2-t-butyldimethylsilyl-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran | 905752-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-t-butyldimethylsilyl-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran
• 英文别名: [2-[tert-butyl(dimethyl)silyl]-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1-benzofuran-7-yl] acetate
• CAS: 905752-39-8
• 化学式: C₂₇H₃₄O₈Si
• 分子量: 514.648
• InChiKey: BUMRSFXRRGWGQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  93.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-t-butyldimethylsilyl-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran 在 四溴化碳 、 溴 、 三乙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 乙醚 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 40.17h， 生成 dibenzyl 6-methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzofuran-7-yl phosphate
  参考文献：
  名称：

  [EN] METHOD FOR TREATING ACUTE MYELOID LEUKEMIA
  [FR] MÉTHODE DE TRAITEMENT DE LA LEUCÉMIE AIGUË MYÉLOÏDE

  摘要：

  本发明涉及一种用于治疗急性髓系白血病（AML）的方法，所用药物可为药物组合物或包含目前描述的化合物（I）的试剂盒，或其盐、溶剂化合物或前药。该发明的特定化合物包括2-甲基-7-羟基-3-(3,4,5-三甲氧基苯甲酰)-6-甲氧基苯并呋喃，也称为BNC105，以及6-甲氧基-2-甲基-3-(3,4,5-三甲氧基苯甲酰)苯并呋喃-7-基磷酸二钠，也称为BNC105P。

  公开号：

  WO2019079848A1
• 作为产物：
  描述：

  2-isopropoxy-3-methoxy-6-iodophenol 在 吡啶 、 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-t-butyldimethylsilyl-7-acetoxy-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran
  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

• Combination Therapy for Treating Proliferative Diseases
  申请人：Kremmidiotis Gabriel

  公开号：US20110130367A1

  公开（公告）日：2011-06-02

  The present invention relates generally to new chemical combinations and methods for their use in the treatment of proliferative diseases and in particular cancer.

  本发明一般涉及新的化学组合物以及它们在治疗增殖性疾病，特别是癌症中的应用方法。
• 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。
• [EN] TREATMENT OF MACULAR DEGENERATION<br/>[FR] TRAITEMENT DE LA DÉGÉNÉRESCENCE MACULAIRE
  申请人：BIONOMICS LTD

  公开号：WO2011022781A1

  公开（公告）日：2011-03-03

  The present invention relates generally to methods for treating macular degeneration, and in particular age-related macular degeneration, involving the use of specific benzofuran based compounds.

  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。
• COMBINATION TREATMENT PROTOCOL
  申请人：Bionomics Limited

  公开号：US20180042887A1

  公开（公告）日：2018-02-15

  The present disclosure provides a combination and a method for treating chronic lymphocytic leukemia (CLL).

  本公开提供了一种用于治疗慢性淋巴细胞白血病（CLL）的组合物和方法。
• [EN] COMBINATION THERAPY INVOLVING A VASCULAR DISRUPTING AGENT AND AN AGENT WHICH TARGETS HYPOXIA<br/>[FR] POLYTHÉRAPIE COMPRENANT UN AGENT DE PERTURBATION VASCULAIRE ET UN AGENT CIBLANT L'HYPOXIE
  申请人：BIONOMICS LTD

  公开号：WO2013177633A1

  公开（公告）日：2013-12-05

  The present invention provides a method for treating a proliferative disease in a patient. The method comprises administering to a patient in need thereof: a) a vascular disrupting agent and (b) at least one hypoxia targeting agent. Preferred combinations are BNC105 and Pazopanib and BNC 105 and Bortezomib.

  本发明提供了一种治疗患有增殖性疾病的患者的方法。该方法包括向需要的患者施用：a) 血管破坏剂和 (b) 至少一种缺氧靶向药物。首选组合是BNC105和帕唑帕尼以及BNC105和硼替佐米。