(E)-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-4-oxo-2-butenoic acid | 23328-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-4-oxo-2-butenoic acid
• 英文别名: 3-(2-naphthoyl)acrylic acid；4-[2]naphthyl-4-oxo-trans-crotonic acid；4-[2]Naphthyl-4-oxo-trans-crotonsaeure；β-(2-naphthoyl)acrylic acid；trans-3-(2-Naphthoyl)acrylsaeure；β-Naphthoylacrylsaeure；(E)-4-naphthalen-2-yl-4-oxobut-2-enoic acid
• CAS: 23328-06-5
• 化学式: C₁₄H₁₀O₃
• 分子量: 226.232
• InChiKey: BMCVUHWZFQWKRR-BQYQJAHWSA-N

物化性质

• 熔点：
  158-161 °C(Solv: hexane (110-54-3); benzene (71-43-2))
• 沸点：
  436.6±37.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-4-oxo-2-butenoic acid 在 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-4-oxo-4-(5,6,7,8-tetrahydronaphtalenyl)-2-butenoic acid cyclohexylamide
  参考文献：
  名称：

  (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalcone–aroylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization

  摘要：

  Antiproliferative activity of twenty-nine (E)-4-aryl-4-oxo-2-butenoic acid amides against three human tumor cell lines (HeLa, FemX, and K562) is reported. Compounds showed antiproliferative activity in one-digit micromolar to submicromolar concentrations. The most active derivatives toward all the cell lines tested bear alkyl substituents on the aroyl moiety of the molecules. Fourteen compounds showed tubulin assembly inhibition at concentrations <20 mu M. The most potent inhibitor of tubulin assembly was unsubstituted compound 1, with IC50 = 2.9 mu M. Compound 23 had an oral LD50 in vivo of 45 mg/kg in mice. Cell cycle analysis on K562 cells showed that compounds 1, 2 and 23 caused accumulation of cells in the G2/M phase, but inhibition of microtubule polymerization is not the principal mode of action of the compounds. Nevertheless, they may be useful leads for the design of a new class of antitubulin agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.006
• 作为产物：
  描述：

  3-bromo-4-naphthalen-2-yl-4-oxo-butyric acid 在 sodium acetate 、 溶剂黄146 作用下， 生成 (E)-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-4-oxo-2-butenoic acid
  参考文献：
  名称：

  Martin; Stoffyn, Bulletin des Societes Chimiques Belges, 1950, vol. 59, p. 83,87

  摘要：

  DOI：

文献信息

• Hydrogen-Bond-Directed Formal [5 + 1] Annulations of Oxindoles with Ester-Linked Bisenones: Facile Access to Chiral Spirooxindole δ-Lactones
  作者：Shuai Zhao、Jun-Bing Lin、Yuan-Yuan Zhao、Yong-Min Liang、Peng-Fei Xu

  DOI：10.1021/ol500547e

  日期：2014.3.21

  A novel bifunctional thiourea catalyzed formal [5 + 1] cycloaddition of oxindoles and ester-linked bisenones was successfully developed. This strategy involves two sequential Michael additions, leading to spirooxindole δ-lactones with three contiguous stereocenters including an all-carbon quaternary center with high diastereo- and enantioselectivites. In addition, a remarkable N-substituent effect

  一种新型的双功能硫脲催化了羟吲哚和酯连接的双硒酮的正式[5 +1]环加成反应。该策略涉及两个连续的迈克尔加成，从而产生具有三个连续立体中心的螺环吲哚δ-内酯，包括具有高非对映体和对映体选择性的全碳四元中心。另外，在反应性和选择性上观察到了显着的N-取代作用。
• Studies on hypolipidemic agents. IV. 3-(4-(Phenylthio)benzoyl)propionic acid derivatives.
  作者：Kazuya KAMEO、Yumiko ASAMI、Kunio OGAWA、Tohru MATSUNAGA、Shiuji SAITO、Kazuyuki TOMISAWA、Kaoru SOTA

  DOI：10.1248/cpb.37.1260

  日期：——

  2-Acetylthio-3-benzoylpropionic acid derivatives having two benzene rings or condensed-ring moieties were prepared, and tested for hypolipidemic activity in normal rats. Some of these compounds were active. 2-Acetylthio-3-[4-(phenylthio)benzoyl]propionic acid (10) and its derivatives seemed to have the most potent hypocholesterolemic activities. Compound 10 showed strong activity, especially in cholesterol-fed rats.

  合成了具有两个苯环或缩合环结构的2-乙酰硫代-3-苯甲酰丙酸衍生物，并在正常大鼠中测试了其降脂活性。其中一些化合物具有活性。2-乙酰硫代-3-[4-(苯硫基)苯甲酰]丙酸（10）及其衍生物似乎具有最强的降胆固醇活性。化合物10表现出强烈的活性，尤其是在胆固醇喂养的大鼠中。
• Diuretic 2,6-diaryl-4-pyridine carboxylic acids
  申请人：The Upjohn Company

  公开号：US04377586A1

  公开（公告）日：1983-03-22

  The present invention provides a novel method of inducing diuresis by administering certain 2,6-diaryl-4-pyridinecarboxylic acid derivatives. Also provided are novel compounds and pharmaceutical compositions to be used in this method.

  本发明提供了一种通过给予特定的2,6-二芳基-4-吡啶羧酸衍生物来诱导利尿的新方法。同时提供了用于该方法的新化合物和药物组合物。
• 10.1016/j.bioorg.2024.107427
  作者：Lei, Yan-Hua、Tang, Qing、Ni, Yang、Li, Cai-Hua、Luo, Peng、Huang, Kun、Chen, Xin、Zhu, Yong-Xia、Wang, Ning-Yu

  DOI：10.1016/j.bioorg.2024.107427

  日期：——

  therapy. Here, we designed and synthesized a series of p300/CBP targeted low molecular weight PROTACs by assembling the covalent ligand of RNF126 E3 ubiquitin ligase and the bromodomain ligand of the p300/CBP. The optimal molecule could effectively degrade p300 and CBP through the ubiquitin–proteasome system in time- and concentration-dependent manners, with half-maximal degradation (DC) concentrations

  组蛋白乙酰转移酶 CREB ​​结合蛋白 (CBP) 及其同源蛋白 p300 是关键的转录激活因子，可以激活癌基因转录，为癌症治疗提供了有希望的靶点。在这里，我们通过组装RNF126 E3泛素连接酶的共价配体和p300/CBP的溴结构域配体，设计并合成了一系列p300/CBP靶向的低分子量PROTAC。最佳分子可以通过泛素-蛋白酶体系统以时间和浓度依赖性方式有效降解 p300 和 CBP，MV4- 中 p300/CBP 的半最大降解 (DC) 浓度为 208.35/454.35 nM 和 82.24/79.45 nM处理 72 小时后的 11 和 Molm13 细胞系。 p300/CBP 的降解依赖于泛素-蛋白酶体途径及其与靶蛋白和 RNF126 的同时相互作用。在一系列 p300/CBP 依赖性癌细胞中表现出良好的抗增殖活性。它可以转录抑制c-Myc的表达，诱导细胞周期停滞在G0/G1期
• Julia; Bonnet, Bulletin de la Societe Chimique de France, 1957, p. 1354,1357
  作者：Julia、Bonnet

  DOI：——

  日期：——