5-nitro-2-(2-phenylethyl)-1H-isoindole-1,3(2H)-dione | 147291-34-7

• 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-nitro-2-(2-phenylethyl)-1H-isoindole-1,3(2H)-dione
• 英文别名: 5-nitro-2-phenethyl-isoindoline-1,3-dione；5-Nitro-2-phenaethyl-isoindolin-1,3-dion；N-(2-phenylethyl)-4-nitrophthalimide；5-nitro-2-(2-phenylethyl)isoindole-1,3-dione
• CAS: 147291-34-7
• 化学式: C₁₆H₁₂N₂O₄
• 分子量: 296.282
• InChiKey: XDVUFCJLGXGIJU-UHFFFAOYSA-N

物化性质

• 沸点：
  482.8±38.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-nitro-2-(2-phenylethyl)-1H-isoindole-1,3(2H)-dione 在 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5-Amino-2-phenethylisoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis, Insecticidal Activities, and 3D-QASR of N-Pyridylpyrazole Amide Derivatives Containing a Phthalimide as Potential Ryanodine Receptor Activators

  摘要：

  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.

  DOI：

  10.1021/acs.jafc.2c03971
• 作为产物：
  描述：

  4-硝基邻苯二甲酸酐 、 2-苯乙胺 以 甲苯 为溶剂， 反应 2.5h， 以to yield the title compound (24.5 g, 89%)的产率得到5-nitro-2-(2-phenylethyl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Bicyclic fibrinogen antagonists

  摘要：

  分子式为：##STR1## 其中A.sup.1至A.sup.5形成一个七元环，其中含有一个可选择的取代氮原子；D.sup.1至D.sup.4形成一个取代的六元环，可选择包含最多两个氮原子；R最好是至少一个含有取代基的酸基；R*是H、Q-C.sub.1-6烷基、Q-C.sub.1-6氧代烷基、Q-C.sub.2-6烯基、Q-C.sub.3-4氧代烯基、Q-C.sub.3-4氧代炔基、Q-C.sub.2-4炔基、C.sub.3-6环烷基、Ar或Het中的一个或多个基团；Q是H、C.sub.3-6环烷基、Het或Ar；R.sup.6最好是一种含有碱性氮原子的取代基；是血小板聚集抑制剂。

  公开号：

  US05939412A1

文献信息

• Bicyclic fibrinogen antagonists
  申请人：SmithKline Beecham Corporation

  公开号：US06403578B1

  公开（公告）日：2002-06-11

  This invention relates to compounds of the formulae: wherein A1 is O, S, N—R1 or CHR1; A4 is N—R4 or CHR4; R2 is a sidechain containing an acid or ester group; R1, R4 and R5 are substituents such as H, alkyl and aryl alkyl, and R6 is a sidechain containing a nitrogen group; and pharmaceutically acceptable salts thereof, which are effective for inhibiting platelet aggregation, pharmaceutical compositions for effecting such activity, and a method for inhibiting platelet aggregation.

  这项发明涉及以下式的化合物：其中A1为O、S、N—R1或CHR1；A4为N—R4或CHR4；R2为含有酸或酯基团的侧链；R1、R4和R5为H、烷基和芳基烷基等取代基；R6为含有氮基团的侧链；以及其药学上可接受的盐，这些化合物对抑制血小板聚集具有有效作用，用于实现此活性的药物组合物，以及抑制血小板聚集的方法。
• 4-Nitrophthalimides. I. Derivatives of Alkyl Halides Giving a Saponification Equivalent¹
  作者：John H. Billman、R. Vincent Cash

  DOI：10.1021/ja01106a503

  日期：1953.5
• Design, Synthesis and Protection Against Pentylenetetrazole-induced Seizure of N-aryl Derivatives of the Phthalimide Pharmacophore
  作者：Asghar Davood、Hamed Shafaroodi、Mohsen Amini、Alireza Nematollahi、Mehrshad Shirazi、Maryam Iman

  DOI：10.2174/157340612802084289

  日期：2012.9.1

  A series of compounds including N-aryl substituents of phthalimide and 4-nitrophthalimide were synthesized and evaluated for their anticonvulsant properties. The in vivo screening data suggest that all the analogs have the ability to protect against pentylenetetrazole-induced seizures. These compounds exerted their maximal effects 30 min after administration. The most potent compound in both, tonic and clonic seizure was 1-naphthyl derivative (comp. 6), which was more active than the reference drug known as Phenytoin. Using an open pore model of the Na channel, these anticonvulsants were docked in the active site and examined in relation to the residues identified by mutagenesis as important for their binding energies. Docking studies revealed that all compounds (1-13) interacted mainly with residues II-S6 of NaV1.2 by making hydrogen bonds and additional hydrophobic interactions with domain I and II in the channel's inner pore.
• BICYCLIC FIBRINOGEN ANTAGONISTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0593603A1

  公开（公告）日：1994-04-27
• US5693636A
  申请人：——

  公开号：US5693636A

  公开（公告）日：1997-12-02