3-nitro-N-(p-hydroxy-phenethyl) phthalimide

• 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: 3-nitro-N-(p-hydroxy-phenethyl) phthalimide
• 英文别名: N-[2-(4-hydroxyphenyl)ethyl]-3-nitrophthalimide；2-[2-(4-hydroxyphenyl)ethyl]-4-nitroisoindole-1,3-dione
• 化学式: C₁₆H₁₂N₂O₅
• 分子量: 312.282
• InChiKey: SEGBPKYKYYUUEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 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：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-nitro-N-(p-hydroxy-phenethyl) phthalimide 在 palladium-carbon catalyst 作用下， 以 methanol (20 ml)-ethanol (50 ml)-acetic acid 、 水 、 氢气 为溶剂， 以24.1%的产率得到3-amino-N-[2-(4-hydroxyphenyl)ethyl]phthalimide
  参考文献：
  名称：

  Compounds and pharmaceutical use thereof

  摘要：

  公式（I）##STR1##中的化合物，其中每个符号如说明书中所定义，其药用可接受的盐及其医药用途。本发明的化合物（I）及其药用可接受的盐对大麻素受体具有选择性作用，尤其是外周受体，对中枢系统的副作用较小，并且具有卓越的免疫调节作用、抗炎作用、抗过敏作用和对肾炎的治疗效果。因此，它们作为大麻素受体，尤其是外周大麻素受体的激动剂和拮抗剂，免疫调节剂，自身免疫性疾病的治疗剂，抗炎剂，抗过敏剂和肾炎的治疗剂是有用的。

  公开号：

  US06017919A1
• 作为产物：
  描述：

  对羟基苯乙胺 、 3-硝基邻苯二甲酸酐 在 溶剂黄146 作用下， 以 水 为溶剂， 生成 3-nitro-N-(p-hydroxy-phenethyl) phthalimide
  参考文献：
  名称：

  Synthesis of PPAR-γ Activators Inspired by the Marine Natural Product, Paecilocin A

  摘要：

  一系列N-取代的邻苯二甲酰亚胺衍生物是基于自然PPAR-γ激动剂paecilocin A及合成先导物的药效团研究合成的。向邻苯二甲酰亚胺骨架引入亲水和疏水基团得到了化合物3-14。化合物7在使用大鼠肝Ac2F细胞的荧光素酶测定中显示出显著的PPAR-γ激活。对接模拟表明，邻苯二甲酰亚胺头部的自由羟基和适当的亲水尾部（包括苯基连接器）对PPAR-γ激活是有益的。化合物7和罗西格列酮以浓度依赖的方式激活PPAR-γ，EC50值分别为0.67 μM和0.028 μM。这些邻苯二甲酰亚胺衍生物可进一步作为新型PPAR-γ配体进行研究。

  DOI：

  10.3390/md12020926

文献信息

• NOVEL COMPOUNDS AND PHARMACEUTICAL USE THEREOF
  申请人：Japan Tobacco Inc.

  公开号：EP0887340A1

  公开（公告）日：1998-12-30

  The compounds of the formula (I) wherein each symbol is as defined in the specification, pharmaceutically acceptable salts thereof and pharmaceutical use thereof. The Compound (I) and pharmaceutically acceptable salts thereof of the present invention selectively act on cannabinoid receptors, particularly peripheral receptors, cause less side effects on the central system, and have superior immunoregulating action, antiinflammatory action, antiallergic action and therapeutic effect on nephritis. Therefore, they are useful as cannabinoid receptor, particularly peripheral cannabinoid receptor activators and antagonists, immunoregulators, therapeutic agents for autoimmune diseases, antiinflammatory agents, antiallergic agents and therapeutic agents for nephritis.

  式 (I) 的化合物 其中各符号如说明书中所定义，其药学上可接受的盐及其制药用途。本发明的化合物(I)及其药学上可接受的盐选择性地作用于大麻素受体，特别是外周受体，对中枢系统的副作用较小，具有优越的免疫调节作用、抗炎作用、抗过敏作用和对肾炎的治疗作用。因此，它们可用作大麻素受体（特别是外周大麻素受体）激活剂和拮抗剂、免疫调节剂、自身免疫性疾病治疗剂、抗炎剂、抗过敏剂和肾炎治疗剂。
• Synthesis and Properties of Dendrimers Possessing the Same Fluorophore(s) Located Either Peripherally or Off-Center
  作者：Grégory Franc、Serge Mazères、Cédric-Olivier Turrin、Laure Vendier、Carine Duhayon、Anne-Marie Caminade、Jean-Pierre Majoral

  DOI：10.1021/jo701462f

  日期：2007.11.1

  Two series of phosphorus dendrimers functionalized by maleimide derivatives are synthesized, as well as three new monomeric maleimide derivatives, of which two are characterized by X-ray diffraction. The first series of phosphorus dendrimers possesses maleimide derivatives as end groups (6-48, from generation 0 to generation 3). The second series of dendrimers possesses a single copy of the same maleimide derivative linked "off-center" to a cyclotriphosphazene core, leading, to dissymmetrical dendrimers; this series is synthesized from generation 0 to generation 2. The fluorescence properties of both series of dendrimers and of monomers are studied, affording new information. First, the presence of labile hydrogen extinguishes the fluorescence. Second, the grafting of the fluorophore(s) directly to the core affords highly fluorescent compounds. Finally, an original influence of the 'branches possessing phosphorhydrazone linkages toward the fluorescence properties is shown.
• US6017919A
  申请人：——

  公开号：US6017919A

  公开（公告）日：2000-01-25
• Compounds and pharmaceutical use thereof
  申请人：Japan Tobacco Inc.

  公开号：US06017919A1

  公开（公告）日：2000-01-25

  The compounds of the formula (I) ##STR1## wherein each symbol is as defined in the specification, pharmaceutically acceptable salts thereof and pharmaceutical use thereof. The Compound (I) and pharmaceutically acceptable salts thereof of the present invention selectively act on cannabinoid receptors, particularly peripheral receptors, cause less side effects on the central system, and have superior immunoregulating action, antiinflammatory action, antiallergic action and therapeutic effect on nephritis. Therefore, they are useful as cannabinoid receptor, particularly peripheral cannabinoid receptor activators and antagonists, immunoregulators, therapeutic agents for autoimmune diseases, antiinflammatory agents, antiallergic agents and therapeutic agents for nephritis.

  公式（I）##STR1##中的化合物，其中每个符号如说明书中所定义，其药用可接受的盐及其医药用途。本发明的化合物（I）及其药用可接受的盐对大麻素受体具有选择性作用，尤其是外周受体，对中枢系统的副作用较小，并且具有卓越的免疫调节作用、抗炎作用、抗过敏作用和对肾炎的治疗效果。因此，它们作为大麻素受体，尤其是外周大麻素受体的激动剂和拮抗剂，免疫调节剂，自身免疫性疾病的治疗剂，抗炎剂，抗过敏剂和肾炎的治疗剂是有用的。
• Synthesis of PPAR-γ Activators Inspired by the Marine Natural Product, Paecilocin A
  作者：Bin Xiao、Mingzhi Su、Eun Kim、Jongki Hong、Hae Chung、Hyung Kim、Jun Yin、Jee Jung

  DOI：10.3390/md12020926

  日期：——

  A series of N-substituted phthalimide derivatives were synthesized based on a pharmacophore study of paecilocin A (a natural PPAR-γ agonist) and synthetic leads. The introduction of hydrophilic and hydrophobic groups to the phthalimide skeleton yielded compounds 3–14. Compound 7 showed significant PPAR-γ activation in a luciferase assay using rat liver Ac2F cells. Docking simulations showed that a free hydroxyl group on the phthalimide head and a suitable hydrophilic tail, including a phenyl linker, were beneficial for PPAR-γ activation. Compound 7 and rosiglitazone concentration-dependently activated PPAR-γ with EC50 values of 0.67 μM and 0.028 μM, respectively. These phthalimide derivatives could be further investigated as a new class of PPAR-γ ligands.

  一系列N-取代的邻苯二甲酰亚胺衍生物是基于自然PPAR-γ激动剂paecilocin A及合成先导物的药效团研究合成的。向邻苯二甲酰亚胺骨架引入亲水和疏水基团得到了化合物3-14。化合物7在使用大鼠肝Ac2F细胞的荧光素酶测定中显示出显著的PPAR-γ激活。对接模拟表明，邻苯二甲酰亚胺头部的自由羟基和适当的亲水尾部（包括苯基连接器）对PPAR-γ激活是有益的。化合物7和罗西格列酮以浓度依赖的方式激活PPAR-γ，EC50值分别为0.67 μM和0.028 μM。这些邻苯二甲酰亚胺衍生物可进一步作为新型PPAR-γ配体进行研究。