(2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine | 127767-94-6

• 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-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
• 英文别名: (4-nitrophenyl)methyl (2S,4S)-4-acetylsulfanyl-2-[[2-(dimethylamino)-2-oxoethoxy]methyl]pyrrolidine-1-carboxylate
• CAS: 127767-94-6
• 化学式: C₁₉H₂₅N₃O₇S
• 分子量: 439.489
• InChiKey: BFAYAHDKYINJFB-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-Acetylthio-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 在 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 4-Nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(dimethylcarbamoyl)methyloxymethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  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-(dimethylcarbamoyl)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

• US4983596A
  申请人：——

  公开号：US4983596A

  公开（公告）日：1991-01-08
• Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems—I. 2-alkoxymethyl derivatives
  作者：Hidenori Azami、Hideo Tsutsumi、Keiji Matsuda、David Barrett、Kouji Hattori、Takashi Nakajima、Satoru Kuroda、Toshiaki Kamimura、Masayoshi Murata

  DOI：10.1016/s0968-0896(97)00142-9

  日期：1997.11

  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.