5-(1,3-benzodioxol-5-ylmethyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(1,3-benzodioxol-5-ylmethyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol
• 英文别名: 5-(1,3-Benzodioxol-5-ylmethyl)-2,3-dihydroimidazo[1,2-b]isoindol-5-ol
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: AFMNHKBYDLREAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  胡椒乙酸 生成 5-(1,3-benzodioxol-5-ylmethyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol
  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

文献信息

• The imidazo[2,1-a]isoindole system. A new skeletal basis for antiplasmodial compounds
  作者：Esther del Olmo、Marlon Garcı́a Armas、Mª Inés Ybarra、Josè Luis López、Patricia Oporto、Alberto Giménez、Eric Deharo、Arturo San Feliciano

  DOI：10.1016/s0960-894x(03)00509-2

  日期：2003.8

  imidazo[2,1-a]isoindole and pyrimido[2,1-a]isoindole derivatives related to the natural dihydrostilbenoid isonotholaenic acid is reported. The evaluation was performed on cultures of F32 strain of Plasmodium falciparum and potent representative compounds were also evaluated in the ferriprotoporphyrin IX biomineralization inhibition test (FBIT). Compounds having the imidazo[2,1-a]isoindole skeleton

  报道了一些与天然二氢苯乙烯基异戊二烯酸相关的二氢苯乙烯基酰胺，邻苯二酮，咪唑并[2,1-a]异吲哚和嘧啶基[2,1-a]异吲哚衍生物的体外抗血浆活性。对恶性疟原虫的F32菌株的培养物进行了评估，并且还在铁原卟啉IX生物矿化抑制试验（FBIT）中评估了有效的代表性化合物。具有咪唑并[2，1-a]异吲哚骨架的化合物活性最高，该组中的一种化合物与氯喹一样有效，但通过抑制血红素生物矿化的机制起作用。
• Leishmanicidal activity of some stilbenoids and related heterocyclic compounds
  作者：Esther del Olmo、Marlon Garcı́a Armas、Jose Luis López-Pérez、Victoria Muñoz、Eric Deharo、Arturo San Feliciano

  DOI：10.1016/s0960-894x(01)00387-0

  日期：2001.8

  the leishmanicidal activity of some natural and semisynthetic dihydrostilbenoids and several compounds of other series of dihydrostilbamides, isoindoles, phthalazinones, imidazoisoindoles and pyrimidoisoindoles. The evaluation was performed in vitro, on cultures of cutaneous, mucocutaneous and visceral strains of Leishmania spp. The most potent and selective compounds of these series were the dihydrostilbene

  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。
• 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。
• 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.