(2E)-1-(3',4',5'-trimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one | 130768-87-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-1-(3',4',5'-trimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
• 英文别名: (E)-1-(3,4,5-trimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；3,3',4,4',5,5'-hexamethoxychalcone；3,4,5,3',4',5'-hexamethoxy-chalcone；3,4,5,3',4',5'-Hexamethoxy-chalkon；(E)-1,3-bis(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 130768-87-5
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: WOJJYHZSZSSQJL-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2E)-1-(3',4',5'-trimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one 在 sodium hydroxide 、 双氧水 作用下， 生成 (3,4,5-Trimethoxy-phenyl)-[3-(3,4,5-trimethoxy-phenyl)-oxiranyl]-methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents

  摘要：

  A series of substituted chalcones and their corresponding pyrazoles were synthesized and evaluated for in vitro cytotoxic activity against a panel of human cancer cell lines. Out of 93 compounds screened, 8 compounds, 1s, 3i,j,n, 4i,j,n and 4s, showed marked activity. Compounds 4j,n and 4s were found to be the most promising in this study. SAR is also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.121
• 作为产物：
  描述：

  3,4,5-三甲氧基苯基原醇甲酯 在 chromium(III) oxide 、 sodium hydroxide 、 硫酸 作用下， 生成 (2E)-1-(3',4',5'-trimethoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Mauthner, Journal fur praktische Chemie (Leipzig 1954), 1915, vol. <2> 92, p. 200

  摘要：

  DOI：

文献信息

• NBS-mediated cyclization of trans-cinnamic alcohols
  作者：Meng-Yang Chang、Chung-Yu Tsai、Ming-Hao Wu

  DOI：10.1016/j.tet.2013.05.110

  日期：2013.8

  An efficient and straightforward three-step synthetic route toward 2,4-disubstituted-3-bromooxetanes 5 with the trans–trans contiguous stereogenic centers is developed from functionalized chalcones 3 via NaBH4-mediated reduction of chalcones 3, followed by NBS-mediated electrophilic cyclization of the resulting trans-cinnamic alcohols 4 in good yield. Skeleton 3 is prepared by Claisen–Schmidt condensation

  通过NaBH 4介导的查耳酮3还原反应，再由NBS介导的亲电反应，从功能化的查耳酮3中开发出一种有效，直接的三步合成路线，以2,4-二取代-3-溴氧杂环丁烷5为反式-反式连续立体中心。以高收率将所得反式肉桂醇4环化。骨架3是通过Claisen-Schmidt缩合取代的芳基醛1和芳基甲基酮或叔丁基甲基酮2制备的。合成路线获得了高收率，并且整个反应过程仅花费了一天。研究了骨架3的取代作用，各种反应条件和合理的机理。
• Synthesis and biological evaluation of 3′,4′,5′-trimethoxychalcone analogues as inhibitors of nitric oxide production and tumor cell proliferation
  作者：Yerra Koteswara Rao、Shih-Hua Fang、Yew-Min Tzeng

  DOI：10.1016/j.bmc.2009.10.022

  日期：2009.12

  anti-proliferative compound in the series with IC50 values of 1.8 and 2.2 μM toward liver cancer Hep G2 and colon cancer Colon 205 cell lines, respectively. 2,3,3′,4′,5′-Pentamethoxychalcone (1), 3,3′,4,4′,5,5′-hexamethoxychalcone (3), 2,3′,4,4′,5,5′-hexamethoxychalcone (5), 2-hydroxy-3,3′,4′,5′-tetramethoxychalcone (10), 11 and 14 showed significant anti-proliferation actions in Hep G2 and Colon 205

  合成了一系列23 3'，4'，5'-三甲氧基查耳酮类似物，它们对LPS /IFN-γ处理的巨噬细胞中一氧化氮（NO）的抑制作用，并研究了肿瘤细胞的增殖。4-羟基-3,3'，4'，5'-四甲氧基查尔酮（7），3,4-二羟基-3'，4'，5'-三甲氧基查尔酮（11），3-羟基-3'，4,4 '，5'-四甲氧基查耳酮（14）和3,3'，4'，5'-四甲氧基查耳酮（15）是产生NO最有效的生长抑制剂，IC 50值为0.3、1.5、1.3和0.3分别为μM。肿瘤细胞增殖测定结果表明，几种化合物对不同的癌细胞系表现出有效的抑制活性。查尔酮15是该系列中最有效的抗增殖化合物，对肝癌Hep G2和结肠癌Colon 205细胞系的IC 50值分别为1.8和2.2μM。2,3,3'，4'，5'-五甲氧基查耳酮（1），3,3'，4,4'，5,5'-六甲氧基查耳酮（3），2,3'，4,4'，5， 5'-六甲氧基查耳酮（5），2-羟基-3
• [EN] 2-BENZYL-INDANONE COMPOUNDS AS ANTICANCER AGENT AND A PROCESS FOR PREPARATION THEREOF<br/>[FR] COMPOSÉS 2-BENZYL-INDANONE EN TANT QU'AGENTS ANTICANCÉREUX ET PROCÉDÉ DE PRÉPARATION DE CEUX-CI
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2017009860A1

  公开（公告）日：2017-01-19

  The anticancer activity of gallic acid compounds has been invented, in order to obtain new potent and cost effective molecule using in vitro cytotoxicity assay. The invention particularly relates to the gallic acid based new molecules i.e. 2-benzyl indanones represented by structure 1, possessing anticancer activity against human cancer cell lines. The compound also exhibited tubulin polymerisation inhibition. 2-(3',4'-methylenedioxybenzyl)-3-(3",4",5"-trimethoxyphenyl)-indanone- 1 (2), possessing molecular formulae as C29H30O9 was synthesized from gallic acid, exhibits potent in-vivo anticancer activity. Compound 2 was evaluated for acute oral activity in Swiss albino mice and it was found to be well tolerated by the experimental animals up to 300mg/kg body weight. (Formula 1, Formula 2).

  已发明了没食子酸化合物的抗癌活性，以便利用体外细胞毒性试验获得新的有效且具有成本效益的分子。该发明特别涉及基于没食子酸的新分子，即结构1所代表的2-苄基茚酮，具有针对人类癌细胞系的抗癌活性。该化合物还表现出微管聚合抑制作用。从没食子酸合成的2-(3',4'-亚甲二氧基苄基)-3-(3",4",5"-三甲氧基苯基)-茚酮-1（2），其分子式为C29H30O9，表现出强大的体内抗癌活性。化合物2在瑞士白化小鼠中进行了急性口服活性评估，发现在300毫克/千克体重的剂量下，实验动物耐受良好。（公式1、公式2）。
• 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。
• TISSUE-PRESERVING LIQUID AND TISSUE-PRESERVING METHOD
  申请人：Osaka University

  公开号：EP2878197A1

  公开（公告）日：2015-06-03

  The present invention provides a tissue preservation sol ution that has good quality for preservation of tissues, org ans and cells, and is useful in the fields of regenerative m edicine, transplantation medicine, etc. The tissue preserva tion solution of the present invention comprises a compound having a Nrf2 activating effect. Preferable compounds havin g a Nrf2 activating effect are electrophiles, and in particu lar, ebselen and tert-butylhydroquinone. A preferable basal solution of the tissue preservation solution is Hank's bala nced salt solution.

  本发明提供了一种组织保存液，它具有良好的组织、器官和细胞保存质量，可用于再生医学、移植医学等领域。本发明的组织保存液包含一种具有 Nrf2 激活作用的化合物。具有 Nrf2 激活作用的化合物最好是嗜电化合物，特别是依布硒和叔丁基对苯二酚。组织保存溶液的基质溶液最好是汉克巴尔德盐溶液。