4-(6-amino-3aR-methyl-2-trifluoromethyl-3,3a-dihydro-imidazo[1,5-b]pyrazol-4-ylideneamino)-2-trifluoromethyl-benzonitrile | 949572-87-6

• 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-(6-amino-3aR-methyl-2-trifluoromethyl-3,3a-dihydro-imidazo[1,5-b]pyrazol-4-ylideneamino)-2-trifluoromethyl-benzonitrile
• 英文别名: 2-(Trifluoromethyl)-4-[[2-(trifluoromethyl)3abeta-methyl-6-amino-3H-1,5,6a-triazapentalene-4(3aH)-ylidene]amino]benzonitrile；4-[[(3aR)-6-amino-3a-methyl-2-(trifluoromethyl)-3H-imidazo[1,5-b]pyrazol-4-ylidene]amino]-2-(trifluoromethyl)benzonitrile
• CAS: 949572-87-6
• 化学式: C₁₅H₁₀F₆N₆
• 分子量: 388.275
• InChiKey: GGBBMNCXWGYSRP-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(6-amino-3aR-methyl-2-trifluoromethyl-3,3a-dihydro-imidazo[1,5-b]pyrazol-4-ylideneamino)-2-trifluoromethyl-benzonitrile 、 4-碘苯异氰酸酯 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以54%的产率得到1-[4-(4-cyano-3-trifluoromethyl-phenylimino)-3aR-methyl-2-trifluoromethyl-3a,4-dihydro-3H-imidazo[1,5-b]pyrazol-6-yl]-3-(4-iodo-phenyl)-urea
  参考文献：
  名称：

  NOVEL IMIDAZOLOPYRAZOLE DERIVATIVES USEFUL AS SELECTIVE ANDROGEN RECEPTOR MODULATORS

  摘要：

  本发明涉及新型咪唑吡唑酮衍生物，含有它们的药物组合物以及它们在治疗受雄激素受体调节的疾病和症状中的用途。

  公开号：

  US20070197616A1
• 作为产物：
  描述：

  N-(4-氰基-3-三氟甲基苯基)甲基丙烯酰胺 在 劳森试剂 、 sodium hydride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 、 甲苯 为溶剂， 反应 6.5h， 生成 4-(6-amino-3aR-methyl-2-trifluoromethyl-3,3a-dihydro-imidazo[1,5-b]pyrazol-4-ylideneamino)-2-trifluoromethyl-benzonitrile
  参考文献：
  名称：

  Serendipitous discovery of novel imidazolopyrazole scaffold as selective androgen receptor modulators

  摘要：

  A novel imidazolopyrazole derivative has been fortuitously discovered as potent selective androgen receptor modulator with in vivo efficacy. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.035

文献信息

• NOVEL IMIDAZOLOPYRAZOLE DERIVATIVES USEFUL AS SELECTIVE ANDROGEN RECEPTOR MODULATORS
  申请人：Zhang Xuqing

  公开号：US20070197616A1

  公开（公告）日：2007-08-23

  The present invention is directed to novel imidazolopyrazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.

  本发明涉及新型咪唑吡唑酮衍生物，含有它们的药物组合物以及它们在治疗受雄激素受体调节的疾病和症状中的用途。
• US7655683B2
  申请人：——

  公开号：US7655683B2

  公开（公告）日：2010-02-02
• [EN] NOVEL IMIDAZOLOPYRAZOLE DERIVATIVES USEFUL AS SELECTIVE ANDROGEN RECEPTOR MODULATORS<br/>[FR] NOUVEAUX DÉRIVÉS D'IMIDAZOLOPYRAZOLE UTILES COMME MODULATEURS SÉLECTIFS DU RÉCEPTEUR DE L'ANDROGÈNE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2007092727A1

  公开（公告）日：2007-08-16

  [EN] The present invention is directed to iraidazolopyrazole derivatives of formula (I), pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by the androgen receptor.
  [FR] La présente invention concerne des dérivés d'imidazolopyrazole de formule (I), des compositions pharmaceutiques les contenant, ainsi que leur utilisation dans le traitement de troubles et de conditions modulées par le récepteur de l'androgène.
• Design, Synthesis, and in Vivo SAR of a Novel Series of Pyrazolines as Potent Selective Androgen Receptor Modulators
  作者：Xuqing Zhang、Xiaojie Li、George F. Allan、Tifanie Sbriscia、Olivia Linton、Scott G. Lundeen、Zhihua Sui

  DOI：10.1021/jm0613976

  日期：2007.8.1

  A novel series of pyrazolines 2 have been designed, synthesized, and evaluated by in vivo screening as tissue-selective androgen receptor modulators (SARMs). Structure- activity relationships (SAR) were investigated at the R-1 to R-6 positions as well as the core pyrazoline ring and the anilide linker. Overall, strong electron-withdrawing groups at the RI and 2 positions and a small group at the R1 and RI position are optimal for AR agonist activity. The (S)-isomer of 7c exhibits more potent AR agonist activity than the corresponding (R)-isomer. (S)-7c exhibited an overall partial androgenic effect but full anabolic effect via oral administration in castrated rats. It demonstrated a noticeable antiandrogenic effect on prostate in intact rats with endogenous testosterone. Thus, (S)-7c is a tissue-selective nonsteroidal androgen receptor modulator with agonist activity on muscle and mixed agonist and antagonist activity on prostate.
• Serendipitous discovery of novel imidazolopyrazole scaffold as selective androgen receptor modulators
  作者：Xuqing Zhang、Xiaojie Li、George F. Allan、Tifanie Sbriscia、Olivia Linton、Scott G. Lundeen、Zhihua Sui

  DOI：10.1016/j.bmcl.2006.10.035

  日期：2007.1

  A novel imidazolopyrazole derivative has been fortuitously discovered as potent selective androgen receptor modulator with in vivo efficacy. (c) 2006 Elsevier Ltd. All rights reserved.