(S)-3-mercapto-N-phenacylpyrrolidine | 181959-69-3

• 英文名称: (S)-3-mercapto-N-phenacylpyrrolidine
• 英文别名: (S)-1-(2-oxo-2-phenylethyl)-3-mercaptopyrrolidine；1-phenyl-2-[(3S)-3-sulfanylpyrrolidin-1-yl]ethanone
• CAS: 181959-69-3
• 化学式: C₁₂H₁₅NOS
• 分子量: 221.323
• InChiKey: XPOZVRBJPSSRQT-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 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：
  21.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  p-nitrobenzyl (5R,6R)-6-((S)-1-hydroxypropyl)-2-methylsulfinylpenem-3-carboxylate 、 (S)-3-mercapto-N-phenacylpyrrolidine 以79%的产率得到p-nitrobenzyl (5R,6R)-6-((S)-1-hydroxypropyl)-2-((S)-1-phenacylpyrrolidin-3-yl)thiopenem-3-carboxylate
  参考文献：
  名称：

  PENEM DERIVATIVES AND ANTIMICROBIAL AGENT CONTAINING THE SAME

  摘要：

  公开号：

  EP0757051B1
• 作为产物：
  描述：

  (S)-3-benzoylthio-1-(2-oxo-2-phenylethyl)pyrrolidine 在 碳酸氢钠 、 水 、 二氯甲烷 、 Sodium sulfate-III 作用下， 以 甲醇 、 sodium hydroxide 、 二氯甲烷 为溶剂， 反应 0.42h， 生成 (S)-3-mercapto-N-phenacylpyrrolidine
  参考文献：
  名称：

  Penem derivatives and antimicrobial agent containing the same

  摘要：

  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。

  公开号：

  US20050004092A1

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。
• Carbapenem derivatives and antimicrobial agents comprising the same
  申请人：SUNTORY LIMITED

  公开号：EP0826687A1

  公开（公告）日：1998-03-04

  Carbapenem derivatives represented by the following Formula I, wherein R1 represents hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, R2 represents hydrogen or a protective group for carboxyl, and R3 represents methyl or ethyl; and pharmaceutically acceptable salts thereof are antimicrobial agents effective against, inter alia, methicillin-resistant Staphylococcus aureus. The analogous compounds in which (a) R1 is a substituted or unsubstituted alkyl, alkenyl, aralkyl or acyl group, R2 is a carboxyl-protecting group or or (b) R1 is a substituted or unsubstituted alkyl, alkenyl, aralkyl, aryl, heterocyclic or acyl group, R2 is a carboxyl-protecting group and the hydroxyl group is protected are novel process intermediates.

  由下式 I 代表的碳青霉烯类衍生物、 其中 R1 代表氢、取代或未取代的芳基或取代或未取代的杂环基，R2 代表氢或羧基保护基团，R3 代表甲基或乙基；及其药学上可接受的盐类是对耐甲氧西林金黄色葡萄球菌等有效的抗菌剂。(a) R1 是取代或未取代的烷基、烯基、芳烷基或酰基，R2 是羧基保护基团，或 (b) R1 是取代或未取代的烷基、烯基、芳烷基、芳基、杂环基或酰基，R2 是羧基保护基团且羟基受到保护的类似化合物是新型工艺中间体。
• 5,6-<i>cis</i>-Penems:  Broad-Spectrum Anti-Methicillin-Resistant <i>Staphylococcus aureus</i> β-Lactam Antibiotics
  作者：Masaji Ishiguro、Rie Tanaka、Koushi Namikawa、Takaaki Nasu、Hidekazu Inoue、Takashi Nakatsuka、Yoshiaki Oyama、Seiichi Imajo

  DOI：10.1021/jm9703348

  日期：1997.7.1

  5,6-cis-Penem derivatives have been synthesized and evaluated as anti-MRSA antibiotics. The cis-penems 5 and 6 showed potent activities against not only MRSA but also a wide variety of bacteria including beta-lactamase-producing microorganisms. These compounds were designed to have high affinity to the penicillin-binding protein 2a of MRSA and to form stable acyl intermediates with beta-lactamases by blocking the deacylating water molecule.
• Diazepinones as antiviral agents
  申请人：——

  公开号：US20040116410A1

  公开（公告）日：2004-06-17

  The invention is novel compounds of formula (I) which exhibit an improved therapeutic index and improved metabolic stability which are useful in the treatment and/or prevention of herpes viral infections. Novel intermediates useful in the synthesis of the final compounds are also part of the invention.
• US6051569A
  申请人：——

  公开号：US6051569A

  公开（公告）日：2000-04-18