3-(4-methylthiobenzylidene)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: 3-(4-methylthiobenzylidene)isobenzofuran-1(3H)-one
• 英文别名: (Z)-3-(4-methylsulfanylbenzylidene)isobenzofuran-1-one；(3Z)-3-[(4-methylsulfanylphenyl)methylene]isobenzofuran-1-one；(3Z)-3-[(4-methylsulfanylphenyl)methylidene]-2-benzofuran-1-one
• 化学式: C₁₆H₁₂O₂S
• 分子量: 268.336
• InChiKey: AAIXFCYNLDGODK-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methylthiobenzylidene)isobenzofuran-1(3H)-one 在 一水合肼 作用下， 以 甲苯 为溶剂， 以50%的产率得到4-(4-methylsulfanylbenzyl)phthalazin-1(2H)-one
  参考文献：
  名称：

  作为抗真菌剂的取代的 Phthalazin-1(2H)-ones 的合成、生物评价和结构研究

  摘要：

  合成了 25 种多取代的酞嗪酮衍生物，并测试了它们对一组致病性和临床上重要的酵母菌和丝状真菌的抗真菌活性。其中，化合物 4-(4-chlorobenzyl)-2-methylphthalazin-1(2H)-one (5) 对皮肤癣菌和新型隐球菌的标准化菌株以及一些临床分离株表现出显着的抗真菌活性。对化合物 5 进行的物理化学研究揭示了其构象和电子特性，为我们未来设计新型相关抗真菌类似物提供了有用的数据。

  DOI：

  10.3390/molecules18033479
• 作为产物：
  描述：

  4-ethynylthioanisole 、 2-溴苯甲酸 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.5h， 以72%的产率得到3-(4-methylthiobenzylidene)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  Pd/C-mediated synthesis of (Z)-3-alkylidenephthalides of potential pharmacological interest

  摘要：

  The coupling of o-bromobenzoic acid with terminal alkynes using 10% Pd/C-Et3N-CuI-PPh3 as a catalyst system leads to the synthesis of (Z)-3-alkylidenephthalides as the major product along with the traces of isocoumarin when the reaction was performed in 1,4-dioxane. The methodology afforded a range of compounds including (Z)-3-(4-(methylsulfonyl)benzylidene)isobenzofuran-1(3H)-one of potential pharmacological interest. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.121

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。
• Anti-HIV activity of stilbene-related heterocyclic compounds
  作者：Luis M. Bedoya、Esther del Olmo、Rocío Sancho、Bianca Barboza、Manuela Beltrán、Ana E. García-Cadenas、Sonsoles Sánchez-Palomino、José L. López-Pérez、Eduardo Muñoz、Arturo San Feliciano、José Alcamí

  DOI：10.1016/j.bmcl.2006.04.087

  日期：2006.8

  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.
• 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.
• [1,3]Diazaheterofused isoindolol derivatives displaying anxiolytic-like effects on mice
  作者：Alejandro Zamilpa、Maribel Herrera-Ruiz、Esther Del Olmo、José L. López-Pérez、Jaime Tortoriello、Arturo San Feliciano

  DOI：10.1016/j.bmcl.2007.04.080

  日期：2007.7

  Anxiolytic-like effects induced on mice by several compounds with imidazo[2,1-a]isoindolol (II), pyrimido[2,1-a]isoindolol (III) and [1,3]diazepino[2,l-a]isoindolol (IV) structures have been evaluated through the elevated plus-maze test. The evaluation has been based on measuring the spent time and counting the number of entries of mice in the open arms of the maze. Single intraperitoneal administration of imidazoisoindolol Ile and pyrimidoisoindolols IIIa, IIIe and IIIg induced significant increments in these behavioural parameters. (C) 2007 Elsevier Ltd. All rights reserved.
• Anxiolytic effects of benzalphthalides
  作者：Alejandro Zamilpa、Maribel Herrera-Ruiz、Esther del Olmo、José L. López-Pérez、Jaime Tortoriello、Arturo San Feliciano

  DOI：10.1016/j.bmcl.2005.06.031

  日期：2005.8

  Anxiolytic effects induced by benzalphthalides oil mice have been evaluated. The evaluation was based on the spent time and the number of entries of animals into the open arms in the elevated plus maze test. Single administration of benzalphthalides I and 11 induced significant increments in both parameters, thus revealing their potentiality as new leads for the development of non-benzodiazepinic and non-nitrogenated antianxiety agents. (c) 2005 Elsevier Ltd. All rights reserved.