4-(3-endo-hydroxy-3-exo-isopropyl-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile | 1196118-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(3-endo-hydroxy-3-exo-isopropyl-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile
• CAS: 1196118-67-8
• 化学式: C₂₁H₂₄N₂O
• 分子量: 320.434
• InChiKey: LHEMVXVTFBTVBC-LFUKPOHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  47.26
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-(3-oxo-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile 、 异丙基氯化镁 在 cerium(III) chloride bis(lithium chloride) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以28%的产率得到4-(3-endo-hydroxy-3-exo-isopropyl-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships, and Characterization of Novel Nonsteroidal and Selective Androgen Receptor Modulators

  摘要：

  Herein we describe the discovery of ACP-105 (1), a novel and potent nonsteroidal selective androgen receptor modulator (SARM) with partial agonist activity relative to the natural androgen testosterone. Compound 1 was developed from a series of compounds found in a HTS screen using the receptor selection and amplification technology (R-SAT). In vivo, 1 improved anabolic parameters in a 2-week chronic study in castrated male rats. In addition to compound 1, a number of potent antiandrogens were discovered from the same series of compounds whereof one compound, 13, had antagonist activity at the AR T877A mutant involved in prostate cancer.

  DOI：

  10.1021/jm901149c

文献信息

• Synthesis, Structure−Activity Relationships, and Characterization of Novel Nonsteroidal and Selective Androgen Receptor Modulators
  作者：Nathalie Schlienger、Birgitte W. Lund、Jan Pawlas、Fabrizio Badalassi、Fabio Bertozzi、Rasmus Lewinsky、Alma Fejzic、Mikkel B. Thygesen、Ali Tabatabaei、Stefania Risso Bradley、Luis R. Gardell、Fabrice Piu、Roger Olsson

  DOI：10.1021/jm901149c

  日期：2009.11.26

  Herein we describe the discovery of ACP-105 (1), a novel and potent nonsteroidal selective androgen receptor modulator (SARM) with partial agonist activity relative to the natural androgen testosterone. Compound 1 was developed from a series of compounds found in a HTS screen using the receptor selection and amplification technology (R-SAT). In vivo, 1 improved anabolic parameters in a 2-week chronic study in castrated male rats. In addition to compound 1, a number of potent antiandrogens were discovered from the same series of compounds whereof one compound, 13, had antagonist activity at the AR T877A mutant involved in prostate cancer.