2-氰基哌啶盐酸盐 | 117921-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 2-氰基哌啶盐酸盐
• 英文名称: rac-2-piperidinecarbonitrile hydrochloride
• 英文别名: (+/-)-piperidine-2-carbonitrile; hydrochloride；(+/-)-Piperidin-2-carbonitril; Hydrochlorid；Piperidine-2-carbonitrile hydrochloride；piperidine-2-carbonitrile;hydrochloride
• CAS: 117921-54-7
• 化学式: C₆H₁₀N₂*ClH
• 分子量: 146.62
• InChiKey: DSAFWCGACOBUOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.07
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.8
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319

反应信息

• 作为反应物：
  描述：

  2-氰基哌啶盐酸盐 、 N-苄氧羰基甘氨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到benzyl N-[2-(2-cyanopiperidin-1-yl)-2-oxoethyl]carbamate
  参考文献：
  名称：

  Constrained Peptidomimetics Reveal Detailed Geometric Requirements of Covalent Prolyl Oligopeptidase Inhibitors

  摘要：

  Prolyl oligopeptidases cleave peptides on the carboxy side of internal proline residues and their inhibition has potential in the treatment of human brain disorders. Using our docking program FITTED, we have designed a series of constrained covalent inhibitors, built from a series of bicyclic scaffolds, to study the optimal shape required for these small molecules. These structures bear nitrile functional groups that we predicted to covalently bind to the catalytic serine of the enzyme. Synthesis and biological assays using human brain-derived astrocytic cells and endothelial cells and human fibroblasts revealed that these compounds act as selective inhibitors of prolyl oligopeptidase activity compared to prolyl-dipeptidyl-aminopeptidase activity, are able to penetrate the cells and inhibit intracellular activities in intact living cells. This integrated computational and experimental study shed light oil the binding mode of inhibitors in the enzyme active site and will guide the design of future drug-like molecules.

  DOI：

  10.1021/jm901013a
• 作为产物：
  描述：

  1-叔丁氧羰基-2-哌啶甲酰胺 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.75h， 以92%的产率得到2-氰基哌啶盐酸盐
  参考文献：
  名称：

  Constrained Peptidomimetics Reveal Detailed Geometric Requirements of Covalent Prolyl Oligopeptidase Inhibitors

  摘要：

  Prolyl oligopeptidases cleave peptides on the carboxy side of internal proline residues and their inhibition has potential in the treatment of human brain disorders. Using our docking program FITTED, we have designed a series of constrained covalent inhibitors, built from a series of bicyclic scaffolds, to study the optimal shape required for these small molecules. These structures bear nitrile functional groups that we predicted to covalently bind to the catalytic serine of the enzyme. Synthesis and biological assays using human brain-derived astrocytic cells and endothelial cells and human fibroblasts revealed that these compounds act as selective inhibitors of prolyl oligopeptidase activity compared to prolyl-dipeptidyl-aminopeptidase activity, are able to penetrate the cells and inhibit intracellular activities in intact living cells. This integrated computational and experimental study shed light oil the binding mode of inhibitors in the enzyme active site and will guide the design of future drug-like molecules.

  DOI：

  10.1021/jm901013a

文献信息

• Hypervalent iodine oxidation of amines using iodosobenzene: Synthesis of nitriles, ketones and lactams
  作者：Robert M Moriarty、Radhe K Vaid、Michael P Duncan、Masahito Ochiai、Minako Inenaga、Yoshimitsu Nagao*

  DOI：10.1016/s0040-4039(00)88473-7

  日期：1988.1

  Primary aliphatic amines on oxidation with iodosobenzene in CH2Cl2 or H2O yield the corresponding nitriles, while primary cycloalkylamines give the corresponding cyclic ketones. Lactams are obtained by the oxidation of cyclic amines. (S)(−) Nicotine () is oxidized to ()-cotinine (). The intermediary imine involved in these processes was trapped in the case of piperidine as the α-aminonitrile.

  在CH 2 Cl 2或H 2 O中与碘代苯氧化时，伯脂肪族伯胺生成相应的腈，而伯环烷基伯胺则生成相应的环酮。内酰胺通过环胺的氧化获得。（S）（-）尼古丁（）被氧化为（）-烟碱（）。在哌啶为α-氨基腈的情况下，与这些过程有关的中间亚胺被捕集。
• MORIARTY, ROBERT M.;VAID, RADHE K.;DUNCAN, MICHAEL P.;OCHIAI, MASAHITO;IN+, TETRAHEDRON LETT., 29,(1988) N 52, C. 6913-6916
  作者：MORIARTY, ROBERT M.、VAID, RADHE K.、DUNCAN, MICHAEL P.、OCHIAI, MASAHITO、IN+

  DOI：——

  日期：——