(2E)-2-氰基-3-(4-羟基-3-甲氧基苯基)丙烯酰胺 | 138175-49-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: (2E)-2-氰基-3-(4-羟基-3-甲氧基苯基)丙烯酰胺
• 英文名称: (E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylamide
• 英文别名: Akos bbs-00008114；(E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• CAS: 138175-49-2
• 化学式: C₁₁H₁₀N₂O₃
• 分子量: 218.212
• InChiKey: XGWRIMMSDUGXTL-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  96.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-2-氰基-3-(4-羟基-3-甲氧基苯基)丙烯酰胺 在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以69%的产率得到(E)-3-[5'-((E)-2-Carbamoyl-2-cyano-vinyl)-6,2'-dihydroxy-5,3'-dimethoxy-biphenyl-3-yl]-2-cyano-acrylamide
  参考文献：
  名称：

  Structural Studies on Bioactive Compounds. 32. Oxidation of Tyrphostin Protein Tyrosine Kinase Inhibitors with Hypervalent Iodine Reagents

  摘要：

  Hydroxylated styrenes (tyrphostins) undergo oxidation by hypervalent iodine oxidants such as [(diacetoxy)iodo]benzene (DAIB) to give a range of products depending on the structure of the phenolic substrate, the solvent, the oxidant stoichiometry, and the purification strategy. Conditions have been developed to modify the phenolic component of the tyrphostin without affecting the appended substituted-vinyl moiety. Novel products include: unstable 2-acyloxy-2-methoxy-4-(substituted-vinyl)cyclohexadienones and their rearrangement products 2-acyloxy-4-hydroxy-3 -methoxy-1-(substituted-vinyl)benzenes; phenyliodoniophenolates and their rearrangement products iodophenoxytyrphostins; and 3,3'-dialkoxy-2,2'-dihydroxy-5,5'-di(substituted-vinyl)biphenyls. None of these oxidation products displayed enhanced activity in vitro in the NCI 60-cell line panel or in a panel of human breast cancer cell lines, compared to their tyrphostin precursors. The inhibitory activity of three representative tyrphostins (3e,n, 28) was not modulated by aerobic/anaerobic conditions in MCF-7 and MDA 468 cells and was independent of EGFR status in clones of ZR75B cells transfected with this receptor. Basal growth of MCF-7 cells was unaffected by co-administration of the growth factors EGF, TGF-alpha, IGF-I, and IGF-II, and the new agents did not inhibit EGFR and c-erbB2 autaphosphorylation in cell lysates from MDA 468 or SkBr3 cells, respectively, suggesting that receptor tyrosine kinases are not targets for these compounds. Growth stimulation by the tyrphostin 3n in the ER+ breast cell lines MCF-7, T47D, and ZR75-1 was abolished by 1 mu M tamoxifen, suggesting that this compound has estrogen agonist activity.

  DOI：

  10.1021/jm990947f
• 作为产物：
  描述：

  2-(4-hydroxy-3-methoxybenzylidene)malononitrile 在 copper(II) acetate monohydrate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 7.0h， 以93%的产率得到(2E)-2-氰基-3-(4-羟基-3-甲氧基苯基)丙烯酰胺
  参考文献：
  名称：

  LQFM184：一种新型的宽紫外辐射范围吸收剂化合物

  摘要：

  由于紫外线辐射是人类皮肤的关键环境压力因素，因此使用防晒霜已成为必不可少的日常工作。本研究侧重于作为光保护剂的新型杂环衍生物 LQFM184 的设计、合成、热/化学稳定性和功效/安全性评估。该化合物在氧化和高温条件下表现出稳定性。它还揭示了在 260-340 nm (UVA/UVB) 处的吸收，主带在 298 nm，肩带接近 334 nm。LQFM184 显示出与其他现有紫外线过滤剂相互作用的能力，促进防晒系数的增加。就急性毒性而言，其估计 LD50 为 > 300-2000 mg/kg，可能诱发急性口服全身毒性危害的可能性较低。此外，我们的数据表明，该化合物没有眼睛刺激性、皮肤致敏性或潜在的光毒性。综上所述，这些发现使 LQFM184 成为一种很有前景的成分，可以单独使用或与其他紫外线过滤剂结合使用，用于具有广谱保护作用的防晒霜等化妆品中。

  DOI：

  10.1111/php.13349

文献信息

• Tellurium(IV) tetrachloride catalysed facile knoevenagel reaction
  作者：Rahat H. Khan、Raj K. Mathur、Anil C. Ghosh

  DOI：10.1080/00397919608086741

  日期：1996.2

  Abstract Non-enolisable aldehydes (I) and active methylene compounds (II) react in the presence of tellurium(IV) tetrachloride (catalytic) to give the corresponding α, β-unsaturated carbonyl compounds (III) in excellent yields and high purity.

  摘要 不可烯醇化的醛 (I) 和活性亚甲基化合物 (II) 在四氯化碲 (IV)（催化）存在下反应，以优异的收率和高纯度反应生成相应的 α, β-不饱和羰基化合物 (III)。
• Zinc chloride as a new catalyst for knoevenagel condensation
  作者：P. Shanthan Rao、R.V. Venkataratnam

  DOI：10.1016/s0040-4039(00)93564-0

  日期：1991.10
• Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases
  作者：Christoph Nitsche、Christian Steuer、Christian D. Klein

  DOI：10.1016/j.bmc.2011.10.061

  日期：2011.12

  The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a K(i)-value of 35.7 mu M at the Dengue and 44.6 mu M at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles
  作者：Yingtian Liu、Xinxin Dang、Yu He、Hudong Bai、Xuehong Chen、Jun-Long Li、Junting Fan、Hezhong Jiang、Jiahong Li

  DOI：10.1080/00397911.2018.1542496

  日期：2019.3.4

  A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions with good to excellent yield.[GRAPHICS].
• Bose, D. Subhas; Narsaiah, A. Venkat, Journal of Chemical Research - Part S, 2001, # 1, p. 36 - 38
  作者：Bose, D. Subhas、Narsaiah, A. Venkat

  DOI：——

  日期：——