(20S,22R,25R)-1α,3α-dihydroxyspirost-5-ene | 861849-15-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (20S,22R,25R)-1α,3α-dihydroxyspirost-5-ene
• 英文别名: (1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14S,16S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14,16-diol
• CAS: 861849-15-2
• 化学式: C₂₇H₄₂O₄
• 分子量: 430.628
• InChiKey: QMQIQBOGXYYATH-RGWRIEHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (20S,22R,25R)-1α,3α-dihydroxyspirost-5-ene 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 正己烷 为溶剂， 反应 4.0h， 生成 (20S,22R,25R)-1α,3α-diacetoxyspirosta-5,7-diene
  参考文献：
  名称：

  Preparations of vitamin D analogs, spirostanols and furostanols from diosgenin and their cytotoxic activities

  摘要：

  Vitamin D analogs 12 and 13 having a spiro ring in the side chain, various spirostanols 18-21, 26, 27, 29 and 37, and furostanols 34-36 having SCN and SeCN groups at the 26 position were prepared from diosgenin 1 via (20S,22R,25R)-spirost-1 alpha,2 alpha-epoxy-4,6-dien-3-one 19 as a key intermediate. The cytotoxic activities of these derivatives as well as 1 on scarcely P-gp-expressed HCT 116 cells and P-gp-overexpressed Hep G2 cells were examined by MTT assay. Furostanols 34 (IC50 value: 4.9 +/- 0.3 mu M) and 36 (IC50 value: 1.3 +/- 0.2 mu M) exhibited marked cytotoxic effects on HCT 116 cells, and spirostanol 29 (IC50 value: 2.4 0.8 mu M) and furostanol 36 (IC50 value: 2.8 +/- 0.4 mu M) on Hep G2 cells. Furthermore, the effects of vitamin D analog 12, spirostanol 26 and furostanol 36 on apoptosis-signaling pathways were investigated. Compounds 12 and 26 overexpressed p53 and Bax mRNAs, while compound 36 overexpressed only Bax mRNA. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.02.003
• 作为产物：
  描述：

  1α,2α-epoxy-(25R)-spirostan-4,6-dien-3-one 在 氨 、 sodium 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以44.1%的产率得到(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene
  参考文献：
  名称：

  Preparations of vitamin D analogs, spirostanols and furostanols from diosgenin and their cytotoxic activities

  摘要：

  Vitamin D analogs 12 and 13 having a spiro ring in the side chain, various spirostanols 18-21, 26, 27, 29 and 37, and furostanols 34-36 having SCN and SeCN groups at the 26 position were prepared from diosgenin 1 via (20S,22R,25R)-spirost-1 alpha,2 alpha-epoxy-4,6-dien-3-one 19 as a key intermediate. The cytotoxic activities of these derivatives as well as 1 on scarcely P-gp-expressed HCT 116 cells and P-gp-overexpressed Hep G2 cells were examined by MTT assay. Furostanols 34 (IC50 value: 4.9 +/- 0.3 mu M) and 36 (IC50 value: 1.3 +/- 0.2 mu M) exhibited marked cytotoxic effects on HCT 116 cells, and spirostanol 29 (IC50 value: 2.4 0.8 mu M) and furostanol 36 (IC50 value: 2.8 +/- 0.4 mu M) on Hep G2 cells. Furthermore, the effects of vitamin D analog 12, spirostanol 26 and furostanol 36 on apoptosis-signaling pathways were investigated. Compounds 12 and 26 overexpressed p53 and Bax mRNAs, while compound 36 overexpressed only Bax mRNA. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.02.003

文献信息

• Preparations of vitamin D analogs, spirostanols and furostanols from diosgenin and their cytotoxic activities
  作者：Hong-Ji Quan、Jyunichi Koyanagi、Fusao Komada、Setsuo Saito

  DOI：10.1016/j.ejmech.2005.02.003

  日期：2005.7

  Vitamin D analogs 12 and 13 having a spiro ring in the side chain, various spirostanols 18-21, 26, 27, 29 and 37, and furostanols 34-36 having SCN and SeCN groups at the 26 position were prepared from diosgenin 1 via (20S,22R,25R)-spirost-1 alpha,2 alpha-epoxy-4,6-dien-3-one 19 as a key intermediate. The cytotoxic activities of these derivatives as well as 1 on scarcely P-gp-expressed HCT 116 cells and P-gp-overexpressed Hep G2 cells were examined by MTT assay. Furostanols 34 (IC50 value: 4.9 +/- 0.3 mu M) and 36 (IC50 value: 1.3 +/- 0.2 mu M) exhibited marked cytotoxic effects on HCT 116 cells, and spirostanol 29 (IC50 value: 2.4 0.8 mu M) and furostanol 36 (IC50 value: 2.8 +/- 0.4 mu M) on Hep G2 cells. Furthermore, the effects of vitamin D analog 12, spirostanol 26 and furostanol 36 on apoptosis-signaling pathways were investigated. Compounds 12 and 26 overexpressed p53 and Bax mRNAs, while compound 36 overexpressed only Bax mRNA. (c) 2005 Elsevier SAS. All rights reserved.