3-(3-isopropoxy-4-methoxyphenyl)-4,5,6-trimethoxy-2-(3,4,5-trimethoxybenzoyl)-1H-inden-1-one | 445483-14-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(3-isopropoxy-4-methoxyphenyl)-4,5,6-trimethoxy-2-(3,4,5-trimethoxybenzoyl)-1H-inden-1-one
• 英文别名: 4,5,6-Trimethoxy-3-(4-methoxy-3-propan-2-yloxyphenyl)-2-(3,4,5-trimethoxybenzoyl)inden-1-one
• CAS: 445483-14-7
• 化学式: C₃₂H₃₄O₁₀
• 分子量: 578.616
• InChiKey: QUBUKDUCFWZJIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-(3-isopropoxy-4-methoxyphenyl)-4,5,6-trimethoxy-2-(3,4,5-trimethoxybenzoyl)-1H-inden-1-one 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以76%的产率得到3-(3-Hydroxy-4-methoxyphenyl)-4,5,6-trimethoxy-2-(3,4,5-trimethoxybenzoyl)inden-1-one
  参考文献：
  名称：

  The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4

  摘要：

  A series of aryl- and aroyl-substituted chalcone analogues of the tubulin binding agent combretastatin A4 (1) were prepared, using a recently introduced one-pot palladium-mediated hydrostannylation-coupling reaction sequence. These chalcones were converted to indanones by Nazarov cyclisation, followed by oxidation to give the corresponding indenones. Indenones were also prepared using a palladium-mediated formal [3+2]-cycloaddition process between ortho-halobenzaldehydes and diarylpropynones. All compounds were assessed as inhibitors of tubulin polymerisation, but only E-31 had activity similar to that of 1. However, compound E-31 did not exhibit antiproliferative activity against the MCF-7 cell line. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.006
• 作为产物：
  描述：

  β,β-dibromo-3-isopropoxy-4-methoxystyrene 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 正丁基锂 、 甲烷磺酸 、 三正丁基氢锡 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 85.0h， 生成 3-(3-isopropoxy-4-methoxyphenyl)-4,5,6-trimethoxy-2-(3,4,5-trimethoxybenzoyl)-1H-inden-1-one
  参考文献：
  名称：

  The concise synthesis of chalcone, indanone and indenone analogues of combretastatin A4

  摘要：

  A series of aryl- and aroyl-substituted chalcone analogues of the tubulin binding agent combretastatin A4 (1) were prepared, using a recently introduced one-pot palladium-mediated hydrostannylation-coupling reaction sequence. These chalcones were converted to indanones by Nazarov cyclisation, followed by oxidation to give the corresponding indenones. Indenones were also prepared using a palladium-mediated formal [3+2]-cycloaddition process between ortho-halobenzaldehydes and diarylpropynones. All compounds were assessed as inhibitors of tubulin polymerisation, but only E-31 had activity similar to that of 1. However, compound E-31 did not exhibit antiproliferative activity against the MCF-7 cell line. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.006

文献信息

• [EN] SYNTHESIS FOR THE PREPARATION OF COMPOUNDS FOR SCREENING AS POTENTIAL TUBULIN BINDING AGENTS<br/>[FR] SYNTHESE DESTINEE A LA PREPARATION DE COMPOSES DE CRIBLAGE UTILISES COMME AGENTS DE FIXATION A LA TUBULINE
  申请人：UNIV AUSTRALIAN

  公开号：WO2002060872A1

  公开（公告）日：2002-08-08

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物以用作潜在的微管聚合抑制剂筛选的方法。本发明还提供了具有微管聚合抑制剂活性的化学化合物。
• Synthesis for the preparation of compounds for screening as potential tubulin binding agents
  申请人：Flynn Luke Bernard

  公开号：US20050130221A1

  公开（公告）日：2005-06-16

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物的方法，用于筛选作为潜在微管聚合抑制剂的化合物。本发明还提供具有微管聚合抑制剂活性的化学化合物。
• 潜在的なチューブリン結合剤としてのスクリーニング用化合物の調製のための合成
  申请人：——

  公开号：JP2004528296A

  公开（公告）日：2004-09-16

  本発明は、潜在的なチューブリン重合阻害剤としてスクリーニングするための化学化合物の合成方法に関する。また、本発明は、チューブリン重合阻害剤活性を持つ化学化合物を提供する。

  本发明涉及一种合成化合物的方法，用于筛选潜在的微管蛋白聚合抑制剂。本发明还提供了具有管蛋白聚合抑制剂活性的化合物。
• SYNTHESIS FOR THE PREPARATION OF COMPOUNDS FOR SCREENING AS POTENTIAL TUBULIN BINDING AGENTS
  申请人：THE AUSTRALIAN NATIONAL UNIVERSITY

  公开号：EP1363880A1

  公开（公告）日：2003-11-26
• EP1363880A4
  申请人：——

  公开号：EP1363880A4

  公开（公告）日：2008-10-08