2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-1-ethylsulfanyl-propan-2-ol | 882977-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-1-ethylsulfanyl-propan-2-ol
• 英文别名: 2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-1-ethylsulfanylpropan-2-ol；2-(5,6-dichloro-1-methylbenzimidazol-2-yl)-1-ethylsulfanylpropan-2-ol
• CAS: 882977-77-7
• 化学式: C₁₃H₁₆Cl₂N₂OS
• 分子量: 319.255
• InChiKey: IOLJDXIXPZOELY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-1-ethylsulfanyl-propan-2-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到2-(5,6-Dichloro-1-methylbenzimidazol-2-yl)-1-ethylsulfonylpropan-2-ol
  参考文献：
  名称：

  Synthesis and SAR of potent and selective androgen receptor antagonists: 5,6-Dichloro-benzimidazole derivatives

  摘要：

  The synthesis and in vivo SAR of 5,6-dichloro-benzimidazole derivatives as novel selective androgen receptor antagonists are described. During screening of 2-alkyl benzimidazoles, it was found that a trifluoromethyl group greatly enhances antagonist activity in the prostate. Benzimidazole I is a potent AR antagonist in the rat prostate (ID50 = 0.15 mg/day). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.071
• 作为产物：
  描述：

  2-(5,6-dichloro-1H-benzimidazol-2-yl)propan-2-ol 在 sodium hydroxide 、 三氯异氰尿酸 、 苄基三乙基氯化铵 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 乙腈 为溶剂， 生成 2-(5,6-dichloro-1-methyl-1H-benzoimidazol-2-yl)-1-ethylsulfanyl-propan-2-ol
  参考文献：
  名称：

  Synthesis and SAR of potent and selective androgen receptor antagonists: 5,6-Dichloro-benzimidazole derivatives

  摘要：

  The synthesis and in vivo SAR of 5,6-dichloro-benzimidazole derivatives as novel selective androgen receptor antagonists are described. During screening of 2-alkyl benzimidazoles, it was found that a trifluoromethyl group greatly enhances antagonist activity in the prostate. Benzimidazole I is a potent AR antagonist in the rat prostate (ID50 = 0.15 mg/day). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.071

文献信息

• [EN] NOVEL BENZIMIDAZOLE DERIVATIVES USEFUL AS SELECTIVE ANDROGEN RECEPTOR MODULATORS (SARMS)<br/>[FR] MODULATEURS SELECTIFS DU RECEPTEUR D'ANDROGENE A BASE DE DERIVES BENZIMIDAZOLIQUES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006039243A1

  公开（公告）日：2006-04-13

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

  本发明涉及新型苯并咪唑衍生物，含有它们的药物组合物以及它们在治疗由雄激素受体调节的疾病和症状中的应用。
• Novel benzimidazole derivatives useful as selective androgen receptor modulators (SARMS)
  申请人：Ng Raymond

  公开号：US20060111402A1

  公开（公告）日：2006-05-25

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

  本发明涉及新型苯并咪唑衍生物、包含它们的药物组合物及其在调节雄激素受体所致的疾病和症状中的应用。
• Novel benzimidazole derivatives useful as selective androgen receptor modulators (sarms)
  申请人：Ng Raymond

  公开号：US20060116412A1

  公开（公告）日：2006-06-01

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

  本发明涉及新的苯并咪唑衍生物、包含它们的药物组合物及其在治疗由雄激素受体调节的疾病和症状中的应用。
• Novel Benzimidazole Derivatives Useful as Selective Androgen Receptor Modulators (SARMS)
  申请人：Ng Raymond

  公开号：US20090258909A1

  公开（公告）日：2009-10-15

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

  本发明涉及新型苯并咪唑衍生物，包含它们的制药组合物以及它们在治疗由雄激素受体调节的疾病和症状中的应用。
• NOVEL BENZIMIDAZOLE DERIVATIVES USEFUL AS SELECTIVE ANDROGEN RECEPTOR MODULATORS (SARMS)
  申请人：Ng Raymond

  公开号：US20080119522A1

  公开（公告）日：2008-05-22

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

  本发明涉及新型苯并咪唑衍生物、包含它们的药物组合物以及它们在治疗通过雄激素受体调节的疾病和症状中的应用。