(3S,4S)-4-Methylpyrrolidin-3-amine | 113617-67-7

• 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: (3S,4S)-4-Methylpyrrolidin-3-amine
• CAS: 113617-67-7；113617-69-9；116729-74-9；144238-34-6；144238-35-7；149714-40-9
• 化学式: C₅H₁₂N₂
• 分子量: 100.164
• InChiKey: SLTMFXXAJKCIPQ-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-Methylpyrrolidin-3-amine 在 sodium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 2.5h， 生成 7-((3R,4R)-3-Amino-4-methyl-pyrrolidin-1-yl)-1-tert-butyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
  参考文献：
  名称：

  氟萘啶和喹诺酮类作为抗菌剂。2.新的1-叔丁基7-取代的衍生物的合成和结构-活性关系。

  摘要：

  已经制备了许多7-取代的1-叔丁基-6-氟喹诺酮-3-羧酸和7-取代的1-叔丁基-6-氟-1,8-萘啶-3-羧酸。经测试具有抗菌活性。其中7-氨基吡咯烷基20b和7-二氮杂双环萘啶18b是体外和体内最有效的化合物。还讨论了理化数据和急性毒性。考虑到体外和体内的微生物活性，低毒性和药代动力学特征，化合物18b BMY 40062表现出最有利的总体性能，并被选择用于临床评估。

  DOI：

  10.1021/jm00167a010

文献信息

• Quinoline derivatives, pharmaceutical composition and method of use
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US04886810A1

  公开（公告）日：1989-12-12

  The present invention relates to quinoline derivatives of the formula ##STR1## wherein Z is an amino group or a halogen atom, R is ##STR2## in which R.sub.1 is a hydrogen atom, a lower alkyl or haloalkyl group, R.sub.2 is a hydrogen atom or a lower alkyl group, R.sub.3 is a lower alkyl or haloalkyl group, R.sub.4 is a hydrogen atom or a lower alkyl group, R.sub.5 and R.sub.6 are the same or different and each represents a hydrogen atom or a lower alkyl group, or R.sub.5 and R.sub.6, together with the nitrogen atom to which they are attached, form a heterocyclic ring, and n is 0 or 1, with the proviso that when Z is an amino group, R is (B); and esters thereof and salts thereof and processes for preparation thereof. These compounds show excellent antibacterial activity and are useful antibacterial agents.

  本发明涉及式（I）的喹啉衍生物：其中Z是氨基或卤素原子，R是式（II）：其中R1是氢原子、低碳基或卤代低碳基，R2是氢原子或低碳基，R3是低碳基或卤代低碳基，R4是氢原子或低碳基，R5和R6相同或不同，分别代表氢原子或低碳基，或R5和R6与它们所连接的氮原子形成杂环环，n为0或1，但当Z是氨基时，R为（B）；以及它们的酯和盐以及其制备方法。这些化合物表现出优异的抗菌活性，是有用的抗菌剂。
• 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.