核酸荧光探针TOTO单体噻唑橙的合成研究

Synthesis of Fluorescent Dye Thiazole Orange

研究设计了以 2 巯基苯并噻唑和 4 甲基喹啉为主要原料 ,合成核酸荧光探针TOTO单体噻唑橙 (TO)的工艺路线。采用碘甲烷和对甲苯磺酸甲酯 ,先后对 2 巯基苯并噻唑进行了氮甲基化和巯甲基化反应 ,收率分别为 92 4 %和 91%。其后 ,用 4 甲基喹啉与 1,3 二溴丙烷反应 ,并将其产物与两步甲基化后产物反应 ,合成了目的产物TO ,后两步收率分别为 5 2 5 %和6 1 2 %。经核磁共振谱鉴定产品结构正确 。

An improved method for the synthesis of fluorescent dye TOTO monomer thiazole orange(TO) is described.The starting materials are commercially available 2 mercaptobenzothiazole and 4 methylquinoline.2 Methylthio N methylbenzothiazole p toluenesulfonate(Ⅰ) is prepared through N methylation and S methylation of 2 mercaptobenzothiazole with iodomethane and methyl p toluenesulfonate in 92 4% and 91% yield respectively. 4 Methyl 1 (3 bromopropyl)quinolinium bromide(Ⅱ) is prepared by reaction of 4 methylquinoline and 1,3 dibromopropane in 52 5% yield.Thiazole orange (TO) is formed by the reaction of Ⅰand Ⅱ and then iodinated with potassium iodide in 61 2% yield.The assigned structures are confirmed to be correct by NMR spectroscopy.