(25R)-1α,3β,26-triacetoxyfurosta-5,7,20(22)-triene | 861675-01-6

• 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: (25R)-1α,3β,26-triacetoxyfurosta-5,7,20(22)-triene
• 英文别名: [(2R)-4-[(2R,4S,8S,9S,12S,13R,14S,16R)-14,16-diacetyloxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-1(20),6,18-trien-6-yl]-2-methylbutyl] acetate
• CAS: 861675-01-6
• 化学式: C₃₃H₄₆O₇
• 分子量: 554.724
• InChiKey: XSGYAKAWCWJNOM-UNYHWMDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (25R)-1α,3β,26-triacetoxyfurosta-5,7,20(22)-triene 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以213 mg的产率得到(2R,4S,8S,9S,12S,13R,14S,16R)-6-[(3R)-4-hydroxy-3-methylbutyl]-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-1(20),6,18-triene-14,16-diol
  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：

  (20S,22R,25R)-1α,3β-diacetoxyspirost-5-ene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 正己烷 为溶剂， 反应 12.0h， 生成 (25R)-1α,3β,26-triacetoxyfurosta-5,7,20(22)-triene
  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