12β-hydroxypyrazino<2,3-b;5,6-b'>bis<(25R)-5α-spirost-14-en-12'-one> | 153711-21-8

• 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: 12β-hydroxypyrazino<2,3-b;5,6-b'>bis<(25R)-5α-spirost-14-en-12'-one>
• CAS: 153711-21-8
• 化学式: C₅₄H₇₄N₂O₆
• 分子量: 847.191
• InChiKey: DKNNIUHEFLTCSZ-YVSPKZTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  62
• 可旋转键数：
  0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙二醇 、 12β-hydroxypyrazino<2,3-b;5,6-b'>bis<(25R)-5α-spirost-14-en-12'-one> 在 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以41%的产率得到
  参考文献：
  名称：

  Chemo-, regio-, and stereoselectivity of F-ring opening reactions in the cephalostatin series

  摘要：

  In an effort to prepare unsymmetrical cephalostatin analogues with multi-functionality, we tried the route of selective opening of the spiroketal joining rings E and F. In this study, we have tested several borane complexes (like borane-9-BBN, borane-(N-tosyl)-D-valine, and borane-catechol) with some bis-steroidal pyrazine derivatives like 3, 4, and 16 aiming at opening ring-F at only one spiro-system of the dimer. Upon testing these borane reagents, satisfying results were obtained in the case of the ketomethylene 4 using the catechol-borane complex. The structures of the resulting mono-opened and also some double-opened spiro dimers have been completely confirmed. Some of the prepared compounds were tested against three cancer cell lines: HM02 (stomach cancer), HEP G2 (hepatocellular cancer), and MCF 7 (breast cancer). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.043
• 作为产物：
  描述：

  pyrazino<2,3-b;5,6-b'>bis<(25R)-5α-spirost-14-ene>-12,12'-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以47%的产率得到12β-hydroxypyrazino<2,3-b;5,6-b'>bis<(25R)-5α-spirost-14-en-12'-one>
  参考文献：
  名称：

  Droegemueller, Michael; Jautelat, Rolf; Winterfeldt, Ekkerhard, Angewandte Chemie, 1996, vol. 108, # 13/14, p. 1669 - 1671

  摘要：

  DOI：

文献信息

• Kramer, Andreas; Ullmann, Ulrike; Winterfeldt, Ekkehard, Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 2865 - 2868
  作者：Kramer, Andreas、Ullmann, Ulrike、Winterfeldt, Ekkehard

  DOI：——

  日期：——
• Chemo-, regio-, and stereoselectivity of F-ring opening reactions in the cephalostatin series
  作者：M. Nawasreh

  DOI：10.1016/j.bmc.2007.09.043

  日期：2008.1

  In an effort to prepare unsymmetrical cephalostatin analogues with multi-functionality, we tried the route of selective opening of the spiroketal joining rings E and F. In this study, we have tested several borane complexes (like borane-9-BBN, borane-(N-tosyl)-D-valine, and borane-catechol) with some bis-steroidal pyrazine derivatives like 3, 4, and 16 aiming at opening ring-F at only one spiro-system of the dimer. Upon testing these borane reagents, satisfying results were obtained in the case of the ketomethylene 4 using the catechol-borane complex. The structures of the resulting mono-opened and also some double-opened spiro dimers have been completely confirmed. Some of the prepared compounds were tested against three cancer cell lines: HM02 (stomach cancer), HEP G2 (hepatocellular cancer), and MCF 7 (breast cancer). (c) 2007 Elsevier Ltd. All rights reserved.
• Droegemueller, Michael; Jautelat, Rolf; Winterfeldt, Ekkerhard, Angewandte Chemie, 1996, vol. 108, # 13/14, p. 1669 - 1671
  作者：Droegemueller, Michael、Jautelat, Rolf、Winterfeldt, Ekkerhard

  DOI：——

  日期：——