3-(ω-bromoheptoxy)estra-1,3,5(10)-trien-17-one | 936325-86-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-(ω-bromoheptoxy)estra-1,3,5(10)-trien-17-one
• 英文别名: (8R,9S,13S,14S)-3-(7-bromoheptoxy)-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS: 936325-86-9
• 化学式: C₂₅H₃₅BrO₂
• 分子量: 447.456
• InChiKey: ZKJKXQOXVCTXMY-AHCIIZGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(ω-bromoheptoxy)estra-1,3,5(10)-trien-17-one 、 1-对甲苯基-1H-四唑-5-硫醇 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以95%的产率得到3-(7-[1-(4-methylphenyl)-5-tetrazolylthio]heptyloxy)estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Hybrid molecules of estrone: New compounds with potential antibacterial, antifungal, and antiproliferative activities

  摘要：

  New hybrid molecules of estrone were synthesized as compounds indicating promising biological activity (antibacterial, antimycobacterial, antifungal, and antiproliferative). The prepared molecules contained various heterocyclic units (pyridine, benzylsulfanyl derivatives of pyridine or derivatives of tetrazole) linked to estrone by n-heptyl bridges. The compounds with charge on molecule (the hybrid pyridinium or benzylsulfanylpyridinium salts) exhibited significant biological activity (antibacterial, antimycobacterial, antifungal, and antiproliferative). On the other hand, the compounds not in the form of salts (omega-(1-phenyl-5-tetrazolylthio)heptylethers of estrone) were inactive. The antimycobacterial activities of three different series of tetrazole derivatives (i.e., the hybrid molecules with estrone, tetrazole-5-thiols, and 5-benzylsulfanyl-1-phenyltetrazoles) with the same substituents on phenyl ring were compared. Amongst them, the 5-benzylsulfanyl-1-phenyltetrazoles were the most potent. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.021
• 作为产物：
  描述：

  1,7-二溴庚烷 、 雌酚酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 17.0h， 以75%的产率得到3-(ω-bromoheptoxy)estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Hybrid molecules of estrone: New compounds with potential antibacterial, antifungal, and antiproliferative activities

  摘要：

  New hybrid molecules of estrone were synthesized as compounds indicating promising biological activity (antibacterial, antimycobacterial, antifungal, and antiproliferative). The prepared molecules contained various heterocyclic units (pyridine, benzylsulfanyl derivatives of pyridine or derivatives of tetrazole) linked to estrone by n-heptyl bridges. The compounds with charge on molecule (the hybrid pyridinium or benzylsulfanylpyridinium salts) exhibited significant biological activity (antibacterial, antimycobacterial, antifungal, and antiproliferative). On the other hand, the compounds not in the form of salts (omega-(1-phenyl-5-tetrazolylthio)heptylethers of estrone) were inactive. The antimycobacterial activities of three different series of tetrazole derivatives (i.e., the hybrid molecules with estrone, tetrazole-5-thiols, and 5-benzylsulfanyl-1-phenyltetrazoles) with the same substituents on phenyl ring were compared. Amongst them, the 5-benzylsulfanyl-1-phenyltetrazoles were the most potent. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.021