2-(4-methylphenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid | 110784-06-0

• 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-(4-methylphenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
• 英文别名: 1,3-Dioxo-2-(p-tolyl)isoindoline-5-carboxylic acid；2-(4-methylphenyl)-1,3-dioxoisoindole-5-carboxylic acid
• CAS: 110784-06-0
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: DRPUWRHXSUVQLL-UHFFFAOYSA-N

物化性质

• 熔点：
  258-259 °C
• 沸点：
  547.1±60.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 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：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三苯基氢氧化锡 、 2-(4-methylphenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid 在 硫酸 作用下， 以 乙醇 、 丙酮 为溶剂， 以88%的产率得到triphenylstannyl 1,3-dioxo-2-(p-tolyl)isoindoline-5-carboxylate
  参考文献：
  名称：

  Design, synthesis, molecular docking studies of organotin-drug derivatives as multi-target agents against antibacterial, antifungal, α-amylase, α-glucosidase and butyrylcholinesterase

  摘要：

  A series of organotin esters has been synthesized using a diverse array of drugs containing carboxylic function with triphenyl/tributyltin. The synthesized derivatives were bioevaluated for antibacterial, anti fungal and enzyme inhibition (alpha-amylase, alpha-glucosidase and butyrylcholinesterase) activities. Interestingly, compound 3c was found to be most potent in all bioassay and showed higher activity than the standards in case of antibacterial and antifungal activity.The molecular docking was utilized to ascertain the mechanism and mode of action towards the molecular targets indicating that ligands and complexes were stabilized at the active site by electrostatic and hydrophobic forces, consistent with the corresponding experimental results. Docking simulation providing additional information about the possibilities of the inhibitory potential of the compounds against the 1j7t and 1EAI. It has been predicted by in silico calculation and investigation of the binding pattern that compound 3c can serve as the potential surrogate for hit to lead generation and design of novel antibacterial and anti-leishmanial agents. (C) 2017 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2017.05.036
• 作为产物：
  描述：

  乙烷,三氯氟- 、 偏苯三酸酐 反应 0.5h， 生成 2-(4-methylphenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
  参考文献：
  名称：

  Mechanochemical synthesis of phthalimides with crystal structures of intermediates and products

  摘要：

  邻苯二甲酸酐与苯胺衍生物在固态下通过研磨（或揉合）成功合成了酞亚胺。选定的产品和中间体通过结晶学方法进行结晶和表征，为涉及共晶作为中间体的固态反应性提供了潜在的合理性。

  DOI：

  10.1039/c5ce00038f

文献信息

• 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
• 1,3-DIOXOISOINDOLE DERIVATIVES HAVING SELECTIVE ANTAGONISM OF T-TYPE CALCIUM CHANNEL
  申请人：Cho Yong Seo

  公开号：US20070259867A1

  公开（公告）日：2007-11-08

  The present invention relates to 1,3-dioxoisoindole derivatives of Formula (1) or pharmaceutically acceptable salts thereof, a preparation method thereof and use thereof as a T-type calcium channel antagonist, based on the fact that 1,3-dioxoisoindole derivatives of Formula (1) show selective antagonistic activity against T-type calcium channel, thus being effective in treating brain diseases, cardiac diseases and neurogenic pains: wherein R 1 is a phenyl or a benzyl group, optionally substituted with a moiety selected from the group consisting of a halogen atom, a C 1 -C 6 alkoxy, a C 1 -C 6 alkyl, and a cyano group; R 2 is a heterocyclic group selected from the group consisting of piperidinyl, pyrrolidinyl, morpholinyl, and piperazinyl groups, wherein the heterocyclic group is optionally substituted with a C 1 -C 6 alkyl group; and n is 1 or 2.

  本发明涉及公式（1）的1,3-二氧杂异吲哚衍生物或其药学上可接受的盐，其制备方法和用作T型钙通道拮抗剂的用途，基于公式（1）的1,3-二氧杂异吲哚衍生物显示出选择性拮抗T型钙通道的活性，因此对治疗脑部疾病，心脏疾病和神经痛有效。其中，R1是苯基或苄基，可选地被取代为来自卤素原子，C1-C6烷氧基，C1-C6烷基和氰基的基团中选出的一个基团；R2是选自哌啶基，吡咯烷基，吗啉基和哌嗪基的杂环基团，其中该杂环基团可选地被C1-C6烷基取代；n为1或2。
• Design, Synthesis, and Structure−Activity Relationships of Phthalimide-Phenylpiperazines:  A Novel Series of Potent and Selective α₁_a-Adrenergic Receptor Antagonists
  作者：Gee-Hong Kuo、Catherine Prouty、William V. Murray、Virginia Pulito、Linda Jolliffe、Peter Cheung、Sally Varga、Mary Evangelisto、Jian Wang

  DOI：10.1021/jm9905918

  日期：2000.6.1

  Beginning from the screening hit and literature alpha(1)-adrenergic compounds, a hybridized basic skeleton A was proposed as the pharmacophore for potent and selective alpha(1a)-AR antagonists. Introduction of a hydroxy group to increase the flexibility afforded B which served as the screening model and resulted in the identification of the second-generation lead 1. Using the Topliss approach, a number of potent and selective alpha(1a)-AR antagonists were discovered. In all cases, binding affinity and selectivity at the alpha(1a)-AR of S-hydroxy enantiomers were higher than those of the R-hydroxy enantiomers. As compared to the des-hydroxy analogues, the S-hydroxy enantiomers had slightly lower binding affinity at alpha(1a)-AR but gained more than 2-fold selectivity for alpha(1a)-AR over alpha(1b)-AR, and 2- to 6-fold selectivity for alpha(1a)-AR over alpha(1d)-AR. They also had less cross activities against a panel of 25-35 peripheral and CNS receptors. The S-hydroxy enantiomers 23 and 24 (K-i = 0.29 nM, 0.33 nM; alpha(1b)/alpha(1a) >5690, >6060; alpha(1d)/alpha(1a) = 186, 158, respectively) were slightly less potent but much more selective at alpha(1a)-AR than tamsulosin (K-i = 0.13 nM, alpha(1d)/alpha(1a)= 14.8, alpha(1d)/alpha(1a) = 1.4). In the functional assay, the S-hydroxy enantiomers 20, 23, and 24 were less potent than tamsulosin in inhibiting contractions of rat prostate tissue but more selective in the inhibition of tissue contractions of rat prostate versus rat aorta. Compound 24 was selected as the development candidate for the treatment of BPH.
• PESTICIDALLY ACTIVE SEMI-CARBAZONES AND THIOSEMICARBAZONES DERIVATIVES
  申请人：Syngenta Participations AG

  公开号：US20180007907A1

  公开（公告）日：2018-01-11

  Compounds of formula (I), wherein the substituents are as defined in claim 1, and agrochemically acceptable salts and enantiomers thereof, can be used as insecticides.
• US7319098B2
  申请人：——

  公开号：US7319098B2

  公开（公告）日：2008-01-15