(E)-2-(3,4-dimethoxybenzylidene)-2,3-dihydro-1H-inden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (E)-2-(3,4-dimethoxybenzylidene)-2,3-dihydro-1H-inden-1-one
• 英文别名: (E)-2-(3,4-dimethoxybenzyliden)-2,3-dihydro-1H-inden-1-one；2-(3,4-Dimethoxybenzylidene)-1-indanone；(2E)-2-[(3,4-dimethoxyphenyl)methylidene]-3H-inden-1-one
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: FJGZVPFZRZDBNC-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-isothiocyanatooxindole 、 (E)-2-(3,4-dimethoxybenzylidene)-2,3-dihydro-1H-inden-1-one 在 3-[[[3,5-双（三氟甲基）苯基]氨基]-4-[[（（8α，9S）-6''-甲氧基七氢呋喃-9-基]氨基]-3-环丁烯-1,2-二酮 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到
  参考文献：
  名称：

  3-异硫氰酸酯基羟吲哚与环外α，β不饱和酮的对映选择性催化级联迈克尔/环化反应途中到-3,2'-吡咯烷基bispirooxindoles †

  摘要：

  研究表明，在存在奎宁衍生的叔氨基-方酸酰胺催化剂的情况下，3-异硫氰酸根合吲哚与环外α，β-不饱和酮之间的级联迈克尔/环化反应可以有效地进行，并提供包含两个螺-季四元的3,2'-吡咯烷基二螺氧基辛多烯和三个连续的立体中心，作为单一的非对映异构体，具有出色的对映选择性（最高99：1 er）。

  DOI：

  10.1039/c6ob02187e
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 1-茚酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-2-(3,4-dimethoxybenzylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  3-异硫氰酸酯基羟吲哚与环外α，β不饱和酮的对映选择性催化级联迈克尔/环化反应途中到-3,2'-吡咯烷基bispirooxindoles †

  摘要：

  研究表明，在存在奎宁衍生的叔氨基-方酸酰胺催化剂的情况下，3-异硫氰酸根合吲哚与环外α，β-不饱和酮之间的级联迈克尔/环化反应可以有效地进行，并提供包含两个螺-季四元的3,2'-吡咯烷基二螺氧基辛多烯和三个连续的立体中心，作为单一的非对映异构体，具有出色的对映选择性（最高99：1 er）。

  DOI：

  10.1039/c6ob02187e

文献信息

• Anticancer and Tubulin Polymerisation Inhibition Activity of Benzylidene Indanones and Process of Preparing the Same
  申请人：Council of Scientific and Industrial Research

  公开号：US20130079396A1

  公开（公告）日：2013-03-28

  The present invention relates to benzylidene indanones of general formula 1. The compounds exhibited tubulin polymerisation inhibition. A series of compounds 2-benzylidene 3-(3,4,5-trimethoxyphenyl) indanones having general formulae 1 were synthesized from gallic acid through a chemical process. 2-(3,4-Methylenedioxybenzylidine), 3-(3,4,5-trimethoxyphenyl), 4,5,6-trimethoxyindanone (8), a representative compound of this series possessing the molecular formulae C 29 H 28 O 9 , was synthesized from gallic acid and exhibits potent anticancer activity. Compound 8 was evaluated for acute oral activity in Swiss albino mice and found to be safe up to 300 mg/kg body weight. The anticancer activity of the compounds has been determined, in order to obtain new potent and cost effective molecules using an in vitro cytotoxicity assay.

  本发明涉及一般式1的苯甲基亚甲基吲哚酮。这些化合物表现出微管聚合抑制作用。通过化学过程从没食子酸合成了一系列一般式1的2-苯甲基亚甲基3-(3,4,5-三甲氧基苯基)吲哚酮。这个系列的代表化合物2-(3,4-亚甲二氧基苯甲亚甲基)、3-(3,4,5-三甲氧基苯基)、4,5,6-三甲氧基吲哚酮（8），其分子式为C29H28O9，由没食子酸合成，表现出强大的抗癌活性。化合物8在瑞士白化小鼠中进行急性口服活性评估，发现在体重为300毫克/千克时是安全的。通过体外细胞毒性测定，已确定这些化合物的抗癌活性，以获得新的有效且成本效益高的分子。
• In vitro and in silico insights into tyrosinase inhibitors with (E)-benzylidene-1-indanone derivatives
  作者：Hee Jin Jung、Sang Gyun Noh、Yujin Park、Dongwan Kang、Pusoon Chun、Hae Young Chung、Hyung Ryong Moon

  DOI：10.1016/j.csbj.2019.07.017

  日期：——

  Tyrosinase is a key enzyme responsible for melanin biosynthesis and is effective in protecting skin damage caused by ultraviolet radiation. As part of ongoing efforts to discover potent tyrosinase inhibitors, we systematically designed and synthesized thirteen (E)-benzylidene-l-indanone derivatives (BID1-13) and determined their inhibitory activities against tyrosinase. Among the compounds evaluated, BID3 was the most potent inhibitor of mushroom tyrosinase (IC50 = 0.034 mu M, monophenolase activity; IC50 = 1.39 mu M, diphenolase activity). Kinetic studies revealed that BID3 demonstrated a mixed type of tyrosinase inhibition with K-i value of 2.4 mu M using L-DOPA as a substrate. In silico molecular docking simulations demonstrated that BID3 can bind to the catalytic and allosteric sites of tyrosinase to inhibit enzyme activity which confirmed in vitro experimental studies between BID3 and tyrosinase. Furthermore, melanin contents decreased and cellular tyrosinase activity was inhibited after BID3 treatment. These observations revealed that BID3 is a potent tyrosinase inhibitor and potentially could be used as a whitening agent for the treatment of pigmentation-related disorders. (C) 2019 The Authors. Published by Elsevier B.V. on behalf of Research Network of Computational and Structural Biotechnology.
• Levai, Albert, Scientia Pharmaceutica, 1996, vol. 64, # 3-4, p. 523 - 530
  作者：Levai, Albert

  DOI：——

  日期：——
• EGR1 TARGETING MOLECULES FOR THE TREATMENT OF INFLAMMATORY AND HYPERPROLIFERATIVE CONDITIONS
  申请人：The Medical Research, Infrastructure and Health Services Fund of the Tel Aviv Medical Center

  公开号：US20180289728A1

  公开（公告）日：2018-10-11

  A method of treating an inflammation or a hyperproliferative disease in a subject in need thereof is disclosed. The method comprising administering to the subject a therapeutically effective amount of a compound selected from the group consisting of: a compound represented by Formula I: or a pharmaceutically acceptable salt thereof, a compound represented by Formula II: and a compound represented by Formula III: wherein the variables in Formulae I, II and III are as defined in the specification.
• US8633242B2
  申请人：——

  公开号：US8633242B2

  公开（公告）日：2014-01-21