2',7-dibenzyloxy-4'-(t-butyldimethylsilyloxy)isoflavone | 1186507-10-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 2',7-dibenzyloxy-4'-(t-butyldimethylsilyloxy)isoflavone
• 英文别名: 2',7-dibenzyloxy-4'-(t-butyldimethylsilyloxy)-isoflavone；2',7-Dibenzyloxy-4'-(t-butlydimethylsilyloxy)-isoflavone；3-[4-[tert-butyl(dimethyl)silyl]oxy-2-phenylmethoxyphenyl]-7-phenylmethoxychromen-4-one
• CAS: 1186507-10-7
• 化学式: C₃₅H₃₆O₅Si
• 分子量: 564.753
• InChiKey: BYZXQXWCMBVJDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.0
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2',7-dibenzyloxy-4'-(t-butyldimethylsilyloxy)isoflavone 在 锂硼氢 、 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到2',7-dibenzyloxy-4'-(tert-butyldimethylsilyloxy)isoflav-3-ene
  参考文献：
  名称：

  METHODS FOR SYNTHESIZING GLYCINOLS, GLYCEOLLINS I AND II, COMPOSITIONS OF SELECTED INTERMEDIATES, AND THERAPEUTIC USES THEREOF

  摘要：

  公开并声明了两种不同的方法，用于合成甘油素I和甘油素II，作为混合物和其纯形式。立体化学异构体和各种合成中间体也被合成并声明为其新颖的物质组成。所有化合物及其混合物均声明用于制剂，用于治疗或预防癌症，或具有作为选择性雌激素受体调节剂的效用，这些制剂包括增强食品、膳食补充剂和伦理药物代理。

  公开号：

  US20110144195A1
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 哌啶 、 盐酸 、 thallium(III) nitrate trihydrate 、 水 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 41.0h， 生成 2',7-dibenzyloxy-4'-(t-butyldimethylsilyloxy)isoflavone
  参考文献：
  名称：

  METHODS FOR SYNTHESIZING GLYCINOLS, GLYCEOLLINS I AND II, COMPOSITIONS OF SELECTED INTERMEDIATES, AND THERAPEUTIC USES THEREOF

  摘要：

  公开并声明了两种不同的方法，用于合成甘油素I和甘油素II，作为混合物和其纯形式。立体化学异构体和各种合成中间体也被合成并声明为其新颖的物质组成。所有化合物及其混合物均声明用于制剂，用于治疗或预防癌症，或具有作为选择性雌激素受体调节剂的效用，这些制剂包括增强食品、膳食补充剂和伦理药物代理。

  公开号：

  US20110144195A1

文献信息

• METHODS FOR SYNTHESIZING GLYCINOLS, GLYCEOLLINS I AND II, COMPOSITIONS OF SELECTED INTERMEDIATES, AND THERAPEUTIC USES THEREOF
  申请人：Erhardt Paul W.

  公开号：US20110144195A1

  公开（公告）日：2011-06-16

  Two distinct methods are disclosed and claimed for synthesizing glyceollin I plus glyceollin II as a mixture and as their pure forms. Stereochemical isomers and various synthetic intermediates are also synthesized and claimed for their novel compositions of matter. All compounds and their mixtures are claimed for use in formulations that are useful to treat or prevent cancer, or that have utility as selective estrogen receptor modulators, such formulations including enhanced or medical foods, dietary supplements and ethical pharmaceutical agents.

  公开并声明了两种不同的方法，用于合成甘油素I和甘油素II，作为混合物和其纯形式。立体化学异构体和各种合成中间体也被合成并声明为其新颖的物质组成。所有化合物及其混合物均声明用于制剂，用于治疗或预防癌症，或具有作为选择性雌激素受体调节剂的效用，这些制剂包括增强食品、膳食补充剂和伦理药物代理。
• Methods for synthesizing glycinols, glyceollins I and II, compositions of selected intermediates, and therapeutic uses thereof
  申请人：Erhardt Paul W.

  公开号：US08563599B2

  公开（公告）日：2013-10-22

  Two distinct methods are disclosed and claimed for synthesizing glyceollin I plus glyceollin II as a mixture and as their pure forms. Stereochemical isomers and various synthetic intermediates are also synthesized and claimed for their novel compositions of matter. All compounds and their mixtures are claimed for use in formulations that are useful to treat or prevent cancer, or that have utility as selective estrogen receptor modulators, such formulations including enhanced or medical foods, dietary supplements and ethical pharmaceutical agents.

  本发明揭示了两种不同的方法，用于合成甘豆素I和甘豆素II，作为混合物和纯形式。还合成了立体化学异构体和各种合成中间体，并声明了它们的新颖物质组成。所有化合物及其混合物均声明用于制剂，可用于治疗或预防癌症，或具有作为选择性雌激素受体调节剂的效用，这些制剂包括增强型或医疗食品、膳食补充剂和道德制药剂。
• Biomimetic Syntheses and Antiproliferative Activities of Racemic, Natural (−), and Unnnatural (+) Glyceollin I
  作者：Rahul S. Khupse、Jeffrey G. Sarver、Jill A. Trendel、Nicole R. Bearss、Michael D. Reese、Thomas E. Wiese、Stephen M. Boue、Matthew E. Burow、Thomas E. Cleveland、Deepak Bhatnagar、Paul W. Erhardt

  DOI：10.1021/jm101619e

  日期：2011.5.26

  A 14-step biomimetic synthetic route to glyceollin I (1.5% overall yield) was developed and deployed to produce the natural enantiomeric form in soy, its unnatural stereoisomer, and a racemic mixture. Enantiomeric excess was assessed by asymmetric NMR shift reagents and chiral HPLC. Antiproliferative effects were measured in human breast, ovarian, and prostate cancer cell lines, with all three chiral forms exhibiting growth inhibition (GI) in the low to mid mu M range for all cells. The natural enantiomer, and in some cases the racemate, gave significantly greater GI than the unnatural stereoisomer for estrogen receptor positive (ER+) versus ER- breast/ovarian cell lines as well as for androgen receptor positive (AR(+)) versus AR(-) prostate cancer cells. Surprisingly, differences between ER+ and ER- cell lines were not altered by media estrogen conditions. These results suggest the antiproliferative mechanism of glyceollin I stereoisomers may be more complicated than strictly ER interactions.