(R)-1-(1-benzylpyrrolidin-3-yl)cyclopropylamine | 851388-54-0

• 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: (R)-1-(1-benzylpyrrolidin-3-yl)cyclopropylamine
• 英文别名: (3R)-3-(1-aminocyclopropyl)-1-benzylpyrrolidine；(R)-1-(1-Benzylpyrrolidin-3-YL)cyclopropanamine；1-[(3R)-1-benzylpyrrolidin-3-yl]cyclopropan-1-amine
• CAS: 851388-54-0
• 化学式: C₁₄H₂₀N₂
• 分子量: 216.326
• InChiKey: CVIWGPQILYTQHX-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-(1-benzylpyrrolidin-3-yl)cyclopropylamine 在 Pd/C (30%) 、 氢气 、 碳酸氢钠 、 溶剂黄146 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 溶剂黄146 、 1,2-二氯乙烷 、 乙腈 为溶剂， 60.0 ℃ 、413.7 kPa 条件下， 反应 29.0h， 生成 1-cyclopropyl-7-fluoro-9-methyl-8-{3-[1-(methylpiperidin-4-ylamino)cyclopropyl]pyrrolidin-1-yl}-4-oxo-4H-quinolizine-3-carboxylic acid
  参考文献：
  名称：

  Development of a Dual-Acting Antibacterial Agent (TNP-2092) for the Treatment of Persistent Bacterial Infections

  摘要：

  The clinical management of prosthetic joint infections and other persistent bacterial infections represents a major unmet medical need. The rifamycins are one of the most potent antibiotic classes against persistent bacterial infections, but bacteria can develop resistance to rifamycins rapidly and the clinical utility of the rifamycin class is typically limited to antibiotic combinations to minimize the development of resistance. To develop a better therapy against persistent bacterial infections, a series of rifamycin based bifunctional molecules were designed, synthesized, and evaluated with the goal to identify a dual-acting drug that maintains the potent activity of rifamycins against persistent pathogens and at the same time minimize the development of rifamycin resistance. TNP-2092 was identified as a drug candidate and is currently in an early stage of clinical development for the treatment of prosthetic joint infections.

  DOI：

  10.1021/acs.jmedchem.6b00485
• 作为产物：
  描述：

  (S)-3-羟基-1-苄基吡咯烷 在 titanium(IV) isopropylate 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 18.0h， 生成 (R)-1-(1-benzylpyrrolidin-3-yl)cyclopropylamine
  参考文献：
  名称：

  Development of a Dual-Acting Antibacterial Agent (TNP-2092) for the Treatment of Persistent Bacterial Infections

  摘要：

  The clinical management of prosthetic joint infections and other persistent bacterial infections represents a major unmet medical need. The rifamycins are one of the most potent antibiotic classes against persistent bacterial infections, but bacteria can develop resistance to rifamycins rapidly and the clinical utility of the rifamycin class is typically limited to antibiotic combinations to minimize the development of resistance. To develop a better therapy against persistent bacterial infections, a series of rifamycin based bifunctional molecules were designed, synthesized, and evaluated with the goal to identify a dual-acting drug that maintains the potent activity of rifamycins against persistent pathogens and at the same time minimize the development of rifamycin resistance. TNP-2092 was identified as a drug candidate and is currently in an early stage of clinical development for the treatment of prosthetic joint infections.

  DOI：

  10.1021/acs.jmedchem.6b00485

文献信息

• (R/S) rifamycin derivatives, their preparations and pharmaceutical compositions
  申请人：Ding Z. Charles

  公开号：US20060019986A1

  公开（公告）日：2006-01-26

  Rifamycin derivatives having the following structure of general formula I (both hydroquinone and corresponding quinone (C 1 -C 4 ) forms): or its salts, hydrates or prodrugs thereof; wherein a preferred R 1 comprises hydrogen or acetyl and a prefered R 2 comprises hydrogen, methyl or other lower alkyls; wherein asterik (*) denotes the carbon bearing the chiral center, wherein absolute configuration is assigned as R or S. Methods of preparation of the aforementioned rifamycin derivatives are also described. The compounds exhibit antimicrobial activities, including activities against drug-resistant microorganisms.

  具有以下一般式I结构（包括羟基喹酮和相应的醌（C1-C4）形式）的利福霉素衍生物或其盐、水合物或前药；其中优选的R1包括氢或乙酰基，优选的R2包括氢、甲基或其他较低的烷基；其中星号（*）表示手性中心的碳原子，绝对构型为R或S。还描述了前述利福霉素衍生物的制备方法。这些化合物表现出抗微生物活性，包括对耐药微生物的活性。
• Intermediates for the production of optically active cyclopropylamine derivatives and process for the production of the intermediates
  申请人：Fujita Masao

  公开号：US20070117988A1

  公开（公告）日：2007-05-24

  The present invention provides intermediates needed for production of an optically active compound represented by formula (6), which enable the compound (6) to be readily synthesized in simple production steps without optical resolution, and also provides a process for producing the intermediates. A process for producing an optically active compound represented by formula (4): wherein R 1 represents a protecting group for the amino group, or a salt thereof, characterized in that a reagent prepared from an titanium(IV) reagent and an alkylmetal compound is reacted with an optically active compound represented by formula (3): wherein R 1 has the same meaning as defined above, if needed, in the presence of a Lewis acid.

  本发明提供了制备光学活性化合物（式（6）所代表）所需的中间体，使得该化合物（6）能够在简单的生产步骤中无需光学分辨即可被合成，并且提供了制备这些中间体的方法。一种用于制备光学活性化合物（式（4）所代表）的方法：其中R1代表氨基保护基或其盐，其特征在于将由钛（IV）试剂和烷基金属化合物制备的试剂与光学活性化合物（式（3）所代表）反应，其中R1具有与上述定义相同的含义，必要时在Lewis酸的存在下进行反应。
• INTERMEDIATES FOR THE PRODUCTION OF OPTICALLY ACTIVE CYCLOPROPYLAMINE DERIVATIVES AND PROCESS FOR THE PRODUCTION OF THE INTERMEDIATES
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1693364B1

  公开（公告）日：2015-05-20
• J. Med. Chem. 2016, 59, 6645-6657
  作者：

  DOI：——

  日期：——
• (R/S) RIFAMYCIN DERIVATIVES, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS
  申请人：Cumbre Pharmaceuticals Inc.

  公开号：EP1768987B1

  公开（公告）日：2009-04-01