(2S)-1-(4-phenylbutanoyl)pyrrolidine-2-carbaldehyde | 102826-53-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S)-1-(4-phenylbutanoyl)pyrrolidine-2-carbaldehyde
• CAS: 102826-53-9
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: FBGVVDIHVBDJQB-AWEZNQCLSA-N

物化性质

• 沸点：
  426.0±45.0 °C(predicted)
• 密度：
  1.160±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-1-(4-phenylbutanoyl)pyrrolidine-2-carbaldehyde 在 四氯化钛 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成
  参考文献：
  名称：

  4-Phenylbutanoyl-2( S )-acylpyrrolidines and 4-phenylbutanoyl- l -prolyl-2( S )-acylpyrrolidines as prolyl oligopeptidase inhibitors

  摘要：

  New 4-phenylbutanoyl-2(S)-acylpyrrolidines and 4-phenylbutanoyl-L-prolyl-2(S)-acylpyrrolidines were synthesized. Their inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. In the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were the best inhibitors having IC50 values of 30 and 23 nM, respectively. This series of compounds shows that that P1 pyrrolidine ring, which is common in most POP inhibitors, can be replaced by either a cyclopentyl ring or a phenyl ring, causing only a slight decrease in the inhibitory activity. In the series of 4-phenylbutanoyl-L-prolyl-2(S)- acyl-pyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were not as active as in the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, The hydroxyacetyl derivative did however show high inhibitors activity. This compound is structurally similar to JTP-4819, which is one of the most potent prolyl oligopeptidase inhibitors. The acyl group in the two series of new compounds seems to bind to different sites of the enzyme, since the second series of ne compounds did not show the same cyclopentanecarbonyl or benzoyl specificity as the first series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00061-5
• 作为产物：
  描述：

  4-苯基丁酰氯 在 pyridine-SO3 complex 、 sodium carbonate 、 三乙胺 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (2S)-1-(4-phenylbutanoyl)pyrrolidine-2-carbaldehyde
  参考文献：
  名称：

  4-Phenylbutanoyl-2( S )-acylpyrrolidines and 4-phenylbutanoyl- l -prolyl-2( S )-acylpyrrolidines as prolyl oligopeptidase inhibitors

  摘要：

  New 4-phenylbutanoyl-2(S)-acylpyrrolidines and 4-phenylbutanoyl-L-prolyl-2(S)-acylpyrrolidines were synthesized. Their inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. In the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were the best inhibitors having IC50 values of 30 and 23 nM, respectively. This series of compounds shows that that P1 pyrrolidine ring, which is common in most POP inhibitors, can be replaced by either a cyclopentyl ring or a phenyl ring, causing only a slight decrease in the inhibitory activity. In the series of 4-phenylbutanoyl-L-prolyl-2(S)- acyl-pyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were not as active as in the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, The hydroxyacetyl derivative did however show high inhibitors activity. This compound is structurally similar to JTP-4819, which is one of the most potent prolyl oligopeptidase inhibitors. The acyl group in the two series of new compounds seems to bind to different sites of the enzyme, since the second series of ne compounds did not show the same cyclopentanecarbonyl or benzoyl specificity as the first series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00061-5

文献信息

• Novel biologically active compound having anti-prolyl endopeptidase activity
  申请人：SUNTORY LIMITED

  公开号：EP0172458A2

  公开（公告）日：1986-02-26

  A novel compound that exhibits inhibitory activity against prolyl endopeptidase and a method for chemical synthesis of said compound, as well as its use as a prolyl endopeptidase inhibitor and an anti-amnesic agent that contains said compound as the active ingredient are provided.

  本研究提供了一种对脯氨酰内肽酶具有抑制活性的新型化合物和一种化学合成该化合物的方法，以及该化合物作为脯氨酰内肽酶抑制剂和含有该化合物作为活性成分的抗氧化剂的用途。
• Neue Pyrrolidin-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel sowie deren Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0286929A2

  公开（公告）日：1988-10-19

  Die Erfindung betrifft Pyrrolidin-Derivate der allgemeinen Formel in welcher R¹, R², R³, R⁴, R⁵, R⁶, R⁷ und R⁸ die in der Beschreibung angegebenen Bedeutungen haben, X Sauerstoff, Imino oder N-Alkylimino bedeutet, m = 0-5 ist, n = 0-2 ist und s = 0 oder 1 ist, Verfahren zu ihrer Herstellung, sie enthaltende Mittel sowie deren Verwendung.

  本发明涉及通式如下的吡咯烷衍生物 其中 R¹、R²、R³、R⁴、R⁵、R⁶、R⁷ 和 R⁸ 具有说明中给出的含义，X 表示氧、亚氨基或 N-烷基亚氨基，m = 0-5，n = 0-2，s = 0 或 1。
• TANAKA, TAKAHARU;HIGUCHI, NAOKI;SAITOH, MASAYUKI;HASHIMOTO, MASAKI
  作者：TANAKA, TAKAHARU、HIGUCHI, NAOKI、SAITOH, MASAYUKI、HASHIMOTO, MASAKI

  DOI：——

  日期：——
• US4743616A
  申请人：——

  公开号：US4743616A

  公开（公告）日：1988-05-10
• 4-Phenylbutanoyl-2( S )-acylpyrrolidines and 4-phenylbutanoyl- l -prolyl-2( S )-acylpyrrolidines as prolyl oligopeptidase inhibitors
  作者：Erik A.A Wallén、Johannes A.M Christiaans、Susanna M Saario、Markus M Forsberg、Jarkko I Venäläinen、Hanna M Paso、Pekka T Männistö、Jukka Gynther

  DOI：10.1016/s0968-0896(02)00061-5

  日期：2002.7

  New 4-phenylbutanoyl-2(S)-acylpyrrolidines and 4-phenylbutanoyl-L-prolyl-2(S)-acylpyrrolidines were synthesized. Their inhibitory activity against prolyl oligopeptidase from pig brain was tested in vitro. In the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were the best inhibitors having IC50 values of 30 and 23 nM, respectively. This series of compounds shows that that P1 pyrrolidine ring, which is common in most POP inhibitors, can be replaced by either a cyclopentyl ring or a phenyl ring, causing only a slight decrease in the inhibitory activity. In the series of 4-phenylbutanoyl-L-prolyl-2(S)- acyl-pyrrolidines, the cyclopentanecarbonyl and benzoyl derivatives were not as active as in the series of 4-phenylbutanoyl-2(S)-acylpyrrolidines, The hydroxyacetyl derivative did however show high inhibitors activity. This compound is structurally similar to JTP-4819, which is one of the most potent prolyl oligopeptidase inhibitors. The acyl group in the two series of new compounds seems to bind to different sites of the enzyme, since the second series of ne compounds did not show the same cyclopentanecarbonyl or benzoyl specificity as the first series. (C) 2002 Elsevier Science Ltd. All rights reserved.