4-(6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)benzaldehyde | 1007347-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)benzaldehyde
• CAS: 1007347-59-2
• 化学式: C₂₃H₂₆O₂Si
• 分子量: 362.544
• InChiKey: DWJVOSVJBPRUSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)benzaldehyde 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以76%的产率得到(4-(6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)phenyl)methanol
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling studies of novel ACD- and ABD-ring steroidomimetics as inhibitors of CYP17

  摘要：

  Two novel classes of non-steroidal substrate mimetics were synthesised and examined for their potency as inhibitors of human CYP17. Selected compounds were tested for inhibition of hepatic CYP enzymes 3A4, 1A2, 2C9 and 2C19. The most promising compound 15 showed a good inhibition of the target enzyme (31% and 66% at 0.2 and 2 mu M, respectively), and little inhibition of the most important hepatic enzyme CYP3A4 (6% and 19% inhibition at 0.2 and 2 mu M, respectively) and the key enzyme of glucocorticoid biosynthesis CYP11B1 (3% and 23% inhibition at 0.2 and 2 mu M, respectively). Docking studies revealed that this compound does not assume the same binding mode as steroidal ligands. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.079
• 作为产物：
  描述：

  4-甲酰基苯硼酸 、 (6-溴萘-2-基氧基)-叔丁基二甲基硅烷 在 palladium diacetate 四丁基溴化铵 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 16.0h， 以91%的产率得到4-(6-(tert-butyldimethylsilyloxy)naphthalen-2-yl)benzaldehyde
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modelling studies of novel ACD- and ABD-ring steroidomimetics as inhibitors of CYP17

  摘要：

  Two novel classes of non-steroidal substrate mimetics were synthesised and examined for their potency as inhibitors of human CYP17. Selected compounds were tested for inhibition of hepatic CYP enzymes 3A4, 1A2, 2C9 and 2C19. The most promising compound 15 showed a good inhibition of the target enzyme (31% and 66% at 0.2 and 2 mu M, respectively), and little inhibition of the most important hepatic enzyme CYP3A4 (6% and 19% inhibition at 0.2 and 2 mu M, respectively) and the key enzyme of glucocorticoid biosynthesis CYP11B1 (3% and 23% inhibition at 0.2 and 2 mu M, respectively). Docking studies revealed that this compound does not assume the same binding mode as steroidal ligands. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.079

文献信息

• CYP17 Inhibitors. Annulations of Additional Rings in Methylene Imidazole Substituted Biphenyls: Synthesis, Biological Evaluation and Molecular Modelling
  作者：Mariano A. E. Pinto-Bazurco Mendieta、Matthias Negri、Qingzhong Hu、Ulrike E. Hille、Carsten Jagusch、Kerstin Jahn-Hoffmann、Ursula Müller-Vieira、Dirk Schmidt、Thomas Lauterbach、Rolf W. Hartmann

  DOI：10.1002/ardp.200700251

  日期：2008.10

  originating from two classes of annulated biphenyls were synthesized as mimetics of the steroidal A‐ and C‐rings and examined for their potency as inhibitors of human CYP17. Selected compounds were tested for inhibition of the hepatic CYP enzyme 3A4. Potent CYP17 inhibitors were found for each class, compound 9 (17 and 71% at 0.2 and 2 μM, respectively) and 21 (591 nM). Compound 21 showed only weak inhibition

  合成了来自两类环联苯的 21 种新化合物，作为甾体 A 和 C 环的模拟物，并检查了它们作为人类 CYP17 抑制剂的效力。测试所选化合物对肝 CYP 酶 3A4 的抑制作用。对每一类都发现了有效的 CYP17 抑制剂，化合物 9（分别为 17% 和 71%，浓度为 0.2 和 2 μM）和 21（591 nM）。化合物 21 仅显示出对 CYP3A4 的微弱抑制（分别为 32% 和 64%，在 2 μM 和 10 μM 时）。然而，这两种化合物都表现出对糖皮质激素形成酶 CYP11B1 的中度至强抑制作用。最有趣的化合物停靠在我们的蛋白质模型中。它们绑定到我们之前发布的一种模式中。确定了新的相互作用区域。