17α-acetoxy-16α-acetoxymethyl-3-methoxyestra-1,3,5(10)-triene | 53973-44-7

• 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: 17α-acetoxy-16α-acetoxymethyl-3-methoxyestra-1,3,5(10)-triene
• 英文别名: 16α-acetoxymethyl-3-methoxyestra-1,3,5(10)-triene-17α-acetate；[(8R,9S,13S,14S,16S,17R)-17-acetyloxy-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]methyl acetate
• CAS: 53973-44-7
• 化学式: C₂₄H₃₂O₅
• 分子量: 400.515
• InChiKey: UTXJMSGCLVYGFL-UQDMXIALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  17α-acetoxy-16α-acetoxymethyl-3-methoxyestra-1,3,5(10)-triene 在 氨 、 sodium 、 叔丁醇 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 1.5h， 以86%的产率得到16α-hydroxymethyl-17α-hydroxyestra-4-en-3-one
  参考文献：
  名称：

  Stereocontrolled synthesis of the four 16-hydroxymethyl-19-nortestosterone isomers and their antiproliferative activities

  摘要：

  Novel 16-hydroxymethyl-19-nortestosterone diastereomers were prepared by Birch reduction from the corresponding 3-methoxy-16-hydroxymethylestra-1,3,5(10)-trien-17-ol isomers with known configurations. The synthesized compounds are 16 alpha- and 16 beta-hydroxymethyl-substituted 19-nortestosterone and their 17 alpha-epimers. To prepare 17 alpha-19-nortestosterone, the Mitsunobu inversion reaction of 19-nortestosterone with different alkyl and aryl carboxylic acids was chosen. Deacylation of the new compounds by the Zemplen method yielded the required 17 alpha-19-nortestosterone.The antiproliferative activities of the structurally related compounds were determined in vitro through microculture tetrazolium assays on a panel of human adherent cervical (HeLa, SiHa and C33A), breast (MCF-7, MDA-MB-231, MDA-MB-361 and T47D) and ovarian (A2780) cell lines. The 17 alpha epimer of 19-nortestosterone demonstrated considerable activity, selectively for HeLa cells, with a calculated IC50 of 0.65 mu M. The reference compound, cisplatin, displayed an order of magnitude higher IC50 (12.4 mu M). The cancer selectivity of 17 alpha-19-nortestosterone was tested by MTT assay performed with noncancerous human fibroblast cell line MRC-5. The results indicated that 17 alpha-19-nortestosterone selectively disturbs the viability of HeLa cells without greatly affecting other cancer cell types and intact fibroblasts. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.12.003
• 作为产物：
  描述：

  17β-acetoxy-16α-acetoxymethyl-3-methoxyestra-1,3,5(10)-triene 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 151.0h， 生成 17α-acetoxy-16α-acetoxymethyl-3-methoxyestra-1,3,5(10)-triene
  参考文献：
  名称：

  Schneider, Gyula; Hackler, Laszlo; Sohar, Pal, Liebigs Annalen der Chemie, 1988, p. 679 - 684

  摘要：

  DOI：

文献信息

• SCHNEIDER, GYULA;HACKLER, LASZLO;SOHAR, PAL, LIEBIGS ANN. CHEM.,(1988) N 7, 679-683
  作者：SCHNEIDER, GYULA、HACKLER, LASZLO、SOHAR, PAL

  DOI：——

  日期：——
• SCHNEIDER, GYULA;VASS, ANDRAS;VINCZE, IREN;SOHAR, PAL, LIEBIGS ANN. CHEM.,(1988) N 3, 267-273
  作者：SCHNEIDER, GYULA、VASS, ANDRAS、VINCZE, IREN、SOHAR, PAL

  DOI：——

  日期：——