| 1609552-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• CAS: 1609552-93-3
• 化学式: C₃₄H₃₃NO₃
• 分子量: 503.641
• InChiKey: IKOMHGKAVINVIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.54
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  58.56
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以70%的产率得到6-(3-adamantan-1-yl-4-hydroxyphenyl)-naphthalene-2-carboxylic acid hydroxyamide
  参考文献：
  名称：

  Influence of the adamantyl moiety on the activity of biphenylacrylohydroxamic acid-based HDAC inhibitors

  摘要：

  To investigate the influence of the adamantyl group on the biological properties of known HDAC inhibitors with a 4-phenylcinnamic skeleton, a series of compounds having the adamantyl moiety in the cap structure were synthesized and compared to the corresponding hydroxamic acids lacking this group. An unexpected finding was the substantial reduction of inhibitory activity toward the tested enzymes, in particular HDAC6, following the introduction of the adamantyl group. In spite of the reduced ability to function as HDAC inhibitors, the compounds containing the adamantyl moiety still retained a good efficacy as antiproliferative and proapoptotic agents. A selected compound (2c; ST3056) of this series exhibited an appreciable antitumor activity against the colon carcinoma xenograft HCT116. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.021
• 作为产物：
  描述：

  6-溴-2-萘甲酸 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 potassium acetate 、 三乙胺 、 联硼酸频那醇酯 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 5.17h， 生成
  参考文献：
  名称：

  Influence of the adamantyl moiety on the activity of biphenylacrylohydroxamic acid-based HDAC inhibitors

  摘要：

  To investigate the influence of the adamantyl group on the biological properties of known HDAC inhibitors with a 4-phenylcinnamic skeleton, a series of compounds having the adamantyl moiety in the cap structure were synthesized and compared to the corresponding hydroxamic acids lacking this group. An unexpected finding was the substantial reduction of inhibitory activity toward the tested enzymes, in particular HDAC6, following the introduction of the adamantyl group. In spite of the reduced ability to function as HDAC inhibitors, the compounds containing the adamantyl moiety still retained a good efficacy as antiproliferative and proapoptotic agents. A selected compound (2c; ST3056) of this series exhibited an appreciable antitumor activity against the colon carcinoma xenograft HCT116. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.021