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具有诱导细胞分化作用及癌和皮肤病化学治疗作用的维甲类化合物,不仅要求分子一端有疏水性、另一端为极性羧基和整个分子的共轭性,而且分子的构象也起重要作用。本文合成的N(4羧基苯基)3,5双叔丁基4羟基苯甲酰胺(2)具有与全反式维甲酸(ATRA,1)相似性质的基团配置和构象,表现有维甲酸的生物活性。然而N甲基化合物3,由于构象的完全不同,丧失了活性。用X线晶体学、紫外和核磁共振等方法研究了化合物2、3和ATRA的结构异同。
The retinoids, which have the effect of inducing cell differentiation and chemotherapy of cancer and dermatosis, require not only the hydrophobicity of one end of the molecule but also the conjugation of the polar carboxyl group with the whole molecule at the other end, and the conformation of the molecule also plays an important role. In this paper, the synthesis of N (4 carboxyl phenyl) 3,5 di-tert-butyl 4 hydroxybenzamide (2) with all-trans retinoic acid (ATRA, 1) similar to the nature of the group configuration And conformation, showing the biological activity of retinoic acid. However, N-methyl compound 3, due to a completely different conformation, loses its activity. X-ray crystallography, UV and NMR methods were used to investigate the similarities and differences between ATRA and 2,3.