(2S,4R)-2-carboxymethyloxymethyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine | 117811-73-1

• 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)-2-carboxymethyloxymethyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
• 英文别名: 2-[[(2S,4R)-4-hydroxy-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidin-2-yl]methoxy]acetic acid
• CAS: 117811-73-1
• 化学式: C₁₅H₁₈N₂O₈
• 分子量: 354.317
• InChiKey: GVHXTOYRQCWFAC-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2-carboxymethyloxymethyl-4-hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 在 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 (2S,4R)-4-methanesulfonyloxy-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
• 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 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 43.0h， 生成 (2S,4R)-2-carboxymethyloxymethyl-4-hydroxy-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-pyrolidinylthio-1-azabicyclo-[3.2.0]hept-2-ene-2-carboxylic acid
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04963543A1

  公开（公告）日：1990-10-16

  3-pyrrolidinylthio-1-azabicyclo[3.2.0]hepten-2-ene-2-carboxylic acid derivatives are prepared.

  制备了3-吡咯烷基硫基-1-氮杂双环[3.2.0]庚烯-2-烯-2-羧酸衍生物。
• 3-pyrrolidinylthio-1-azabicyclo-(3.2.0)hept-2-ene-2-carboxylic acid
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05061804A1

  公开（公告）日：1991-10-29

  3-thio pyrrolidines are intermediates for carbapenams.

  3-硫代吡咯烷是碳青霉烯的中间体。
• 3-pyrrolidinylthio-1-azabicyclo(3.2.0)-hept-2-ene-2-carboxylic acid
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04822787A1

  公开（公告）日：1989-04-18

  This invention consists of 3-pyrrolidinylthio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds and their use as antimicrobial agents in the treatment of infectious diseases.

  这项发明涉及3-吡咯烷基硫基-1-氮杂双环[3.2.0]庚-2-烯-2-羧酸化合物及其在治疗传染病中作为抗微生物药物的用途。
• 3-Pyrrolidinylthio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds and processes for the preparation thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0272456A1

  公开（公告）日：1988-06-29

  A compound 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 protected or unprotected ureido(lower)alkyl, R5 is hydrogen, lower alkanimidoyl or imino-protective group, and A is lower alkylene, and pharmaceutically acceptable salts thereof, processes or their preparation and pharmaceutical compositions comprising them. The invention also relates to intermediate compounds of the formula

  式.的化合物 其中 R1 为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 是受保护或未受保护的脲基（低级）烷基、 R5 是氢、低级烷酰基或亚氨基保护基团，以及 A 是低级亚烷基，及其药学上可接受的盐、制备工艺或包含它们的药物组合物。本发明还涉及式中的中间体化合物
• 3-Pyrrolidinylthio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid derivatives and processes for the preparation thereof
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0280771A1

  公开（公告）日：1988-09-07

  A compound 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 lower alkyl having suitable substituent(s), heterocyclic group optionally substituted by suitable substituent(s), or lower alkylsulfonyl,     R⁵ is hydrogen, lower alkanimidoyl or imino-protective group,     A is lower alkylene, and     X is sulfur, oxygen, imino or protected imino, provided that     when X is oxygen,     then R⁴ is not "protected or unprotected ureido(lower)alkyl", and pharmaceutically acceptable salts thereof, processes for their preparation and pharmaceutical compositions comprising them as an active ingredient. The invention also relates to intermediates of the formula and a process for the preparation thereof.

  一种式......的化合物 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 是具有适当取代基的低级烷基、任选被适当取代基取代的杂环基团或低级烷基磺酰基、 R⁵ 是氢、低级烷酰基或亚氨基保护基团、 A 是低级亚烷基，以及 X 是硫、氧、亚氨基或保护亚氨基、 条件是 当 X 为氧时 则 R⁴ 不是 "受保护或未受保护的脲基（低级）烷基"、 及其药学上可接受的盐、制备工艺和包含它们作为活性成分的药物组合物。本发明还涉及式 及其制备工艺。