(R,S)-ethyl 5-(1-hydroxyethyl)-1H-pyrrole-2-carboxylate | 635313-71-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (R,S)-ethyl 5-(1-hydroxyethyl)-1H-pyrrole-2-carboxylate
• 英文别名: ethyl 5-(1-hydroxyethyl)-1H-pyrrole-2-carboxylate
• CAS: 635313-71-2
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: ZGGVRGSNPVPJNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,S)-ethyl 5-(1-hydroxyethyl)-1H-pyrrole-2-carboxylate 在 戴斯-马丁氧化剂 作用下， 以96%的产率得到ethyl 5-acetyl-pyrrole-2-carboxylate
  参考文献：
  名称：

  2-Aminobenzimidazoles as potent ITK antagonists: de novo design of a pyrrole system targeting additional hydrogen bonding interaction

  摘要：

  Based on information from molecular modeling, a series of 2-aminobenzimidazoles with pyrrole moieties were designed and synthesized as ITK antagonists. Results showed that a significant improvement of intrinsic and cell-based potency was achieved. X-ray crystallographic analysis of an inhibitor complex with ITK confirmed the prediction from the de novo design that the pyrrole moiety of the inhibitor would form an additional hydrogen bonding interaction with Glu436 in the catalytic domain, and hence improve overall binding affinity of the inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.10.057
• 作为产物：
  描述：

  吡咯-2-羧酸乙酯 在 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 5.25h， 生成 (R,S)-ethyl 5-(1-hydroxyethyl)-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: synthesis and mechanism of action

  摘要：

  13C NMR 和质谱研究已用于证明 N-磺酰羟甲基吡咯抑制剂 (10) 对 α-胰凝乳蛋白酶的抑制是非共价的。已合成了在替代的 C2 位置引入吸电子基团（酰基取代基）的羟基烷基吡咯，并且还显示出可使 α-胰凝乳蛋白酶失活。对此类的 SAR 研究表明，在 C2 处掺入苯丙氨酸是有利的，但在 C5 处引入疏水取代基几乎没有什么好处。

  DOI：

  10.1039/b302411c

文献信息

• 2-Aminobenzimidazoles as potent ITK antagonists: de novo design of a pyrrole system targeting additional hydrogen bonding interaction
  作者：Ho Yin Lo、Jörg Bentzien、Andre White、Chuk C. Man、Roman W. Fleck、Steven S. Pullen、Hnin Hnin Khine、Josephine King、Joseph R. Woska、John P. Wolak、Mohammed A. Kashem、Gregory P. Roth、Hidenori Takahashi

  DOI：10.1016/j.tetlet.2008.10.057

  日期：2008.12

  Based on information from molecular modeling, a series of 2-aminobenzimidazoles with pyrrole moieties were designed and synthesized as ITK antagonists. Results showed that a significant improvement of intrinsic and cell-based potency was achieved. X-ray crystallographic analysis of an inhibitor complex with ITK confirmed the prediction from the de novo design that the pyrrole moiety of the inhibitor would form an additional hydrogen bonding interaction with Glu436 in the catalytic domain, and hence improve overall binding affinity of the inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.
• Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: synthesis and mechanism of action
  作者：Derek C. Martyn、Andrea J. Vernall、Bruce M. Clark、Andrew D. Abell

  DOI：10.1039/b302411c

  日期：——

  13C NMR and mass spectrometry studies have been used to demonstrate that the inhibition of α-chymotrypsin by N-sulfonylhydroxymethylpyrrole inhibitors (10) is non-covalent. Hydroxyalkylpyrroles in which an electron-withdrawing group (acyl substituent) is introduced at the alternative C2 position have been synthesised and also shown to inactivate α-chymotrypsin. SAR studies on this class suggests that the incorporation of phenylalanine at C2 is favoured, however, there is little gain in introducing a hydrophobic substituent at C5.

  13C NMR 和质谱研究已用于证明 N-磺酰羟甲基吡咯抑制剂 (10) 对 α-胰凝乳蛋白酶的抑制是非共价的。已合成了在替代的 C2 位置引入吸电子基团（酰基取代基）的羟基烷基吡咯，并且还显示出可使 α-胰凝乳蛋白酶失活。对此类的 SAR 研究表明，在 C2 处掺入苯丙氨酸是有利的，但在 C5 处引入疏水取代基几乎没有什么好处。