3-(2,5-dimethoxyphenyl)-1-phenyl-2-propenone | 81885-90-7

• 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: 3-(2,5-dimethoxyphenyl)-1-phenyl-2-propenone
• 英文别名: 3-(2,5-Dimethoxyphenyl)-1-phenylprop-2-en-1-one
• CAS: 81885-90-7
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: CFTGFQGJNBMNFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-(2,5-dimethoxyphenyl)-1-phenyl-2-propenone 、 肼甲酰亚胺酰胺一氯化氢 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以42%的产率得到(Z)-2-((E)-3-(2,5-dimethoxyphenyl)-1-phenylallylidene)hydrazinecarboximidamide
  参考文献：
  名称：

  Rational design, synthesis and in vitro evaluation of allylidene hydrazinecarboximidamide derivatives as BACE-1 inhibitors

  摘要：

  BACE-1 (beta-secretase) is considered to be one of the promising targets for treatment of Alzheimer's disease as it catalyzes the rate limiting step of A beta-42 production. Herein, we report a novel class of allylidene hydrazinecarboximidamide derivatives as moderately potent BACE-1 inhibitors, having aminoguanidine substitution on allyl linker with two aromatic groups on either side. A library of derivatives was designed based on the docking studies, synthesized and evaluated for BACE-1 inhibition in vitro. The designed ligands displayed interactions with the catalytic aspartate dyad through guanidinium functionality. Further, the aromatic rings placed on either side of the linker occupied S1 and S3 active site regions contributing to the activity. These ligands were also predicted to follow Lipinski rule and cross blood brain barrier. Compound 2.21, having high docking score, was found to be most active with IC50 of 6.423 mu M indicating good correlation with docking prediction. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.044
• 作为产物：
  描述：

  2,5-二甲氧基苯甲醛 、 苯乙酮 在 硫酸 、 溶剂黄146 作用下， 反应 10.0h， 生成 3-(2,5-dimethoxyphenyl)-1-phenyl-2-propenone
  参考文献：
  名称：

  3,5-二芳基-4,5-二氢-1H-吡唑甲醛作为非嘌呤黄嘌呤氧化酶抑制剂的设计、合成、生物学评价：通过黄嘌呤氧化酶抑制追踪抗癌机制

  摘要：

  黄嘌呤氧化酶 (XO) 主要用于开发抗高尿酸血症/抗痛风剂，因为它催化黄嘌呤和次黄嘌呤转化为尿酸。由于催化过程中活性氧 (ROS) 的产生和致癌物质的代谢活化，XO 在各种癌症中的过度表达非常相关。在此，我们报告了一系列 3,5-二芳基-4,5-二氢-1 H-吡唑甲醛衍生物 ( 2a - 2x) 作为黄嘌呤氧化酶抑制剂 (XOI)。开发了一种对接模型，用于预测我们的新型化合物的 XO 抑制活性。此外，我们的化合物抗癌活性导致 2D 和 3D 培养模型中的低 XO 表达和 XO 携带癌细胞。合成的化合物的阵列中，图2b和2米成为具有IC强效抑制剂XO 50值分别为 9.32 ± 0.45 µM 和 10.03 ± 0.43 µM。这两种化合物均诱导细胞凋亡，在 G1 期停止细胞周期进程，提高 ROS 水平，改变线粒体膜电位，并抑制抗氧化酶。由于我们的化合物诱导的氧化应激增加，细胞中 miRNA

  DOI：

  10.1016/j.bioorg.2020.104620

文献信息

• Lithium hydroxide mediated synthesis of 3,4-disubstituted pyrroles
  作者：Ratnesh Sharma、Kapil Kumar、Mangilal Chouhan、Vikas Grover、Vipin A. Nair

  DOI：10.1039/c3ra42569j

  日期：——

  LiOH·H2O in ethanol was found to be an effective reagent for the synthesis of 3,4-disubstituted pyrrole derivatives by the van Leusen method. In situ formation of chalcones from aromatic aldehydes and enolisable ketones, and their subsequent reaction with tosylmethyl isocyanide resulted in the formation and precipitation of pyrrole derivatives from the reaction medium, in good yields. The solvation effect of the polar medium facilitates the reaction.

  在乙醇中，LiOH·H2O被发现是通过van Leusen方法合成3,4-二取代吡咯衍生物的有效试剂。从芳香醛和可烯醇化的酮原位形成的查尔酮，与对甲苯磺酰甲基异氰化物的后续反应导致了吡咯衍生物在反应介质中形成并沉淀，产率良好。极性溶剂的溶剂化效应促进了反应的进行。
• A boron–nitrogen transborylation enabled, borane-catalysed reductive cyanation of enones
  作者：Kieran Benn、Kieran Nicholson、Thomas Langer、Stephen P. Thomas

  DOI：10.1039/d1cc03649a

  日期：——

  introduction of a nitrile group into organic molecules and an orthogonal route for the installation of a wide array of functional groups using simple transformations. Cyanation methods are dominated by transition metal catalysis and the use of hydrogen cyanide gas. Here, the electrophilic cyanation of enones was achieved using a main-group catalyst and a non-toxic, electrophilic cyanide source. This protocol

  氰化提供了一种将腈基引入有机分子的简单方法，以及使用简单转化安装各种官能团的正交途径。氰化方法主要是过渡金属催化和使用氰化氢气体。在这里，烯酮的亲电氰化是使用主基催化剂和无毒的亲电氰化物源实现的。该协议适用于广泛的底物范围，包括那些含有可还原官能团的底物。机理研究表明，氨基硼烷中间体经过 B-N 转移（B -N / B- H 交换）以实现催化转化。
• Design, synthesis, biological evaluation of 3,5-diaryl-4,5-dihydro-1H-pyrazole carbaldehydes as non-purine xanthine oxidase inhibitors: Tracing the anticancer mechanism via xanthine oxidase inhibition
  作者：Gaurav Joshi、Manisha Sharma、Sourav Kalra、Navnath S. Gavande、Sandeep Singh、Raj Kumar

  DOI：10.1016/j.bioorg.2020.104620

  日期：2021.2

  (2a-2x) as xanthine oxidase inhibitors (XOIs). A docking model was developed for the prediction of XO inhibitory activity of our novel compounds. Furthermore, our compounds anticancer activity results in low XO expression and XO-harboring cancer cells both in 2D and 3D-culture models are presented and discussed. Among the array of synthesized compounds, 2b and 2m emerged as potent XO inhibitors having

  黄嘌呤氧化酶 (XO) 主要用于开发抗高尿酸血症/抗痛风剂，因为它催化黄嘌呤和次黄嘌呤转化为尿酸。由于催化过程中活性氧 (ROS) 的产生和致癌物质的代谢活化，XO 在各种癌症中的过度表达非常相关。在此，我们报告了一系列 3,5-二芳基-4,5-二氢-1 H-吡唑甲醛衍生物 ( 2a - 2x) 作为黄嘌呤氧化酶抑制剂 (XOI)。开发了一种对接模型，用于预测我们的新型化合物的 XO 抑制活性。此外，我们的化合物抗癌活性导致 2D 和 3D 培养模型中的低 XO 表达和 XO 携带癌细胞。合成的化合物的阵列中，图2b和2米成为具有IC强效抑制剂XO 50值分别为 9.32 ± 0.45 µM 和 10.03 ± 0.43 µM。这两种化合物均诱导细胞凋亡，在 G1 期停止细胞周期进程，提高 ROS 水平，改变线粒体膜电位，并抑制抗氧化酶。由于我们的化合物诱导的氧化应激增加，细胞中 miRNA
• Rational design, synthesis and in vitro evaluation of allylidene hydrazinecarboximidamide derivatives as BACE-1 inhibitors
  作者：Priti Jain、Pankaj K. Wadhwa、Shilpa Rohilla、Hemant R. Jadhav

  DOI：10.1016/j.bmcl.2015.11.044

  日期：2016.1

  BACE-1 (beta-secretase) is considered to be one of the promising targets for treatment of Alzheimer's disease as it catalyzes the rate limiting step of A beta-42 production. Herein, we report a novel class of allylidene hydrazinecarboximidamide derivatives as moderately potent BACE-1 inhibitors, having aminoguanidine substitution on allyl linker with two aromatic groups on either side. A library of derivatives was designed based on the docking studies, synthesized and evaluated for BACE-1 inhibition in vitro. The designed ligands displayed interactions with the catalytic aspartate dyad through guanidinium functionality. Further, the aromatic rings placed on either side of the linker occupied S1 and S3 active site regions contributing to the activity. These ligands were also predicted to follow Lipinski rule and cross blood brain barrier. Compound 2.21, having high docking score, was found to be most active with IC50 of 6.423 mu M indicating good correlation with docking prediction. (C) 2015 Elsevier Ltd. All rights reserved.