3-benzyloxy-13β-D-homoestra-1,3,5(10),16-tetraen-17a-one | 439267-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-benzyloxy-13β-D-homoestra-1,3,5(10),16-tetraen-17a-one
• 英文别名: (4aS,4bR,10bS,12aS)-12a-methyl-8-phenylmethoxy-4,4a,4b,5,6,10b,11,12-octahydrochrysen-1-one
• CAS: 439267-00-2
• 化学式: C₂₆H₂₈O₂
• 分子量: 372.507
• InChiKey: UZMQRGFUZZJVMO-BIATYSSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-13β-D-homoestra-1,3,5(10),16-tetraen-17a-one 在 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 生成 3-hydroxy-13β-D-homoestra-1,3,5(10)-trien-17a-one
  参考文献：
  名称：

  Syntheses and antiproliferative effects of d-homo- and d-secoestrones

  摘要：

  Substituted and/or heterocyclic d-homoestrone derivatives were synthetized via the intramolecular cyclization of a δ-alkenyl-d-secoaldehyde, -d-secoalcohol or -d-secocarboxylic acid of estrone 3-benzyl ether. The d-secoalcohol was modified at three sites in the molecule. The in vitro antiproliferative activities of the new d-homo- and d-secoestrone derivatives were determined on HeLa, MCF-7, A431 and A2780 cells through use of MTT assay. d-Homoalcohols 3 and 5 displayed cell line-selective cytostatic effects against ovarian and cervical cell lines, respectively. Two d-secoestrones (6 and 12c) proved to be effective, with IC50 values comparable with those of the reference agent cisplatin. A selected compound (6) was tested by tubulin polymerization assay and its cancer specificity was additionally determined by using noncancerous human fibroblast cells.

  DOI：

  10.1016/j.steroids.2014.05.015
• 作为产物：
  描述：

  16,17-seco-3-benzyloxy-13β-estra-1,3,5(10),16-tetraen-1-al 在 对甲苯磺酸 、 Jones reagent 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 25.0h， 生成 3-benzyloxy-13β-D-homoestra-1,3,5(10),16-tetraen-17a-one
  参考文献：
  名称：

  Syntheses and antiproliferative effects of d-homo- and d-secoestrones

  摘要：

  Substituted and/or heterocyclic d-homoestrone derivatives were synthetized via the intramolecular cyclization of a δ-alkenyl-d-secoaldehyde, -d-secoalcohol or -d-secocarboxylic acid of estrone 3-benzyl ether. The d-secoalcohol was modified at three sites in the molecule. The in vitro antiproliferative activities of the new d-homo- and d-secoestrone derivatives were determined on HeLa, MCF-7, A431 and A2780 cells through use of MTT assay. d-Homoalcohols 3 and 5 displayed cell line-selective cytostatic effects against ovarian and cervical cell lines, respectively. Two d-secoestrones (6 and 12c) proved to be effective, with IC50 values comparable with those of the reference agent cisplatin. A selected compound (6) was tested by tubulin polymerization assay and its cancer specificity was additionally determined by using noncancerous human fibroblast cells.

  DOI：

  10.1016/j.steroids.2014.05.015

文献信息

• Stereoselective Synthesis of New Halogen-containing D-Homoestrone Derivatives
  作者：É. Frank、E. Mernyák、J. Wölfling、Gy. Schneider

  DOI：10.1055/s-2002-20455

  日期：——

  The Lewis acid-induced cyclization of the 3-methyl and 3-benzyl ethers of an unsaturated secoestrone aldehyde furnished D-homosteroids containing 16β-oriented halogens on the sterane skeleton.

  路易斯酸诱导的不饱和癸烯雌酮醛的 3-甲基和 3-苄基醚的环化提供了在甾烷骨架上含有 16β 取向卤素的 D-同型甾体。
• Synthesis and receptor-binding examinations of the normal and 13-epi-D-homoestrones and their 3-methyl ethers
  作者：János Wölfling、Erzsébet Mernyák、Éva Frank、George Falkay、Árpád Márki、Renáta Minorics、Gyula Schneider

  DOI：10.1016/s0039-128x(02)00181-2

  日期：2003.3

  An effective epimerization of the normal estrone 3-methyl and 3-benzyl ethers by using o-phenylenediamine and AcOH made the possibility for facile entry into the 13alpha-estrone series. Combination of this synthetic methodology with an isolation step carried out by means of the Girard-P reagent, the corresponding ethers of 13-epi-estrone were obtained in excellent yields. The 3-hydroxy and 3-methoxy D-homoestrone derivatives in both the normal and the 13alpha-estrone series were then synthesized and tested in vitro in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities (RBAs) are lower than that of the reference compound 3,17beta-estradiol. The progesterone receptor-binding affinities of the four D-homo derivatives were also tested showing low values for 13alpha-D-homoestrone and its 3-methyl ether. Pharmacologically, these 13alpha-D-homoestrone derivatives are estrogen receptor-selective molecules. (C) 2002 Elsevier Science Inc. All rights reserved.
• Synthesis of novel halogen-containing d-homoestrone and 13α-d-homoestrone derivatives by Lewis acid-induced intramolecular Prins reaction
  作者：János Wölfling、Éva Frank、Erzsébet Mernyák、Gábor Bunkóczi、Jose A Cvesta Seijo、Gyula Schneider

  DOI：10.1016/s0040-4020(02)00742-1

  日期：2002.8

  A simple synthetic route has been developed for the synthesis of16-halo-D-homosteroids in both the normal and 13-epiestrone series by the Lewis acid-catalyzed cyclization of an unsaturated secoestrone aldehyde and its 13alpha isomer. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Syntheses and antiproliferative effects of d-homo- and d-secoestrones
  作者：Erzsébet Mernyák、Johanna Szabó、Ildikó Bacsa、Judit Huber、Gyula Schneider、Renáta Minorics、Noémi Bózsity、István Zupkó、Mónika Varga、Zsolt Bikádi、Eszter Hazai、János Wölfling

  DOI：10.1016/j.steroids.2014.05.015

  日期：2014.9

  Substituted and/or heterocyclic d-homoestrone derivatives were synthetized via the intramolecular cyclization of a δ-alkenyl-d-secoaldehyde, -d-secoalcohol or -d-secocarboxylic acid of estrone 3-benzyl ether. The d-secoalcohol was modified at three sites in the molecule. The in vitro antiproliferative activities of the new d-homo- and d-secoestrone derivatives were determined on HeLa, MCF-7, A431 and A2780 cells through use of MTT assay. d-Homoalcohols 3 and 5 displayed cell line-selective cytostatic effects against ovarian and cervical cell lines, respectively. Two d-secoestrones (6 and 12c) proved to be effective, with IC50 values comparable with those of the reference agent cisplatin. A selected compound (6) was tested by tubulin polymerization assay and its cancer specificity was additionally determined by using noncancerous human fibroblast cells.