3,5,4'-trimethoxy-3'-amino-cis-stilbene | 586410-12-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,5,4'-trimethoxy-3'-amino-cis-stilbene
• 英文别名: (Z)-5-(3,5-dimethoxystyryl)-2-methoxyaniline；cis-3,4',5-Trimethoxy-3'-aminostilbene；5-[(Z)-2-(3,5-dimethoxyphenyl)ethenyl]-2-methoxyaniline
• CAS: 586410-12-0
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: OEQWGVQMUXYOJC-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5,4'-trimethoxy-3'-amino-cis-stilbene 以 1,4-二氧六环 为溶剂， 反应 50.0h， 生成 (Z)-{5-[2-(3,5-dimethoxyphenyl)-ethenyl]-2-methoxyphenyl}carbamic acid 2-[2-(2-hydroxyethoxy)ethoxy]ethyl ester
  参考文献：
  名称：

  STILBENE DERIVATIVES AS NEW CANCER THERAPEUTIC AGENTS

  摘要：

  Stilbene衍生物表现出对多种癌细胞的杀灭和抑制生长活性，并且在体内有效地抑制肿瘤生长。Stilbene衍生物可用于治疗以细胞过度增殖为特征的疾病，包括人类恶性肿瘤和非恶性疾病，如肝硬化。Stilbenes也可以破坏肿瘤中的异常血管，实现血管破坏效应以抑制肿瘤生长。水溶性的Stilbene衍生物前药形式在体内抑制肿瘤生长方面特别有用。

  公开号：

  US20080261982A1
• 作为产物：
  描述：

  3-硝基-4-甲氧基苯甲醛 在 正丁基锂 、 sodium dithionite 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 2.0h， 生成 3,5,4'-trimethoxy-3'-amino-cis-stilbene
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Resveratrol and Analogues as Apoptosis-Inducing Agents

  摘要：

  Resveratrol 1 (3,4',5-trihydroxy-trans-stilbene), a phytoalexin present in grapes and other food products, has recently been suggested as a potential cancer chemopreventive agent based on its striking inhibitory effects on cellular events associated with cancer initiation, promotion, and progression. This triphenolic stilbene has also displayed in vitro growth inhibition in a number of human cancer cell lines. In this context, a series of cis- and trans-stilbene-based resveratrols were prepared with the aim of discovering new lead compounds with clinical potential. All the synthesized compounds were tested in vitro for cell growth inhibition and the ability to induce apoptosis in HL60 promyelocytic leukemia cells. The tested trans-stilbene derivatives were less potent than their corresponding cis isomers, except for trans-resveratrol, whose cis isomer was less active. The best results were obtained with compounds 11b and 7b, the cis-3,5-dimethoxy derivatives of rhapontigenin 10a (3,5,3'-trihydroxy-4'methoxy-trans-stilbene) and its 3'-amino derivative 10b, respectively, which showed apoptotic activity at nanomolar concentrations. The corresponding trans isomers 12b and 8b were less active both as antiproliferative and as apoptosis-inducing agents. Of interest, 11b and 7b were active toward resistant HL60R cells and their activity was higher than that of several classic chemotherapeutic agents. The flow cytometry assay showed that at 50 nM compounds 7b or 11b were able to recruit almost all cells in the apoptotic sub-G(0)-G(1) peek, thus suggesting that the main mechanism of cytotoxicity of these compounds could be the activation of apoptosis. These data indicate unambiguously that structural alteration of the stilbene motif of resveratrol can be extremely effective in producing potent apoptosis-inducing agents.

  DOI：

  10.1021/jm030785u

文献信息

• Novel Antiproliferative Chimeric Compounds with Marked Histone Deacetylase Inhibitory Activity
  作者：Elisa Giacomini、Angela Nebbioso、Alfonso Ciotta、Cristina Ianni、Federico Falchi、Marinella Roberti、Manlio Tolomeo、Stefania Grimaudo、Antonietta Di Cristina、Rosaria Maria Pipitone、Lucia Altucci、Maurizio Recanatini

  DOI：10.1021/ml5000959

  日期：2014.9.11

  approach, new chimeric molecules were designed and synthesized by combining in single chemical entities structural features of SAHA, targeting histone deacetylases (HDACs), with substituted stilbene or terphenyl derivatives previously obtained by us and endowed with antiproliferative and pro-apoptotic activity. The new chimeric derivatives were characterized with respect to their cytotoxic activity and their

  考虑到我们对寻找潜在的抗肿瘤药物的兴趣，并鉴于癌症的多因素机制性质，在本工作中，利用多功能配体方法，通过在单个化学实体中结合SAHA的结构特征，设计并合成了新的嵌合分子，靶向组蛋白脱乙酰基酶（HDACs），并由我们先前获得的具有取代基的二苯乙烯或三联苯衍生物赋予抗增殖和促凋亡活性。就它们的细胞毒性活性以及它们对不同肿瘤细胞系上的细胞周期进程的影响以及它们对HDAC的抑制而言，对新的嵌合衍生物进行了表征。其中，反式-6表现出最有趣的生物学特征，
• NOVEL 3,4,5-TRIMETHOXYSTYRYLARYLAMINOPROPENONES AS POTENTIAL ANTICANCER AGENTS
  申请人：Council of Scientific and Industrial Research

  公开号：US20150322009A1

  公开（公告）日：2015-11-12

  The present invention relate to compounds of general formula A. The invention also provides the synthesis of 3,4,5-trimethoxystyrylarylaminopropenones useful as potential antitumor agents against human cancer cell lines and a process for the preparation thereof. wherein: R=H, OMe, Cl, F, OH, Me X=aryl, heteroaryl

  本发明涉及一般式A的化合物。该发明还提供了3,4,5-三甲氧基苯乙烯基芳基氨基丙酮的合成方法，该方法可作为潜在的抗人类癌细胞系的抗肿瘤剂，并提供其制备过程。其中：R=H，OMe，Cl，F，OH，Me，X=芳基，杂环芳基。
• [EN] N-((3,4,5-TRIMETHOXYSTYRYL)ARYL)CINNAMAMIDE COMPOUNDS AS POTENTIAL ANTICANCER AGENTS AND PROCESS FOR THE PREPARATION THEREOF<br/>[FR] COMPOSÉS N-((3,4,5-TRIMÉTHOXYSTYRYL)ARYL)CINNAMAMIDE À UTILISER EN TANT QU'AGENTS ANTICANCÉREUX POTENTIELS ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2016027282A1

  公开（公告）日：2016-02-25

  The present invention provides a compound of general formula A, useful as potential anticancer agents against human cancer cell lines and process for the preparation thereof. [Formula should be entered here] General formula A where in B selected from aryl, heteroaryl and fused heteroaryl ring R and X selected from H, hydroxy, alkyl, alkoxy, prop-2-ynyloxy, allyloxy, halo, alkylhalides, alkoxy halides, nitro, amine.

  本发明提供了一种通用公式A的化合物，该化合物可用作潜在的抗人类癌细胞系的抗癌剂，并提供了其制备方法。[公式应在此处输入]通用公式A，其中B选自芳基、杂芳基和融合的杂芳基环，R和X选自H、羟基、烷基、烷氧基、丙-2-炔氧基、烯丙氧基、卤素、烷基卤素、烷氧基卤素、硝基、胺基。
• 3,4,5-TRIMETHOXYSTYRYLARYLAMINOPROPENONES for the treatment of cancer
  申请人：Council of Scientific and Industrial Research

  公开号：EP2942345A1

  公开（公告）日：2015-11-11

  The present invention relate to compounds of general formula A. The invention also provides the synthesis of 3,4,5-trimethoxystyrylarylaminopropenones useful as potential antitumor agents against human cancer cell lines and a process for the preparation thereof.

  本发明涉及通式 A 的化合物。本发明还提供了 3,4,5-三甲氧基苯乙烯基氨基丙烯酮的合成及其制备方法，该化合物可作为潜在的抗肿瘤剂用于人类癌细胞系。
• Induction of tumor hypoxia for cancer therapy
  申请人：Virginia Commonwealth University

  公开号：US10159676B2

  公开（公告）日：2018-12-25

  Methods and compositions for enhancing the ability of hypoxia-activated bioreductive agents to kill tumor cells within solid tumors are provided. Local regions of hypoxia are created within a tumor, or within a region containing a tumor, resulting in enhanced activation of hypoxia-activated bioreductive agents (e.g. tirapazamine) within the local region. The activated hypoxia-activated bioreductive agents kill tumor cells in the hypoxic region by catalyzing DNA stand breakage within the tumor cells. Because the activity is localized, side effects that typically occur as a result of systemic administration of bioreductive agents are reduced.

  本文提供了增强缺氧激活生物还原剂杀死实体瘤内肿瘤细胞能力的方法和组合物。在肿瘤内或含有肿瘤的区域内形成局部缺氧区域，从而增强局部区域内缺氧激活的生物还原剂（如替拉帕扎胺）的活化。活化的缺氧活化生物还原剂通过催化肿瘤细胞内的 DNA 支架断裂，杀死缺氧区域内的肿瘤细胞。由于生物还原剂的活性是局部的，因此可减少因全身使用生物还原剂而产生的副作用。