(E)-3-(4"-methoxy-3''-nitrophenyl)-1-(3',4',5'-trimethoxyphenyl)-2-propen-1-one | 527750-17-0

• 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: (E)-3-(4"-methoxy-3''-nitrophenyl)-1-(3',4',5'-trimethoxyphenyl)-2-propen-1-one
• 英文别名: (2E)-3-(4-methoxy-3-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；(E)-3-(4-methoxy-3-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 527750-17-0
• 化学式: C₁₉H₁₉NO₇
• 分子量: 373.362
• InChiKey: QISDFKAAGWGUJL-FNORWQNLSA-N

物化性质

• 熔点：
  143-145 °C
• 沸点：
  574.4±50.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-(4"-methoxy-3''-nitrophenyl)-1-(3',4',5'-trimethoxyphenyl)-2-propen-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 57.0h， 生成 (3-(4-methoxy-3-nitrophenyl)oxiran-2-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  海胆胚胎模型作为可靠的体内表型筛选来表征选择性抗有丝分裂分子。比较比较Combretapyrazoles，-isoxazoles，-1,2,3-triazoles和-pyrroles作为微管蛋白结合剂

  摘要：

  通过改进的方案合成了一系列新颖的和已报道的康布雷他汀类似物，包括二芳基吡唑，-异恶唑，-1,2,3-三唑和-吡咯，以使用体内海胆胚胎测定法和专家小组评估其抗有丝分裂的抗微管蛋白活性。人类癌细胞 对这些化合物进行了系统的比较结构-活性关系研究。吡唑1i和1p，异恶唑3a和三唑7b被发现是所有测试化合物中最有效的抗有丝分裂剂，分别导致海胆胚胎的裂解改变分别为1、0.25、1和0.5 nM。这些试剂对人癌细胞显示出可比的细胞毒性。结构-活性关系研究表明，被3,4,5-三甲氧基苯基环A和4-甲氧基苯基环B取代的化合物表现出最高的活性。B环中的3-羟基对于二芳基异恶唑系列的抗增殖活性至关重要，而对二芳基吡唑的效力则不是必需的。具有3,4,5-三甲氧基取代的环A和3-羟基-4-甲氧基取代的环B的异恶唑3比各自的吡唑1具有更高的活性。与同一组的其他芳药效团取代的唑类，二芳基的1，4,5- diarylisoxazoles

  DOI：

  10.1021/acscombsci.8b00113
• 作为产物：
  描述：

  3',4',5'-三甲氧基苯乙酮 、 3-羟基-4-硝基苯甲醛 以62%的产率得到(E)-3-(4"-methoxy-3''-nitrophenyl)-1-(3',4',5'-trimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  一种组蛋白去乙酰化酶和微管双靶点抑制剂及其制备方法

  摘要：

  本发明公开了一种组蛋白去乙酰化酶和微管双靶点抑制剂及其制备方法，该抑制剂如I)或II)所示：该抑制剂同时具有微管和组蛋白去乙酰化酶的双重抑制活性。

  公开号：

  CN109651199B

文献信息

• SYNTHESIS AND CYTOTOXIC PROPERTIES OF NITRO- AND AMINOCHALCONES
  作者：Hari N. Pati、Herman L. Holt、Regan LeBlanc、John Dickson、Michelle Stewart、Toni Brown、Moses Lee

  DOI：10.1007/s00044-004-0122-7

  日期：2005.1

  Twenty-two nitro- and aminochalcones were synthesized and characterized. Their cytotoxic properties were determined by a 3-day continuous exposure MTT assay with murine melanoma B16 cells. The aminochalcones were generally more cytotoxic than their nitro precursors. Aminochalcone 18, which has an IC50 value of 0.24 μM, was the most potent compound. The results demonstrated that the number and position

  合成并表征了22个硝基和氨基查耳酮。通过用鼠黑素瘤B16细胞进行3天连续暴露MTT测定来确定它们的细胞毒性特性。氨基查耳酮通常比其硝基前体更具细胞毒性。IC50值为0.24μM的氨基查耳酮18是最有效的化合物。结果表明，环A中甲氧基的数量和位置增强了查耳酮的细胞毒性。B环上氨基的位置也影响细胞毒性。
• Towards dual photodynamic and antiangiogenic agents: design and synthesis of a phthalocyanine-chalcone conjugate
  作者：Sinem Tuncel、Jérémie Fournier-dit-Chabert、Florian Albrieux、Vefa Ahsen、Sylvie Ducki、Fabienne Dumoulin

  DOI：10.1039/c2ob06809e

  日期：——

  A phthalocyanine–chalcone conjugate has been designed to combine the vascular disrupting effect of chalcones with the photodynamic effect of phthalocyanines. This potential dual photodynamic and antiangiogenic agent was obtained by the condensation of a tetrahydroxylated non-peripherally substituted Zn(II) phthalocyanine with an amino chalcone converted into the corresponding activated isocyanate. The conjugate was fully characterized.

  一种酞菁-查尔酮共轭物被设计用于将查尔酮的血管破坏作用与酞菁的光动力作用相结合。这种潜在的双重光动力和抗血管生成剂是通过将四羟基非外围取代的Zn（II）酞菁与氨基查尔酮缩合转化成相应的活性异氰酸酯而获得的。该共轭物已被完全表征。
• Combretastatin a-4 derivatives having antineoplastic activity
  申请人：Lawrence James Nicholas

  公开号：US20050065213A1

  公开（公告）日：2005-03-24

  Compounds are disclosed that are designed to mimic the activity of combretastatin A-4 based on chalcone, aurone, or indanone structures, or involving benzoquinone or quinone rings. The anti-cancer activity of exemplified compounds is demonstrated in a range of in vitro and in vivo assays.

  公开了一些化合物，这些化合物是基于查尔酮、金合欢素或茚酮结构设计的，或涉及苯醌或醌环，旨在模仿紫杉醇A-4的活性。在一系列体外和体内试验中，展示了这些化合物的抗癌活性。
• Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity
  作者：Sylvie Ducki、David Rennison、Meiko Woo、Alexander Kendall、Jérémie Fournier Dit Chabert、Alan T. McGown、Nicholas J. Lawrence

  DOI：10.1016/j.bmc.2009.09.039

  日期：2009.11

  The alpha-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G(2)/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 mu M; CA4, 0.10 mu M) and compete with [H-3] colchicine for binding to tubulin (8% [H-3] colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity. (C) 2009 Elsevier Ltd. All rights reserved.
• The synthesis and Angiotensin Converting Enzyme (ACE) inhibitory activity of chalcones and their pyrazole derivatives
  作者：Marco Bonesi、Monica R. Loizzo、Giancarlo A. Statti、Sylvie Michel、François Tillequin、Francesco Menichini

  DOI：10.1016/j.bmcl.2010.01.113

  日期：2010.3

  A series of chalcones (1-9) and pyrazoles (10-18) was prepared to investigate their potential activity as Angiotensin I-Converting Enzyme (ACE) inhibitors. Their structures were verified by elemental analysis, UV, IR, MS, H-1 NMR, C-13 NMR, and 2D NMR experiments. Among tested compounds, chalcone 7 exerted the highest activity with an IC50 value of 0.219 mM, while the most potent pyrazole was 15 (IC50 value of 0.213 mM). (C) 2010 Elsevier Ltd. All rights reserved.