Synthesis of Nucleophilic Adducts of Thiols (￥°). Addition of Cysteine to ￥a-Nitrostyrene Derivatives

摘要

The addition reactions of cysteine without blocking amino and carboxyl groups to substituted and unsubstituted モ-nitro-styrene derivatives were investigated. モ-Nitrostyrene(1a), p-methyl-モ-nitrostyrene(1b), 3,4,5-trimethoxy-モ -nitrostyrene(1c), -3,4-methylenedioxy-モ -nitrostyrene(1d), o-, m- and p-chloro-モ -nitrostyrene (1e, 1f, 1g) and o-, m- and p-methoxy-モ-nitrostyrene (1h, 1i, 1j) easily undergo addition reactions with cysteine to form S-(2-nitro-1-phenylethyl)-L-cysteine(3a), S-[2-nitro-1-(p-methyl)phenylethyl]-L-cysteine(3b) , S-[2-nitro-1-(3`,4`,5`-trimethoxy)phenylethyl]-L-c ysteine(3c), S-[2-nitro-1-( -3`,4`-methylenedioxy)phenylethyl]-L-cysteine(3d), S-[2-nitro-1-(o-chloro)phenylethyl]-L-cysteine(3e) , S-[2-nitro-1-(m-chloro)-phenylethyl]-L-cysteine(3f ), S-[2-nitro-1-(p-chloro)phenylethyl]-L-cysteine(3g) , S-[2-nitro-1-(o-methoxy)phenylethyl]-L-cysteine(3 h), S-[2-nitro-1-(m-methoxy)phenylethyl]-L-cysteine(3 i) and S-[2-nitro-1-(p-methoxy)phenylethyl]-L-cysteine(3j ), respectively. The structure of adducts were confirmed by means of UV-spectrum, IR-spectrum, molecular weight measurement and elemental analysis. The various factors effecting the yield of cysteine adducts to モ-nitrostyrene derivatives were also studied.