2-benzyl-2,5,6,7-tetrahydro-4H-isoindol-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-benzyl-2,5,6,7-tetrahydro-4H-isoindol-4-one
• 英文别名: 2-benzyl-6,7-dihydro-5H-isoindol-4-one
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: RJRAYQZJKFWDDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzyl-2,5,6,7-tetrahydro-4H-isoindol-4-one 在 potassium tert-butylate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 51.0h， 生成 8-benzyl-3,5,6,8-tetrahydro-2H-pyrrolo[3,4-h]quinazolin-2-one
  参考文献：
  名称：

  Synthesis of a new class of pyrrolo[3,4-h]quinazolines with antimitotic activity

  摘要：

  A new series of pyrrolo[3,4-h]quinazolines was conveniently prepared with a broad substitution pattern. A large number of derivatives was obtained and the cellular cytotoxicity was evaluated in vitro against 5 different human tumor cell lines with GI(50) values reaching the low micromolar level (1.3-19.8 mu M). These compounds were able to induce cell death mainly by apoptosis through a mitochondrial dependent pathway. Selected compounds showed antimitotic activity and a reduction of tubulin polymerization in a concentration-dependent manner. Moreover, they showed anti-angiogenic properties since reduced in vitro endothelial cell migration and disrupted HUVEC capillary-like tube network in Matrigel. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.014
• 作为产物：
  描述：

  2-环己烯-1-酮 在 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 32.5h， 生成 2-benzyl-2,5,6,7-tetrahydro-4H-isoindol-4-one
  参考文献：
  名称：

  氯二嗪的吲哚和吡咯的光化学介导的扩环：合成方法和热危害评估

  摘要：

  我们证明，吡啶盐和喹啉盐可以通过将芳基氯二嗪中的单个 C 原子插入母体 N-烷基吡咯或吲哚来获得。扩环的氮化产物被激活，进行氧化和氢化，加速了进一步的结构多样化。利用差示扫描量热法的洞察力，已经开发了使用二嗪嗪作为卡宾前体的更安全的方法。

  DOI：

  10.1002/anie.202305081

文献信息

• [EN] NEW THERAPEUTIC AGENTS FOR THE TREATMENT OF HAEMATOLOGICAL PATHOLOGIES<br/>[FR] NOUVEAUX AGENTS THÉRAPEUTIQUES POUR LE TRAITEMENT DE PATHOLOGIES HÉMATOLOGIQUES
  申请人：UNIV DEGLI STUDI DI PALERMO

  公开号：WO2021038452A1

  公开（公告）日：2021-03-04

  The present invention relates to compounds having a tetracyclic system and the use thereof as new therapeutic agents in the treatment of acute myeloid leukemia (AML), preferably in FLT3/ITD hemizygote patients resistant to conventional therapies. The invention also relates to 5,7-dihydro-4H-[1,3]thiazolo[4,5-e]isoindol-2-amine compounds useful as intermediates for the synthesis of tetracyclic imidazo[2',1':2,3][1,3]thiazolo[4,5-e]isoindole compounds.

  该发明涉及具有四环系统的化合物及其作为新的治疗剂在治疗急性髓样白血病（AML）中的用途，优选用于对传统疗法具有抗药性的FLT3/ITD半合子患者。该发明还涉及5,7-二氢-4H-[1,3]噻唑并[4,5-e]异吲哚-2-胺化合物，可用作合成四环咪唑并[2',1':2,3][1,3]噻唑并[4,5-e]异吲哚化合物的中间体。
• Preparation of Pyrroles by Dehydrogenation of Pyrrolidines with Manganese Dioxide
  作者：Bernard Bonnaud、Dennis C. H. Bigg

  DOI：10.1055/s-1994-25500

  日期：——

  The dehydrogenation of pyrrolidines by activated manganese dioxide provides a fairly general and mild method for the preparation of substituted pyrroles.

  活化的二氧化锰对吡咯烷进行脱氢反应，提供了一种相当普遍且温和的方法用于制备取代吡咯。
• Insight on [1,3]thiazolo[4,5-e]isoindoles as tubulin polymerization inhibitors
  作者：Virginia Spanò、Marilia Barreca、Roberta Rocca、Roberta Bortolozzi、Ruoli Bai、Anna Carbone、Maria Valeria Raimondi、Antonio Palumbo Piccionello、Alessandra Montalbano、Stefano Alcaro、Ernest Hamel、Giampietro Viola、Paola Barraja

  DOI：10.1016/j.ejmech.2020.113122

  日期：2021.2

  A series of [1,3]thiazolo[4,5-e]isoindoles has been synthesized through a versatile and high yielding multistep sequence. Evaluation of the antiproliferative activity of the new compounds on the full NCI human tumor cell line panel highlighted several compounds that are able to inhibit tumor cell proliferation at micromolar-submicromolar concentrations. The most active derivative 11g was found to cause

  通过通用且高产率的多步骤序列合成了一系列[1,3]噻唑并[4,5- e ]异吲哚。对新化合物在完整的NCI人肿瘤细胞系中的抗增殖活性的评估突出了几种能够在微摩尔-亚微摩尔浓度下抑制肿瘤细胞增殖的化合物。发现最活跃的衍生物11g沿着线粒体途径，导致细胞周期停滞在G2 / M期并诱导HeLa细胞凋亡，使其成为发现新抗有丝分裂药物的先导化合物。
• Pyrrolo[3,4-h]quinolinones a new class of photochemotherapeutic agents
  作者：Paola Barraja、Patrizia Diana、Alessandra Montalbano、Anna Carbone、Giampietro Viola、Giuseppe Basso、Alessia Salvador、Daniela Vedaldi、Francesco Dall’Acqua、Girolamo Cirrincione

  DOI：10.1016/j.bmc.2011.02.023

  日期：2011.4

  nitrogen isosters of the angular furocoumarin angelicin, with the aim of obtaining new photochemotherapeutic agents with increased antiproliferative activity and lower undesired toxic effects. A versatile synthetic pathway was approached to allow the isolation of derivatives of the new ring system with a good substitution pattern on the pyrrole moiety. Photobiological screenings of the new compounds

  合成吡咯并[3,4- h ]喹啉-2-酮作为角呋喃香豆素当归的氮等价物，目的是获得具有增加的抗增殖活性和较低的不良毒性作用的新型光化学治疗剂。寻求一种通用的合成途径以分离具有在吡咯部分上的良好取代模式的新环系统的衍生物。新化合物的光生物学筛选显示出强大的光毒性作用和很大的UVA剂量依赖性，在亚微摩尔水平下达到IC 50值。诱导的细胞光细胞毒性与线粒体和溶酶体的参与，细胞周期谱的改变和膜脂质过氧化的凋亡有关。
• Pyrano[2,3-e]isoindol-2-ones, new angelicin heteroanalogues
  作者：Paola Barraja、Virginia Spanò、Diana Patrizia、Anna Carbone、Girolamo Cirrincione、Daniela Vedaldi、Alessia Salvador、Giampietro Viola、Francesco Dall’Acqua

  DOI：10.1016/j.bmcl.2009.01.096

  日期：2009.3

  synthesis of the pyrano[2,3-e]isoindol-2-one ring system, an heteroanalogue of angelicin, is reported. Our synthetic approach consists of the annelation of the pyran ring on the isoindole moiety using 5-dialkylamino- or 5-hydroxymethylene intermediates as building blocks. The photoantiproliferative activity of the new derivatives was studied. Some of them bearing the benzyl group at the 8 position

  据报道，吡喃并[2,3 - e ] isoindol-2-one环系统，即当归的杂类似物，可以方便地合成。我们的合成方法包括使用5-二烷基氨基-或5-羟基亚甲基中间体作为结构单元，使吡喃环在异吲哚部分上的成环反应。研究了新衍生物的光抗增殖活性。其中一些在8位带有苄基的化合物在微摩尔范围内具有IC 50活性。细胞的细胞毒性涉及细胞凋亡，细胞周期概况的改变和膜的光损伤。