2-bromo-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-benzo[b]furan | 905752-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-benzo[b]furan
• 英文别名: 2-bromo-3-(3,4,5-trimethoxybenzoyl)-6-methoxy-benzofuran；2-Bromo-3-(3,4,5-trimethoxybenzoyl)-6-methoxybenzofuran；(2-bromo-6-methoxy-1-benzofuran-3-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 905752-26-3
• 化学式: C₁₉H₁₇BrO₆
• 分子量: 421.244
• InChiKey: UOSNIQFPVNZJES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-bromo-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-benzo[b]furan 、 1-甲基-4-(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)-1H-吡唑 在 四(三苯基膦)钯 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以65%的产率得到2-(1-methyl-1H-pyrazol-4-yl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)benzo[b]furan
  参考文献：
  名称：

  3-芳基-2-溴苯并[ b ]呋喃的高效合成与取代

  摘要：

  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。

  DOI：

  10.1021/jo701656z
• 作为产物：
  描述：

  2-碘-5-甲氧基苯酚 在 溴 、 palladium diacetate 、 sodium carbonate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-bromo-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-benzo[b]furan
  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。
• A THERAPEUTIC PROTOCOL FOR TREATING OVARIAN CANCER
  申请人：Bionomics Limited

  公开号：US20170119727A1

  公开（公告）日：2017-05-04

  The present invention is directed to a pharmaceutical combination for treating proliferative disease comprising a compound of formula (I), or a salt, solvate or prodrug thereof, carboplatin or cisplatin, and gemcitabine. The present invention is further directed to a therapeutic protocol to manage ovarian cancer treatment in a female subject involving the administration of the combination to an ovarian cancer subject with recurrent or persistent ovarian cancer following treatment with platinum-based therapy. Kits comprising the combination as well as the use of the combination in the treatment of a proliferative disease are further contemplated.

  本发明涉及一种用于治疗增生性疾病的药物组合，包括化合物(I)的盐、溶剂化合物或前药，卡铂或顺铂，以及吉西他滨。本发明还涉及一种治疗方案，用于管理女性患者的卵巢癌治疗，包括将该组合物用于在接受过以铂为基础的治疗后出现复发或持续性卵巢癌的卵巢癌患者。还考虑了包含该组合物的试剂盒以及该组合物在治疗增生性疾病中的应用。
• SUBSTITUTED BENZOFURANS, BENZOTHIOPHENES, BENZOSELENOPHENES AND INDOLES AND THEIR USE AS TUBULIN POLYMERISATION INHIBITORS
  申请人：Chaplin Jason Hugh

  公开号：US20100004208A1

  公开（公告）日：2010-01-07

  The present invention relates generally to substituted benzofurans, benzothiophenes, and indoles and their use as tubulin polymerisation inhibitors.

  本发明涉及取代苯并呋喃、苯并噻吩和吲哚，以及它们作为微管聚合抑制剂的用途。
• COMBINATION THERAPY FOR TREATING PROLIFERATIVE DISEASES
  申请人：Kremmidiotis Gabriel

  公开号：US20120149665A1

  公开（公告）日：2012-06-14

  A pharmaceutical composition of a tubulin polymerisation inhibitor and an mTOR inhibitor and a method of treating proliferative disease with a combination of a tubulin polymerisation inhibitor and an mTOR inhibitor.

  一种包含微管聚合抑制剂和mTOR抑制剂的药物组合物，以及使用微管聚合抑制剂和mTOR抑制剂的组合物治疗增殖性疾病的方法。
• Tubulin polymerisation inhibitors
  申请人：Biononics Limited

  公开号：US08278290B2

  公开（公告）日：2012-10-02

  The present invention relates to compounds of general formula (I) as tublin polymerization inhibitors and methods for preparing such compounds.

  本发明涉及一般式（I）化合物作为微管聚合抑制剂和制备这些化合物的方法。