4-(1-(2-cyanoethyl)-4,4-dimethyl-2-oxopyrrolidin-3-yloxy)-2-(trifluoromethyl)benzonitrile | 1356347-04-0

• 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: 4-(1-(2-cyanoethyl)-4,4-dimethyl-2-oxopyrrolidin-3-yloxy)-2-(trifluoromethyl)benzonitrile
• 英文别名: 4-[1-(2-cyanoethyl)-4,4-dimethyl-2-oxopyrrolidin-3-yl]oxy-2-(trifluoromethyl)benzonitrile
• CAS: 1356347-04-0
• 化学式: C₁₇H₁₆F₃N₃O₂
• 分子量: 351.328
• InChiKey: YUZDOKGVYDKRFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(1-(2-cyanoethyl)-4,4-dimethyl-2-oxopyrrolidin-3-yloxy)-2-(trifluoromethyl)benzonitrile 以602.63 mg的产率得到(R)-(+)-4-(1-(2-cyanoethyl)-4,4-dimethyl-2-oxopyrrolidin-3-yloxy)-2-(trifluoromethyl)benzonitrile
  参考文献：
  名称：

  Discovery of 3-aryloxy-lactam analogs as potent androgen receptor full antagonists for treating castration resistant prostate cancer

  摘要：

  High throughput cell-based screening led to the identification of 3-aryloxy lactams as potent androgen receptor (AR) antagonists. Refinement of these leads to improve the ADME profile and remove residual agonism led to the discovery of 12, a potent full antagonist with greater oral bioavailability. Improvements in the ADME profile were realized by designing more ligand-efficient molecules with reduced molecular weights and lower lipophilicities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.068
• 作为产物：
  描述：

  4-氟-2-(三氟甲基)苯甲腈 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 148.0h， 生成 4-(1-(2-cyanoethyl)-4,4-dimethyl-2-oxopyrrolidin-3-yloxy)-2-(trifluoromethyl)benzonitrile
  参考文献：
  名称：

  Discovery of 3-aryloxy-lactam analogs as potent androgen receptor full antagonists for treating castration resistant prostate cancer

  摘要：

  High throughput cell-based screening led to the identification of 3-aryloxy lactams as potent androgen receptor (AR) antagonists. Refinement of these leads to improve the ADME profile and remove residual agonism led to the discovery of 12, a potent full antagonist with greater oral bioavailability. Improvements in the ADME profile were realized by designing more ligand-efficient molecules with reduced molecular weights and lower lipophilicities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.068

文献信息

• Discovery of 3-aryloxy-lactam analogs as potent androgen receptor full antagonists for treating castration resistant prostate cancer
  作者：Chuangxing Guo、Susan Kephart、Martha Ornelas、Javier Gonzalez、Angelica Linton、Mason Pairish、Asako Nagata、Samantha Greasley、Jeff Elleraas、Natilie Hosea、Jon Engebretsen、Andrea N. Fanjul

  DOI：10.1016/j.bmcl.2011.11.068

  日期：2012.1

  High throughput cell-based screening led to the identification of 3-aryloxy lactams as potent androgen receptor (AR) antagonists. Refinement of these leads to improve the ADME profile and remove residual agonism led to the discovery of 12, a potent full antagonist with greater oral bioavailability. Improvements in the ADME profile were realized by designing more ligand-efficient molecules with reduced molecular weights and lower lipophilicities. (C) 2011 Elsevier Ltd. All rights reserved.