α-(4-chlorophenyl)-α-phenyl-5-pyrimidinemethanol | 108394-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-(4-chlorophenyl)-α-phenyl-5-pyrimidinemethanol
• 英文别名: Phenyl-(4-chlorophenyl)-(5-pyrimidinyl)carbinol；(4-chlorophenyl)-phenyl-pyrimidin-5-ylmethanol
• CAS: 108394-95-2
• 化学式: C₁₇H₁₃ClN₂O
• 分子量: 296.756
• InChiKey: QJYBUDJACCWKFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴嘧啶 、 4-氯二苯甲酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 α-(4-chlorophenyl)-α-phenyl-5-pyrimidinemethanol
  参考文献：
  名称：

  Biological Evaluation of 5-Substituted Pyrimidine Derivatives as Inhibitors of Brassinosteroid Biosynthesis

  摘要：

  我们合成了一系列 5-取代的嘧啶衍生物，并测试了它们抑制铜绿素生物合成的能力。这些化合物的生物活性通过茎伸长法进行了评估。在合成的化合物中，α-（4-氯苯基）-α-苯基-5-嘧啶甲醇（DPPM 4）在光照下对延缓芹菜茎的伸长有很强的抑制作用。施用 10 nM 黄铜内酯可逆转这种抑制作用，但 1 μM GA3 则不能。DPPM 4 还影响拟南芥在黑暗中的生长。经 DPPM 4 处理的拟南芥在黑暗中的表型与黄铜类固醇缺乏的突变体相似，下胚轴短小，子叶开裂。同时施用 10 nM 的黄铜素内酯可恢复这些生物变化，而施用 1 μM GA3 则无法恢复，这表明 DPPM 4 的主要作用部位是黄铜素类固醇生物合成途径。

  DOI：

  10.1271/bbb.65.817

文献信息

• Aromatase inhibition by 5-substituted pyrimidines and dihydropyrimidines
  作者：Harold M. Taylor、C. David Jones、James D. Davenport、Kenneth S. Hirsch、T. J. Kress、Dix Weaver

  DOI：10.1021/jm00391a016

  日期：1987.8

  The inhibition of estrogen biosynthesis has been suggested to be an effective treatment of hormone-dependent diseases, particularly breast cancer. Several series of 5-substituted pyrimidine derivatives have been synthesized and tested for their ability to inhibit the enzyme aromatase (estrogen synthetase). Compounds were evaluated in an in vitro assay that measured the inhibition of rat ovarian microsomal aromatase activity. Greatest inhibitory activity was achieved in the cases of diarylpyrimidinemethanols and diarylpyrimidinyl methanes which were substituted in the 4- and 4'-positions with electron-withdrawing substituents, particularly Cl.
• TAYLOR, H. M.;JONES, C. D.;DAVENPORT, J. D.;HIRSCH, K. S.;KRESS, T. J.;WE+, J. MED. CHEM., 30,(1987) N 8, 1359-1365
  作者：TAYLOR, H. M.、JONES, C. D.、DAVENPORT, J. D.、HIRSCH, K. S.、KRESS, T. J.、WE+

  DOI：——

  日期：——
• Biological Evaluation of 5-Substituted Pyrimidine Derivatives as Inhibitors of Brassinosteroid Biosynthesis
  作者：Jing-Ming WANG、Tadao ASAMI、Shigeo YOSHIDA、Noboru MUROFUSHI

  DOI：10.1271/bbb.65.817

  日期：2001.1

  A series of 5-substituted pyrimidine derivatives was synthesized, and their ability to inhibit brassinosteroid biosynthesis was tested. The biological activity of these compounds was evaluated by the cress stem elongation method. Among the synthesized compounds, α-(4-chlorophenyl)-α-phenyl-5-pyrimidinemethanol (DPPM 4) exhibited potent inhibitory activity for retarding cress stem elongation in the light. This inhibition was reversed by the application of 10 nM brassinolide, but not by 1 μM GA3. DPPM 4 also affected Arabidopsis growth in the dark. DPPM 4-treated Arabidopsis had phenotypes like those of brassinosteroid-deficient mutants, with short hypocotyls and open cotyledons, in the dark. These biological changes were restored by the co-application of 10 nM brassinolide, but not by 1 μM GA3, suggesting that the primary site of action of DPPM 4 was the brassinosteroid biosynthetic pathway.

  我们合成了一系列 5-取代的嘧啶衍生物，并测试了它们抑制铜绿素生物合成的能力。这些化合物的生物活性通过茎伸长法进行了评估。在合成的化合物中，α-（4-氯苯基）-α-苯基-5-嘧啶甲醇（DPPM 4）在光照下对延缓芹菜茎的伸长有很强的抑制作用。施用 10 nM 黄铜内酯可逆转这种抑制作用，但 1 μM GA3 则不能。DPPM 4 还影响拟南芥在黑暗中的生长。经 DPPM 4 处理的拟南芥在黑暗中的表型与黄铜类固醇缺乏的突变体相似，下胚轴短小，子叶开裂。同时施用 10 nM 的黄铜素内酯可恢复这些生物变化，而施用 1 μM GA3 则无法恢复，这表明 DPPM 4 的主要作用部位是黄铜素类固醇生物合成途径。