2-萘甲氧基-3-丁炔基胞苷的合成与性质研究

Synthesis and Characterization of 2-Naphthalene Methoxy-3-Butynyl Cytidine

本研究以3-丁炔-1-醇和2-溴甲基萘为原料,合成萘甲氧基取代的中间产物2-萘甲氧基-3-丁炔。2-萘甲氧基-3-丁炔通过与5-碘胞苷的Sonogashira反应合成得到2-萘甲氧基-3-丁炔基胞苷,其结构通过核磁共振( 1H NMR 和 13 C NMR)以及质谱(MS)证实。2-萘甲氧基-3-丁炔基胞苷的光谱性质及细胞活性的研究结果表明,在不同溶剂中化合物对粘度和极性的变化敏感;天然核苷对其影响较小,当插入寡聚核酸中时能够保持其荧光性;合成得到的核苷发光性较强,具有成为荧光探针并用来探索生物分子结构、动力学和识别作用的潜在价值。

The intermediate 2-naphthalene methoxyl-3-butyne was synthesized from 3-butyne-1-alcohol and 2-bromomethyl naphthalene. 2-naphthalene methoxy-3-butynyl cytidine was synthesized by Sonogashira reaction with 2-naphthalene methoxyl-3-butyne and 5-iodocytidine,and its structure was confirmed by nuclear magnetic resonance(1H NMR and 13C NMR) and mass spectrometry(MS). The spectral properties and cellular activities of 2-naphthalene methoxy-3-butynyl cytidine showed that the compounds in different solvents were sensitive to changes in viscosity and polarity. Natural nucleoside had little effect on its fluorescence property after being inserted into oligonucleotide. The synthesized nucleosides with strong luminescence had the potential value of becoming fluorescent probes to explore the molecular structure kinetics and recognition of biomolecules.