Methanopterin과 관련된 6-[1-(4-Ribitylanilino)ethyl]-1,3,7-trimethyllumazine의 합성

Abstract

Methanopterin의 pteridine부분과 관련있는 구조를 가지는 6-[1-(4-ribityl-anilino)ethyl]-1,3,7-trimethyllumazine (2)를 합성하였다. 4-Ribitylaniline 유도체는 D-ribose와 N-benzoyl-4-bromoaniIine (7)을출발 물질로 하여 여러 단계를 거쳐 합성되었다. 6-Acetyl-1,3,7-trimethyllumazine (4)는 Timmis 반응을 이용하여 4-amino-1,3-dimethyl-5-nitrosouracil (3)과 2,4-pentanedione을 반응시켜 얻을 수 있었다. 화합물 4는 N a B H 4 에 의한 환원반응과 뒤이은 S O C l 2 에 의한 염소화반응으로 6-(1-chloroethyl)-1,3,7-trimethyllumazine (6)으로 변환되었다. 화합물 6과 4-(2,3:4,5-di-O-isopropylidene-D-ribityl)aniline (13)의 친핵성 치환반응으로 6-[1-{4-(2,3:4,5-di-O-isopropylidene-D-ribityl)anilino}ethyl]-1,3,7-trimethyllumazine (14)가 합성되었다 목표 화합물 2는 산 촉매하에서 화합물 14를 가수분해하여 얻어졌다. 6-[1-(4-ribitylanilino)ethyl]-1,3,7-trimethyllumazine (2), which is related to pteridine moiety of methanopterin, was synthesized. 4-Ribitylaniline derivative was prepared from D-ribose and N-benzoyl-4-bromoaniline (7) as the starting materials through several steps. 6-Acetyl-1,3,7-trimethyllumazine (4) was obtained from the reaction of 4-amino-1,3-dimethyl-5-nitrosouracil (3) with 2,4-pentanedione by Timmis reaction. Compound 4 was converted to 6-(1-chloroethyl)-1,3,7-trimethyllumazin (6) by the reduction with sodium borohydride and followed by chlorination with thionyl chloride. The nucleophilic displacement reaction of compound 6 with 4-(2,3:4,5-di-O-iso-propylidene-D-ribityl)aniline (13) in anhydrous DMF yielded 6-[1-{4-(2,3:4,5-di-O-isopropylidene-D-ribityl)anilino}ethyl]-1,3,7-trimethyllumazine (14). The target molecule 2 was obtained by the hydrolysis of compound 14 in the presence of an acid catalyst.