(2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine | 127768-05-2

• 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,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine
• 英文别名: benzyl (2S,4R)-2-(2-fluoroethoxymethyl)-4-methylsulfonyloxypyrrolidine-1-carboxylate
• CAS: 127768-05-2
• 化学式: C₁₆H₂₂FNO₆S
• 分子量: 375.418
• InChiKey: IPOQMGSXNWJGFZ-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  90.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine 在 palladium on activated charcoal 盐酸 、 calcium hydroxide 、 sodium hydroxide 、 氢气 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 14.0h， 生成 allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)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)-Cbz-4-甲磺酰氧基脯氨酸甲酯 在 sodium hydroxide 、 sodium tetrahydroborate 、 N,N-二乙基-1,1,2,3,3,3-六氟丙胺 、 三氟化硼乙醚 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 (2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine
  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
  申请人：Fujisawa Pharmaceutical Company, Ltd.

  公开号：US04983596A1

  公开（公告）日：1991-01-08

  The invention relates to a compound of antimicrobial activity, of the formula: ##STR1## in which R.sup.1 is carboxy or protected carboxy, R.sup.2 is hydroxy(lower)alkyl or protected hydroxy(lower)alkyl, R.sup.3 is hydrogen or lower alkyl, R.sup.4 is 2-fluoroethyl, 2-chloroethyl, 2-fluoropropyl or 4-fluorobutyl, R.sup.5 is hydrogen, lower alkanimidoyl, unsubstituted lower cycloalkenyl or substituted by a group consisting of oxo and amino, or imino-protective group, and A is lower alkylene, or pharmaceutically acceptable salts thereof.

  该发明涉及一种具有抗微生物活性的化合物，其化学式为：##STR1##其中R.sup.1是羧基或保护羧基，R.sup.2是羟基(较低)烷基或保护羟基(较低)烷基，R.sup.3是氢或较低烷基，R.sup.4是2-氟乙基，2-氯乙基，2-氟丙基或4-氟丁基，R.sup.5是氢，较低烷基亚胺基，未取代的较低环烯基或由氧代和氨基组成的取代基，或亚胺保护基，A是较低烷基，或其药用可接受盐。
• 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
• 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.