2-((phenylamino)methyl)isoindoline-1,3-dione | 13314-96-0

• 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-((phenylamino)methyl)isoindoline-1,3-dione
• 英文别名: 2-[(phenylamino)methyl]-isoindole-1,3-dione；N-anilinomethyl-phthalimide；N-Anilinomethyl-phthalimid；2-[(phenylamino)methyl]-1H-isoindole-1,3(2H)-dione；2-(anilinomethyl)-1H-isoindole-1,3(2H)-dione；2-(anilinomethyl)isoindole-1,3-dione
• CAS: 13314-96-0
• 化学式: C₁₅H₁₂N₂O₂
• mdl: MFCD00221821
• 分子量: 252.272
• InChiKey: YQBGAGYLFPRNEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  2-((phenylamino)methyl)isoindoline-1,3-dione 、 phenylsulfone 、 聚合甲醛 以72%的产率得到
  参考文献：
  名称：

  MESSINGER P.; MEYER H., ARCH. PHARM., 1979, 312, NO 12, 1007-1010

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(toluene-4-sulfonylmethyl)-aniline 以30%的产率得到
  参考文献：
  名称：

  MESSINGER P., PHARMAZIE , 1976, 31, NO 1, 16-18

  摘要：

  DOI：

文献信息

• Isoindole-1,3-dione derivatives as RSK2 inhibitors: synthesis, molecular docking simulation and SAR analysis
  作者：Wei Zhou、Shiliang Li、Weiqiang Lu、Jun Yuan、Yufang Xu、Honglin Li、Jin Huang、Zhenjiang Zhao

  DOI：10.1039/c5md00469a

  日期：——

  RSK2 (p90 ribosomal S6 kinase 2) is a serine/threonine kinase expressed in a variety of cancers. Molecular-targeted inhibition of RSK2 as a potential therapeutic strategy for human cancers has been documented. In this work, a series of isoindole-1,3-dione derivatives as novel RSK2 inhibitors were designed and synthesized from a hit discovered in our previous study. Some compounds were confirmed to

  RSK2（p90核糖体S6激酶2）是在多种癌症中表达的丝氨酸/苏氨酸激酶。已经证明了分子靶向抑制RSK2作为人类癌症的潜在治疗策略。在这项工作中，从我们先前的研究中发现的命中物中，设计并合成了一系列新型RSK2抑制剂异吲哚-1,3-二酮衍生物。已确认某些化合物是中等有效的RSK2抑制剂，IC 50值约为0.5μM。通过分子对接进行结构-活性关系分析和结合模式研究。
• Crystal Structure, Conformation and Vibrational Analysis of a Mannich Base: 2-[(phenylamino) methyl]-isoindole-1,3-dione
  作者：S. Franklin、D. Tamilvendan、G. Venkatesa Prabhu、T. Balasubramanian

  DOI：10.1007/s10870-011-0055-1

  日期：2011.8

  The crystal structure of 2-[(phenylamino) methyl]-isoindole-1,3-dione, C15H12N2O2, crystallizes in the triclinic space group Pī with cell parameters of a = 7.1176 (2) Å, b = 8.5533 (3) Å, c = 10.9163 (4) Å, α = 95.937 (2)°, β = 102.975 (2)°, γ = 108.474 (2)°, V = 603.18 (4) Å3 and Z = 2. This indole derivative is a Mannich base in which a methyl group bridges the molecules of phthalimide and aniline molecules. The dihedral angle between the phthalimide and aniline is 75.47 (3)°. The molecules of the title compound forms a centrosymmetric hydrogen-bonded dimer through a pair of N–H···O hydrogen bonds. C–H···π and an extensive π···π interactions, in addition, stabilize the molecular structure. The compound presented here is V-shaped, the angle at the methyl bridge [N–C–N] being 115.04 (12)°. Present study reports the conformation and hydrogen bonding interactions which play an important role in biological functions. Vibration analysis complement the structure analysed. The crystal structure of 2-[(phenylamino) methyl]-isoindole-1,3-dione is a Mannich base compound in which a phenylamine and phthalimide molecules are bridged by a methyl group.

  2-[(苯基氨基)甲基]-异吲哚-1,3-二酮（C15H12N2O2）的水晶结构以三斜晶系Pī为空间群，晶胞参数为a=7.1176(2)Å、b=8.5533(3)Å、c=10.9163(4)Å、α=95.937(2)°、β=102.975(2)°、γ=108.474(2)°、V=603.18(4)Å3和Z=2。这种吲哚衍生物是一种曼尼希碱，其中甲基桥连了邻苯二甲酰亚胺分子和苯胺分子。邻苯二甲酰亚胺和苯胺之间的二面角为75.47(3)°。标题化合物的分子通过一对N-H·O氢键形成中心对称的氢键二聚体。此外，C-H·π和广泛的π·π相互作用稳定了分子结构。此处介绍的化合物呈V形，甲基桥[N-C-N]处的角度为115.04(12)°。本研究报告了构象和氢键相互作用，它们在生物功能中起着重要作用。振动
• Sachs, Chemische Berichte, 1898, vol. 31, p. 3234
  作者：Sachs

  DOI：——

  日期：——
• Identification of Amines. I. N-(Arylaminomethyl)-phthalimides
  作者：Meldrum B. Winstead、Harold W. Heine

  DOI：10.1021/ja01612a068

  日期：1955.4
• Potent novel nonsteroidal androgen antagonists with a phthalimide skeleton
  作者：Hiroyuki Miyachi、Akihiko Azuma、Takuya Kitamoto、Kozue Hayashi、Shigeaki Kato、Masafumi Koga、Bunzo Sato、Yuichi Hashimoto

  DOI：10.1016/s0960-894x(97)00249-7

  日期：1997.6

  Anti-androgenic activity of various phthalimide analogs was evaluated based on inhibition of androgen-induced activation of nuclear androgen receptor (CAT assay) and on growth inhibition of the androgen-dependent clonal cell Line SC-3. Some compounds showed very potent androgen-antagonistic activity. (C) 1997 Elsevier Science Ltd.