2-(1,3-dibenzoylimidazolidin-2-yl)imidazole hydrochloride | 65276-01-9

• 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: 2-(1,3-dibenzoylimidazolidin-2-yl)imidazole hydrochloride
• 英文别名: [3-benzoyl-2-(1H-imidazol-2-yl)imidazolidin-1-yl]-phenylmethanone;hydrochloride
• CAS: 65276-01-9
• 化学式: C₂₀H₁₈N₄O₂*ClH
• 分子量: 382.849
• InChiKey: LMYXNMYOUOJXFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(1,3-dibenzoylimidazolidin-2-yl)imidazole hydrochloride 在 盐酸 、 水 作用下， 生成 2-咪唑甲醛
  参考文献：
  名称：

  Schiff’s Base Imidazole Derivatives Synthesis and Evaluation for their Anti-Inflammatory Activity

  摘要：

  This study is focused on the synthesis and exploration of Schiff’s base imidazole derivatives with the aim of assessing their anti-inflammatory activity. A series of compounds were synthesized and characterized using spectroscopic techniques. In-silico docking analysis was employed to identify potential active ingredients. The anti-inflammatory properties of these derivatives were then investigated using paw edema model induced by carrageenan followed by assessment of TNF-α and IL-1β as inflammatory cytokines. Results showed that specific Schiff’s base Imidazole derivatives, notably C1IN, C2IN, C4IN, C5IN, and C11IN, demonstrate significant effectiveness in alleviating paw edema and reducing the level of IL-1β and TNF-α. The findings emphasize the potential of these developed derivatives as viable options for anti-inflammatory intervention. The observed reduction in paw edema and cytokine levels signifies a promising anti-inflammatory profile, positioning these compounds as candidates for further exploration and development. The study contributes valuable insights into the anti-inflammatory properties of imidazole derivatives, suggesting their potential therapeutic applications in inflammatory conditions. Future research should delve deeper into mechanistic aspects and conduct additional preclinical studies to validate the translational potential of these derivatives in anti-inflammatory pharmacotherapy. This research opens avenues for the development of novel anti-inflammatory agents with potential clinical relevance.

  DOI：

  10.13005/ojc/400119
• 作为产物：
  描述：

  2-(1,3-二苯甲酰基-4-咪唑啉-2-基)咪唑盐酸盐 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 0.2h， 生成 2-(1,3-dibenzoylimidazolidin-2-yl)imidazole hydrochloride
  参考文献：
  名称：

  IMIDAZOLE-2-CARBOXALDEHYDE

  摘要：

  DOI：

  10.15227/orgsyn.060.0072

文献信息

• NMR Characterization of Hydrate and Aldehyde Forms of Imidazole-2-carboxaldehyde and Derivatives
  作者：Juan Manuel Lázaro Martínez、Pablo Nicolás Romasanta、Ana Karina Chattah、Graciela Yolanda Buldain

  DOI：10.1021/jo902588s

  日期：2010.5.21

  The existence and stability of the aldehyde-hydrate form of imidazole-2-carboxaldehyde (4) were studied using FTIR together with solution- and solid-state NMR experiments. The results allowed us to conclude that the hydrate form was stable and precipitated at pH = 8.0 and that the aldehyde form was isolated at p = 6.5 and 9.5. Moreover, the presence of the aldehyde-hydrate form was studied through NMR experiments in D2O at both alkaline and acidic pH. In addition, the tautomeric forms of the 2-substituted imidazole compounds were also analyzed to investigate the influence of the hybridization on the carbon adjacent to the imidazole ring, by C-13 NMR in DMSO-d(6), acetone-d(6), and CDCl3. The presence of the syn- and anti-isomers of oxime 8 obtained from 4 were characterized by solid-state NMR and variable-temperature NMR experiments in acetone-d(6).
• BASTIAANSEN, L. A. M.;VAN, DIER, P. M.;GODEFROI, E. F., ORG. SYNTH. VOL. 60., NEW YORK E.A., 1981, 72-77
  作者：BASTIAANSEN, L. A. M.、VAN, DIER, P. M.、GODEFROI, E. F.

  DOI：——

  日期：——
• BASTIAANSEN L. A. M.; GODEFROI E. F., J. ORG. CHEM., 1978, 43, NO 8, 1603-1604
  作者：BASTIAANSEN L. A. M.、 GODEFROI E. F.

  DOI：——

  日期：——
• IMIDAZOLE-2-CARBOXALDEHYDE
  作者：Bastiaansen, Leonard A. M.、Van Lier, Pieter M.、Godefroi, Erik F.

  DOI：10.15227/orgsyn.060.0072

  日期：——
• Schiff’s Base Imidazole Derivatives Synthesis and Evaluation for their Anti-Inflammatory Activity
  作者：Divya Singh、Rajeev Kharb、Satish Kumar Sharma

  DOI：10.13005/ojc/400119

  日期：2024.2.25

  This study is focused on the synthesis and exploration of Schiff’s base imidazole derivatives with the aim of assessing their anti-inflammatory activity. A series of compounds were synthesized and characterized using spectroscopic techniques. In-silico docking analysis was employed to identify potential active ingredients. The anti-inflammatory properties of these derivatives were then investigated using paw edema model induced by carrageenan followed by assessment of TNF-α and IL-1β as inflammatory cytokines. Results showed that specific Schiff’s base Imidazole derivatives, notably C1IN, C2IN, C4IN, C5IN, and C11IN, demonstrate significant effectiveness in alleviating paw edema and reducing the level of IL-1β and TNF-α. The findings emphasize the potential of these developed derivatives as viable options for anti-inflammatory intervention. The observed reduction in paw edema and cytokine levels signifies a promising anti-inflammatory profile, positioning these compounds as candidates for further exploration and development. The study contributes valuable insights into the anti-inflammatory properties of imidazole derivatives, suggesting their potential therapeutic applications in inflammatory conditions. Future research should delve deeper into mechanistic aspects and conduct additional preclinical studies to validate the translational potential of these derivatives in anti-inflammatory pharmacotherapy. This research opens avenues for the development of novel anti-inflammatory agents with potential clinical relevance.