(4S)-4-acetyl-1-[(1S)-1-phenylethyl]pyrrolidin-2-one | 143408-60-0

• 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: (4S)-4-acetyl-1-[(1S)-1-phenylethyl]pyrrolidin-2-one
• CAS: 143408-60-0
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: MSTQWPYYJTYBNO-GWCFXTLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-4-acetyl-1-[(1S)-1-phenylethyl]pyrrolidin-2-one 在 硼烷四氢呋喃络合物 、 20% palladium(II) hydroxide on carbon 、 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 60.0h， 生成 N-[1-[(3S)-pyrrolidin-3-yl]ethyl]cyclopropanamine
  参考文献：
  名称：

  Exploration of the Activity of 7-Pyrrolidino-8-methoxyisothiazoloquinolones against Methicillin-Resistant Staphylococcus aureus (MRSA)

  摘要：

  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.

  DOI：

  10.1021/jm101604v

文献信息

• Individual stereoisomers of 7-(3-aminoalkyl)-1-pyrrolidinyl)-quinolones as antibacterial agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0909759A2

  公开（公告）日：1999-04-21

  Individual stereoisomers of 7-[3-(1-aminoalkyl)-1-pyrrolidinyl]-quinolones are described, their therapeutic advantages as antibacterial agents, as well as a novel method for the preparation and isolation of such stereoisomers.

  介绍了 7-[3-(1-氨基烷基)-1-吡咯烷基]-喹诺酮类化合物的单个立体异构体、它们作为抗菌剂的治疗优势以及制备和分离此类立体异构体的新方法。
• INDIVIDUAL STEREOISOMERS OF 7- 3-(1-AMINOALKYL)-1-PYRROLIDINYL]-QUINOLONES AND NAPHTHYRIDONES AS ANTIBACTERIAL AGENTS
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0559774B1

  公开（公告）日：1999-07-07
• US5344940A
  申请人：——

  公开号：US5344940A

  公开（公告）日：1994-09-06
• US5461165A
  申请人：——

  公开号：US5461165A

  公开（公告）日：1995-10-24
• US5563155A
  申请人：——

  公开号：US5563155A

  公开（公告）日：1996-10-08