[[amino-(4-methylphenyl)methylidene]amino] ethyl carbonate | 31827-21-1

• 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: [[amino-(4-methylphenyl)methylidene]amino] ethyl carbonate
• CAS: 31827-21-1
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: GZEMZJLXAGHDBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [[amino-(4-methylphenyl)methylidene]amino] ethyl carbonate 在 copper(l) iodide 、 水 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 4-(4-{[5-oxo-3-(p-tolyl)-1,2,4-oxadiazol-4(5H)-yl]methyl}-1H-1,2,3-triazol-1-yl)benzoic acid
  参考文献：
  名称：

  Discovery of novel heterocyclic derivatives containing oxadiazolone or pyrimidinone cores as DPP‐4 inhibitors

  摘要：

  Type 2 diabetes is a chronic disease characterized by insulin resistance and alterations in incretin secretion, such as the glucagon‐like peptide‐1 (GLP‐1) hormone. GLP‐1 plays a crucial role in signaling insulin production in the pancreas, with its activity regulated by the dipeptidyl peptidase 4 (DPP‐4) enzyme. DPP‐4 presents an intriguing strategy for controlling type 2 diabetes. This study focuses on synthesizing 22 novel oxadiazolone and pyrimidinone derivatives, in vitro DPP‐4 inhibition, and elucidating binding modes through molecular docking simulations. Nine compounds showed promising inhibitory activity, with IC50 values ranging from 0.3 to 1.86 mM. Molecular docking simulations revealed interactions between these compounds and critical residues in the enzyme's active site, such as Arg125, Glu206, Ser630, and His740. This investigation introduces a new class of DPP‐4 inhibitors, providing insights into the design of more potent molecules as potential candidates for combating type 2 diabetes. The findings contribute to developing innovative therapeutics for managing this prevalent metabolic disorder.

  DOI：

  10.1002/jhet.4811
• 作为产物：
  描述：

  对甲苯腈 在 盐酸羟胺 、 碳酸氢钠 、 三乙胺 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 生成 [[amino-(4-methylphenyl)methylidene]amino] ethyl carbonate
  参考文献：
  名称：

  New oxadiazol‐5‐ones derivatives and their performance as angiotensin‐converting enzyme (ACE) inhibitors

  摘要：

  Angiotensin‐converting enzyme inhibitors are widely used in treating arterial hypertension, acting on the renin‐angiotensin‐aldosterone system and controlling blood pressure. We present a novel, greener, and faster methodology to assess the 1,2,4‐oxadiazol‐5‐one ring and perform molecular modifications to obtain angiotensin‐converting enzyme (ACE) inhibitors using this heterocyclic core. Molecular docking simulations indicate that the tested compounds exhibited an affinity for the ACE binding site, with scores comparable to the commercial inhibitor lisinopril. However, in vitro assays revealed that the compounds were ineffective in inhibiting ACE activity. The lack of inhibition may be related to the compounds' more apolar nature. These results emphasize the importance of integrating computational and experimental approaches in developing new drugs, providing valuable insights for planning future studies to optimize the activity of synthesized compounds.

  DOI：

  10.1002/jhet.4835

文献信息

• Schubart, Chemische Berichte, 1889, vol. 22, p. 2441
  作者：Schubart

  DOI：——

  日期：——
• Heterocycles from nitrile oxides. 3. 1,2,4-Oxadiazol-5(4H)-ones
  作者：Ahmad Q. Hussein

  DOI：10.1021/je00047a037

  日期：1987.1
• Kawashima, Etsuko; Ando, Yuko; Tabei, Katsumi, Heterocycles, 1987, vol. 26, # 4, p. 1015 - 1028
  作者：Kawashima, Etsuko、Ando, Yuko、Tabei, Katsumi、Miyamae, Hiroshi

  DOI：——

  日期：——
• KAWASHIMA, ETSUKO;ANDO, YUKO;TABEI, KATSUMI;MIYAMAE, HIROSHI, HETEROCYCLES, 26,(1987) N 4, 1015-1028
  作者：KAWASHIMA, ETSUKO、ANDO, YUKO、TABEI, KATSUMI、MIYAMAE, HIROSHI

  DOI：——

  日期：——
• HUSSELN AHMAD Q., J. CHEM. AND ENG. DATA, 32,(1987) N 1, 127-128
  作者：HUSSELN AHMAD Q.

  DOI：——

  日期：——