3-(((((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)carbonyl)amino)propanoic acid | 151869-51-1

• 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-(((((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)carbonyl)amino)propanoic acid
• CAS: 151869-51-1
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: ROAYBCCZJWTCPO-QLDGJZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  92.7
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(((((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)carbonyl)amino)propanoic acid 、 (氨基亚甲基)双磷酸四乙酯 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以100%的产率得到(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl (3-((bis(diethoxyphosphoryl)methyl)amino)-3-oxopropyl)carbamate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel estradiol–bisphosphonate conjugates as bone-specific estrogens

  摘要：

  Bone deficiency causes osteoporosis and often decreases quality of life in patients with rheumatoid arthritis. Estrogens are known to protect elderly women from bone loss. Synthesis of new estradiol-bisphosphonate conjugates (E-2-BPs) was accomplished and their in vivo activity as bone-specific estrogens were examined. Among them, MCC-565 showed selective estrogenic activity in bones; but it showed little estrogenic activity in the uterus. We also found that the linker moiety in E2-BPs was essential for the absorption and specificity of the conjugates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.041
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.0h， 以83%的产率得到3-(((((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)carbonyl)amino)propanoic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel estradiol–bisphosphonate conjugates as bone-specific estrogens

  摘要：

  Bone deficiency causes osteoporosis and often decreases quality of life in patients with rheumatoid arthritis. Estrogens are known to protect elderly women from bone loss. Synthesis of new estradiol-bisphosphonate conjugates (E-2-BPs) was accomplished and their in vivo activity as bone-specific estrogens were examined. Among them, MCC-565 showed selective estrogenic activity in bones; but it showed little estrogenic activity in the uterus. We also found that the linker moiety in E2-BPs was essential for the absorption and specificity of the conjugates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.041