(Z)-4-(4-pyrrolidinophenylmethylene)-3-(4-fluorophenyl)-5(4H)-isoxazolone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (Z)-4-(4-pyrrolidinophenylmethylene)-3-(4-fluorophenyl)-5(4H)-isoxazolone
• 英文别名: (4Z)-3-(4-fluorophenyl)-4-[(4-pyrrolidin-1-ylphenyl)methylidene]-1,2-oxazol-5-one
• 化学式: C₂₀H₁₇FN₂O₂
• 分子量: 336.366
• InChiKey: ZUPZXTAXIZNDRJ-AQTBWJFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-苯基吡咯烷 在 磷酸 、 盐酸羟胺 、 三氯氧磷 作用下， 反应 2.0h， 生成 (Z)-4-(4-pyrrolidinophenylmethylene)-3-(4-fluorophenyl)-5(4H)-isoxazolone
  参考文献：
  名称：

  Anti-Androgens with full antagonistic activity toward human prostate tumor LNCaP cells with mutated androgen receptor

  摘要：

  Anti-androgens were designed based on the principle of inhibiting the folding of helix 12 of the nuclear androgen receptor. The prepared anti-androgens exhibited full antagonistic activity toward human prostate tumor LNCaP cells with T877A point-mutated nuclear androgen receptor, as far as examined, towards which other known anti-androgens, including hydroxyflutamide, are inactive or act as androgen agonists. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00575-4

文献信息

• Novel Non-Steroidal/Non-Anilide Type Androgen Antagonists with an Isoxazolone Moiety
  作者：Toshiyasu Ishioka、Asako Kubo、Yukiko Koiso、Kazuo Nagasawa、Akiko Itai、Yuichi Hashimoto

  DOI：10.1016/s0968-0896(01)00421-7

  日期：2002.5

  3-Substitutcd (Z)-4-(4-N,N-dialkylaminophenylmethylene)-5(4H)-isoxazolones and related compounds were designed and prepared as candidates for structurally novel androgen antagonists. Several compounds showed potent anti-androgenic activity as assessed by nuclear androgen receptor binding assay and growth inhibition assay using androgen-dependent Shionogi carcinoma cells SC-3. They were approximately 10-220 times more potent than flutamide in these assay systems, They also showed anti-androgenic activity toward prostate tumor cell line LNCaP, which has an aberrant nuclear androgen receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.