Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Nucleophilic Adducts of Thiols (Ⅳ). Addition of Glutathione to $\beta$-Nitrostyrene Derivatives

  • Kim, Tae-Rin (Department of Chemistry, College of Sciences, Korea University) ;
  • Choi, Sung-Yong (Department of Chemistry, College of Sciences, Korea University) ;
  • Choi, Won-Sik (Department of Chemistry, Kangreung National University)
  • Published : 1983.04.20
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Abstract

The addition products of glutathione to ${\beta}$ -nitrostyrene derivatives were synthesized. ${\beta}$ -Nitrostyrene (1a), p-methyl-${\beta}$-nitrostyrene (1b), 3,4,5-trimethoxy-${\beta}$-nitrostyrene (1c), o-, m- and p-chloro-${\beta}$-nitrostyrene (1e, 1f, 1g) and o-, m- and p-methoxy-${\beta}$-nitrostyrene (1h, 1i, 1j) undergo addition reactions with glutathione to form S-(2-nitro-1-phenylethyl)-L-glutathione (5a), S-[2-nitro-1-(p-methyl)phenylethyl]-L-glutatione (5b), S-[2-nitro-1-(3', 4', 5'-trimethoxy)phenylethyl]-L-glutathione (5c), S-[2-nitro-1-(o-chloro)phenylethyl]-L-glutathione (5e), S-[2-nitro-1-(m-choro)phenylethyl]-L-glutathione (5f), S-[2-nitro-1-(p-chloro)phenylethyl]-L-glutathione (5g), S-[2-nitro-x-(o-methoxy)-phenylethyl]-L-glutathion e(5h), S-[2-nitro-x-(m-methoxy)phenylethyl]-L-glutathion e (5i), and S-[2-nitro-1-(p-methoxy)phenylethy])-L-glutathione (5j), respectively. The structure of adducts were identified by UV and IR-spectra, molecular weight measurement, and elemental analysis.

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