4-苯基-1-[(2S)-2-(吡咯烷-1-羰基)吡咯烷-1-基]丁烷-1-酮 | 112603-82-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-苯基-1-[(2S)-2-(吡咯烷-1-羰基)吡咯烷-1-基]丁烷-1-酮
• 中文别名: N-(N-(苯基)丁酰-L-脯氨酰)吡咯烷
• 英文名称: SUAM-1221
• 英文别名: N-[N-(γ-phenyl)butyryl-L-prolyl]pyrrolidine；N-(4-Phenylbutanoyl)-L-prolylpyrrolidine；N-[N-(4-phenylbutanoyl)-L-prolyl]pyrrolidine；N-(N-(Phenyl)butyryl-L-prolyl)pyrrolidine；4-phenyl-1-[(2S)-2-(pyrrolidine-1-carbonyl)pyrrolidin-1-yl]butan-1-one
• CAS: 112603-82-4
• 化学式: C₁₉H₂₆N₂O₂
• 分子量: 314.428
• InChiKey: HDRSLHFTJYMQIL-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-苯基丁酸 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 4-苯基-1-[(2S)-2-(吡咯烷-1-羰基)吡咯烷-1-基]丁烷-1-酮
  参考文献：
  名称：

  Synthesis of Prolyl Endopeptidase Inhibitors and Evaluation of Their Structure-Activity Relationships: In Vitro Inhibition of Prolyl Endopeptidase from Canine Brain.

  摘要：

  通过对一种已知的脯氨酰内肽酶（PEP）抑制剂（N-[N-（4-苯基丁酰基）-L-脯氨酰]吡咯烷；SUAM-1221）进行化学修饰，合成了几种芳基烷酰基衍生物（V-1-27），并测试了其对犬脑中 PEP 的体外抑制活性。其中，4-（2-噻吩基）丁酰衍生物（V-24-27）显示出比 SUAM-1221 更强的 PEP 抑制活性。本文讨论了这些化合物的结构-活性关系。

  DOI：

  10.1248/cpb.41.1583

文献信息

• Pyrrolidineamide derivative of acylamino acid and pharmaceutical
  申请人：Suntory Limited

  公开号：US04826870A1

  公开（公告）日：1989-05-02

  A compound of the general formula: ##STR1## wherein m is an integer of 1 to 7, n is 0 or an integer of 1 to 5, R.sup.1 is the phenyl, a substituted phenyl, the phenoxy, a substituted phenoxy or a saturated or unsaturated straight alkyl having 5 to 18 carbon atoms, R.sup.2 is hydrogen atom, R.sup.3 is hydrogen atom, a branched or unbranched alkyl having 3 to 5 carbon atoms, the phenyl, hydroxyphenyl, benzyloxyphenyl, an alkylthio having 1 to 3 carbon atoms in its alkyl moiety, amino, carboxyl, hydroxy, benzyloxy, indolyl or imidazolyl, or R.sup.2 and R.sup.3 together form a single bond between the carbon atom and the nitrogen atom, and a pharmaceutical composition containing said compound are provided. The compound is effective in curing amnesia because of its anti-prolyl endopeptidase activity.

  通式为：##STR1## 其中m为1到7的整数，n为0或1到5的整数，R.sup.1为苯基、取代苯基、苯氧基、取代苯氧基或具有5到18个碳原子的饱和或不饱和直链烷基，R.sup.2为氢原子，R.sup.3为氢原子、具有3到5个碳原子的支链或非支链烷基、苯基、羟基苯基、苄氧基苯基、在其烷基部分具有1到3个碳原子的烷基硫基、氨基、羧基、羟基、苄氧基、吲哚基或咪唑基，或R.sup.2和R.sup.3共同形成碳原子和氮原子之间的单键，以及含有上述化合物的药物组合物。该化合物由于其抗脯氨酸内切肽酶活性而有效治疗遗忘症。
• Pyrrolidineamide derivatives of acylamino acid and pharmaceutical
  申请人：Suntory Limited

  公开号：US05198458A1

  公开（公告）日：1993-03-30

  A compound of the general formula: ##STR1## wherein m is an integer of 1 to 7, n is 0 or an integer of 1 to 5, R.sup.1 is the phenyl, a substituted phenyl, the phenoxy, a substituted phenoxy or a saturated or unsaturated straight alkyl having 5 to 18 carbon atoms, R.sup.2 is hydrogen atom, R.sup.3 is hydrogen atom, a branched or unbranched alkyl having 3 to 5 carbon atoms, the phenyl, hydroxyphenyl, benzyloxyphenyl, an alkylthio having 1 to 3 carbon atoms in its alkyl moiety, amino, carboxyl, hydroxy, benzyloxy, indolyl or imidazolyl, or R.sup.2 and R.sup.3 together form a single bond between the carbon atom and the nitrogen atom, and a pharmaceutical composition containing said compound are provided. The compound is effective in curing amnesia because of its anti-prolyl endopeptidase activity.

  一种通式为：##STR1## 其中m为1至7的整数，n为0或1至5的整数，R.sup.1为苯基、取代苯基、苯氧基、取代苯氧基或具有5至18个碳原子的饱和或不饱和直链烷基，R.sup.2为氢原子，R.sup.3为氢原子、具有3至5个碳原子的分支或直链烷基、苯基、羟基苯基、苯甲氧基苯基、其烷基部分中具有1至3个碳原子的烷基硫基、氨基、羧基、羟基、苯甲氧基、吲哚基或咪唑基，或R.sup.2和R.sup.3一起形成碳原子和氮原子之间的单键，以及含有该化合物的药物组合物。该化合物由于其抗脯氨酰内切肽酶活性，对治疗健忘症有效。
• Pyrrolidineamide derivative of acylamino acid, pharmaceutical composition and use
  申请人：SUNTORY LIMITED

  公开号：EP0232849A2

  公开（公告）日：1987-08-19

  A compound of the general formula: wherein m is an integer of I to 7, n is 0 or an integer of I to 5, R' is the phenyl, a substituted phenyl, the phenoxy, a substituted phenoxy or a saturated or unsaturated straight alkyl having 5 to 18 carbon atoms, R2 is hydrogen atom, R3 is hydrogen atom, a branched or unbranched alkyl having 3 to 5 carbon atoms, the phenyl, hydroxyphenyl, benzyloxyphenyl, an alkylthio having I to 3 carbon atoms in its alkyl moiety, amino, carboxyl, hydroxy, benzyloxy, indolyl or imidazolyl, or R2 and R3 together form a single bond between the carbon atom and the nitrogen atom, and a pharmaceutical composition containing said compound are provided. The compound is effective in curing amnesia because of its anti-prolyl endopeptidase activity and may be used in the preparation of an anti-prolyl endopeptidase medicament, and. in the preparation of a medicament for treating brain malfunction.

  通式如下的化合物 其中 m 为 I 至 7 的整数、 n 是 0 或 I 至 5 的整数、 R'是苯基、取代的苯基、苯氧基、取代的苯氧基或具有 5 至 18 个碳原子的饱和或不饱和直烷基，R2 是氢原子、 R3 是氢原子、具有 3 至 5 个碳原子的支链或未支链烷基、苯基、羟基苯基、苄氧基苯基、在其烷基中具有 I 至 3 个碳原子的烷硫基、氨基、羧基、羟基、苄氧基、吲哚基或咪唑基，或 R2 和 R3 一起在碳原子和氮原子之间形成单键，以及含有所述化合物的药物组合物。由于该化合物具有抗脯氨酰内肽酶活性，因此能有效治疗健忘症，可用于制备抗脯氨酰内肽酶药物，以及用于制备治疗脑功能障碍的药物。
• CHOLINESTERASE ACTIVATOR
  申请人：ZERIA PHARMACEUTICAL CO., LTD.

  公开号：EP0754454A1

  公开（公告）日：1997-01-22

  The invention relates to a cholinesterase activator comprising, as an active ingredient, a compound represented by the following general formula (I): wherein A means a group such as a phenyl group or indanyl group, B denotes a group such as a prolyl group or thioprolyl group, and m stands for an integer of 0-5. The cholinesterase activator according to the invention has a strongly activating action on cholinesterase, in particular, a selectively activating action on peripheral cholinesterase and is also high in safety. It is hence useful as an agent for preventing and treating the side effects of central cholinesterase inhibitors, in particular, hepatopathy, and an agent for preventing and treating the side effects of various medicines manifested on the basis of a cholinesterase-inhibiting action.

  本发明涉及一种胆碱酯酶激活剂，其活性成分包括由以下通式（I）代表的化合物： 其中 A 表示苯基或茚基等基团，B 表示脯氨酰基或噻丙酰基等基团，m 代表 0-5 的整数。 本发明的胆碱酯酶激活剂对胆碱酯酶有强烈的激活作用，特别是对外周胆碱酯酶有选择性激活作用，而且安全性高。因此，它可用作预防和治疗中枢性胆碱酯酶抑制剂副作用（尤其是肝病）的药物，以及预防和治疗以胆碱酯酶抑制作用为基础的各种药物副作用的药物。
• METHOD AND PHARMACEUTICAL COMPOSITION FOR INHIBITING PI3K/AKT/MTOR SIGNAL PATH
  申请人：Targeted Therapeutics, LLC

  公开号：EP2905032A1

  公开（公告）日：2015-08-12

  The present invention relates to a pharmaceutical composition of PRCP antagonist, PREP antagonist, or PRCP-PREP dual antagonist. The present invention also relates to a pharmaceutical composition jointly using PRCP antagonist and mTOR antagonist, or jointly using PREP antagonist and mTOR antagonist, or jointly using PRCP-PREP dual antagonist and mTOR antagonist. In addition, the present invention also relates to a method for utilizing the pharmaceutical compositions to treat and prevent cancers and diseases related to insulin receptor substrate protein and PI3K/AKT/mTOR signal pathway.

  本发明涉及一种由 PRCP 拮抗剂、PREP 拮抗剂或 PRCP-PREP 双拮抗剂组成的药物组合物。本发明还涉及一种联合使用 PRCP 拮抗剂和 mTOR 拮抗剂，或联合使用 PREP 拮抗剂和 mTOR 拮抗剂，或联合使用 PRCP-PREP 双拮抗剂和 mTOR 拮抗剂的药物组合物。此外，本发明还涉及一种利用药物组合物治疗和预防与胰岛素受体底物蛋白和 PI3K/AKT/mTOR 信号通路有关的癌症和疾病的方法。