1-(3,4-dichlorophenyl)-3-methylenepyrrolidine-2,5-dione | 63233-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-(3,4-dichlorophenyl)-3-methylenepyrrolidine-2,5-dione
• 英文别名: 1-(3,4-Dichlorophenyl)-3-methylidenepyrrolidine-2,5-dione
• CAS: 63233-85-2
• 化学式: C₁₁H₇Cl₂NO₂
• mdl: MFCD28384442
• 分子量: 256.088
• InChiKey: RRVVAMBFQCFXLM-UHFFFAOYSA-N

物化性质

• 熔点：
  125 °C(Solv: hexane (110-54-3))
• 沸点：
  398.3±52.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3,4-dichlorophenyl)-3-methylenepyrrolidine-2,5-dione 、 1,3-二苯基异苯并呋喃 以 二氯甲烷 为溶剂， 反应 48.0h， 以76%的产率得到
  参考文献：
  名称：

  酸诱导的N-芳基衣康酰亚胺和1,3-二苯基异苯并呋喃的加合物的重排

  摘要：

  用强酸处理N-芳基衣康酰亚胺和1,3-二苯基异苯并呋喃的几种Diels-Alder加合物会引起骨骼重排，从而导致2-芳基-6,10b-二苯基苯并[ h ]异喹啉-1,3（2 H，10b H）-二酮。

  DOI：

  10.1016/j.tetlet.2014.06.107
• 作为产物：
  描述：

  衣康酸酐 在 sodium acetate 、 乙酸酐 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 1-(3,4-dichlorophenyl)-3-methylenepyrrolidine-2,5-dione
  参考文献：
  名称：

  N-Aryl-3-mercaptosuccinimides as Antivirulence Agents Targeting Pseudomonas aeruginosa Elastase and Clostridium Collagenases

  摘要：

  In light of the global antimicrobial-resistance crisis, there is an urgent need for novel bacterial targets and antibiotics with novel modes of action. It has been shown that Pseudomonas aeruginosa elastase (LasB) and Clostridium histolyticum (Hathewaya histolytica) collagenase (CoIH) play a significant role in the infection process and thereby represent promising antivirulence targets. Here, we report novel N-aryl-3-mercaptosuccinimide inhibitors that target both LasB and CoIH, displaying potent activities in vitro and high selectivity for the bacterial over human metalloproteases. Additionally, the inhibitors demonstrate no signs of cytotoxicity against selected human cell lines and in a zebrafish embryo toxicity model. Furthermore, the most active CoIH inhibitor shows a significant reduction of collagen degradation in an ex vivo pig-skin model.

  DOI：

  10.1021/acs.jmedchem.0c00584

文献信息

• Facile One-Pot Synthesis of Benzo[h]isoquinolines via Strong Acid Triggered [1,2]-Sigmatropic Rearrangement: A Theoretical and Experimental Studies
  作者：V.M. Boitsov、N.A. Knyazev、S.V. Shmakov、S.Yu. Vyazmin、D.M. Nikolaev、O.B. Chakchir、A.V. Stepakov

  DOI：10.14233/ajchem.2019.22074

  日期：2019.8.10

  to this ring system has been reported yet. Herein, a facile one-pot synthesis from N-aryl itaconimides and 1,3-diarylisobenzofuran via strong acid triggered skeletal rearrangement reaction is described. Theoretical study for this rearrangement is provided at M11/cc-pVDZ level of theory. Antitumor activity of obtained benzo[h]isoquinoline derivatives against human erythroleukemia K562 cell line was evaluated

  苯并[h]异喹啉支架作为刚性亚基而备受关注，可用于构建生物活性产品。然而，尚未报道该环系统的高产率合成途径。本文描述了通过强酸引发的骨架重排反应从 N-芳基衣康酰亚胺和 1,3-二芳基异苯并呋喃进行简单的一锅合成。在 M11/cc-pVDZ 理论水平上提供了这种重排的理论研究。通过MTS测定评估了所获得的苯并[h]异喹啉衍生物对人红白血病K562细胞系的体外抗肿瘤活性。
• Stereoselective cycloaddition of diphenylisobenzofuran to N-arylitaconimides
  作者：A. P. Molchanov、A. V. Stepakov、V. M. Boitsov、R. R. Kostikov

  DOI：10.1007/s11172-013-0138-6

  日期：2013.4

  A reaction of 1,3-diphenylisobenzofuran with N-arylitaconimides gives the [4+2] cycloaddition products with the 11′-oxaspiro[pyrrolidine-3,9′-tricyclo[6.2.1.0 2,7 ]undeca-2′,4′,6′-triene-2,5-dione] skeleton as a single diastereomer.

  1,3-二苯基异苯并呋喃与N-芳基衣康酰亚胺的反应得到单一的非对映异构体的[4+2]环加成产物，其骨架为11′-氧杂螺[吡咯烷-3,9′-三环[6.2.1.0 2,7]十一碳-2′,4′,6′-三烯-2,5-二酮]。
• Synthesis of Cyclic Imides (Methylphtalimides, Carboxylic Acid Phtalimides and Itaconimides) and Evaluation of their Antifungal Potential
  作者：Dorimar Stiz、Rogério Corrêa、Felicia D. D';Auria、Giovanna Simonetti、Valdir Cechinel-Filho

  DOI：10.2174/1573406412666160229150833

  日期：2016.9.27

  BACKGROUND This paper describes the synthesis of three different subfamilies of cyclic imides: methylphtalimides, carboxyl acid phtalimides and itaconimides. METHODS Fifteen compounds (five of each sub-family) were obtained by the reaction of appropriated anhydrides and different aromatic amines, using the manual Topliss method. Their structures were confirmed by spectral data (IR and NMR). The antifungal

  背景技术本文描述了环状酰亚胺的三个不同亚家族的合成：甲基邻苯二甲酰亚胺，羧酸邻苯二甲酰亚胺和衣康酰亚胺。方法使用适当的酸酐和不同的芳族胺，使用手动Topliss方法反应，可得到15种化合物（每个子家族5种）。通过光谱数据（IR和NMR）证实了它们的结构。通过肉汤微量稀释研究合成的化合物的抗真菌活性，以确定最小抑制浓度（MIC）。还针对最具活性的物质评估了抑制生物膜形成或破坏成熟的白色念珠菌生物膜的能力。结果结果表明，只有衣康酰亚胺亚胺11-15表现出强大而有希望的抗真菌特性，MIC100在1至64μgmL-1之间，比参考药物氟康唑的功效高出几倍。在浓度为64μgmL-1的情况下，化合物11-15抑制了64％至95％的生物膜形成，并破坏了78％至99％的成熟生物膜。在计算机模拟评估中进行了ADME（吸收，分布，代谢和排泄），以预测所研究的分子是否为良好的候选药物。结论Itaconimides
• A novel synthetic approach to hydroimidazo[1,5-<i>b</i>]pyridazines by the recyclization of itaconimides and HPLC–HRMS monitoring of the reaction pathway
  作者：Dmitry Yu Vandyshev、Khidmet S Shikhaliev、Andrey Yu Potapov、Michael Yu Krysin、Fedor I Zubkov、Lyudmila V Sapronova

  DOI：10.3762/bjoc.13.252

  日期：——

  The novel cascade two-stage reaction between itaconimides and 1,2-diamino-4-phenylimidazole proceeds regio- and chemoselectively to form tetrahydroimidazo[1,5-b]pyridazines and includes nucleophilic C-addition by the activated C=C double bond and subsequent intramolecular recyclization of the intermediate with the amino group involved.

  在咪唑酰亚胺和1,2-二氨基-4-苯基咪唑之间进行的新型级联双级反应以区域和化学选择性形成四氢咪唑并[1,5-b]吡嗪，并包括通过活性C=C双键的亲核C-加成和随后的中间体内分子回收化，其中氨基参与其中。
• A novel method for the synthesis of pyrimido[1,2-a]benzimidazoles
  作者：Dmitriy Yu. Vandyshev、Khidmet S. Shikhaliev、Anna V. Kokonova、Andrei Yu. Potapov、Maria G. Kolpakova、Artem L. Sabynin、Fedor I. Zubkov

  DOI：10.1007/s10593-016-1914-7

  日期：2016.7

  Condensation of 1,2-diaminobenzimidazole with N-arylitaconimides was studied. It was found that 2-(10-amino-N-aryl-2-oxo-2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazol-3-yl)acetamides were formed in the course of this reaction upon brief heating to reflux of the reagent mixture in 2-propanol in the presence of catalytic amounts of acetic acid.

  研究了1,2-二氨基苯并咪唑与N-芳基衣康酰亚胺的缩合反应。发现在该反应过程中形成了2-（10-氨基-N-芳基-2-氧代-2,3,4,10-四氢嘧啶基[1,2 - a ]苯并咪唑-3-基）乙酰胺。在催化量的乙酸存在下，短暂加热反应混合物在2-丙醇中的回流。