pyrrole-3-carboxaldehyde oxime | 32597-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: pyrrole-3-carboxaldehyde oxime
• 英文别名: (E)-N-(1H-Pyrrol-3-ylmethylidene)hydroxylamine；N-(1H-pyrrol-3-ylmethylidene)hydroxylamine
• CAS: 32597-35-6
• 化学式: C₅H₆N₂O
• 分子量: 110.115
• InChiKey: BYNPPKBMTMCMDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.4
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  pyrrole-3-carboxaldehyde oxime 在 乙醇 、 sodium 作用下， 以64%的产率得到(1H-吡咯-3-基)甲胺
  参考文献：
  名称：

  Refinement of the Benzodiazepine Receptor Site Topology by Structure−Activity Relationships of New N-(Heteroarylmethyl)indol-3-ylglyoxylamides

  摘要：

  N-(Heteroaryiniethyl)indol-3-ylglyoxylamides (1-26) were synthesized and evaluated as ligands of the benzodiazepine receptor (BzR) to probe the hydrogen bonding properties of the so-called S, site of the BzR by means of suitable heterocyclic side chains. SARs were developed in light of our hypothesis of binding modes A and B. Pyrrole and furan derivatives adopting mode A (2, 8, 10, 20, 22) turned out to be more potent (K-i values < 35 nM) than their analogues lacking hydrogen bonding heterocyclic side chains. These data suggest that the most potent indoles interact with a hydrogen bond acceptor/donor (HBA/D) group located within the S, site of the BzR. Compounds 1, 2, 8, 19, 20, and 22, tested at recombinant rat (alpha(1)beta(2)gamma(2),, alpha(2)beta(2)gamma(2), and alpha(5)beta(3)gamma(2) BzRs, elicited selectivity for the alpha(1)beta(2)gamma(2) isoform. On the basis of published mutagenesis studies and the present SARs, we speculate that the S, HBA/D group might be identified as the hydroxyl of alpha(1)-Tyr209 or of other neighboring amino acids.

  DOI：

  10.1021/jm0511841
• 作为产物：
  描述：

  吡咯-3-甲醛 在 盐酸羟胺 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 0.5h， 以94%的产率得到pyrrole-3-carboxaldehyde oxime
  参考文献：
  名称：

  Refinement of the Benzodiazepine Receptor Site Topology by Structure−Activity Relationships of New N-(Heteroarylmethyl)indol-3-ylglyoxylamides

  摘要：

  N-(Heteroaryiniethyl)indol-3-ylglyoxylamides (1-26) were synthesized and evaluated as ligands of the benzodiazepine receptor (BzR) to probe the hydrogen bonding properties of the so-called S, site of the BzR by means of suitable heterocyclic side chains. SARs were developed in light of our hypothesis of binding modes A and B. Pyrrole and furan derivatives adopting mode A (2, 8, 10, 20, 22) turned out to be more potent (K-i values < 35 nM) than their analogues lacking hydrogen bonding heterocyclic side chains. These data suggest that the most potent indoles interact with a hydrogen bond acceptor/donor (HBA/D) group located within the S, site of the BzR. Compounds 1, 2, 8, 19, 20, and 22, tested at recombinant rat (alpha(1)beta(2)gamma(2),, alpha(2)beta(2)gamma(2), and alpha(5)beta(3)gamma(2) BzRs, elicited selectivity for the alpha(1)beta(2)gamma(2) isoform. On the basis of published mutagenesis studies and the present SARs, we speculate that the S, HBA/D group might be identified as the hydroxyl of alpha(1)-Tyr209 or of other neighboring amino acids.

  DOI：

  10.1021/jm0511841