5-amino-2-[(4-fluorophenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione | 1021096-70-7

• 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: 5-amino-2-[(4-fluorophenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione
• 英文别名: ZHAWOC3199；5-Amino-2-[(4-fluorophenyl)methyl]isoindole-1,3-dione
• CAS: 1021096-70-7
• 化学式: C₁₅H₁₁FN₂O₂
• 分子量: 270.263
• InChiKey: IUFKMDFEFLOPAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-2-[(4-fluorophenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione 在 sodium hypochlorite 、 sodium chlorite 、 2,2,6,6-四甲基哌啶氧化物 、 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 、 sodium phosphate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 20.0~40.0 ℃ 、100.0 kPa 条件下， 反应 8.0h， 生成 5-{4-[({2-[(4-fluorophenyl)methyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl}carbamoyl)methyl]-phenoxy}pentanoic acid
  参考文献：
  名称：

  Development of a Non-Hydroxamate Dual Matrix Metalloproteinase (MMP)-7/-13 Inhibitor

  摘要：

  基质金属蛋白酶7（MMP-7）是MMP超家族的成员，能够降解胶乳蛋白、明胶、纤维连接蛋白和蛋白多糖等细胞外基质蛋白。MMP-7是癌症小分子药物开发的验证靶点。MMP-13在酶类中是对II型胶原的降解效率最高的贡献者，并且是关节炎和癌症的验证靶点。我们开发了双重MMP-7/-13抑制剂ZHAWOC6941，其IC50值分别为2.2μM（MMP-7）和1.2μM（MMP-13），在广泛的MMP亚型中具有选择性。它保留了MMP-1、-2、-3、-8、-9、-12和-14，使其成为针对性多药理学方法的有价值调节剂。

  DOI：

  10.3390/molecules22091548
• 作为产物：
  描述：

  4-硝基邻苯二甲酰亚胺 在 palladium on activated charcoal 、 甲酸铵 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 16.0h， 生成 5-amino-2-[(4-fluorophenyl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione
  参考文献：
  名称：

  A new series of N2-substituted-5-(p-toluenesulfonylamino)phthalimide analogues as α-glucosidase inhibitors

  摘要：

  Several members of a new family of non-sugar-type alpha-glycosidase inhibitors, bearing a 5-(p-toluenesulfonylamino)phthalimide moiety and various substituent at the N2 position, were synthesized and their activities were investigated. The newly synthesized compounds displayed different inhibition profile towards yeast alpha-glycosidase and rat intestinal alpha-glycosidase. Almost all the compounds had strong inhibitory activities against yeast alpha-glycosidase. Regarding rat intestinal alpha-glycosidase, only analogs with N2-aromatic substituents displayed varying degrees of inhibitory activities on rat intestinal maltase and lactase and nearly all compounds showed no inhibition against rat intestinal alpha-amylase. Structure-activity relationship studies indicated that 5-(p-toluenesulfonylamino)phthalimide moiety is a favorable scaffold to exert the alpha-glucosidase inhibitory activity and substituents at the N2 position have considerable influence on the efficacy of the inhibition activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.011

文献信息

• Synthesis, Insecticidal Activities, and 3D-QASR of <i>N</i>-Pyridylpyrazole Amide Derivatives Containing a Phthalimide as Potential Ryanodine Receptor Activators
  作者：Lu Zhang、Ruijia Chen、Xiaoyang Li、Xiaoyong Xu、Zhiping Xu、Jiagao Cheng、Yanli Wang、Yuxin Li、XuSheng Shao、Zhong Li

  DOI：10.1021/acs.jafc.2c03971

  日期：2022.10.5

  To develop potent and environment-friendly insecticides, novel N-pyridylpyrazole amide derivatives containing a phthalimide were designed and synthesized. The preliminary bioassay results showed that most of the target compounds exhibited good insecticidal activities. For oriental armyworm (Mythimna separata), compounds E5, E29, E30, and E33 displayed higher than 90% lethal rates at 25 mg L-1. In particular, compound E33 displayed 60% mortality at a lower concentration of 6.25 mg L-1. Besides, compound E33 also showed a 30% lethal rate at 5 mg L-1 against diamondback moth (DBM) (Plutella xylostella). Molecular docking between the most active compound E33 and DBM ryanodine receptor (RyR), comparative molecular field analysis (CoMFA), and density functional theory (DFT) calculations were conducted and discussed. Furthermore, according to vitro studies using a calcium imaging technique, compound E33 was a potent novel lead targeting insect RyR.
• Development of a Non-Hydroxamate Dual Matrix Metalloproteinase (MMP)-7/-13 Inhibitor
  作者：Thomas Fischer、Rainer Riedl

  DOI：10.3390/molecules22091548

  日期：——

  Matrix metalloproteinase 7 (MMP-7) is a member of the MMP superfamily and is able to degrade extracellular matrix proteins such as casein, gelatin, fibronectin and proteoglycan. MMP-7 is a validated target for the development of small molecule drugs against cancer. MMP-13 is within the enzyme class the most efficient contributor to type II collagen degeneration and is a validated target in arthritis and cancer. We have developed the dual MMP-7/-13 inhibitor ZHAWOC6941 with IC50-values of 2.2 μM (MMP-7) and 1.2 μM (MMP-13) that is selective over a broad range of MMP isoforms. It spares MMP-1, -2, -3, -8, -9, -12 and -14, making it a valuable modulator for targeted polypharmacology approaches.

  基质金属蛋白酶7（MMP-7）是MMP超家族的成员，能够降解胶乳蛋白、明胶、纤维连接蛋白和蛋白多糖等细胞外基质蛋白。MMP-7是癌症小分子药物开发的验证靶点。MMP-13在酶类中是对II型胶原的降解效率最高的贡献者，并且是关节炎和癌症的验证靶点。我们开发了双重MMP-7/-13抑制剂ZHAWOC6941，其IC50值分别为2.2μM（MMP-7）和1.2μM（MMP-13），在广泛的MMP亚型中具有选择性。它保留了MMP-1、-2、-3、-8、-9、-12和-14，使其成为针对性多药理学方法的有价值调节剂。
• A new series of N2-substituted-5-(p-toluenesulfonylamino)phthalimide analogues as α-glucosidase inhibitors
  作者：Xiaoli Bian、Qian Wang、Changhu Ke、Guilan Zhao、Yiping Li

  DOI：10.1016/j.bmcl.2013.02.011

  日期：2013.4

  Several members of a new family of non-sugar-type alpha-glycosidase inhibitors, bearing a 5-(p-toluenesulfonylamino)phthalimide moiety and various substituent at the N2 position, were synthesized and their activities were investigated. The newly synthesized compounds displayed different inhibition profile towards yeast alpha-glycosidase and rat intestinal alpha-glycosidase. Almost all the compounds had strong inhibitory activities against yeast alpha-glycosidase. Regarding rat intestinal alpha-glycosidase, only analogs with N2-aromatic substituents displayed varying degrees of inhibitory activities on rat intestinal maltase and lactase and nearly all compounds showed no inhibition against rat intestinal alpha-amylase. Structure-activity relationship studies indicated that 5-(p-toluenesulfonylamino)phthalimide moiety is a favorable scaffold to exert the alpha-glucosidase inhibitory activity and substituents at the N2 position have considerable influence on the efficacy of the inhibition activities. (C) 2013 Elsevier Ltd. All rights reserved.