(E)-3-(4-hydroxy-3-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one | 1352346-97-4

• 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-(4-hydroxy-3-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one
• CAS: 1352346-97-4
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: UWLUYCAMCMIRGK-KRXBUXKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one 在 potassium carbonate 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 1-(4,5-Dihydro-5-(3-methoxy-4-(prop-2-ynyloxy)phenyl)-3-(4-nitrophenyl)pyrazol-1-yl)ethanone
  参考文献：
  名称：

  通过点击化学合成1,2,3-三唑系留双功能杂化物及其细胞毒性研究

  摘要：

  考虑到目前使用的大多数抗癌药物的耐药性，已合成了吡唑基查耳酮和由三唑环束缚的对硝基苄基官能团的分子杂合物，并评估了其对三种人类癌细胞系（THP，COLO-205）的细胞毒性研究，A-549）。初步研究的结果显示出细胞毒性活性对电子因子的显着依赖性。萘基（JGPT-11）和三甲氧基苯基环（JGPT-6）作为环A的放置被证明对增强细胞毒性潜力极为有利。因此，我们在本文中报道了新型分子杂合体的合成和细胞毒性研究。对JGPT-11和6的生物学机理的详细研究正在进行中。

  DOI：

  10.1007/s00044-012-0312-7
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以84%的产率得到(E)-3-(4-hydroxy-3-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Discovery of a Locally and Orally Active CXCL12 Neutraligand (LIT-927) with Anti-inflammatory Effect in a Murine Model of Allergic Airway Hypereosinophilia

  摘要：

  We previously reported Chalcone-4 (1) that binds the chemokine CXCL12, not its cognate receptors CXCR4 or CXCR7, and neutralizes its biological activity. However, this neutraligand suffers from limitations such as poor chemical stability, solubility, and oral activity. Herein, we report on the discovery of pyrimidinone 57 (LIT-927), a novel neutraligand of CXCL12 which displays a higher solubility than 1 and is no longer a Michael acceptor. While both 1 and 57 reduce eosinophil recruitment in a murine model of allergic airway hypereosinophilia, 57 is the only one to display inhibitory activity following oral administration. Thereby, we here describe 57 as the first orally active CXCL12 neutraligand with anti-inflammatory properties. Combined with a high binding selectivity for CXCL12 over other chemokines, 57 represents a powerful pharmacological tool to investigate CXCL12 physiology in vivo and to explore the activity of chemokine neutralization in inflammatory and related diseases.

  DOI：

  10.1021/acs.jmedchem.8b00657

文献信息

• Synthesis and cdc25B inhibitory activity evaluation of chalcones
  作者：Fei Zhao、Qing-Jie Zhao、Jing-Xia Zhao、Da-Zhi Zhang、Qiu-Ye Wu、Yong-Sheng Jin

  DOI：10.1007/s10600-013-0563-7

  日期：2013.5

  A library of sixty-five chalcones was prepared for screening against the protein phosphatase, cdc25B. From this library, thirteen compounds were found having good inhibitory activity. Two compounds have excellent activity and can be used for the design of more potent antiproliferative agents.

  制备了一个包含六十五种查尔酮的库，用于针对蛋白磷酸酶cdc25B进行筛选。从这个库中，发现了十三种具有良好抑制活性的化合物。其中两种化合物表现出极佳的活性，可用于设计更有效的抗增殖剂。
• Synthesis and biological activity of new chalcone scaffolds as prospective antimicrobial agents
  作者：Sangeeta Narwal、Sanjiv Kumar、Prabhakar Kumar Verma

  DOI：10.1007/s11164-020-04359-6

  日期：2021.4

  group which is liable for the antimicrobial activity of the chalcone is additionally of vast use in further chemical modification into a variety of heterocyclic compounds. A new series of chalcone derivatives was synthesized and characterized by spectral analysis (IR, 1H-NMR, 13C-NMR, MS and elemental analysis) and evaluated for its in vitro antimicrobial activity against bacterial (Gram negative and Gram

  Chalcones是含有两个芳香环的开链类黄酮，由3个碳原子的α-，β-不饱和羰基链连接。的，β对查尔酮的抗微生物活性负责的不饱和酮基在进一步化学修饰成各种杂环化合物中还具有广泛的用途。合成了一系列新的查尔酮衍生物，并通过光谱分析（IR，1H-NMR，13C-NMR，MS和元素分析）进行了表征，并使用以下方法评估了其对细菌（革兰氏阴性和革兰氏阳性）和真菌菌株的体外抗菌活性管稀释法。抗菌筛查结果显示，一些化合物系列1（MICpa = 1.16 µM），3（MICbs = 1.82 µM），6（MICan = 2.09 µM），8（MICec和se = 0.94和1.88 µM）和17（MICsa （ca = 0.91和1.81 µM）对革兰氏阳性和革兰氏阴性细菌和真菌菌株均显示出最有希望的抗菌活性，
• Synthesis and anticancer activity of chalcones derived from vanillin and isovanillin
  作者：Saiharish Raghavan、Prasath Manogaran、Balasubramanian Kalpattu Kuppuswami、Ganesh Venkatraman、Krishna Kumari Gadepalli Narasimha

  DOI：10.1007/s00044-015-1453-2

  日期：2015.12

  An array of chalcones from vanillin/isovanillin and differently substituted acetophenones were synthesized and assessed for their anticancer activity against A549, MCF7 and MIA PaCa-2 cell lines using MTT assay. Some of the chalcones exhibited good anticancer activity with IC50 values below 10 mu M. Compound 5f with IC50 values 5.4 +/- A 0.7, 10.45 +/- A 2.15 and 13.0 +/- A 1.68 A mu M on MIA PaCa-2, A549 and MCF7, respectively, was more potent than curcumin and hence was analyzed for changes in cell morphology, inhibition of cell migration, mechanism of cell death and arrest of cell cycle progression on MIA PaCa-2 cells.
• Synthesis, molecular docking, antiproliferative and radical scavenging activities of vanillin derived 1,3,5-trisubstituted 2-pyrazolines
  作者：Deshpande, Shreenivas R.、Malagi, Prasad V.、Jalihal, Prabhu C.、Mandalmari, Manappa T.

  DOI：10.56042/ijc.v61i7.64634

  日期：——
• Discovery of a Locally and Orally Active CXCL12 Neutraligand (LIT-927) with Anti-inflammatory Effect in a Murine Model of Allergic Airway Hypereosinophilia
  作者：Pierre Regenass、Dayana Abboud、François Daubeuf、Christine Lehalle、Patrick Gizzi、Stéphanie Riché、Muriel Hachet-Haas、François Rohmer、Vincent Gasparik、Damien Boeglin、Jacques Haiech、Tim Knehans、Didier Rognan、Denis Heissler、Claire Marsol、Pascal Villa、Jean-Luc Galzi、Marcel Hibert、Nelly Frossard、Dominique Bonnet

  DOI：10.1021/acs.jmedchem.8b00657

  日期：2018.9.13

  We previously reported Chalcone-4 (1) that binds the chemokine CXCL12, not its cognate receptors CXCR4 or CXCR7, and neutralizes its biological activity. However, this neutraligand suffers from limitations such as poor chemical stability, solubility, and oral activity. Herein, we report on the discovery of pyrimidinone 57 (LIT-927), a novel neutraligand of CXCL12 which displays a higher solubility than 1 and is no longer a Michael acceptor. While both 1 and 57 reduce eosinophil recruitment in a murine model of allergic airway hypereosinophilia, 57 is the only one to display inhibitory activity following oral administration. Thereby, we here describe 57 as the first orally active CXCL12 neutraligand with anti-inflammatory properties. Combined with a high binding selectivity for CXCL12 over other chemokines, 57 represents a powerful pharmacological tool to investigate CXCL12 physiology in vivo and to explore the activity of chemokine neutralization in inflammatory and related diseases.