Quinone 유도체의 합성에 관한 연구

Abstract

Quinones are widely distributed in nature and play essential biological roles. They also occur as substances of potential toxicological significance in environmental pollutants, and some are used as anticancer drugs. Considerable interest has been focused on quinone compounds since the agents with a naphthoquinone framework such as anthracyclines and mitoxantrones had been developed. In this study, many compounds having multiple skeletal structure of naphthoquinone were synthesized and carried out anti-cancer activity test. From 2-formyl-1,4,5,8-tetramethoxynaphthalene, new leading compounds of 20 species were produced. 2-formyl-1,4,5,8-tetramethoxynaphthalene which is second material was synthesized by this 4 step of reaction, methylation (86%), bromination (85%), methoxylation (61%) and formylation (96%) from 1,5-naphthalen diol. To compose 2-substituted 1,4,5,8-tetramethoxynaphthalene with leading compound of naphthaoquinone, chromium (Ⅵ) oxide and cerium (Ⅳ) ammonium nitrate (CAN) was used then 6-substituted compound of CrO and 2-substituted compound was obteined mainly. MTT experiments showed that the compounds containing naphthoquinone moiety exhibited potent bioactivities against AML-2 cell in vitro and 2-substituted 5,8-dimethoxy-1,4-naphthoquinone derivatives exhibited higher antitumor activity than 6-substituted 5,8-dimethoxy-1,4-naphthoquinone derivatives.