(Z)-3-(3,4,5-trimethoxyphenylmethylidene)isobenzofuran-1(3H)-one | 148345-05-5

• 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-(3,4,5-trimethoxyphenylmethylidene)isobenzofuran-1(3H)-one
• 英文别名: (Z)-3-(3',4',5'-trimethoxy)benzylidenephthalide；(3Z)-3-[(3,4,5-trimethoxyphenyl)methylene]isobenzofuran-1-one；(3Z)-3-[(3,4,5-trimethoxyphenyl)methylidene]-2-benzofuran-1-one
• CAS: 148345-05-5
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: GITAAAKDURRRPS-ZSOIEALJSA-N

物化性质

• 沸点：
  472.2±45.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-3-(3,4,5-trimethoxyphenylmethylidene)isobenzofuran-1(3H)-one 在 肼 作用下， 以97%的产率得到4-(3,4,5-Trimethoxy-benzyl)-2H-phthalazin-1-one
  参考文献：
  名称：

  某些类胡萝卜素和相关杂环化合物的杀菌活性。

  摘要：

  我们已经评估了一些天然和半合成的二氢二苯乙烯类化合物和其他系列的二氢二苯乙烯酰胺，异吲哚，邻苯二氮酮，咪唑异吲哚和嘧啶异吲哚的几种化合物的杀菌活性。评估是在体外对利什曼原虫属的皮肤，粘膜皮肤和内脏菌株的培养物进行的。这些系列中最有效和选择性最大的化合物是二氢sti哌啶。

  DOI：

  10.1016/s0960-894x(01)00387-0
• 作为产物：
  描述：

  苯酐 、 3,4,5-三甲氧基苯乙酸 在 sodium acetate 作用下， 以 甲苯 为溶剂， 生成 (Z)-3-(3,4,5-trimethoxyphenylmethylidene)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  咪唑并[2,1 - a ]异吲哚-5-醇衍生物及其相关化合物的抗疟活性

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2011.08.043

文献信息

• Synthesis, Bioevaluation and Structural Study of Substituted Phthalazin-1(2H)-ones Acting as Antifungal Agents
  作者：Marcos Derita、Esther del Olmo、Bianca Barboza、Ana García-Cadenas、José López-Pérez、Sebastián Andújar、Daniel Enriz、Susana Zacchino、Arturo San Feliciano

  DOI：10.3390/molecules18033479

  日期：——

  important yeasts and filamentous fungi. Among them, the compound 4-(4-chlorobenzyl)-2-methylphthalazin-1(2H)-one (5) exhibited a remarkable antifungal activity against standardised strains of dermatophytes and Cryptococcus neoformans, as well as against some clinical isolates. A physicochemical study performed on compound 5 revealed its conformational and electronic characteristics, providing us with useful

  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。
• Copper-Catalyzed Preparation of γ-Alkylidenebutenolides and Isocoumarins under Mild Palladium-Free Conditions
  作者：Samuel Inack-Ngi、Raphaël Rahmani、Laurent Commeiras、Gaëlle Chouraqui、Jérôme Thibonnet、Alain Duchêne、Mohamed Abarbri、Jean-Luc Parrain

  DOI：10.1002/adsc.200800757

  日期：2009.3

  Abstractmagnified imageA general and efficient copper(I)‐catalyzed cross‐coupling and heterocyclization reaction of terminal alkynes and β‐iodo‐α,β‐unsaturated acid derivatives has been developed under very mild conditions. This method provides easy access from good to excellent yields of a variety of 5‐ylidenebutenolides and 3‐substituted isocoumarins with excellent regio‐ and stereoselectivity. This procedure does not require the use of any expensive supplementary additives, and is palladium‐free.
• 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.