3-(3-Dimethylamino-propyl)-2-(4-methyl-3-nitro-phenyl)-thiazolidin-4-one | 751467-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-Dimethylamino-propyl)-2-(4-methyl-3-nitro-phenyl)-thiazolidin-4-one
• 英文别名: 3-[3-(Dimethylamino)propyl]-2-(4-methyl-3-nitrophenyl)-1,3-thiazolidin-4-one
• CAS: 751467-62-6
• 化学式: C₁₅H₂₁N₃O₃S
• 分子量: 323.416
• InChiKey: GLVQBCJWIWUNCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  94.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3-Dimethylamino-propyl)-2-(4-methyl-3-nitro-phenyl)-thiazolidin-4-one 在 铁粉 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2-(3-Amino-4-methyl-phenyl)-3-(3-dimethylamino-propyl)-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 2-(substituted phenyl)-3-[3-(N,N-dimethylamino)propyl]-1,3-thiazolidin-4-ones acting as H1-histamine antagonists

  摘要：

  2-(Substituted-phenyl)-3-[3-(N,N-dimethylamino)propyl]-1,3-thiazolidin-4-ones (1-15) showed dependence of the potency of the H-1-histamine antagonism on the m- and p-substituents suggesting that the aromatic moiety binds the receptor by a strong pi-interaction. Electron-withdrawing substituents decrease the potency while the electron-donating alkyl substituents, enhancing the aryl HOMO energy, increase the antihistamine activity. The m-substituents with the capability to form hydrogen bonds, seems to share an extrainteraction with hydrogen accepting or donating groups of the histamine receptor and exhibits very high potency. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00064-6
• 作为产物：
  描述：

  4-甲基-3-硝基苯甲醛 以 苯 为溶剂， 生成 3-(3-Dimethylamino-propyl)-2-(4-methyl-3-nitro-phenyl)-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 2-(substituted phenyl)-3-[3-(N,N-dimethylamino)propyl]-1,3-thiazolidin-4-ones acting as H1-histamine antagonists

  摘要：

  2-(Substituted-phenyl)-3-[3-(N,N-dimethylamino)propyl]-1,3-thiazolidin-4-ones (1-15) showed dependence of the potency of the H-1-histamine antagonism on the m- and p-substituents suggesting that the aromatic moiety binds the receptor by a strong pi-interaction. Electron-withdrawing substituents decrease the potency while the electron-donating alkyl substituents, enhancing the aryl HOMO energy, increase the antihistamine activity. The m-substituents with the capability to form hydrogen bonds, seems to share an extrainteraction with hydrogen accepting or donating groups of the histamine receptor and exhibits very high potency. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00064-6

文献信息

• Synthesis and structure–activity relationships of 2-(substituted phenyl)-3-[3-(N,N-dimethylamino)propyl]-1,3-thiazolidin-4-ones acting as H1-histamine antagonists
  作者：M.Vittoria Diurno、Orazio Mazzoni、Gaetano Correale、Isabel Gomez Monterrey、Antonio Calignano、Giovanna La Rana、Adele Bolognese

  DOI：10.1016/s0014-827x(99)00064-6

  日期：1999.9

  2-(Substituted-phenyl)-3-[3-(N,N-dimethylamino)propyl]-1,3-thiazolidin-4-ones (1-15) showed dependence of the potency of the H-1-histamine antagonism on the m- and p-substituents suggesting that the aromatic moiety binds the receptor by a strong pi-interaction. Electron-withdrawing substituents decrease the potency while the electron-donating alkyl substituents, enhancing the aryl HOMO energy, increase the antihistamine activity. The m-substituents with the capability to form hydrogen bonds, seems to share an extrainteraction with hydrogen accepting or donating groups of the histamine receptor and exhibits very high potency. (C) 1999 Elsevier Science S.A. All rights reserved.