(E)-2-(3,4,5-trimethoxybenzylidene)-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-(3,4,5-trimethoxybenzylidene)-2,3-dihydro-1H-inden-1-one
• 英文别名: (E)-2-(3,4,5-trimethoxybenzyliden)-2,3-dihydro-1H-inden-1-one；2,3-dihydro-2-(3,4,5-trimethoxybenzylidene)-1H-inden-1-one；2-(3,4,5-Trimethoxybenzylidene)-1-indanone；(2E)-2-[(3,4,5-trimethoxyphenyl)methylidene]-3H-inden-1-one
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: OFVGYTVXPWPBMR-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲醛肟 、 (E)-2-(3,4,5-trimethoxybenzylidene)-2,3-dihydro-1H-inden-1-one 在 sodium hypochlorite 作用下， 以 氯仿 、 水 为溶剂， 反应 2.0h， 以62%的产率得到3'-phenyl-4'-(3,4,5-trimethoxyphenyl)-4'H-spiro[indene-2,5'-isoxazol]-1(3H)-one
  参考文献：
  名称：

  3'，4'-双（3,4,5-三取代）-4'H-螺[茚-2,5'-异恶唑] -1（3H）-1衍生物的设计，合成及体外细胞毒性评价作为有希望的抗癌药

  摘要：

  设计并合成了一系列新的3'，4'-双（3,4,5-三甲氧基苯基）-4'H-螺[茚-2,5'-异恶唑] -1（3H）-衍生物。评估了合成化合物对几种不同人类癌细胞的细胞毒性作用。其中，化合物9e对T47D细胞显示出最有效的体外抗增殖活性，IC 50值为0.07±0.01 µM。另一个强效衍生物9h对T47D细胞的IC 50值为0.12±0.07 µM，与阳性对照（科尔基辛？顺铂？长春新碱？长春碱？阿霉素？塞来昔布）相当。讨论了构效关系，并提出了对所开发化合物的抗微管蛋白和COX-2抑制作用。

  DOI：

  10.2174/1570180811666140704172442
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 1-茚酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (E)-2-(3,4,5-trimethoxybenzylidene)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  3'，4'-双（3,4,5-三取代）-4'H-螺[茚-2,5'-异恶唑] -1（3H）-1衍生物的设计，合成及体外细胞毒性评价作为有希望的抗癌药

  摘要：

  设计并合成了一系列新的3'，4'-双（3,4,5-三甲氧基苯基）-4'H-螺[茚-2,5'-异恶唑] -1（3H）-衍生物。评估了合成化合物对几种不同人类癌细胞的细胞毒性作用。其中，化合物9e对T47D细胞显示出最有效的体外抗增殖活性，IC 50值为0.07±0.01 µM。另一个强效衍生物9h对T47D细胞的IC 50值为0.12±0.07 µM，与阳性对照（科尔基辛？顺铂？长春新碱？长春碱？阿霉素？塞来昔布）相当。讨论了构效关系，并提出了对所开发化合物的抗微管蛋白和COX-2抑制作用。

  DOI：

  10.2174/1570180811666140704172442

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 2D-QSAR study of dispiropyrrolodinyl-oxindole based alkaloids as cholinesterase inhibitors
  作者：Aladdin M. Srour、Dina H. Dawood、Mohammed N.A. Khalil、Zienab M. Nofal

  DOI：10.1016/j.bioorg.2018.10.030

  日期：2019.3

  In this work, we describe the regioselective synthesis of some new dispiro[indene-2,3'-pyrrolidine-2',3″-indoline]-1,2″(3H)-dione 4-29 attributable to the previously described methods. All the new chemical entities were assessed in-vitro as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes; while no significant inhibitory activity for the tested compounds were assigned

  在这项工作中，我们描述了一些新的双螺并[indene-2,3'-吡咯烷-2'，3“-二氢吲哚] -1,2”（3H）-二酮4-29的区域选择性合成，这归因于前述方法。所有新的化学实体均作为乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）酶的抑制剂进行了体外评估。尽管对被测化合物没有明显的抑制活性，但化合物4,27、29、28和15对BChE酶的活性最高，IC50分别为13.7 µM，21.8 µM，22.1 µM，22.9 µM和24.9 µM。至多奈哌齐（IC50 = 0.72 µM）。发现化合物4具有混合型抑制模式，即新化学实体的生物活性（N = 26，n = 5，R2 = 0.893，R2 cvOO = 0.831，R2 cvMO = 0.838，F = 33.32，s2 = 0 。
• Formation of Dimers of Some 2-Substituted Indan-1-one Derivatives during Base-Mediated Cross-Aldol Condensation
  作者：Gaurav Narang、Dharam Paul Jindal、Birinder Jit、Ranju Bansal、Brian S. Potter、Rex A. Palmer

  DOI：10.1002/hlca.200690028

  日期：2006.2

  Unexpected dimers of some 2-substituted indan-1-one derivatives were isolated during aldol condensation of indan-1-one with various aldehydes in the presence of KOH (see Scheme). Monomeric products, usually expected from aldol condensation, further underwent a base-catalyzed nucleophilic addition reaction to their dimeric form in some cases. The structures of these dimers were characterized by using

  在KOH存在下，在茚满-1-酮与各种醛的醛醇缩合反应中，分离出某些2-取代的茚满-1-酮衍生物的意外的二聚体（参见方案）。通常从醛醇缩合预期的单体产物在某些情况下进一步经历碱催化的亲核加成反应为其二聚体形式。这些二聚体的结构通过使用各种光谱技术进行表征，在一种情况下，通过高分辨率晶体学分析确定了结构细节。
• Stereoselective synthesis of dispiropyrrolidinyl oxindole derivatives and evaluation of their antibacterial efficacy
  作者：Bishwa Narayan Kondoli、Divya Vemula、Umarani Brahma、Vasundhra Bhandari、Pratap Chandra Acharya

  DOI：10.1016/j.molstruc.2023.135808

  日期：2023.9

  pharmaceutical industry is continuously striving to develop new antibacterial agents. Herein, we have reported stereoselective synthesis of dispiropyrrolidinyl oxindole derivatives using 1,3-dipolar cycloaddition reaction, between arylidene indanone derivatives as dipolarophile and azomethine ylides formed in situ from isatin and sarcosine in a multicomponent reaction (MCR) mode. The reaction condition was optimized

  抗菌素耐药性是一场全球性的健康危机，其主要原因是抗菌药物的过度使用和误用。因此，制药行业不断努力开发新型抗菌剂。在此，我们报道了使用 1,3-偶极环加成反应立体选择性合成二吡咯烷基羟吲哚衍生物，在多组分反应 (MCR) 模式下，亚芳基茚满酮衍生物作为亲偶极试剂和由靛红和肌氨酸原位形成的偶氮甲碱叶立德。优化了反应条件，并使用 NMR 光谱数据确定了二螺产物的绝对构型，并从单晶 X 射线晶体学中进行了确认。新合成的螺衍生物在体外表现良好至中等对六种细菌的抗菌效率。初步的计算机研究表明，这些二螺衍生物对青霉素结合蛋白 3 具有潜在的结合亲和力，它们可以用作未来抗菌药物发现的模板。
• 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.