(2-(tert-butyldimethylsilyl)-7-hydroxy-6-methoxybenzofuran-3-yl)(3,4,5-trimethoxyphenyl)methanone | 1007198-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-(tert-butyldimethylsilyl)-7-hydroxy-6-methoxybenzofuran-3-yl)(3,4,5-trimethoxyphenyl)methanone
• CAS: 1007198-30-2
• 化学式: C₂₅H₃₂O₇Si
• 分子量: 472.61
• InChiKey: GUBXYHHOPVXBPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  87.36
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2-(tert-butyldimethylsilyl)-7-hydroxy-6-methoxybenzofuran-3-yl)(3,4,5-trimethoxyphenyl)methanone 在 四(三苯基膦)钯 吡啶 、 四溴化碳 、 水 、 溴 、 碳酸氢钠 、 三乙胺 作用下， 以 1,4-二氧六环 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 6.25h， 生成 dibenzyl 6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzofuran-7-yl phosphate
  参考文献：
  名称：

  [EN] TREATMENT OF MACULAR DEGENERATION
  [FR] TRAITEMENT DE LA DÉGÉNÉRESCENCE MACULAIRE

  摘要：

  本发明涉及治疗黄斑变性的方法，特别是涉及使用特定苯并呋喃化合物治疗老年性黄斑变性。

  公开号：

  WO2011022781A1
• 作为产物：
  描述：

  2-isopropoxy-3-methoxy-6-iodophenol 在 aluminum (III) chloride 、 palladium diacetate 、 sodium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2-(tert-butyldimethylsilyl)-7-hydroxy-6-methoxybenzofuran-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Discovery of 7-Hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan (BNC105), a Tubulin Polymerization Inhibitor with Potent Antiproliferative and Tumor Vascular Disrupting Properties

  摘要：

  A structure activity relationship (SAR) guided design of novel tubulin polymerization inhibitors has resulted in a series of benzo[b]furans with exceptional potency toward cancer cells and activated endothelial cells. The potency of early lead compounds has been substantially improved through the synergistic effect of introducing a conformational bias and additional hydrogen bond donor to the pharmacophore. Screening of a focused library of potent tubulin polymerization inhibitors for selectivity against cancer cells and activated endothelial cells over quiescent endothelial cells has afforded 7-hydroxy-6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo-[b]furan (BNC105, 8) as a potent and selective antiproliferative. Because of poor solubility, 8 is administered as its disodium phosphate ester prodrug 9 (BNC105P), which is rapidly cleaved in vivo to return the active 8. 9 exhibits both superior vascular disrupting and tumor growth inhibitory properties compared with the benchmark agent combretastatin A-4 disodium phosphate 5 (CA4P).

  DOI：

  10.1021/jm200454y

文献信息

• An Efficient Synthesis and Substitution of 3-Aroyl-2-bromobenzo[<i>b</i>]furans
  作者：Gurmit S. Gill、Damian W. Grobelny、Jason H. Chaplin、Bernard L. Flynn

  DOI：10.1021/jo701656z

  日期：2008.2.1

  A convenient method for the synthesis of 2-bromo-3-aroyl-benzo[b]furans from readily accessible precursors has been developed. The 2-bromo group has been employed as a versatile synthetic handle in both palladium-mediated couplings and direct nucleophilic substitutions to give access to a wide range of 2-substituted-3-aroyl-benzo[b]furans.

  已经开发了从容易获得的前体合成2-溴-3-芳酰基-苯并[ b ]呋喃的简便方法。2-溴基团已在钯介导的偶联和直接亲核取代中用作通用合成手柄，从而可使用各种2-取代-3-芳酰基-苯并[ b ]呋喃。
• WO2006/84338
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2007/87684
  申请人：——

  公开号：——

  公开（公告）日：——