Institute of Biological Sciences, Faculty of Science and Health, The John Paul II Catholic University of Lublin, Konstantynów 1J/4.03, 20-708 Lublin, Poland.
Faculty of Chemistry, Maria Curie-Sklodowska University in Lublin, Gliniana 33, 20-031 Lublin, Poland.
Molecules. 2022 Aug 27;27(17):5504. doi: 10.3390/molecules27175504.
The series of -symmetric biaryl core-based non-racemic bisphosphines possessing substituents of different electronic properties: both EDG and EWG were obtained in a short sequence of good yielding transformations, started from commercial 1,3-dimethyl-2-nitrobenzene. Several different approaches leading to the desirable ligands were practically evaluated. Notably, the synthesis of the entire series of ligands could be performed with the utilization of a single early-stage precursor DIDAB (6,6'-diiodo-2,2',4,4'-tetramethylbiphenyl-3,3'-diamine), which could be easily obtained in enantiomerically pure form. The obtained compounds at concentrations of 50 and 200 µM showed various biological activity against normal human dermal fibroblast, ranging from inactivity through time-dependent action and ending up with high toxicity.
该系列基于 - 对称联苯的非手性双膦配体具有不同电子性质的取代基：均具有给电子和吸电子基团，它们都是通过商业的 1,3-二甲基-2-硝基苯起始，经过一系列高产率的转化短序列得到的。实际评估了几种不同的方法来获得所需的配体。值得注意的是，整个系列配体的合成都可以利用单个早期阶段的前体 DIDAB（6,6'-二碘-2,2',4,4'-四甲基联苯-3,3'-二胺）来进行，该前体可以很容易地以对映体纯的形式获得。在 50 和 200µM 浓度下获得的化合物对正常人类皮肤成纤维细胞显示出不同的生物活性，从无活性到时间依赖性作用，最终具有高毒性。
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