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Synthesis of boronated meso-arylporphyrins via copper-catalyzed 1,3-dipolar cycloaddition reaction and their binding ability towards albumin and low density lipoproteins
Journal of Organometallic Chemistry ( IF 2.3 ) Pub Date : 2020-03-25 , DOI: 10.1016/j.jorganchem.2020.121248
Valentina A. Ol’shevskaya , Andrei V. Zaitsev , Anton V. Makarenkov , Elena G. Kononova , Alina A. Markova , Alexey A. Kostyukov , Anton E. Egorov , Mikhail A. Klimovich , Olga A. Koroleva , Vladimir A. Kuzmin

A series of novel meso- triazoloporphyrin-carborane conjugates was prepared in good yields via the copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of Zn(II) or Pd(II) 5,10,15,20-tetrakis[4-(2-propargyloxy)-2,3,5,6-tetrafluorophenyl]porphyrin or Zn(II) 5,10,15,20-tetra(p-propargyloxyphenyl)porphyrin with 1-azidomethyl-o-carborane in CH2Cl2. Zinc metalloporphyrins were demetallated under acidic conditions to afford the corresponding free-base triazolo-carborane porphyrins in excellent yields. All new compounds were characterized by MS, NMR and UV–vis spectroscopy and their photophysical properties were studied.



中文翻译:

铜催化的1,3-偶极环加成反应合成硼代的中芳基卟啉及其对白蛋白和低密度脂蛋白的结合能力

通过铜(I)催化的锌(II)或钯(II)5,3,10,15,20-四烷基的惠斯根1,3-偶极环加成反应以高收率制备了一系列新型的内消旋-三唑并卟啉-碳硼烷共轭物[4-(2-炔丙氧基)-2,3,5,6-四氟苯基]卟啉或Zn(II)5,10,15,20-四(p -propargyloxyphenyl)卟啉与1- azidomethyl- ö -carborane在CH 2 Cl 2。将金属卟啉锌在酸性条件下脱金属,以优异的产率得到相应的游离碱三唑-碳硼烷卟啉。所有新化合物均通过MS,NMR和UV-vis光谱进行了表征,并对其光物理性质进行了研究。

更新日期:2020-03-26
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