(2R,4S,8S,9S,12S,13R,14S,16R)-6-[(3R)-4-iodo-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 | 861675-04-9

• 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: (2R,4S,8S,9S,12S,13R,14S,16R)-6-[(3R)-4-iodo-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
• CAS: 861675-04-9
• 化学式: C₂₇H₃₉IO₃
• 分子量: 538.509
• InChiKey: QFOZUZWDCQTHGP-FHMZKFIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,4S,8S,9S,12S,13R,14S,16R)-6-[(3R)-4-iodo-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 、 potassium thioacyanate 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以135 mg的产率得到(25R)-1α,3β-dihydroxy-26-thiocyanatofurosta-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
• 作为产物：
  描述：

  (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene 在 吡啶 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 三甲胺盐酸盐 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 20.17h， 生成 (2R,4S,8S,9S,12S,13R,14S,16R)-6-[(3R)-4-iodo-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