(Z)-3-(3,4-dichlorobenzylidene)isobenzofuran-1(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (Z)-3-(3,4-dichlorobenzylidene)isobenzofuran-1(3H)-one
• 英文别名: 3-(3,4-dichlorobenzylidene)-2-benzofuran-1(3H)-one；(3Z)-3-[(3,4-dichlorophenyl)methylidene]-2-benzofuran-1-one
• 化学式: C₁₅H₈Cl₂O₂
• 分子量: 291.133
• InChiKey: HQTZOLYGVQALEU-ZSOIEALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-(3,4-dichlorobenzylidene)isobenzofuran-1(3H)-one 在 肼 作用下， 以78%的产率得到4-(3,4-Dichloro-benzyl)-2H-phthalazin-1-one
  参考文献：
  名称：

  Anti-HIV activity of stilbene-related heterocyclic compounds

  摘要：

  Viral transcription has not been routinely targeted in the development of new antiviral drugs. This crucial step of the viral cycle depends on the concerted action of cellular and viral proteins such as NF-kappa B and Tat. In the present study, stilbene-related heterocyclic compounds including benzalphthalide, phthalazinone, imidazoindole and pyrimidoisoindole derivatives are tested for their anti-HIV activity. Original assays based on recombinant viruses were used to evaluate HIV replication inhibition and stably transfected cell lines were used to evaluate inhibition of Tat and NF-kappa B proteins. Some of the stilbene-related heterocyclic compounds analysed displayed anti-HIV activity through interference with NF-kappa B and Tat function. Moreover, compounds inhibiting both targets displayed a stronger activity on viral replication. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.087
• 作为产物：
  描述：

  苯酐 生成 (Z)-3-(3,4-dichlorobenzylidene)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  XASIMOTO, SINDZI;OKU, AKIO;ITO, JOSIKUNI

  摘要：

  DOI：

文献信息

• Antimalarial activity of imidazo[2,1-a]isoindol-5-ol derivatives and related compounds
  作者：Esther del Olmo、Bianca Barboza、Louise D. Chiaradia、Alicia Moreno、Juana Carrero-Lérida、Dolores González-Pacanowska、Victoria Muñoz、José L. López-Pérez、Alberto Giménez、Agustín Benito、Antonio R. Martínez、Luis M. Ruiz-Pérez、Arturo San Feliciano

  DOI：10.1016/j.ejmech.2011.08.043

  日期：2011.11

  electron-withdrawing or-donating substituents on different parts of the molecule, as well as those produced by the incorporation of an additional fused ring, were analyzed. Several compounds showed significant antimalarial activity in vitro with IC50 values as low as 60 nM and a certain efficacy in vivo by reducing parasitemia in Plasmodium berghei mouse models.

  介绍并讨论了咪唑并[2,1 - a ]异吲哚-5-醇系列衍生物的合成及其对恶性疟原虫的评价结果。分析了吸电子或供电子取代基对分子不同部分的影响，以及通过引入额外的稠合环所产生的影响。几种化合物在体外显示出显着的抗疟活性，IC 50值低至60 nM，并且通过降低伯氏疟原虫小鼠模型中的寄生虫血症在体内具有一定的功效。
• Lactonization of 2-Alkynylbenzoates for the Assembly of Isochromenones Mediated by BF₃·Et₂O
  作者：Xiang Zhang、Xintong Wan、Ying Cong、Xiaohua Zhen、Qiao Li、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/acs.joc.9b01601

  日期：2019.8.16

  A general and efficient lactonization method of readily available 2-alkynylbenzoates affording biologically important isochromenones has been realized via a solely BF3 center dot Et2O-mediated 6-endo-dig cyclization process under mild conditions. An alternative mechanistic pathway in which BF3 center dot Et2O activates the carbonyl of the ester moiety, rather than the alkyne triple bond, was postulated on the basis of control experiment results. Gram-scale reaction and further application for the assembly of more complex molecules demonstrated the practicability of the protocol.
• Vasorelaxant activity of phthalazinones and related compounds
  作者：Esther del Olmo、Bianca Barboza、Ma Inés Ybarra、José Luis López-Pérez、Rosalía Carrón、Ma Angeles Sevilla、Cinthia Boselli、Arturo San Feliciano

  DOI：10.1016/j.bmcl.2006.02.003

  日期：2006.5

  Several series of dihydrostilbenamide, imidazo[2,1-a]isoindole, pyrimido[2,1-a]isoindole and phthalazinone derivatives were obtained and their vasorelaxant activity was measured on isolated rat aorta rings pre-contracted with phenylephrine (10(-5) M). Some phthalazinones attained, practically, the total relaxation of the organ at micromolar concentrations. For the most potent compound 9h (EC50 = 0.43 mu M) the affinities for alpha(1A), alpha(1B) and alpha(1D) adrenergic sub-receptors were determined. (C) 2006 Elsevier Ltd. All rights reserved.