3-arylamino-1, 4-naphthoquinone 유도체의 합성

Abstract

항응고, 항암성 등 생리활성을 갖는 Naphthoquinone 유도체를 개발하기 위해 2, 3-Dichloro-1 ,4-naphthoquinone 과 N-arylamine (o-fluoroaniline, p-hydroxyaniline, m - chloroaniline, p-sulfadiazine , p-acetoaniline, N, N-dimethyl-1, 4-phenylenediamine)등을 반응시켜서 새로운 2-Chloro-3-(N-arylamino)-1, 4-naphthoquinone 유도체를 합성하였는데 높은 수득률을 보였고 2, 3-Dichloro-1, 4-naphthoquinone과 구조유사체인 2, 3 - Dibromo-1, 4-naphthoquinone과 2, 3-Epoxy-2, 3-dihydro-1, 4-naphthoquinone에도 N-arylamine을 반응시켜서 새로운 2-Bromo-3-(N-arylamino)-1, 4-naphthoquinone 유도체와 2-Hydroxy-3- (N-arylamino)-1, 4-naphthoquinone 유도체를 합성하였다.;2,3-Dichloro-1,4-naphthoquinone was reacted with o-fluoroaniline, p-sulfadiazine, p-acetoanline, N,N-dimethyl-1,4-phenylenediamine as a nucleophyllic substitution to form 2-Chloro-3-(N-arylamino)-1,4-naphthoquinones (1.-6.) in good yield. 2,3-Dibromo-1,4-naphthoquinone was also reacted with o-fluoroaniline, m-aminobenzoic acid, m-chloroaniline, morpholine, P-acetoaniline, N,N-dimethyl-1,4-phenylenediamine as a nucleophyllic substitution to give 2-Bromo-3-(N-arylamino)-1,4-naphthoquinones (7.-12). 2,3-Epoxy-2,3-dihydro-1,4-naphthoquinone was reacted with o-fluoroaniline, P-toluidine, m-chloroaniline, m-nitroaniline, p-amino salicylic acid, P-phenetidine, N,N-dimethyl-1,4-phenylenediamine as a ring opening and dehydrogenation to form 2-Hydroxy-3-(N-arylamino)-1,4-naphthoquinones (13.-21.). These new compounds are expected to have a biological activities such as anticoagulant, crtotoxic.