(E)-2-(2,4-dimethoxybenzyliden)-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-(2,4-dimethoxybenzyliden)-2,3-dihydro-1H-inden-1-one
• 英文别名: (e)-2-(2',4'-Dimethoxybenzylidene)-1-indanone；(2E)-2-[(2,4-dimethoxyphenyl)methylidene]-3H-inden-1-one
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: ZFNBHDZFYPETHF-GXDHUFHOSA-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：

  (E)-2-(2,4-dimethoxybenzyliden)-2,3-dihydro-1H-inden-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以20 %的产率得到(E)-2-(2,4-dihydroxybenzyliden)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  Resorcinol-based hemiindigoid derivatives as human tyrosinase inhibitors and melanogenesis suppressors in human melanoma cells

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114972
• 作为产物：
  描述：

  1-茚酮 、 2,4-二甲氧基苯甲醛 生成 (E)-2-(2,4-dimethoxybenzyliden)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  用X射线晶体学测定某些2-亚芳基苯并环烷酮的细胞毒性与形貌之间的相关性。

  摘要：

  制备了三个系列的2-亚芳基苯并环烷酮1-3，以比较分子的形貌与细胞毒性。这些化合物包含两个芳基环，它们的空间关系受脂环族环的大小和亚芳基芳基环中取代基的性质影响。所有化合物均针对鼠P388和L1210细胞以及人类Molt 4 / C8和CEM T淋巴细胞进行了评估。从这些结果中，出现了1l和2c，1作为有用的先导分子，并且显示1l可显着抑制L1210细胞中的大分子DNA，RNA和蛋白质合成。通过X射线晶体学测定了19种代表性化合物的各种原子间距离，键角和扭转角，在将近40％的病例中，这些数据与细胞毒性之间存在相关性。结构活性关系揭示，一般而言，亚芳基芳基环中基团的空间性质，如通过摩尔折射率值的测量所揭示，比芳基取代基的电子和疏水性质对生物活性的贡献更大。这些化合物显示出极小的鼠毒性，这有利于决定开发这些分子作为细胞毒性和抗癌剂。

  DOI：

  10.1021/jm010559p

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。
• Synthesis and characterization of novel indanone-based spiro-dihydrobenzofuranderivatives
  作者：Meliha Burcu GÜDERE、Neşe DÜRÜ、Yakup BUDAK、Mustafa CEYLAN

  DOI：10.3906/kim-1904-13

  日期：——

  In this study, the synthesis and characterization of novel indanone-based spiro-dihydrobenzofuran derivatives were examined. Firstly, chalcone-like compounds 4a-k, ($E)$-2-benzylidene-2,3-dihydro-1$H$-inden-1-one derivatives, were synthesized by the base-catalyzed addition of benzaldehyde derivatives to 2,3-dihydro-1$H$-inden-1-one. Then Mn(OAc)$_3}$-mediated addition of dimedone (2) to the chalcone-like compounds gave two novel spiro-dihydrobenzofuran isomers: (3$S)$-6,6-dimethyl-3-aryl-6,7-dihydro-3$H$-spiro [benzofuran-2,2'-indene]-1',4(3'$H$,5$H)$-dione (5a-k) and (2'$S)$-6,6-dimethyl-2-aryl-6,7-dihydro-2$H$-spiro[benzofuran-3,2'-indene]-1',4(3'$H$,5$H)$-dione (6a-k) in good yields. The isomers were separated by column chromatography and their structures were elucidated on the basis of spectral data (NMR, IR) and elemental analysis.

  本研究考察了新型茚酮基螺二氢苯并呋喃衍生物的合成和表征。首先，通过苯甲醛衍生物与 2,3-二氢-1$H$-茚-1-酮的碱催化加成，合成了类查耳酮化合物 4a-k，即 ($E)$-2-亚苄基-2,3-二氢-1$H$-茚-1-酮衍生物。然后，Mn(OAc)$_3}$ 介导的二酮 (2) 与类查耳酮化合物的加成反应得到了两种新型螺二氢苯并呋喃异构体： (3$S)$-6,6-dimethyl-3-aryl-6,7-dihydro-3$H$-spiro [benzofuran-2,2'-indene]-1',4(3'$H$,5$H)$-dione (5a-k) 和 (2'$S)$-6、6,7-二氢-2$H$螺[苯并呋喃-3,2'-茚]-1',4(3'$H$,5$H)$二酮 (6a-k)。通过柱色谱法分离了这些异构体，并根据光谱数据（核磁共振、红外）和元素分析阐明了它们的结构。
• 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.
• US8633242B2
  申请人：——

  公开号：US8633242B2

  公开（公告）日：2014-01-21