(2S,4S)-4-Acetylthio-2-(methylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine | 127767-95-7

• 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: (2S,4S)-4-Acetylthio-2-(methylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
• 英文别名: (4-nitrophenyl)methyl (2S,4S)-4-acetylsulfanyl-2-[[2-(methylamino)-2-oxoethoxy]methyl]pyrrolidine-1-carboxylate
• CAS: 127767-95-7
• 化学式: C₁₈H₂₃N₃O₇S
• 分子量: 425.463
• InChiKey: DGQTUWQDOCLYFT-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-Acetylthio-2-(methylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (2S,4S)-4-Mercapto-2-(methylcarbamoyl)methyloxymethyl-(4-nitrobenzyloxycarbonyl)pyrrolidine
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems—I. 2-alkoxymethyl derivatives

  摘要：

  The synthesis and in vitro antibacterial activity of a novel series of 2-alkoxymethyl-4-pyrrolidinylthio-1 beta-methyl carbapenems are described. As a result of these studies, we discovered that FR27743 (19j) containing a novel,2-fluoroethoxymethyl substituent possesses a broad spectrum of antibacterial activity against both Gram-positive and Gram-negative organisms, including Pseudomonas aeruginosa. Furthermore, FR27743 exhibited excellent stability against renal dehydropeptidase-I (DHP-I), good urinary recovery, and superior in vivo activity compared to that for Meropenem against several systemic infections. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00142-9
• 作为产物：
  描述：

  (2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 在 palladium dihydroxide 咪唑 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 potassium tert-butylate 、 氢气 、 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 49.5h， 生成 (2S,4S)-4-Acetylthio-2-(methylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
  参考文献：
  名称：

  Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems—I. 2-alkoxymethyl derivatives

  摘要：

  The synthesis and in vitro antibacterial activity of a novel series of 2-alkoxymethyl-4-pyrrolidinylthio-1 beta-methyl carbapenems are described. As a result of these studies, we discovered that FR27743 (19j) containing a novel,2-fluoroethoxymethyl substituent possesses a broad spectrum of antibacterial activity against both Gram-positive and Gram-negative organisms, including Pseudomonas aeruginosa. Furthermore, FR27743 exhibited excellent stability against renal dehydropeptidase-I (DHP-I), good urinary recovery, and superior in vivo activity compared to that for Meropenem against several systemic infections. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00142-9

文献信息

• 3-pyrrolidinylthio-1-azabicyclo(3.2.0)-hept-2-ene-2-carboxylic acid derivatives and their preparation
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0341557A1

  公开（公告）日：1989-11-15

  3-Pyrrolidinylthio-1-azabicyclo(3.2.0)-hept-2-ene-2-carbocylic acid derivatives of the formula: in which R¹ is carboxy or protected carboxy, R² is hydroxy(lower)alkyl or protected hydroxy(lower)alkyl, R³ is hydrogen or lower alkyl, R⁴ is monohalo(lower)alkyl, mono- or di(lower)alkylamino(lower)alkyl, protected mono(lower)alkylamino­(lower)alkyl, mono- or di(lower)­alkylcarbamoyl(lower)alkyl, or protected or unprotected carboxy­(lower)alkyl, R⁵ is hydrogen, lower alkanimidoyl, lower cycloalkenyl which may have suitable substituent(s) or imino-protective group, and A is lower alkylene, or pharmaceutically acceptable salts thereof, processes for their preparation and pharmaceutical compositions comprising them as an active ingredient.

  式中的 3-吡咯烷基硫基-1-氮杂双环(3.2.0)-庚-2-烯-2-甲酸衍生物： 其中 R¹ 是羧基或受保护的羧基、 R² 是羟基（低级）烷基或受保护的羟基（低级）烷基、 R³ 是氢或低级烷基、 R⁴ 是单卤代（低级）烷基、单-或二（低级）烷基氨基（低级）烷基、受保护的单-（低级）烷基氨基（低级）烷基、单-或二（低级）烷基氨基甲酰基（低级）烷基、或受保护或未受保护的羧基（低级）烷基、 R⁵ 是氢、低级烷氨基甲酰基、低级环烯基（可带有合适的取代基）或亚氨基保护基，以及 A 是低级亚烷基、 或其药学上可接受的盐、其制备工艺以及包含它们作为活性成分的药物组合物。
• US4983596A
  申请人：——

  公开号：US4983596A

  公开（公告）日：1991-01-08