(2S)-2-吲哚啉甲酰胺 | 110660-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: (2S)-2-吲哚啉甲酰胺
• 英文名称: (S)-2,3-dihydro-1H-indole-2-carboxamide
• 英文别名: indoline-2S-carboxamide；(2S)-2,3-dihydro-1H-indole-2-carboxamide
• CAS: 110660-78-1
• 化学式: C₉H₁₀N₂O
• mdl: MFCD11982945
• 分子量: 162.191
• InChiKey: ATEDHUGCKSZDCP-QMMMGPOBSA-N

物化性质

• 沸点：
  425.5±35.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-吲哚啉甲酰胺 在 三乙胺 、 三氯乙酰氯 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 1.0h， 生成 (S)-1-acetyl-2,3-dihydro-1H-indole-2-carbonitrile
  参考文献：
  名称：

  Design, Synthesis, and Tripeptidyl Peptidase II Inhibitory Activity of a Novel Series of (S)-2,3-Dihydro-2-(4-alkyl-1H-imidazol-2-yl)-1H-indoles

  摘要：

  Butabindide, 1, was previously reported as a potent inhibitor (IC50 = 7 nM) of the serine protease enzyme tripeptidyl peptidase II (TPPII), an endogenous protease that degrades cholecystokinin-8 (CCK-8). We found that 1 has some inherent chemical instability, yielding diketopiperazine 2 fairly readily under mimicked physiological conditions. We therefore prepared imidazoles 3, which are void of 1's inherent instability, and have found that our novel analogues maintained comparable TPPII inhibitory activity (e.g.,for 3c, IC50 = 4 nM) as 1.

  DOI：

  10.1021/jm0202831
• 作为产物：
  描述：

  吲哚-3-甲胺 以 甲醇 为溶剂， 生成 (2S)-2-吲哚啉甲酰胺
  参考文献：
  名称：

  Gamma-r-glutamoyl derivatives

  摘要：

  该化合物的化学式为##STR1##其中R.sub.1和R.sub.6分别表示羟基、C.sub.1-C.sub.4-烷氧基、取代的C.sub.1-C.sub.4-烷氧基、氨基或取代的氨基，R.sub.2表示氢、C.sub.1-C.sub.4-烷基或C.sub.2-C.sub.4-烯基，R.sub.3表示环状C.sub.3-C.sub.6-烷基、苯基、被C.sub.1-C.sub.4-烷基、卤素、硝基或C.sub.1-C.sub.4-烷氧基取代的苯基，或者与苯环融合的环状C.sub.3-C.sub.6-烷基，或者R.sub.2和R.sub.3相连，并与相邻的--CH基团和相邻的N原子一起形成饱和或部分饱和的、单环、五元或六元杂环基团，或形成含有五个或六个原子的饱和或部分饱和的双环杂环基团，R.sub.4表示氢或C.sub.1-C.sub.4-烷基，R.sub.5表示酰基基团，可用作降压和心脏活性药物。本发明还涉及制备式I化合物的方法和制药组合物。

  公开号：

  US04678800A1

文献信息

• US4678800A
  申请人：——

  公开号：US4678800A

  公开（公告）日：1987-07-07
• Design, Synthesis, and Tripeptidyl Peptidase II Inhibitory Activity of a Novel Series of (<i>S</i>)-2,3-Dihydro-2-(4-alkyl-1<i>H</i>-imidazol-2-yl)-1<i>H</i>-indoles
  作者：Henry J. Breslin、Tamara A. Miskowski、Michael J. Kukla、William H. Leister、Hans L. De Winter、Diane A. Gauthier、Maria V. F. Somers、Daniëlle C. G. Peeters、Peter W. M. Roevens

  DOI：10.1021/jm0202831

  日期：2002.11.1

  Butabindide, 1, was previously reported as a potent inhibitor (IC50 = 7 nM) of the serine protease enzyme tripeptidyl peptidase II (TPPII), an endogenous protease that degrades cholecystokinin-8 (CCK-8). We found that 1 has some inherent chemical instability, yielding diketopiperazine 2 fairly readily under mimicked physiological conditions. We therefore prepared imidazoles 3, which are void of 1's inherent instability, and have found that our novel analogues maintained comparable TPPII inhibitory activity (e.g.,for 3c, IC50 = 4 nM) as 1.
• Gamma-r-glutamoyl derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US04678800A1

  公开（公告）日：1987-07-07

  A compound of the formula ##STR1## wherein R.sub.1 and R.sub.6 independently represent hydroxy, C.sub.1 -C.sub.4 -alkoxy, substituted C.sub.1 -C.sub.4 - alkoxy, amino, or substituted amino, R.sub.2 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, or C.sub.2 -C.sub.4 -alkenyl, R.sub.3 represents cyclo-C.sub.3 -C.sub.6 -alkyl, phenyl, phenyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen, nitro, or C.sub.1 -C.sub.4 -alkoxy, or cyclo-C.sub.3 -C.sub.6 -alkyl fused with benzene, or wherein R.sub.2 and R.sub.3 are connected and together with the adjacent --CH-group and the adjacent N-atom form a saturated or partially saturated, monocyclic, five- or six-membered heterocyclic group or form a saturated or partially saturated, bicyclic heterocyclic group containing five or six atoms per ring, R.sub.4 represents hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sub.5 represents an acyl group, are useful as antihypertensive and cardioactive agents. The invention also relates to processes for preparing the compounds of the formula I and to pharmaceutical compositions.

  该化合物的化学式为##STR1##其中R.sub.1和R.sub.6分别表示羟基、C.sub.1-C.sub.4-烷氧基、取代的C.sub.1-C.sub.4-烷氧基、氨基或取代的氨基，R.sub.2表示氢、C.sub.1-C.sub.4-烷基或C.sub.2-C.sub.4-烯基，R.sub.3表示环状C.sub.3-C.sub.6-烷基、苯基、被C.sub.1-C.sub.4-烷基、卤素、硝基或C.sub.1-C.sub.4-烷氧基取代的苯基，或者与苯环融合的环状C.sub.3-C.sub.6-烷基，或者R.sub.2和R.sub.3相连，并与相邻的--CH基团和相邻的N原子一起形成饱和或部分饱和的、单环、五元或六元杂环基团，或形成含有五个或六个原子的饱和或部分饱和的双环杂环基团，R.sub.4表示氢或C.sub.1-C.sub.4-烷基，R.sub.5表示酰基基团，可用作降压和心脏活性药物。本发明还涉及制备式I化合物的方法和制药组合物。