(2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine | 199998-81-7

• 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,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine
• 英文别名: (2S,4R)-1-benzyloxycarbonyl-2-[2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl]oxymethyl-4-methanesulfonyloxypyrrolidine；benzyl (2S,4R)-2-[[2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethoxy]methyl]-4-methylsulfonyloxypyrrolidine-1-carboxylate
• CAS: 199998-81-7
• 化学式: C₂₂H₂₇NO₁₁S
• 分子量: 513.522
• InChiKey: DFWSLVBYWJMVEY-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  160
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-4-methanesulfonyloxypyrrolidine 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 N,N-二乙基-1,1,2,3,3,3-六氟丙胺 、 氢气 、 sodium methylate 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 乙腈 为溶剂， 反应 79.75h， 生成 allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoropropyl)oxymethylpyrrolidin-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 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 potassium tert-butylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 (2S,4R)-1-benzyloxycarbonyl-2-{2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl}-oxymethyl-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。
• 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.