(5S,6S,8R,9R,10R,11S,12R,14S,17R,20S,26S,27S,30S,31R,32S,33R,35S,38R,41S)-12,33-bis[(3S)-4-hydroxy-3-methylbutyl]-5,9,11,26,30,32-hexamethyl-29-methylidene-13,34-dioxa-2,23-diazaundecacyclo[22.18.0.03,22.05,20.06,17.09,16.010,14.026,41.027,38.030,37.031,35]dotetraconta-1,3(22),15,23,36-pentaen-8-ol | 552844-02-7

• 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: (5S,6S,8R,9R,10R,11S,12R,14S,17R,20S,26S,27S,30S,31R,32S,33R,35S,38R,41S)-12,33-bis[(3S)-4-hydroxy-3-methylbutyl]-5,9,11,26,30,32-hexamethyl-29-methylidene-13,34-dioxa-2,23-diazaundecacyclo[22.18.0.03,22.05,20.06,17.09,16.010,14.026,41.027,38.030,37.031,35]dotetraconta-1,3(22),15,23,36-pentaen-8-ol
• CAS: 552844-02-7
• 化学式: C₅₅H₈₀N₂O₅
• 分子量: 849.251
• InChiKey: JBDOFAXUKMUPSG-LBDGOGIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  62
• 可旋转键数：
  8
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5S,6S,8R,9R,10R,11S,12R,14S,17R,20S,26S,27S,30S,31R,32S,33R,35S,38R,41S)-12,33-bis[(3S)-4-hydroxy-3-methylbutyl]-5,9,11,26,30,32-hexamethyl-29-methylidene-13,34-dioxa-2,23-diazaundecacyclo[22.18.0.03,22.05,20.06,17.09,16.010,14.026,41.027,38.030,37.031,35]dotetraconta-1,3(22),15,23,36-pentaen-8-ol 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以81%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：

  在 borane-(N-tosyl)-D-valine complex 作用下， 以 四氢呋喃 为溶剂， 反应 168.0h， 以52%的产率得到(5S,6S,8R,9R,10R,11S,12R,14S,17R,20S,26S,27S,30S,31R,32S,33R,35S,38R,41S)-12,33-bis[(3S)-4-hydroxy-3-methylbutyl]-5,9,11,26,30,32-hexamethyl-29-methylidene-13,34-dioxa-2,23-diazaundecacyclo[22.18.0.03,22.05,20.06,17.09,16.010,14.026,41.027,38.030,37.031,35]dotetraconta-1,3(22),15,23,36-pentaen-8-ol
  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