항응고성의 2-Chloro-3-(N-Arylamino)-1,4-Naphthoquinone 유도체 합성

Synthesis of Anticoagulant 2-Chloro-3-(N-Arylamino)-1, 4-Naphthoquinones

Naphthoquinone derivatives have been found to be anticoagulant. In this report, several new 2-chloro-3-(N-arylamino)-naphthoquinone derivatives were synthesized in order to develope mild anticoagulant. 2,3-dichloro-1,4-naphthoquinone was reacted with p-aminobenzoic acid, m-aminobenzoic acid, toluidine, m-nitroaniline, sulfanilamide, sulfathiazole, sulfaguanidine, phenetidine, 2-aminopyrimidine and 3-amino-5-methylisoxazole in EtOH or AcOH afford 2-chloro-3-(p-carboxy anilino)-naphthoquinone (1), 2-chloro-3-(m-carboxyanilino)-naphthoquinone (2), 2-chloro-3-(toluidino)-naphthoquinone (3), 2-chloro-3-(m-nitroanilino)-naphthoquinone (4), 2-chloro-3-(4-sulfanilanilino)-naphthoquinone (5), 2-chloro-3-(4-sulfathiazolino)-naphthoquinone (6), 2-chloro-3-(4-sulfaguanidino)-naphthoquinone (7), 2-chloro-3-(Phenetidino)-naphthoquinone (8), 2-chloro-3-(pyrimidine-2-amino)-naphthoquinone (9) and 2-chloro-3-(5-methylisoxazole-3-amino)-naphthoquinone (10) in good yield.