1-<17'β-hydroxy-3'-methoxy-1',3',5'(10')-estratrien-16β-yl>-methanol | 64336-09-0

• 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: 1-<17'β-hydroxy-3'-methoxy-1',3',5'(10')-estratrien-16β-yl>-methanol
• 英文别名: 16β-hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol；(8R,9S,13S,14S,16R,17S)-16-(hydroxymethyl)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol
• CAS: 64336-09-0
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: LFRSVHPVBIECFA-FTVOKIHPSA-N

物化性质

• 沸点：
  482.7±45.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

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：

  1-<17'β-hydroxy-3'-methoxy-1',3',5'(10')-estratrien-16β-yl>-methanol 在 potassium acetate 作用下， 以 吡啶 为溶剂， 反应 114.0h， 生成 16-acetoxymethyl-3-methoxyestra-1,3,5(10),16-tetraene
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲氧基雌酮 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 1-<17'β-hydroxy-3'-methoxy-1',3',5'(10')-estratrien-16β-yl>-methanol
  参考文献：
  名称：

  A Convenient Synthetic Method for Alpha-Alkylation of Steroidal 17-Ketone: Preparation of 16β(THPO-Heptyl)-Estradiol

  摘要：

  A sequence of three key-steps (activation of steroidal 17-ketone, alkylation and decarboxyalkoxylation) provided an interesting synthetic device to obtain, after reduction, 16 beta-(THPO-heptyl)-estradiol.

  DOI：

  10.1080/00397919508015454

文献信息

• New steroid-fused P-heterocycles
  作者：Éva Frank、Tamás Körtvélyesi、Mátyás Czugler、Zoltán Mucsi、György Keglevich

  DOI：10.1016/j.steroids.2007.02.002

  日期：2007.5

  in the case of the boat conformation, the anisotropic shielding effect of the phenyl group of cyclic phosphonate 4a generates an upfield shift for 17-H, as compared with the corresponding chemical shift for epimer 4b. A similar boat conformation was substantiated for derivatives 4b, 5a, 5b and 6b on the basis of the J(H, H) and J(H, P) coupling constants and also ab initio calculations, regardless

  将雌酮系列中的D环稠合的二氧杂膦酰二氢萘醌（4-6）合成为差向异构对，并通过NMR和计算方法进行研究，以确定其立体结构和主要构象。进行了研究，以评估刚性甾烷骨架对稠合杂环的几何形状的影响，以及13位角甲基的可能的空间效应。此外，P取代基的空间和电子效应在构象平衡上进行了研究。通过单晶X射线分析确认了二氧杂磷氮雌酮3-甲基醚4a的杂环的扭曲舟构型。这与溶液中的观察结果非常吻合，在船的情况下，与差向异构体4b的相应化学位移相比，环状膦酸酯4a的苯基的各向异性屏蔽作用会产生17-H的高场位移。基于J（H，H）和J（H，P）耦合常数以及从头算，无论P构型如何，都对导数4b，5a，5b和6b证实了类似的船形。同时，由于N-双（2-氯乙基）基团强烈的赤道偏爱，6a的杂环似乎向椅子样构象倾斜。不论P配置如何。同时，由于N-双（2-氯乙基）基团强烈的赤道偏爱，6a的杂环似乎向椅子样构象倾斜。不论P配置如何
• Synthesis of some novel D-ring-fused dioxa- and oxazaphosphorinanes in the estrone series
  作者：Éva Frank、Brigitta Kazi、Krisztina Ludányi、György Keglevich

  DOI：10.1016/j.tetlet.2005.12.038

  日期：2006.2

  New types of P-heterocyclic-fused steroids, such as dioxa- and oxazaphosphorinane derivatives, were synthetized from estrone-1,3-dihydroxy and 1,3-aminoalcohol precursors by cyclization with phenylphosphonic dichloride. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereocontrolled synthesis of the four 16-hydroxymethyl-19-nortestosterone isomers and their antiproliferative activities
  作者：Gyula Schneider、Anita Kiss、Erzsébet Mernyák、Zsanett Benke、János Wölfling、Éva Frank、Noémi Bózsity、András Gyovai、Renáta Minorics、István Zupkó

  DOI：10.1016/j.steroids.2015.12.003

  日期：2016.1

  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.
• 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：——