(E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one | 88775-43-3

• 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)-1-(benzo[d][1,3]dioxol-5-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (2E)-1-(1,3-benzodioxol-5-yl)-3-(2,4,5-trimethoxyphenyl)-2-propen-1-one；2,4,5-trimethoxy-3',4'-methylenedioxychalcone；(E)-1-(1,3-benzodioxol-5-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 88775-43-3
• 化学式: C₁₉H₁₈O₆
• 分子量: 342.348
• InChiKey: GXEJRHRTNZOHKM-GQCTYLIASA-N

物化性质

• 沸点：
  534.2±50.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  氰化钾 、 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one 以 乙二醇乙醚 、 水 、 溶剂黄146 为溶剂， 反应 1.0h， 以19.7 g的产率得到4-(3,4-methylenedioxyphenyl)-4-oxo-2-(2,4,5-trimethoxyphenyl)butyronitrile
  参考文献：
  名称：

  Studies on the chemical constituents of rutaceous plants. XLIX. Development of a versatile method for the synthesis of antitumor-active benzo(c)phenanthridine alkaloids. 1. Preparation of various 2,4-bisaryl-4-oxobutyronitriles and 2,4-bisaryl-4-oxobutyramides.

  摘要：

  为了建立一种通用的苯并[c]菲啶生物碱合成方法，对Robinson合成方法进行了改进。通过将两个乙酰苯衍生物（15和16）与十一种苯甲醛衍生物（19a-k）缩合，制备了十三种查尔酮（7a-m）作为基本起始材料。除了一个查尔酮（7m）外，这些查尔酮（7a-l）的氰化反应得到了相应的2,4-双芳基-4-氧代丁腈（8a-l）。还制备了十一种2,4-双芳基-4-氧代丁酰胺（9a-k）。

  DOI：

  10.1248/cpb.31.3024
• 作为产物：
  描述：

  1,2,4-三甲氧基苯 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Studies on the chemical constituents of rutaceous plants. XLIX. Development of a versatile method for the synthesis of antitumor-active benzo(c)phenanthridine alkaloids. 1. Preparation of various 2,4-bisaryl-4-oxobutyronitriles and 2,4-bisaryl-4-oxobutyramides.

  摘要：

  为了建立一种通用的苯并[c]菲啶生物碱合成方法，对Robinson合成方法进行了改进。通过将两个乙酰苯衍生物（15和16）与十一种苯甲醛衍生物（19a-k）缩合，制备了十三种查尔酮（7a-m）作为基本起始材料。除了一个查尔酮（7m）外，这些查尔酮（7a-l）的氰化反应得到了相应的2,4-双芳基-4-氧代丁腈（8a-l）。还制备了十一种2,4-双芳基-4-氧代丁酰胺（9a-k）。

  DOI：

  10.1248/cpb.31.3024

文献信息

• Synthesis, Characterization and Antimicrobial Activities of Chalcones and Their Post Transformation to Pyrazole Derivatives
  作者：D. Ramyashree、K.R. Raghavendra、A. Dileep Kumar、C.B. Vagish、K. Ajay Kumar

  DOI：10.14233/ajchem.2017.20561

  日期：——

  An efficient procedure for the synthesis of trisubstituted pyrazoles was developed. Claisen-Schmidt condensation of 2,4,5-trimethoxybenzaldehyde and substituted acetophenone in the presence of aqueous alkaline bases produced chalcones. The cyclocondensation reaction of chalcones and phenyl hydrazine hydrochloride catalyzed by an acid produced trisubstituted pyrazolines in good yields. The synthesized new compounds were characterized by spectral studies and elemental analysis and some of the intermediate chalcones by single crystal X-ray diffraction studies. The compounds were screened in vitro for their antimicrobial susceptibilities against different bacteria and fungi species.

  开发了一种合成三取代吡唑的高效工艺。在含水碱性条件下，2,4,5-三甲氧基苯甲醛与取代苯乙酮进行克莱森-施密特缩合反应，生成查耳酮。在酸催化下，查耳酮与苯肼盐酸盐发生环化缩合反应，以良好产率生成三取代吡唑啉。通过光谱研究和元素分析对合成的新化合物进行了表征，部分中间体查耳酮通过单晶X射线衍射研究进行了鉴定。对这些化合物进行了体外抗菌活性筛选，测试了它们对不同细菌和真菌种类的抗菌敏感性。
• Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi
  作者：Deise M. Borchhardt、Alessandra Mascarello、Louise Domeneghini Chiaradia、Ricardo J. Nunes、Glaucius Oliva、Rosendo A. Yunes、Adriano D. Andricopulo

  DOI：10.1590/s0103-50532010000100021

  日期：——

  Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC50 values in the range of 20-60 mu M), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series.
• Synthetic compounds from an <i>in house</i> library as inhibitors of falcipain-2 from <i>Plasmodium falciparum</i>
  作者：Jean Borges Bertoldo、Louise Domeneghini Chiaradia-Delatorre、Alessandra Mascarello、Paulo César Leal、Marlon Norberto Sechini Cordeiro、Ricardo José Nunes、Emir Salas Sarduy、Philip Jon Rosenthal、Hernán Terenzi

  DOI：10.3109/14756366.2014.920839

  日期：2015.3.4

  Falcipain-2 (FP-2) is a key cysteine protease from the malaria parasite Plasmodium falciparum. Many previous studies have identified FP-2 inhibitors; however, none has yet met the criteria for an antimalarial drug candidate. In this work, we assayed an in-house library of non-peptidic organic compounds, including (E)-chalcones, (E)-N'-benzylidene-benzohydrazides and alkylesters of gallic acid, and assessed the activity toward FP-2 and their mechanisms of inhibition. The (E)-chalcones 48, 54 and 66 showed the lowest IC50 values (8.5 +/- 0.8 mu M, 9.5 +/- 0.2 mu M and 4.9 +/- 1.3 mu M, respectively). The best inhibitor (compound 66) demonstrated non-competitive inhibition, and using mass spectrometry and fluorescence spectroscopy assays, we suggest a potential allosteric site for the interaction of this compound, located between the catalytic site and the hemoglobin binding arm in FP-2. We combined structural biology tools and mass spectrometry to characterize the inhibition mechanisms of novel compounds targeting FP-2.