Auckland Cancer Society Research Centre, School of Medical Sciences, Auckland 1142, New Zealand.
Waikato Clinical School, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand.
Molecules. 2020 Jun 26;25(12):2950. doi: 10.3390/molecules25122950.
A series of benzene ring substituted ketamine -alkyl esters were prepared from the corresponding substituted norketamines. Few of the latter have been reported since they have not been generally accessible via known routes. We report a new general route to many of these norketamines via the Neber (oxime to α-aminoketone) rearrangement of readily available substituted 2-phenycyclohexanones. We explored the use of the substituents Cl, Me, OMe, CF, and OCF, with a wide range of lipophilic and electronic properties, at all available benzene ring positions. The 2- and 3-substituted compounds were generally more active than 4-substituted compounds. The most generally acceptable substituent was Cl, while the powerful electron-withdrawing substituents CF and OCF provided fewer effective analogues.
一系列苯环取代的酮胺-烷基酯是由相应的取代的去甲酮胺制备的。由于它们通常无法通过已知途径获得，因此很少有报道。我们报告了一种新的一般方法，可以通过易得的取代的 2-苯环己酮的 Neber（肟至α-氨基酮）重排来制备许多这种去甲酮胺。我们探索了在所有可用的苯环位置使用具有广泛亲脂性和电子性质的取代基 Cl、Me、OMe、CF 和 OCF。2-和 3-取代的化合物通常比 4-取代的化合物更活跃。最普遍可接受的取代基是 Cl，而强大的吸电子取代基 CF 和 OCF 提供了较少有效的类似物。
