4-(3-exo-ethynyl-3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile | 870888-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(3-exo-ethynyl-3-endo-hydroxy-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile
• CAS: 870888-75-8
• 化学式: C₂₀H₁₈N₂O
• 分子量: 302.376
• InChiKey: SEMBWNLBKXWPPO-IGOJGBNBSA-N

物化性质

• 沸点：
  530.6±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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 、 乙炔基溴化镁 在 cerium(III) chloride bis(lithium chloride) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以59%的产率得到4-(3-exo-ethynyl-3-endo-hydroxy-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

• Androgen receptor modulators and methods of treating disease using the same
  申请人：Schlienger Nathalie

  公开号：US20070004679A1

  公开（公告）日：2007-01-04

  Disclosed herein are bicycloaryl compounds of Formula (I) that selectively modulate nuclear receptors, preferably the androgen receptor, or a pharmaceutically acceptable salt, ester, amide, or prodrug thereof, and methods of treating disease comprising administering a compound of Formula (I) to a patient in need thereof.

  本文公开了一种公式（I）的双环芳基化合物，其选择性调节核受体，优选为雄激素受体，或其药学上可接受的盐、酯、酰胺或前药，以及包括向需要治疗的患者给予公式（I）化合物的治疗疾病的方法。
• Androgen receptor modulators and method of treating disease using the same
  申请人：Schlienger Nathalie

  公开号：US20060014739A1

  公开（公告）日：2006-01-19

  Disclosed herein are bicycloaryl compounds of Formula (I) that selectively modulate nuclear receptors, preferably the androgen receptor, or a pharmaceutically acceptable salt, ester, amide, or prodrug thereof, and methods of treating disease comprising administering a compound of Formula (I) to a patient in need thereof.

  本文公开了式(I)的双环芳基化合物，其选择性调节核受体，优选为雄激素受体，或其药学上可接受的盐、酯、酰胺或前药，以及通过向需要治疗的患者施用式(I)化合物的方法治疗疾病。
• ANDROGEN RECEPTOR MODULATORS AND METHOD OF TREATING DISEASE USING THE SAME
  申请人：Schlienger Nathalie

  公开号：US20080009489A1

  公开（公告）日：2008-01-10

  Disclosed herein are bicycloaryl compounds of Formula (I) that selectively modulate nuclear receptors, preferably the androgen receptor, or a pharmaceutically acceptable salt, ester, amide, or prodrug thereof, and methods of treating disease comprising administering a compound of Formula (I) to a patient in need thereof.

  本文披露了公式(I)的双环芳基化合物，其有选择性地调节核受体，优选为雄激素受体，或其药学上可接受的盐、酯、酰胺或前药，以及治疗疾病的方法，包括向需要该化合物的患者施用公式(I)的化合物。
• US7268232B2
  申请人：——

  公开号：US7268232B2

  公开（公告）日：2007-09-11
• 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.