(3α,5α)-3-hydroxy-22-iodo-13,23-cyclo-18,21-dinorchol-20-en-23-one | 1291069-89-0

• 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: (3α,5α)-3-hydroxy-22-iodo-13,23-cyclo-18,21-dinorchol-20-en-23-one
• CAS: 1291069-89-0
• 化学式: C₂₁H₂₉IO₂
• 分子量: 440.365
• InChiKey: QPIMBTXEMPIYCJ-PDFUVAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3α,5α)-3-hydroxy-22-iodo-13,23-cyclo-18,21-dinorchol-20-en-23-one 、 2-丙炔-1-醇 在 copper(l) iodide 、 N,N-二异丙基乙胺 、 三苯基膦钯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到(3α,5α)-3-hydroxy-22-(3-(3-hydroxyprop-1-ynyl))-13,23-cyclo-18,21-dinorchol-20-en-23-one
  参考文献：
  名称：

  Novel and efficient synthesis of 22-alkynyl-13,24(23)-cyclo-18,21-dinorchol-22-en-20(23)-one analogues

  摘要：

  The efficient synthesis of some 22-alkynyl-13,24(23)-cyclo-18,21-dinorchol-22-en-20(23)-ones was investigated. 22-Iodocyclo-18,21-dinorcholenones were prepared from cyclo-18,21-dinorcholenones using I(2)/DMAP/pyridine system firstly. The cross coupling reaction of 22-iodocyclo-18,21-dinorcholenones and 1-alkynes was carried out efficiently catalyzed by tetrakis(triphenylphosphine) palladium/cuprous iodide in the presence of base diisopropylethylamine. This strategy offered a very straightforward and efficient method for access to conjugated alkynyl cyclo-18,21-dinorcholenones from the cyclo-18,21-dinorcholenones and 1-alkynes in excellent overall yields. Evaluation of the synthesized compounds for cytotoxicity against KB, HeLa, MKN-28 and MCF-7 cell lines showed that the 22-alkynylcyclodinorchoenones possessing hydroxylethyl and hyclroxylmethyl mono-substituted side chain at the end of alkynyl group have significantly inhibition activity. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.01.005
• 作为产物：
  描述：

  (3α,5α)-3-hydroxy-13,23-cyclo-18,21-dinorchol-20-en-23-one 在 吡啶 、 4-二甲氨基吡啶 、 碘 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 以98%的产率得到(3α,5α)-3-hydroxy-22-iodo-13,23-cyclo-18,21-dinorchol-20-en-23-one
  参考文献：
  名称：

  Novel and efficient synthesis of 22-alkynyl-13,24(23)-cyclo-18,21-dinorchol-22-en-20(23)-one analogues

  摘要：

  The efficient synthesis of some 22-alkynyl-13,24(23)-cyclo-18,21-dinorchol-22-en-20(23)-ones was investigated. 22-Iodocyclo-18,21-dinorcholenones were prepared from cyclo-18,21-dinorcholenones using I(2)/DMAP/pyridine system firstly. The cross coupling reaction of 22-iodocyclo-18,21-dinorcholenones and 1-alkynes was carried out efficiently catalyzed by tetrakis(triphenylphosphine) palladium/cuprous iodide in the presence of base diisopropylethylamine. This strategy offered a very straightforward and efficient method for access to conjugated alkynyl cyclo-18,21-dinorcholenones from the cyclo-18,21-dinorcholenones and 1-alkynes in excellent overall yields. Evaluation of the synthesized compounds for cytotoxicity against KB, HeLa, MKN-28 and MCF-7 cell lines showed that the 22-alkynylcyclodinorchoenones possessing hydroxylethyl and hyclroxylmethyl mono-substituted side chain at the end of alkynyl group have significantly inhibition activity. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.01.005