tertiary butyl (3S)-4-[2-(benzenesulfonyl)oxyethyl]-3-methyl-5-oxo-1-[(1R)-phenylethyl]pyrrolidine-3-carboxylate

• 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: tertiary butyl (3S)-4-[2-(benzenesulfonyl)oxyethyl]-3-methyl-5-oxo-1-[(1R)-phenylethyl]pyrrolidine-3-carboxylate
• 英文别名: (3S)-4-[2-(benzenesulfonyl)oxyethyl]-3-methyl-5-oxo-1-[(1R)-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester；(3S)-4-[2-(benzenesulfonyl)oxyethyl]-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester；tert-butyl (3S)-4-[2-(benzenesulfonyl)oxyethyl]-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate；tert-butyl (3S)-4-[2-(benzenesulfonyloxy)ethyl]-3-methyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate
• 化学式: C₂₆H₃₃NO₆S
• 分子量: 487.617
• InChiKey: URLKYYRGDPBUIU-DCEQETOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tertiary butyl (3S)-4-[2-(benzenesulfonyl)oxyethyl]-3-methyl-5-oxo-1-[(1R)-phenylethyl]pyrrolidine-3-carboxylate 在 盐酸 、 叠氮磷酸二苯酯 、 palladium 10% on activated carbon 、 水 、 氢气 、 sodium hexamethyldisilazane 、 三乙胺 、 红铝 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 48.25h， 生成 7-[(7S)-7-amino-7-methyl-5-azaspiro[2.4]hept-5-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluations of Novel 7-[7-Amino-7-methyl-5-azaspiro[2.4]heptan-5-yl]-8-methoxyquinolines with Potent Antibacterial Activity against Respiratory Pathogens

  摘要：

  Novel 7-[7-amino-7-methyl-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]- 8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 2a and 2b were designed and synthesized to obtain potent antibacterial drugs for the treatment of respiratory tract infections. Among these, compound 2a possessing (S)-configuration for the asymmetrical carbon on the pyrolidine moiety at the C-7 position of the quinolone scaffold exhibited potent in vitro antibacterial activity against respiratory pathogens including Gram-positive (Streptococcus pneumoniae and Staphylococcus aureus), Gram-negative (Haemophilus influenzae and Moraxcella catarrhalis), and atypical strains (Chalmydia pneumoniae and Mycoplasma pneumoniae), as well as multidrug-resistant Streptococcus pneumoniae and quinolone-resistant and methicillin-resistant Staphylococcus aureus). Furthermore, compound 2a showed excellent in vivo activity against the experimental murine pneumonia model due to multidrug resistant Streptococcus pneumoniae (MDRSP) and favorable profiles in preliminary toxicological and nonclinical pharmacokinetic studies.

  DOI：

  10.1021/jm301650g
• 作为产物：
  描述：

  tert-butyl 2-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-4-carboxylate 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium hydride 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 tertiary butyl (3S)-4-[2-(benzenesulfonyl)oxyethyl]-3-methyl-5-oxo-1-[(1R)-phenylethyl]pyrrolidine-3-carboxylate
  参考文献：
  名称：

  HYDRATE FOR MEDICAL PURPOSES

  摘要：

  公开号：

  EP2000467B1

文献信息

• Tri-, tetra-substituted-3-aminopyrrolidine derivative
  申请人：Takahashi Hisashi

  公开号：US20060264428A1

  公开（公告）日：2006-11-23

  A quinolone synthetic antibacterial agent and a therapeutic agent for an infection which exhibit broad spectrum and strong antibacterial activity for both Gram positive and Gram negative bacteria, and which are also highly safe are provided. The compound provided is represented by following formula (I): wherein R 1 and R 2 represent hydrogen atom, or the like; R 3 represents an alkyl group containing 1 to 6 carbon atoms, or the like; R 4 and R 5 independently represents hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or the like, with the proviso that R 4 and R 5 do not simultaneously represent hydrogen atom; or the substituents R 4 and R 5 together represent (a) a 3- to 6-membered cyclic structure including the carbon atom shared by R 4 and R 5 to form a spirocyclic structure with the pyrrolidine ring; R 6 and R 7 independently represents hydrogen atom, an alkyl group containing 1 to 6 carbon atoms, or the like; R 8 represents a halogen-substituted alkyl group containing 1 to 6 carbon atoms, or the like; X 1 represents hydrogen atom or a halogen atom; A represents nitrogen atom or a moiety represented by formula (II):

  提供了一种喹诺酮合成抗菌剂和治疗感染的药物，对革兰氏阳性和革兰氏阴性细菌均表现出广谱和强效的抗菌活性，并且具有很高的安全性。所提供的化合物由以下式（I）表示： 其中R1和R2代表氢原子，或类似物；R3代表含有1至6个碳原子的烷基基团，或类似物；R4和R5独立地代表氢原子，含有1至6个碳原子的烷基基团，或类似物，但R4和R5不同时代表氢原子；或取代基R4和R5一起代表（a）包括由R4和R5共享的碳原子形成螺环结构与吡咯烷环形成螺环结构的3至6成员环结构；R6和R7独立地代表氢原子，含有1至6个碳原子的烷基基团，或类似物；R8代表含有1至6个碳原子的卤代烷基基团，或类似物；X1代表氢原子或卤原子；A代表氮原子或由式（II）表示的基团。
• WO2006/123792
  申请人：——

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• WO2007/37303
  申请人：——

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  公开（公告）日：——
• WO2006/123767
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• US8003666B2
  申请人：——

  公开号：US8003666B2

  公开（公告）日：2011-08-23