1-苄基-3-羟甲基-3-氨基吡咯烷 | 475469-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苄基-3-羟甲基-3-氨基吡咯烷
• 中文别名: (3-氨基-1-苄基-3-吡咯烷)-甲醇；1-苄基3-羟甲基-3-氨基吡咯烷
• 英文名称: 3-amino-1-benzyl-3-hydroxymethylpyrrolidine
• 英文别名: (3-Amino-1-benzylpyrrolidin-3-yl)methanol
• CAS: 475469-13-7
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: JTBHAUAMGKMSLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-苄基-3-羟甲基-3-氨基吡咯烷 在 5percent Pd/C 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (3-羟甲基吡咯烷-3-基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 1

  摘要：

  In an attempt to search for clinically useful antitumor agents, we have discovered that a series of 1,1-disubstituted-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids possessed moderate cytotoxic activity.,We investigated the structure-activity relationships in this series of compounds by changing N-1 and C-7 positions and the core ring structure itself and evaluated the synthesized compounds against several murine and human tumor cell lines. These modifications led us to the following findings. (1) The 2-thiazolyl group at the N-1 position of the naphthyridine structure is the best substituent for antitumor activity. (2) Regarding core ring structure, the naphthyridine derivative is the most active followed by pyridopyrimidine analogue. (3) At the C-7 position, -aminopyrrolidine derivatives are more effective than other amines or thioether derivatives. Finally, the trans-3-amino-4-methoxypyrrolidinyl derivative (43j), and the 3-amino-3-methylpyrrolidinyl derivative (43f) as well as 3-aminopyrrolidinyl derivative (AT-3639, 1) were determined to be effective in in vitro and in vivo antitumor assays, and their activity was comparable to that of etoposide.

  DOI：

  10.1021/jm010057b
• 作为产物：
  描述：

  1-苄基-3-氨基吡咯烷-3-甲酸 在 盐酸 、 红铝 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 1-苄基-3-羟甲基-3-氨基吡咯烷
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 1

  摘要：

  In an attempt to search for clinically useful antitumor agents, we have discovered that a series of 1,1-disubstituted-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids possessed moderate cytotoxic activity.,We investigated the structure-activity relationships in this series of compounds by changing N-1 and C-7 positions and the core ring structure itself and evaluated the synthesized compounds against several murine and human tumor cell lines. These modifications led us to the following findings. (1) The 2-thiazolyl group at the N-1 position of the naphthyridine structure is the best substituent for antitumor activity. (2) Regarding core ring structure, the naphthyridine derivative is the most active followed by pyridopyrimidine analogue. (3) At the C-7 position, -aminopyrrolidine derivatives are more effective than other amines or thioether derivatives. Finally, the trans-3-amino-4-methoxypyrrolidinyl derivative (43j), and the 3-amino-3-methylpyrrolidinyl derivative (43f) as well as 3-aminopyrrolidinyl derivative (AT-3639, 1) were determined to be effective in in vitro and in vivo antitumor assays, and their activity was comparable to that of etoposide.

  DOI：

  10.1021/jm010057b

文献信息

• Renin Inhibitors
  申请人：Baldwin John J.

  公开号：US20090264428A1

  公开（公告）日：2009-10-22

  Described are compounds of the formula (I) which are orally active and bind to aspartic proteases to inhibit their activity. They are useful in the treatment or amelioration of diseases associated with aspartic protease activity. Also described are methods of use of the compounds described herein in ameliorating or treating aspartic protease related disorders in a subject in need thereof.

  本文描述了一种公式（I）的化合物，其具有口服活性并能结合天冬氨酸蛋白酶以抑制其活性。它们可用于治疗或改善与天冬氨酸蛋白酶活性相关的疾病。还描述了在需要改善或治疗天冬氨酸蛋白酶相关疾病的受试者中使用本文所述化合物的方法。
• RENIN INHIBITORS
  申请人：Baldwin John J.

  公开号：US20090275581A1

  公开（公告）日：2009-11-05

  Disclosed are compounds according to Formula I: wherein the variables are defined herein. Such compounds are can bind aspartic proteases to inhibit their activity. They are useful in the treatment or amelioration of diseases associated with aspartic protease activity. Also described herein are methods of antagonizing aspartic protease inhibitors in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a compound according to Formula I.

  本发明涉及公式I所示的化合物，其中变量在此定义。这些化合物能够结合天冬氨酸蛋白酶以抑制其活性。它们可用于治疗或改善与天冬氨酸蛋白酶活性相关的疾病。本发明还描述了拮抗需要受到天冬氨酸蛋白酶抑制剂的受试者的方法，包括向受试者施用公式I所示的化合物的治疗有效量。
• [EN] RENIN INHIBITORS<br/>[FR] INHIBITEURS DE LA RÉNINE
  申请人：VITAE PHARMACEUTICALS INC

  公开号：WO2007117482A2

  公开（公告）日：2007-10-18

  [EN] Disclosed are compounds according to Formula (I): wherein the variables are defined herein. Such compounds are can bind aspartic proteases to inhibit their activity. They are useful in the treatment or amelioration of diseases associated with aspartic protease activity. Also described herein are methods of antagonizing aspartic protease inhibitors in a subject in need thereof comprising administering to the subject a therapeutically effective amount of a compound according to Formula (I).
  [FR] L'invention concerne des composés de formule (I), dans laquelle les variables son spécifiées. Lesdits composés peuvent se lier à des protéases aspartiques de manière à inhiber leur activité. Ils sont utilisés dans le traitement ou l'amélioration de maladies associées à l'activité de la protéase aspartique. L'invention concerne également des méthodes de traitement par antagonisme des inhibiteurs de la protéase aspartique chez un sujet nécessitant les soins, comprenant l'administration au sujet d'une quantité efficace de manière thérapeutique d'un composé de formule (I).
• Synthesis and Structure−Activity Relationships of Novel 7-Substituted 1,4-Dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acids as Antitumor Agents. Part 1
  作者：Kyoji Tomita、Yasunori Tsuzuki、Koh-ichiro Shibamori、Masanori Tashima、Fumie Kajikawa、Yuji Sato、Shigeki Kashimoto、Katsumi Chiba、Katsuhiko Hino

  DOI：10.1021/jm010057b

  日期：2002.12.1

  In an attempt to search for clinically useful antitumor agents, we have discovered that a series of 1,1-disubstituted-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids possessed moderate cytotoxic activity.,We investigated the structure-activity relationships in this series of compounds by changing N-1 and C-7 positions and the core ring structure itself and evaluated the synthesized compounds against several murine and human tumor cell lines. These modifications led us to the following findings. (1) The 2-thiazolyl group at the N-1 position of the naphthyridine structure is the best substituent for antitumor activity. (2) Regarding core ring structure, the naphthyridine derivative is the most active followed by pyridopyrimidine analogue. (3) At the C-7 position, -aminopyrrolidine derivatives are more effective than other amines or thioether derivatives. Finally, the trans-3-amino-4-methoxypyrrolidinyl derivative (43j), and the 3-amino-3-methylpyrrolidinyl derivative (43f) as well as 3-aminopyrrolidinyl derivative (AT-3639, 1) were determined to be effective in in vitro and in vivo antitumor assays, and their activity was comparable to that of etoposide.