Fluorescent sugar and uridine conjugates of 1,8-naphthalimides with methyl and ferrocenyl headgroups
Fluorescent sugar and uridine conjugates of 1,8-naphthalimides with methyl and ferrocenyl headgroups
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DOI：
10.1071/ch04020
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发表时间：
2004-01-01
影响因子：
1.1
通讯作者：
Simpson, J
中科院分区：
文献类型：
--
作者：
Cavigiolio, G;Morgan, JL;Simpson, J
首次合成了具有4-乙炔基-1，8-N-甲基萘酰亚胺接头的两亲性糖和脱氧尿苷缀合物、具有N-十一碳基二茂铁基头基的4-乙炔基脱氧尿苷缀合物和具有2，3，4，6-四-O-乙酸-β-D-吡喃葡萄糖苷头基的1，8-萘酰亚胺。还报道了一种用于糖-乙炔基萘二甲酰亚胺聚合物的新型丙烯酸酯单体前体。乙炔基系链与Co-2（CO）（8）和Co-2（CO）（6）dppm形成络合物。本文还报道了2 '-丙炔基-2，3，4，6-四-O-乙酸酯-β-D-吡喃葡萄糖苷4和4-（2'-丙炔基-2，3，4，6-四-O-乙酸酯-β-D-吡喃葡萄糖苷）-N-甲基-1，8-萘酰亚胺6的单晶X-射线结构。除了Co2复合物之外，糖和脱氧尿苷缀合物是强荧光的。在具有十一烷基二茂铁基头基的脱氧尿苷缀合物中实现“开-关”荧光切换。
The first amphiphilic sugar and deoxyuridine conjugates with a 4-ethynyl-1,8-N-methylnaphthalimide linker, a 4-ethynyldeoxyuridine conjugate with a N-undecylferrocenyl headgroup, and a 1,8-naphthalimide with a 2,3,4,6-tetra-O-acetate-beta-D-glucopyranoside headgroup have been synthesized. A novel acrylate monomeric precursor for sugar-ethynylnaphthalimide polymers is also reported. The ethynyl tether forms complexes with Co-2(CO)(8) and Co-2(CO)(6)dppm. The single-crystal X-ray structures of 2'-propynyl-2,3,4,6-tetra-O-acetate-beta-D-glucopyranoside 4 and 4-(2'-propynyl-2,3,4,6-tetra-O-acetate-beta-D-glucopyranoside)-N-methyl-1,8-naphthalimide 6 are also reported. With the exception of the Co2 complexes, the sugar and deoxyuridine conjugates are strongly fluorescent. 'On-off' fluorescent switching is achieved in the deoxyuridine conjugate with an undecylferrocenyl headgroup.