6-(butyl-methyl-amino)-2-chloro-4-trifluoromethyl-nicotinonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(butyl-methyl-amino)-2-chloro-4-trifluoromethyl-nicotinonitrile
• 英文别名: 6-[Butyl(methyl)amino]-2-chloro-4-(trifluoromethyl)pyridine-3-carbonitrile
• 化学式: C₁₂H₁₃ClF₃N₃
• 分子量: 291.704
• InChiKey: XYXDZNJOXRSCSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(butyl-methyl-amino)-2-chloro-4-trifluoromethyl-nicotinonitrile 在 palladium on activated charcoal TEA 、 氢气 作用下， 生成 6-(butyl-methyl-amino)-4-trifluoromethyl-nicotinonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of amino-pyridines as androgen receptor antagonists for stimulating hair growth and reducing sebum production

  摘要：

  A series of amino-pyridines were synthesized and evaluated for androgen antagonist activities. Among these compounds, (R)-(+)-6-[methyl-(1-phenyl-ethyl)-amino]-4-trifluoromethyl-nicotinonitrile was the most active example of this class. This compound displayed potent androgen receptor antagonist activity as well as favorable pharmacokinetic characteristics for a potential topical agent. It also demonstrated remarkable potency for stimulating hair growth in a male C3H mouse model as well as reducing sebum production in the male Syrian hamster ear model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.059
• 作为产物：
  描述：

  甲基丁胺 、 3-氰基-2,6-二氯-4-(三氟甲基)吡啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-(butyl-methyl-amino)-2-chloro-4-trifluoromethyl-nicotinonitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of amino-pyridines as androgen receptor antagonists for stimulating hair growth and reducing sebum production

  摘要：

  A series of amino-pyridines were synthesized and evaluated for androgen antagonist activities. Among these compounds, (R)-(+)-6-[methyl-(1-phenyl-ethyl)-amino]-4-trifluoromethyl-nicotinonitrile was the most active example of this class. This compound displayed potent androgen receptor antagonist activity as well as favorable pharmacokinetic characteristics for a potential topical agent. It also demonstrated remarkable potency for stimulating hair growth in a male C3H mouse model as well as reducing sebum production in the male Syrian hamster ear model. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.059

文献信息

• [EN] ANDROGEN RECEPTOR MODULATORS<br/>[FR] MODULATEURS DU RECEPTEUR ANDROGENE
  申请人：WARNER LAMBERT CO

  公开号：WO2005049574A1

  公开（公告）日：2005-06-02

  The present invention is directed to a new class of 5-cyano-2-amino pyridines and to their use as androgen receptor modulators. A further aspect of the invention is directed to a new animal model for finding compounds capable of alleviating androgenic alopecia.

  本发明涉及一种新的5-氰基-2-氨基吡啶类化合物及其用作雄激素受体调节剂的用途。该发明的另一个方面涉及一种新的动物模型，用于寻找能够缓解雄激素性脱发的化合物。
• ANDROGEN RECEPTOR MODULATORS
  申请人：Warner-Lambert Company LLC

  公开号：EP1687274A1

  公开（公告）日：2006-08-09
• Androgen receptor modulators
  申请人：Hu Lain-Yen

  公开号：US20070129409A1

  公开（公告）日：2007-06-07

  The present invention is directed to a new class of 5-cyano-2-amino pyridines and to their use as androgen receptor modulators. A further aspect of the invention is directed to a new animal model for finding compounds capable of alleviating androgenic alopecia.