School of Chemistry, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland.
School of Chemistry, Trinity College Dublin, 152-160 Pearse Street, Dublin 2, Ireland.
Bioorg Med Chem Lett. 2023 Jun 15;90:129346. doi: 10.1016/j.bmcl.2023.129346. Epub 2023 May 20.
We present a general efficient green method for the preparation of nitro N,N'-diaryl thioureas via a one-pot method using cyrene as a solvent with almost quantitative yields. This confirmed the viability of cyrene as a green alternative to THF in the synthesis of thiourea derivatives. After screening different reducing conditions, the nitro N,N'-diaryl thioureas were selectively reduced using Zn dust in the presence of water and acid to the corresponding amino N,N'-diaryl thioureas. These were then used to test the installation of the Boc-protected guanidine group with N,N'-bis-Boc protected pyrazole-1-carboxamidine as a guanidylating reagent not requiring mercury(II) activation. Finally, the TFA salts obtained after Boc-deprotection of two sample compounds were tested for their affinity towards DNA showing no binding.
我们提出了一种通用的高效绿色方法，通过一锅法使用金烯作为溶剂制备硝基 N,N'-二芳基硫脲，几乎可以定量产率。这证实了金烯作为四氢呋喃在硫脲衍生物合成中的绿色替代品的可行性。在筛选不同的还原条件后，使用锌粉在水和酸的存在下选择性地将硝基 N,N'-二芳基硫脲还原为相应的氨基 N,N'-二芳基硫脲。然后，使用它们来测试 Boc 保护的胍基与 N,N'-双 Boc 保护的吡唑-1-甲脒的安装，作为不需要汞(II)激活的胍基化试剂。最后，对两个样品化合物的 Boc 脱保护后获得的 TFA 盐进行了 DNA 亲和力测试，显示没有结合。
