycarbonylstyrene Derivatives

Thiol의 친핵성 첨가물의 합성 (Ⅷ). β,β-Diethoxycarbonylstyrene에 대한 L-Glutathione의 첨가
Tae-Rin Kim, Sung-Yong Choi, Joon-Seob Shin

김태린, 최승용, 신준섭
물-메탄올(9:1) 용매 속에서 β,β-diethoxycarbonylstyrene과 L-glutathione을 반응시켜 좋은 수득율로 다음과 같은 화합물을 합성하였다. 즉 S-(2,2-diethoxycarbonyl-1-phenylethyl)-L-glutathione, S-2,2-diethoxycarbonyl-1-(3',4'-methylenedioxy)phenylethyl-L-glutathione, S-2,2-diethoxycarbonyl-1-(3',4',5'-trimethoxy)phenylethyl-L-glutathione, S-2,2-diethoxycarbonyl-1-(4'-hydroxy)phenylethyl-L-glutathione, S-2,2-diethoxycarbonyl-1-(4'-methoxy)phenylethyl-L-glutathione. 위 화합물들의 구조는 원소분석과 분광학적 방법으로 확인하였고 수득율에 미치는 pH와 용매의 영향을 실험한 결과 pH는 4.0에서 8.0사이가 용매는 물-메탄올이 가장 적합하다는 것을 알았다. 한편 이 화합물의 Gram(+) 박테리아에 대한 항균성을 실험한 결과 약함을 알았다.

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.

651 - 655
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