Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Pusztaszeri út 59-67, H-1025 Budapest, Hungary.
Bioorg Med Chem. 2012 Jul 15;20(14):4258-70. doi: 10.1016/j.bmc.2012.05.065. Epub 2012 Jun 5.
N-dienylphenothiazines synthesized from tetrazolo[1,5-a]pyridinium salts by treatment with phenothiazine were subjected to catalytic hydrogenation to yield N-butylphenothiazines, whereas transformation of these dienes with borane dimethyl sulfide (BH(3) × Me(2)S) resulted in selective hydroboration of one double bond and full reduction of the other double bond to give 2-hydroxybutylphenothiazines. Position of the hydroxyl group was supported by NMR spectroscopy and verified by X-ray analysis. Comparison of MDR modulatory activity of the new derivatives revealed that the hydroxybutyl compounds are promising candidates for development of novel MDR inhibitors.
N-二烯基吩噻嗪由四唑并[1,5-a]吡啶𬭩盐与吩噻嗪反应合成，经催化氢化生成 N-正丁基吩噻嗪，而这些二烯与硼烷二甲硫醚（BH(3) × Me(2)S）反应则选择性地使一个双键加氢，另一个双键完全还原，得到 2-羟丁基吩噻嗪。羟基的位置通过 NMR 光谱得到支持，并通过 X 射线分析得到验证。对新衍生物的 MDR 调节活性的比较表明，羟丁基化合物是开发新型 MDR 抑制剂的有前途的候选物。
