(3S,4R)-3-(N-benzyl-N-cyclopropyl)aminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine | 604798-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4R)-3-(N-benzyl-N-cyclopropyl)aminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine
• CAS: 604798-70-1
• 化学式: C₂₃H₂₇FN₂O₂
• 分子量: 382.478
• InChiKey: ZNVHEDOSFGVTHS-UNMCSNQZSA-N

物化性质

• 沸点：
  505.4±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-(N-benzyl-N-cyclopropyl)aminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine 在 palladium 10% on activated carbon 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 N-{[(3R,4R)-4-氟-3-吡咯烷基]甲基}环丙胺
  参考文献：
  名称：

  10-(3-CYCLOPROPYLAMINOMETHYL-1-PYRROLIDINYL)PYRIDOBENZOXAZINECARBOXYLIC ACID DERIVATIVE EFFECTIVE AGAINST RESISTANT BACTERIA

  摘要：

  公开号：

  EP1486500B1
• 作为产物：
  描述：

  (3S,4R)-3-benzylaminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine 、 1-乙氧基-1-三甲硅氧基环丙烷 在 sodium cyanoborohydride 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 (3S,4R)-3-(N-benzyl-N-cyclopropyl)aminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine
  参考文献：
  名称：

  10-(3-CYCLOPROPYLAMINOMETHYL-1-PYRROLIDINYL)PYRIDOBENZOXAZINECARBOXYLIC ACID DERIVATIVE EFFECTIVE AGAINST RESISTANT BACTERIA

  摘要：

  公开号：

  EP1486500B1

文献信息

• Synthesis and Antibacterial Activity of Novel Pyrido[1,2,3-<i>de</i>][1,4]benzoxazine-6-carboxylic Acid Derivatives Carrying the 3-Cyclopropylaminomethyl-4-substituted-1-pyrrolidinyl Group as a C-10 Substituent
  作者：Yoshikazu Asahina、Masaya Takei、Tetsuya Kimura、Yasumichi Fukuda

  DOI：10.1021/jm701428b

  日期：2008.6.1

  Novel pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid derivatives 5-9 carrying a 3-cyclopropylaminomethyl-4-substituted-1-pyrrolidinyl moiety at the C-10 position were synthesized and their in vitro antibacterial activity, intravenous single-dose toxicity, convulsion inductive ability, and phototoxicity were evaluated. It appeared evident that compounds 5a, 6a, 8a, and 9a, which have a cis-oriented 4-methyl or 4-fluoro-3-cyclopropylaminomethyl-1-pyrrolidinyl moiety at the C-10 position, exhibited 2- to 16-fold more potent in vitro antibacterial activity than clinafloxacin against quinolone-resistant Gram-positive clinical isolates. Furthermore, it was obvious that introduction of a fluorine atom to the C-4 position of the 3-cyclopropylaminomethyl-1-pyrrolidinyl moiety reduced intraveneous single-dose acute toxicity and the convulsion inductive ability, and introduction of a fluorine atom to the C-3 methyl group of the pyridobenzoxazine nucleus eliminated the phototoxicity.
• 7-(4-SUBSTITUTED 3- CYCLOPROPYLAMINOMETHYL-1- PYRROLIDINYL) Q UINOLONECARBOXYLIC ACID DERIVATIVE
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：EP1666477B1

  公开（公告）日：2013-07-03