环三磷腈对羟基苯甲醛芳胺衍生物的合成及分子识别功能

Synthesis and Molecular Recognition Function of Cyclotriphosphazene Derivative of p-hydroxybenzaldehyde and Arylamine

以六氯环三磷腈为起始原料,在不同摩尔的2,2-二羟基联苯的保护下合成了化合物(1)和(2),并分别与对羟基苯甲醛芳氨希夫碱进一步反应,经分离纯化后得到4种环三磷腈衍生物。通过红外光谱、核磁共振波谱对化合物进行了结构表征,证实为目标产物。以衍生物为活性小分子,利用紫外光谱研究了4种衍生物对信号分子激活剂磷酸吡哆醛的识别功能和剂-效关系。结果表明,化合物(5)—(8)对磷酸吡哆醛均有很好的识别功能,且多支链的希夫碱基枝化衍生物(6)和(8)具有更好的识别能力,这可能与希夫碱基支链增多,空间阻碍作用增强,限制了其与磷酸吡哆醛间的键合识别作用有关,也提示只有特定结构类型的衍生物才具有磷酸吡哆醛键合识别功能。

Compound （ 1 ） and （2） were prepared under the protection of 2,2 - dihydroxybiphe- nyl at different ratios by taking hexachloro -cylotriphosphazenes as starting material, and in the presence of p - hydroxybenzaldehyde Schiff base, four cyclotriphosphazene derivatives were ob- tained by separating and purifying. The compounds were characterized and confirmed as target products by IR spectroscopy, NMR spectroscopy, as well as took the derivatives as active small molecule, studied for the recognition function and dose - effect relationship of the four derivatives to react with the signal molecular activator pyridoxal phosphate by UV spectroscopy. The result shows that compound （5） - （8）have good recognition ability to pyridoxal phosphate, but the （6） and （8） for branched Schiff base derivatives have better recognition ability. This may be related to steric hindrance effect enhancing with the increasing of the branched - chain Schiff base, which limits to cyclotriphosphazene derivatives bonding recognition with pyridoxal phos- phate. This result also suggests that only specific type of derivative has the ability of bonding recognition function with pyridoxal phosphate.