3-吡咯烷胺,4-甲氧基-1-(苯基甲基)-,(3R,4R)-rel- | 128739-90-2

• 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: 3-吡咯烷胺,4-甲氧基-1-(苯基甲基)-,(3R,4R)-rel-
• 英文名称: (+)-(3S,4S)-3-amino-1-benzyl-4-methoxypyrrolidine
• 英文别名: (3S,4S)-1-Benzyl-4-methoxypyrrolidin-3-amine
• CAS: 128739-90-2
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: XATWULWMGNIFCJ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 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：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-吡咯烷胺,4-甲氧基-1-(苯基甲基)-,(3R,4R)-rel- 以99% ee; 32的产率得到rel-(3R,4R)-1-Benzyl-4-methoxypyrrolidin-3-amine
  参考文献：
  名称：

  Tetrahedron: Asymmetry 2001, 12, 2989-2997

  摘要：

  DOI：
• 作为产物：
  描述：

  1-t-butoxycarbonyl-4-hydroxy-3-methylaminopyrrolidine 以57的产率得到3-吡咯烷胺,4-甲氧基-1-(苯基甲基)-,(3R,4R)-rel-
  参考文献：
  名称：

  Tetrahedron: Asymmetry 2001, 12, 2989-2997

  摘要：

  DOI：

文献信息

• 7-(1-pyrrolidinyl)-3-quinolone- and -naphthyridonecarboxylic acid
  申请人：Bayer Aktiengesellschaft

  公开号：US04990517A1

  公开（公告）日：1991-02-05

  7-(1-Pyrrolidinyl)-3-quinolone- and -naphthyridonecarboxylic acid derivatives as antibacterial agents and feed additives, of the formula ##STR1## in which X.sup.1 is halogen, X.sup.2 is hydrogen, halogen, amino or other radical, R.sup.1 is alkyl, cycloalkyl, optionally substituted phenyl or other radical, R.sup.2 is hydrogen, alkyl or a dioxolylmethyl radical, R.sup.3 is ##STR2## A is N, CH, C-halogen, or the like, or forms a bridge with R.sup.1, and addition products thereof.

  7-(1-吡咯啉基)-3-喹啉基-和-萘啉基羧酸衍生物作为抗菌剂和饲料添加剂，其化学式为##STR1##其中X.sup.1为卤素，X.sup.2为氢、卤素、氨基或其他基团，R.sup.1为烷基、环烷基、可选择取代的苯基或其他基团，R.sup.2为氢、烷基或二氧杂环丙基基团，R.sup.3为##STR2##A为N、CH、C-卤素或类似物，或与R.sup.1形成桥梁的结合物。
• 7-(1-Pyrrolidinyl)-3-chinolon- und -naphthyridoncarbon-säure-Derivate, Verfahren zu ihrer Herstellung sowie substituierte mono-und bicyclische Pyrrolidinderivate als Zwischenprodukte zu ihrer Herstellung, und sie enthaltende antibakterielle Mittel und Futterzusatzstoffe
  申请人：BAYER AG

  公开号：EP0350733A2

  公开（公告）日：1990-01-17

  Die Erfindung betrifft 7-(1-Pyrrolidinyl)-3-chinolon-und -naphthyridoncarbonsäure-Derivate der Formel (I) in welcher X1, X2, R1, R2, R3 und A die in der Beschreibung angegebene Bedeutung haben, Verfahren sowie substituierte (Oxa)Diazabicyclooctane und -nonane als Zwischenprodukte zu ihrer Herstellung, und sie enthaltende antibakterielle Mittel und Futterzusatzstoffe.

  本发明涉及式(I)的 7-(1-吡咯烷基)-3-喹啉酮和-萘啶羧酸衍生物。 其中 X1、X2、R1、R2、R3 和 A 具有描述中给出的含义，以及作为制备它们的中间体的工艺和取代的（氧杂）二氮杂双环辛烷和-壬烷，以及含有它们的抗菌剂和饲料添加剂。
• 7-(1-Pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsäure-Derivate, Verfahren zu ihrer Herstellung sowie substituierte mono- und bicyclische Pyrrolidinderivate als Zwischenprodukte zu ihrer Herstellung, und sie enthaltende antibakterielle Mittel und Futterzusatzstoffe
  申请人：BAYER AG

  公开号：EP0757990A1

  公开（公告）日：1997-02-12

  Die Erfindung betrifft 7-(1-Pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsäure-Derivate der Formel (I) in welcher X1, X2, R1, R2, R3 und A die in der Beschreibung angegebene Bedeutung haben, Verfahren sowie substituierte (Oxa)Diazabicyclooctane und -nonane als Zwischenprodukte zu ihrer Herstellung, und sie enthaltende antibakterielle Mittel und Futterzusatzstoffe.

  本发明涉及式(I)的 7-(1-吡咯烷基)-3-喹啉酮和-萘啶羧酸衍生物。 其中 X1、X2、R1、R2、R3 和 A 具有描述中给出的含义，以及作为制备它们的中间体的工艺和取代的（氧杂）二氮杂双环辛烷和-壬烷，以及含有它们的抗菌剂和饲料添加剂。
• 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.
• 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 2
  作者：Yasunori Tsuzuki、Kyoji Tomita、Koh-ichiro Shibamori、Yuji Sato、Shigeki Kashimoto、Katsumi Chiba

  DOI：10.1021/jm0304966

  日期：2004.4.1

  We have previously reported that a series of 7-substituted 6-fluoro-1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic acids possess moderate cytotoxic activity. In a further attempt to find clinically useful antitumor agents, we investigated the structure-activity relationships (SARs) of a new series of compounds obtained by changing the C-6 position of the fluorine atom in addition to the C-5 and C-7 positions and evaluating their cytotoxic activity against several murine and human tumor cell lines. Our results showed that the 6-unsubstituted 1,8-naphthyridine structure had the most potent cytotoxic activity against murine P388 leukemia twice that of the 6-fluoro analogue. In addition, introduction of an amino group at the C-5 position did not have any substantial effect on the cytotoxic activity, while both the 5-chloro and 5-trifluoromethyl groups decreased the cytotoxic activity by 5- to 10-fold. Moreover, aminopyrrolidine derivatives at the C-7 position showed more potent cytotoxic activity than other amines or carbon derivatives. Among the 7-(3-aminopyrrolidinyl) derivatives, the trans-3-methoxy-4-methylaminopyrrolidinyI derivative (271) was determined to have potent cytotoxic activity in both in vitro and in vivo assays and high water solubility. Finally, the (SS)-isomer (AG-7352, 3) of 271, with a cytotoxic activity against human tumor cell lines more potent than that of etoposide, was selected for further development.