(E)-1-(2-hydroxy-4-(prop-2-yn-1-yloxy)phenyl)-3-phenylprop-2-en-1-one | 1394289-45-2

• 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)-1-(2-hydroxy-4-(prop-2-yn-1-yloxy)phenyl)-3-phenylprop-2-en-1-one
• 英文别名: (E)-1-(2-hydroxy-4-prop-2-ynoxyphenyl)-3-phenylprop-2-en-1-one
• CAS: 1394289-45-2
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: UFWOWFCCFVQHIB-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-hydroxy-4-(prop-2-yn-1-yloxy)phenyl)-3-phenylprop-2-en-1-one 在 copper(ll) sulfate pentahydrate 、 sodium hydride 、 sodium ascorbate 、 苯甲酸 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 2-(2-Amino-6-phenylpyrimidin-4-yl)-5-[(1-hexyltriazol-4-yl)methoxy]phenol
  参考文献：
  名称：

  Synthesis and evaluation of small libraries of triazolylmethoxy chalcones, flavanones and 2-aminopyrimidines as inhibitors of mycobacterial FAS-II and PknG

  摘要：

  A synthetic strategy to access small libraries of triazolylmethoxy chalcones 4{1-20}, triazolylmethoxy flavanones 5{1-10} and triazolylmethoxy aminopyrimidines 6{1-17} from a common substrate 4-propargyloxy-2-hydroxy acetophenone using a set of different reactions has been developed. The chalcones and flavanones were screened against mycobacterial FAS-II pathway using a recombinant mycobacterial strain, against which the most potent compound showed similar to 88% inhibition in bacterial growth and substantially induction of reporter gene activity at 100 mu M concentration. The triazolylmethoxy aminopyrimdines were screened against PknG of Mycobaceterium tuberculosis displaying moderate to good activity (23-53% inhibition at 100 mu M), comparable to the action of a standard inhibitor. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.07.009
• 作为产物：
  描述：

  1-(2-hydroxy-4-(prop-2-yn-1-yloxy)phenyl)ethanone 在 氢氧化钾 、 苯甲醛 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-1-(2-hydroxy-4-(prop-2-yn-1-yloxy)phenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Chalcones having antiproliferative activity

  摘要：

  这项发明涉及一种新型化合物类，其结构与某些天然存在或合成的香豆素相关。该发明还涉及包括这些化合物的药物组合物以及使用这些药物组合物治疗某些疾病的方法。该发明还涉及一种合成这种新型化合物类的工艺。

  公开号：

  US06423740B1

文献信息

• Design, synthesis and anticancer activity of matrine–1H-1,2,3-triazole–chalcone conjugates
  作者：Lihui Zhao、Lina Mao、Ge Hong、Xiaojiao Yang、Tianjun Liu

  DOI：10.1016/j.bmcl.2015.04.051

  日期：2015.6

  A series of novel matrine–1H-1,2,3-triazole–chalcone conjugates was synthesized and their anticancer activity against A549, Bel-7402, Hela, and MCF-7 cancer cells was evaluated. Most of the conjugates displayed higher potency than their components. Compounds 6h and 6i exhibited more potent anticancer activity than 5-fluorouracil against the four tested human cancer cell lines and lower cytotoxicity

  合成了一系列新型苦参碱-1 H -1,2,3-三唑-查耳酮缀合物，并评估了它们对A549，Bel-7402，Hela和MCF-7癌细胞的抗癌活性。大多数缀合物显示出比其组分更高的效价。与5-氟尿嘧啶相比，化合物6h和6i对四种测试的人类癌细胞系表现出更强的抗癌活性，并且对NIH3T3正常细胞的细胞毒性较低。流式细胞仪测试表明化合物6h可以以浓度依赖的方式诱导A549细胞凋亡。此外，6h可以有效抑制小鼠异种移植模型中人肿瘤的生长，而不会引起明显的毒性。
• US6423740B1
  申请人：——

  公开号：US6423740B1

  公开（公告）日：2002-07-23
• Chalcones having antiproliferative activity
  申请人：Indena S.p.A.

  公开号：US06423740B1

  公开（公告）日：2002-07-23

  The invention relates to a novel class of compounds that have structures related to certain naturally occurring or synthetic chalcones. The invention also relates to pharmaceutical compositions comprising the compounds and methods for treating certain disorders using the pharmaceutical compositions. The invention further relates to a process for synthesizing the novel class of compounds.

  这项发明涉及一种新型化合物类，其结构与某些天然存在或合成的香豆素相关。该发明还涉及包括这些化合物的药物组合物以及使用这些药物组合物治疗某些疾病的方法。该发明还涉及一种合成这种新型化合物类的工艺。
• Synthesis and evaluation of small libraries of triazolylmethoxy chalcones, flavanones and 2-aminopyrimidines as inhibitors of mycobacterial FAS-II and PknG
  作者：Namrata Anand、Priyanka Singh、Anindra Sharma、Sameer Tiwari、Vandana Singh、Diwakar K. Singh、Kishore K. Srivastava、B.N. Singh、Rama Pati Tripathi

  DOI：10.1016/j.bmc.2012.07.009

  日期：2012.9

  A synthetic strategy to access small libraries of triazolylmethoxy chalcones 41-20}, triazolylmethoxy flavanones 51-10} and triazolylmethoxy aminopyrimidines 61-17} from a common substrate 4-propargyloxy-2-hydroxy acetophenone using a set of different reactions has been developed. The chalcones and flavanones were screened against mycobacterial FAS-II pathway using a recombinant mycobacterial strain, against which the most potent compound showed similar to 88% inhibition in bacterial growth and substantially induction of reporter gene activity at 100 mu M concentration. The triazolylmethoxy aminopyrimdines were screened against PknG of Mycobaceterium tuberculosis displaying moderate to good activity (23-53% inhibition at 100 mu M), comparable to the action of a standard inhibitor. (C) 2012 Elsevier Ltd. All rights reserved.