N-p-nitrobenzyloxycarbonyl-3-mercaptopyrrolidine | 86063-66-3

• 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: N-p-nitrobenzyloxycarbonyl-3-mercaptopyrrolidine
• 英文别名: (S)-3-mercapto-1-(p-nitrobenzyloxycarbonyl)pyrrolidine；(4-nitrophenyl)methyl 3-sulfanylpyrrolidine-1-carboxylate
• CAS: 86063-66-3
• 化学式: C₁₂H₁₄N₂O₄S
• 分子量: 282.32
• InChiKey: ZVAPAKFZITWAHK-UHFFFAOYSA-N

物化性质

• 沸点：
  457.0±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  76.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-p-nitrobenzyloxycarbonyl-3-mercaptopyrrolidine 生成 (2S,4S)-4-Acetylsulfanyl-2-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanylmethyl]-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  新型4-吡咯烷基硫基碳青霉烯II的合成及其抗菌活性：2-烷基和2-芳基硫代甲基衍生物。

  摘要：

  DOI：

  10.7164/antibiotics.51.374

文献信息

• Penem derivatives and antimicrobial agents containing the same
  申请人：SUNTORY LIMITED

  公开号：EP0774465A1

  公开（公告）日：1997-05-21

  Penem derivatives represented by the following Formula (I): wherein Z represents a hydroxyl group or a fluorine atom, R1 represents a substituted or unsubstituted alkyl, alkenyl, aralkyl group, aryl group, heterocyclic, or acyl group, or a hydrogen atom, and R2 represents a hydrogen atom or a carboxyl-protecting group; and pharmacologically acceptable salts thereof are antibacterial agents effective against, inter alia, methicillin-resistant Staphylococcus aureus. The derivatives and salts are novel except when R1 is ethyl and Z is hydroxyl. The analogous compounds in which R2 is a carboxyl-protecting group and any hydroxyl group represented by Z is protected are novel process intermediates.

  Penem衍生物由以下公式（I）表示：其中Z代表一个羟基团或氟原子，R1代表一个取代或未取代的烷基，烯基，芳基甲基，芳基，杂环基或酰基，或氢原子，R2代表一个氢原子或羧基保护基；及其药理学上可接受的盐是有效的抗菌剂，可用于治疗耐甲氧西林金黄色葡萄球菌等感染。这些衍生物和盐是新颖的，除非R1是乙基且Z是羟基。其中R2是羧基保护基且Z代表的任何羟基被保护的类似化合物是新颖的工艺中间体。
• Penem derivatives and antimicrobial agent containing the same
  申请人：Ishiguro Masaji

  公开号：US20050004092A1

  公开（公告）日：2005-01-06

  A penem derivative represented by the following formula (I): wherein R 1 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkenylthio group, a substituted or unsubstituted aralkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic thio group, a substituted or unsubstituted acylthio group, a mercapto group or a hydrogen atom, and R 2 represents a hydrogen atom or a carboxyl-protecting group; or a pharmacologically acceptable salt thereof. The compound (I) exhibits strong antibacterial activities, and especially, shows strong activities against MRSA. It is therefore useful not only as a general antibacterial agent but also as an antibacterial agent for MRSA against which no general antibacterial agents are recognized to be-effective.

  以下是公式（I）所代表的一种青霉烷衍生物： 其中，R1代表取代或未取代的烷基、取代或未取代的烯基、取代或未取代的芳基烷基、取代或未取代的芳基、取代或未取代的烷基硫基、取代或未取代的烯基硫基、取代或未取代的芳基烷基硫基、取代或未取代的芳基硫基、取代或未取代的杂环基、取代或未取代的杂环硫基、取代或未取代的酰基硫基、巯基或氢原子，R2代表氢原子或羧酸保护基；或其药学上可接受的盐。该化合物（I）表现出强大的抗菌活性，特别是对MRSA表现出强大的活性。因此，它不仅有用作一般抗菌剂，还有用作抗MRSA的抗菌剂，对于这种细菌，一般的抗菌剂被认为无效。
• Azetidinone derivatives, a process for their preparation and their use as intermediates in the preparation of carbapenem antibiotics
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0102239A1

  公开（公告）日：1984-03-07

  Compounds of formula (I): (wherein R' represents hydrogen or a hydroxy-protecting group, R2 and R3 represent hydrogen, alkyl or aryl; R4 represents optionally substituted alkyl, alicyclic heterocyclic, aryl, aromatic heterocyclic, optionally substituted alkenyl or optionally substituted alkynyl; R6 represents hydrogen or a carboxy-protecting group; and R5 represents alkoxy, aryloxy, dialkylamino or diarylamino or two of R6 together represent o-phenylenedioxy or three together represent CH3C (-CH2O-)3) may be prepared by reacting the corresponding carbonyl compound with a compound of formula P(R6)3. Compounds (I) may be cyclised to prepare carbapenem derivatives, many of which have valuable antibiotic activity.

  式(I)化合物： (其中 R' 代表氢或羟基保护基团，R2 和 R3 代表氢、烷基或芳基；R4 代表任选取代的烷基、脂环杂环基、芳基、芳香杂环基、任选取代的烯基或任选取代的炔基；R6 代表氢或羧基保护基团；以及 R5 代表烷氧基、芳氧基、二烷基氨基或二芳基氨基或两个 R6 共同代表邻苯二氧基或三个 R6 共同代表 CH3C (-CH2O-)3)可通过相应的羰基化合物与式 P(R6)3 的化合物反应制备。化合物 (I) 可通过环化制备碳青霉烯衍生物，其中许多具有重要的抗生素活性。
• 1-Hetero-6-/1-Hydroxyethyl/-2-SR8-1-carbadethiapen-2-EM-3-carboxylic acids
  申请人：Merck & Co., Inc.

  公开号：EP0160876A1

  公开（公告）日：1985-11-13

  Disclosed are 1-hetero-6-[1-hydroxyethyl)-2-SR8-1-carbadethiapen-2-em-3-COOR4 compounds having the structure: wherein R4 is, e.g., hydrogen, R8 is, e.g., alkyl and R9 is, e.g., halogen; the pharmaceutically acceptable salt and ester derivatives thereof and use as antibiotics. Also disclosed are processes for the preparation of such compounds and pharmaceutical compositions comprising such compounds.

  公开了具有以下结构的1-hetero-6-[1-羟乙基]-2-SR8-1-carbadethiapen-2-em-3-COOR4化合物：其中R4为氢等，R8为烷基等，R9为卤素等；其药学上可接受的盐和酯衍生物以及作为抗生素的用途。 还公开了制备此类化合物的工艺和包含此类化合物的药物组合物。
• Carbapenem derivatives and compositions containing them
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0160391A1

  公开（公告）日：1985-11-06

  Compounds of formula (I): wherein: one or both of R' and R2 are selected from a variety of organic groups; R3 is an optionally substituted heterocycle; and R4 is hydrogen or optionally substituted alkyl or alkoxy. and salts and esters thereof have valuable antibiotic activity.

  式(I)化合物： 其中 R' 和 R2 中的一个或两个选自各种有机基团； R3 是任选取代的杂环；以及 R4 是氢或任选取代的烷基或烷氧基。 其盐类和酯类具有重要的抗生素活性。