16α-hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol | 64336-08-9

• 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: 16α-hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol
• 英文别名: (8R,9S,13S,14S,16S,17S)-16-(hydroxymethyl)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol
• CAS: 64336-08-9
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: LFRSVHPVBIECFA-PJKJDQBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  16α-hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol 在 吡啶 、 氨 、 sodium 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 16α-hydroxymethyl-17β-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：

  16-hydroxymethylene-3-methoxyestra-1,3,5(10)-trien-17-one 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 52.0h， 生成 16α-hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol
  参考文献：
  名称：

  Schneider, Gyula; Vass, Andras; Vincze, Iren, Liebigs Annalen der Chemie, 1988, p. 267 - 274

  摘要：

  DOI：

文献信息

• New synthesis of steroidal tetrahydrooxazin-2-ones
  作者：Gyula Schneider、László Hackler、Pál Sohár

  DOI：10.1016/s0040-4020(01)81681-1

  日期：1987.1

  In the DMSO/NaHCO3 system, 16α-aminomethyl-, 16α-benzylaminomethyl- and substituted benzylaminomethyl-3-methoxy-17β-tosyloxyestra-1,3, 5(10)-triene (3, 5a-k) do not undergo oxidation, but form a tetrahydrooxa-zin-2-one ring (7, 8a-k) via neighboring group participation. Under similar conditions, 16β-aminomethyl-3-methoxy-17β-tosylestra-1,3,5(10)-triene (4) decomposes into 16-methylene-3-methoxyestra-l

  在DMSO / NaHCO 3系统中，16α-氨基甲基-，16α-苄基氨基甲基-和取代的苄基氨基-3-甲氧基-17β-甲苯磺酰氧基-1,3，5（10）-三烯（3，5a-k）不会发生氧化，但通过相邻基团的参与形成四氢氧杂嗪2酮环（7，8a-k）。在类似条件下，16β-氨基甲基-3-甲氧基-17β-甲苯磺酰基-1,3,5（10）-三烯（4）分解成16-亚甲基-3-甲氧基乙-1,3,5（10）-trien- 17一（12）。
• Schneider, Gyula; Hackler, Laszlo; Sohar, Pal, Liebigs Annalen der Chemie, 1988, p. 679 - 684
  作者：Schneider, Gyula、Hackler, Laszlo、Sohar, Pal

  DOI：——

  日期：——
• Stereocontrolled synthesis of the four possible 3-methoxy and 3-benzyloxy-16-triazolyl-methyl-estra-17-ol hybrids and their antiproliferative activities
  作者：Anita Kiss、János Wölfling、Erzsébet Mernyák、Éva Frank、Zsanett Benke、Seyyed Ashkan Senobar Tahaei、István Zupkó、Sándor Mahó、Gyula Schneider

  DOI：10.1016/j.steroids.2019.108500

  日期：2019.12

  The four possible isomers of each of 3-methoxy- and 3-benzyloxyestra-1,3,5(10)-trien-17-ols (5-8 and 9-12) were converted through 16-p-tosylorcymethyl- or 16-bromomethyl derivatives into their 3-methoxy- and 3-benzyloxy-16-azidomethylestra(1,3,5(10)-triene derivatives (13-16 and 17-20). The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of these compounds with different terminal alkynes afforded novel 1,4-disubstituted diastereomers (21a-f, 22a-f, 23a-f, 24a-f and 25a-f, 26a-f, 27a-f, 28a-f). The antiproliferative activities of the structurally related triazoles were determined in vitro with the microculture tetrazolium assay on four malignant human cell lines of gynecological origin (Hela, SiHa, MCF-7 and MDA-MB-231).
• MESKO, ESZTER;SCHNEIDER, GYULA;DOMBI, GYORGY;ZEIGAN, DIETER, LIEBIGS ANN. CHEM.,(1990) N, C. 419-422
  作者：MESKO, ESZTER、SCHNEIDER, GYULA、DOMBI, GYORGY、ZEIGAN, DIETER

  DOI：——

  日期：——
• 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：——