2-(1-naphthyl)-1H-4-imidazolcarbaldehyde | 279251-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-naphthyl)-1H-4-imidazolcarbaldehyde
• 英文别名: 2-naphthalen-1-yl-1H-imidazole-5-carbaldehyde
• CAS: 279251-02-4
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: CEHYVTNHKAZRAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-叔丁基羟胺盐酸盐 、 2-(1-naphthyl)-1H-4-imidazolcarbaldehyde 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以70%的产率得到(Z)-α-[2-(-Naphthyl)-1H-imidazol-4-yl]-N-tert-butylnitrone
  参考文献：
  名称：

  Synthesis, Structure, and Neuroprotective Properties of Novel Imidazolyl Nitrones

  摘要：

  A new series of imidazolyl nitrones spin traps has been synthesized and evaluated pharmacologically. The salient structural feature of these molecules is the presence of an imidazole moiety substituted by aromatic or heteroaromatic cycles. This connectivity imparts to the nitrone superior neuroprotective properties in vivo and in parallel reduced side effects and toxicity. Thus compound 6a (a 2-phenylimidazolyl nitrone) administered intraperitoneally protects (80%) mice from lethality induced by an intracerebroventricular administration of tert-butyl hydroperoxide (t-BHP) an oxidant capable of inducing neurodegenerative processes. Administration of the archetypal nitrone phenyl-tert-butyl nitrone (PBN) at an equimolar dose also affords some protection (60%) in this test. However, this activity is accompanied by hypothermia, whereas no such effect is apparent for 6a. Moreover, previously prepared nonsubstituted or alkyl-substituted imidazolyl nitrones were shown to be extremely toxic to rats in contrast to the compounds prepared in this study. The observed activities in vivo correlate well with the calculated partition coefficients (ClogP) and HOMO energy level.

  DOI：

  10.1021/jm991154w
• 作为产物：
  描述：

  2-(1-naphthyl)-4-cyano-1H-imidazole 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以39%的产率得到2-(1-naphthyl)-1H-4-imidazolcarbaldehyde
  参考文献：
  名称：

  Synthesis, Structure, and Neuroprotective Properties of Novel Imidazolyl Nitrones

  摘要：

  A new series of imidazolyl nitrones spin traps has been synthesized and evaluated pharmacologically. The salient structural feature of these molecules is the presence of an imidazole moiety substituted by aromatic or heteroaromatic cycles. This connectivity imparts to the nitrone superior neuroprotective properties in vivo and in parallel reduced side effects and toxicity. Thus compound 6a (a 2-phenylimidazolyl nitrone) administered intraperitoneally protects (80%) mice from lethality induced by an intracerebroventricular administration of tert-butyl hydroperoxide (t-BHP) an oxidant capable of inducing neurodegenerative processes. Administration of the archetypal nitrone phenyl-tert-butyl nitrone (PBN) at an equimolar dose also affords some protection (60%) in this test. However, this activity is accompanied by hypothermia, whereas no such effect is apparent for 6a. Moreover, previously prepared nonsubstituted or alkyl-substituted imidazolyl nitrones were shown to be extremely toxic to rats in contrast to the compounds prepared in this study. The observed activities in vivo correlate well with the calculated partition coefficients (ClogP) and HOMO energy level.

  DOI：

  10.1021/jm991154w

文献信息

• Synthesis, Structure, and Neuroprotective Properties of Novel Imidazolyl Nitrones
  作者：Alain Dhainaut、André Tizot、Eric Raimbaud、Brian Lockhart、Pierre Lestage、Solo Goldstein

  DOI：10.1021/jm991154w

  日期：2000.6.1

  A new series of imidazolyl nitrones spin traps has been synthesized and evaluated pharmacologically. The salient structural feature of these molecules is the presence of an imidazole moiety substituted by aromatic or heteroaromatic cycles. This connectivity imparts to the nitrone superior neuroprotective properties in vivo and in parallel reduced side effects and toxicity. Thus compound 6a (a 2-phenylimidazolyl nitrone) administered intraperitoneally protects (80%) mice from lethality induced by an intracerebroventricular administration of tert-butyl hydroperoxide (t-BHP) an oxidant capable of inducing neurodegenerative processes. Administration of the archetypal nitrone phenyl-tert-butyl nitrone (PBN) at an equimolar dose also affords some protection (60%) in this test. However, this activity is accompanied by hypothermia, whereas no such effect is apparent for 6a. Moreover, previously prepared nonsubstituted or alkyl-substituted imidazolyl nitrones were shown to be extremely toxic to rats in contrast to the compounds prepared in this study. The observed activities in vivo correlate well with the calculated partition coefficients (ClogP) and HOMO energy level.