(R)-3-(1-amino-1-methylethyl)-1-benzylpyrrolidine | 157528-57-9

• 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)-3-(1-amino-1-methylethyl)-1-benzylpyrrolidine
• 英文别名: 2-((R)-1-benzylpyrrolidin-3-yl)propan-2-amine；2-[(3R)-1-benzylpyrrolidin-3-yl]propan-2-amine
• CAS: 157528-57-9
• 化学式: C₁₄H₂₂N₂
• 分子量: 218.342
• InChiKey: VKMDDONHDBJSAT-CYBMUJFWSA-N

物化性质

• 沸点：
  305.2±15.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• 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)-3-(1-amino-1-methylethyl)-1-benzylpyrrolidine 在 palladium on carbon 氢气 作用下， 以 乙醇 为溶剂， 45.0 ℃ 、344.75 kPa 条件下， 反应 24.0h， 以95%的产率得到1-((R)-methyl-1-pyrrolidin-3-yl)-ethylamine
  参考文献：
  名称：

  WO2007/14308

  摘要：

  公开号：
• 作为产物：
  描述：

  甲基锂 、 (R)-1-苄基-3-吡咯烷甲腈 在 cerium(III) chloride 作用下， 生成 (R)-3-(1-amino-1-methylethyl)-1-benzylpyrrolidine
  参考文献：
  名称：

  An efficient method for the synthesis of (R)-3-(1-amino-1-methylethyl)pyrrolidines for the antiinfective agent, PD 138312

  摘要：

  DOI：

  10.1016/0957-4166(94)80138-x

文献信息

• Process for chiral
  申请人：Warner-Lambert Company

  公开号：US05347017A1

  公开（公告）日：1994-09-13

  The process for the preparation of chiral 3-(1-amino-1,1-bisalkylmethyl)-1-substituted-pyrrolidines used as key intermediates for the preparation of naphthyridine and quinolone antibacterial agents which comprises reacting readily available chiral 1-substituted-3-pyrrolidinols to their corresponding chiral sulfonate esters; converting the sulfonate esters to chiral 1-substituted-3-cyanopyrrolidines having an inverse configuration, and then dialkylating the chiral cyanopyrrolidines with alkyl lithium in the presence of a Lewis acid without racemization at the asymmetric carbon atom is described.

  用作制备萘啉和喹诺酮抗菌剂的关键中间体的手性3-(1-氨基-1,1-双烷基甲基)-1-取代吡咯烷的制备过程包括将易得的手性1-取代-3-吡咯烷醇与它们对应的手性磺酸酯反应；将磺酸酯转化为具有反向构型的手性1-取代-3-氰基吡咯烷，然后在Lewis酸存在下，用烷基锂与手性氰基吡咯烷进行二烷基化，不发生手性碳原子的消旋。
• Chiral 3-cyano-1-substituted-pyrrolidines
  申请人：Warner-Lambert Company

  公开号：US05466828A1

  公开（公告）日：1995-11-14

  Chiral 3-cyanopyrrolidines of the following formula are disclosed, wherein R' is as defined herein. The compounds are useful as intermediates for naphthyridine and quinoline antibiotics. ##STR1##

  本发明揭示了以下公式的手性3-氰基吡咯烷，其中R'如本文所定义。该化合物可用作萘啶和喹啉类抗生素的中间体。 ##STR1##
• 8-methoxy-9H-isothiazolo[5,4-b]quinoline-3,4-diones and related compounds as anti-infective agents
  申请人：Bradbury James Barton

  公开号：US20070049586A1

  公开（公告）日：2007-03-01

  The invention provides compound and salts of Formula I and II, disclosed herein, which includes compounds of Formula A and Formula B: Such compounds possess useful antimicrobial activity. The variables R 2 , R 3 , R 5 , R 6 , R 7 , and R 9 shown in Formula A and B are defined herein. Certain compounds of Formula I and Formula II disclosed herein are potent and/or selective inhibitors of bacterial DNA synthesis and bacterial replication. The invention also provides antimicrobial compositions, including pharmaceutical compositions, containing one or more compounds of Formula I or Formula II and one or more carriers, excipients, or diluents. Such compositions may contain a compound of Formula I or Formula II as the only active agent or may contain a combination of a compound of Formula I or Formula II and one or more other active agents. The invention also provides methods for treating microbial infections in animals.

  本发明提供了公式I和II的化合物和盐，其中包括公式A和公式B的化合物：这些化合物具有有用的抗微生物活性。公式A和B中显示的变量R2、R3、R5、R6、R7和R9在此定义。本文所披露的公式I和公式II的某些化合物是强效和/或选择性的细菌DNA合成和细菌复制抑制剂。本发明还提供了抗微生物组合物，包括含有公式I或公式II中一个或多个化合物和一个或多个载体、赋形剂或稀释剂的制药组合物。这些组合物可以仅包含公式I或公式II中的一个化合物作为唯一活性剂，也可以包含公式I或公式II中的一个化合物和一个或多个其他活性剂的组合物。本发明还提供了治疗动物微生物感染的方法。
• 8-METHOXY-9H-ISOTHIAZOLO[5,4-B]QUINOLINE-3,4-DIONES AND RELATED COMPOUNDS AS ANTI-INFECTIVE AGENTS
  申请人：Bradbury Barton James

  公开号：US20120040959A1

  公开（公告）日：2012-02-16

  The invention provides compound and salts of Formula I and II, disclosed herein, which includes compounds of Formula A and Formula B: Such compounds possess useful antimicrobial activity. The variables R 2 , R 3 , R 5 , R 6 , R 7 , and R 9 shown in Formula A and B are defined herein. Certain compounds of Formula I and Formula II disclosed herein are potent and/or selective inhibitors of bacterial DNA synthesis and bacterial replication. The invention also provides antimicrobial compositions, including pharmaceutical compositions, containing one or more compounds of Formula I or Formula II and one or more carriers, excipients, or diluents. Such compositions may contain a compound of Formula I or Formula II as the only active agent or may contain a combination of a compound of Formula I or Formula II and one or more other active agents. The invention also provides methods for treating microbial infections in animals.

  本发明提供了公式I和II的化合物和盐，其中包括公式A和公式B的化合物：这些化合物具有有用的抗微生物活性。 公式A和B中显示的变量R2、R3、R5、R6、R7和R9在此定义。 本文所披露的某些公式I和公式II的化合物是细菌DNA合成和细菌复制的有效和/或选择性抑制剂。 本发明还提供了抗微生物组合物，包括含有一个或多个公式I或公式II化合物的制药组合物和一个或多个载体、赋形剂或稀释剂。 这样的组合物可以仅包含公式I或公式II的化合物作为唯一活性剂，也可以包含公式I或公式II的化合物和一个或多个其他活性剂的组合物。 本发明还提供了治疗动物微生物感染的方法。
• Exploration of the Activity of 7-Pyrrolidino-8-methoxyisothiazoloquinolones against Methicillin-Resistant <i>Staphylococcus aureus</i> (MRSA)
  作者：Ha Young Kim、Jason A. Wiles、Qiuping Wang、Godwin C. G. Pais、Edlaine Lucien、Akihiro Hashimoto、David M. Nelson、Jane A. Thanassi、Steven D. Podos、Milind Deshpande、Michael J. Pucci、Barton J. Bradbury

  DOI：10.1021/jm101604v

  日期：2011.5.12

  A series of 7-(3'-substituted)pyrrolidino-8-methoxyisothiazoloquinolone (ITQ) analogues were prepared, and their antibacterial potency against methicillin-sensitive Staphylococcus aureus (MSSA), methicillin-resistant Staphylococcus aureus (MRSA), and Escherichia coli were compared. Many of these analogues had MIC <= 0.25 mu g/mL against quinolone-resistant MRSA strains. The stereochemical preference was explored for a series of 1 ''-methyl-3'-aminomethylpyrrolidine analogues. Antibacterial activity was generally more favorable with 3'-R, 1 ''-S configuration. Substitution on the 3'-aminomethyl nitrogen tended to decrease activity, while potency was maintained with disubstitution or aryl substitution at the 1 ''-carbon. The 7-[(R)-3-((S)-1-aminoethyl)pyrrolidin-1-yl] analogue (6a(R,S)) and the (R)-7-[3-(2-aminopropan-2-yl)pyrrolidin-1-yl] analogue (7a(R)) were found to be the ITQs with the most promising antibacterial profiles. The MICs of these select ITQs versus a panel of clinical MRSA strains were determined, and the ITQs were found to have 8- to 16-fold greater potency than linezolid. These analogues were also evaluated for inhibition of the target enzymes, topoisomerase IV and DNA gyrase, from both wild-type and multidrug resistant strains. The ITQs were up to >30 times more inhibitory against these targets than the fluoroquinolone moxifloxacin.