(E)-3-[benzo(d)1,3-dioxol-5-yl]-1-[naphth-2-yl]prop-2-en-1-one | 52601-57-7

• 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-[benzo(d)1,3-dioxol-5-yl]-1-[naphth-2-yl]prop-2-en-1-one
• 英文别名: (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(naphthalen-2-yl)prop-2-en-1-one；2-<3.4-Methylendioxy-cinnamoyl>-naphthalin；(2E)-1-(2-naphthyl)-3-(1,3-benzodioxol-5-yl)-2-propen-1-one；3t-benzo[1,3]dioxol-5-yl-1-[2]naphthyl-propenone；3t-Benzo[1,3]dioxol-5-yl-1-[2]naphthyl-propenon；3-benzo[1,3]dioxol-5-yl-1-[2]naphthyl-propenone；3-Benzo[1,3]dioxol-5-yl-1-[2]naphthyl-propenon；3-(1,3-Benzodioxol-5-yl)-1-(2-naphthyl)prop-2-en-1-one；(E)-3-(1,3-benzodioxol-5-yl)-1-naphthalen-2-ylprop-2-en-1-one
• CAS: 52601-57-7
• 化学式: C₂₀H₁₄O₃
• 分子量: 302.329
• InChiKey: UIASZIZNIOGSLS-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-[benzo(d)1,3-dioxol-5-yl]-1-[naphth-2-yl]prop-2-en-1-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  国家统计局介导的环化反式-肉桂醇

  摘要：

  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。

  DOI：

  10.1016/j.tet.2013.05.110
• 作为产物：
  描述：

  胡椒醛 、 2-萘乙酮 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-3-[benzo(d)1,3-dioxol-5-yl]-1-[naphth-2-yl]prop-2-en-1-one
  参考文献：
  名称：

  与姜黄素有关的芳族烯酮的合成及生物学评价。

  摘要：

  姜黄素是从香料姜黄中分离得到的天然产物，已显示出广泛的药理活性，包括某些抗癌特性。它已被明确地证明是在体外和体内血管生成的有效抑制剂。使用姜黄素作为抗血管生成类似物设计的先导化合物，已经合成了一系列利用取代的查尔酮骨架的结构相关化合物，并通过已建立的SVR细胞增殖测定法进行了测试。结果产生了范围广泛的化合物，这些化合物等于或超过姜黄素体外抑制内皮细胞生长的能力。由于它们的商业可获得性和相当简单的合成制备方法，这些低分子量化合物是开发未来血管生成抑制剂的诱人线索。

  DOI：

  10.1016/j.bmc.2005.03.054

文献信息

• Synthesis and biological evaluation of naphthalene, furan and pyrrole based chalcones as cytotoxic and antimicrobial agents
  作者：Abhishek Budhiraja、Kanika Kadian、Mandeep Kaur、Vikas Aggarwal、Atul Garg、Sameer Sapra、Kunal Nepali、O. P. Suri、K. L. Dhar

  DOI：10.1007/s00044-011-9733-y

  日期：2012.9

  but in the present study we report the reactions of 1-acetylnaphthalene, 2-acetylfuran and 2-acetylpyrrole with aldehydes, thus getting compounds akin to chalcones. 31 analogues have been synthesised and evaluated for cytotoxic potential against PC-3, OVCAR, IMR-32 and HEP-2. Compound 9 was found to be the most cytotoxic with inhibition ranging from 72 to 88% against the cell lines employed. The synthetics

  摘要查耳酮是一种芳香族酮，可形成多种重要生物化合物（统称为查耳酮）的核心。它们显示出抗菌，抗真菌，抗肿瘤和抗炎特性，并且是类黄酮生物合成的中间体，类黄酮是植物中广泛存在的具有一系列生物活性的物质。这些联芳基丙烯酮对几种癌细胞显示出强力毒性，并在其秋水仙碱结合位点与微管蛋白相互作用。微管蛋白结合分子干扰微管的动态不稳定性，从而破坏微管，诱导细胞周期停滞在M期，形成异常纺锤体并最终导致凋亡性细胞死亡。基本上，Chalcones由C 6 –C 3 –C 6组成单位，但在本研究中，我们报道了1-乙酰基萘，2-乙酰基呋喃和2-乙酰基吡咯与醛的反应，从而得到类似于查耳酮的化合物。已合成了31种类似物，并评估了其对PC-3，OVCAR，IMR-32和HEP-2的细胞毒性。发现化合物9对细胞毒性最大，对所用细胞系的抑制作用范围为72％至88％。还评估了合成物的抗菌活性，发现化合物25最有效。 图形概要合成
• A new series of thiazolyl pyrazoline derivatives linked to benzo[1,3]dioxole moiety: Synthesis and evaluation of antimicrobial and anti-proliferative activities
  作者：Eman Mansour、Asmaa Aboelnaga、Ekhlass M. Nassar、Safaa I. Elewa

  DOI：10.1080/00397911.2019.1695839

  日期：2020.2.1

  compounds show interesting biological properties as antimicrobial and antiproliferative activities, the results of minimum inhibitory concentration showed that pyrazole derivative 7c (MIC: 0.23 mg/mL) showed better results when compared with 11c and 12a (MIC: 0.1–0.125 mg/mL) as obtained from their MIC values. On the other hand, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(naphthalen-2-yl)-4,5-dihydro-1H-pyr

  摘要 2-(5-(Benzo[d][1,3]dioxol-5-yl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4- (4-取代苯基)噻唑 (7) 和噻唑衍生物 (9) 分别通过 4,5-二氢-1H-吡唑 (5a,b) 与取代苯甲酰溴和许多α-卤代化合物的反应合成。此外，(E)-2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(naphthalen-1-yl)-4,5 dihydro-1H-pyrazol-1-yl )-4-甲基-5-(取代的苯基二氮烯基)噻唑(11)通过硫代碳酰胺(5a,b)与腙酰卤的反应制备。此外，硫代酰胺（5a-b）被用作制备噻唑（12a-b）和亚苄基噻唑（13a-b）的起始材料。大多数合成的化合物显示出有趣的生物学特性，如抗菌和抗增殖活性，最低抑菌浓度的结果表明，与 11c 和 12a（MIC：0
• Synthesis of 1-substituted 3,5-diaryl-2-pyrazolines by the reaction of α,β-unsaturated ketones with hydrazines
  作者：Albert Lévai、József Jekö

  DOI：10.1002/jhet.5570430117

  日期：2006.1

  1-Acetyl-, 1-propionyl- and 1-phenyl-3,5-diaryl-2-pyrazolines have been synthesized by the reaction of the appropriate α,β-unsaturated ketones with hydrazine or phenylhydrazine in hot acetic acid or propionic acid. Structures of all new 2-pyrazolines 16-40 have been elucidated by microanalyses, 1H and 13C nmr spectroscopies.

  通过适当的α，β-不饱和酮与肼或苯肼在热乙酸或丙酸中的反应，已经合成了1-乙酰基，1-丙酰基-和1-苯基-3，5-二芳基-2-吡唑啉。所有新的2-吡唑啉16-40的结构已通过微量分析，1 H和13 C nmr光谱学得以阐明。
• Naphthylchalcones induce apoptosis and caspase activation in a leukemia cell line: The relationship between mitochondrial damage, oxidative stress, and cell death
  作者：Evelyn Winter、Louise Domeneghini Chiaradia、Clarissa A.S. de Cordova、Ricardo José Nunes、Rosendo Augusto Yunes、Tânia Beatriz Creczynski-Pasa

  DOI：10.1016/j.bmc.2010.09.025

  日期：2010.11

  In this study, we investigated the effects of 24 chalcone derivatives from 2-naphthylacetophenone toward a lymphoblastic leukemia cell line (L1210). Three compounds, called R7, R13, and R15, presented concentration- and time-dependent cytotoxicity and induced cellular death by apoptosis via mitochondrial injury and oxidative stress. The effects of these compounds appear to occur through different mechanisms because R13 and R7 induced a greater disturbance of mitochondrial potential, and all compounds induced disturbances of cellular ATP content and increased caspase-3 activity before cellular death. These compounds also interfered with antioxidant enzymes activities and GSH content through different mechanisms. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.