(2R,4S)-2-(2-Methyl-2H-pyrazol-3-ylmethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester | 164161-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,4S)-2-(2-Methyl-2H-pyrazol-3-ylmethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (2R,4S)-2-[(2-methylpyrazol-3-yl)methyl]-4-tritylsulfanylpyrrolidine-1-carboxylate
• CAS: 164161-74-4
• 化学式: C₃₂H₃₃N₃O₂S
• 分子量: 523.699
• InChiKey: JKKKYKZUBYFOCW-IHLOFXLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2-(2-Methyl-2H-pyrazol-3-ylmethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester 在 甲醇 、 三乙基硅烷 、 N,N-二甲基乙酰胺 、 Amberlist A-26 、 氨 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 生成 3-{(2R,4S)-1-Allyloxycarbonyl-4-[(4R,5S,6S)-2-allyloxycarbonyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-ylmethyl}-1-carboxymethyl-2-methyl-2H-pyrazol-1-ium; chloride
  参考文献：
  名称：

  Studies on β-lactam antibiotics. Synthesis and antibacterial activity of novel 1β-methylcarbapenems related to FR21818: 5-membered ring analogs

  摘要：

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems 1 are described. Most compounds displayed extremely potent antibacterial activity and high renal DHP-1 stability. The best compound in this series, FR21818 (1a) displayed excellent in vivo efficacy against an MRSA infection in mice. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00230-8
• 作为产物：
  描述：

  (2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-formylpyrrolidine 在 palladium on activated charcoal 二硫化碳 、 三正丁基氢锡 、 甲酸铵 、 sodium methylate 、 sodium hydride 、 碘甲烷 作用下， 生成 (2R,4S)-2-(2-Methyl-2H-pyrazol-3-ylmethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester
  参考文献：
  名称：

  Studies on β-lactam antibiotics. Synthesis and antibacterial activity of novel 1β-methylcarbapenems related to FR21818: 5-membered ring analogs

  摘要：

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems 1 are described. Most compounds displayed extremely potent antibacterial activity and high renal DHP-1 stability. The best compound in this series, FR21818 (1a) displayed excellent in vivo efficacy against an MRSA infection in mice. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00230-8

文献信息

• 3-PYRROLIDINYLTHIO-CARBAPENEM DERIVATIVES AND THEIR ANTIMICROBAL ACTIVITY
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0722447A1

  公开（公告）日：1996-07-24
• [EN] 3-PYRROLIDINYLTHIO-CARBAPENEM DERIVATIVES AND THEIR ANTIMICROBAL ACTIVITY<br/>[FR] DERIVES DE 3-PYRROLIDINYLTHIO-CARBAPENEM ET LEUR ACTIVITE ANTIMICROBIENNE
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：WO1995010520A1

  公开（公告）日：1995-04-20

  (EN) A compound of formula (I), in which R1 is carboxy, etc., R2 is hydroxy(lower)alkyl, etc., R3 is hydrogen or lower alkyl, R4 is 2(or 3)-methylpyridin-4-ylmethyl, etc., and R5 is hydrogen or imino-protective group, or pharmaceutically acceptable salts thereof, which is useful as an antimicrobial agent.(FR) L'invention concerne un composé de formule (I), dans laquelle R1 représente carboxy, etc., R2 représente hydroxyalkyle (inférieur), etc., R3 représente hydrogène ou alkyle inférieur, R4 représente 2(ou 3)-méthylpyridin-4-ylméthyle, etc., et R5 représente hydrogène ou un groupe imino-protecteur. Ce composé et ses sels pharmaceutiquement acceptables s'utilisent comme agents antimicrobiens.
• Studies on β-lactam antibiotics. Synthesis and antibacterial activity of novel 1β-methylcarbapenems related to FR21818: 5-membered ring analogs
  作者：Hidenori Azami、David Barrett、Akira Tanaka、Hiroshi Sasaki、Keiji Matsuda、Minoru Sakurai、Yoshimi Matsumoto、Shuichi Tawara、Toshiyuki Chiba、Kazuo Sakane

  DOI：10.1016/s0960-894x(97)00230-8

  日期：1997.6

  The synthesis and biological activity of the novel series of 1 beta-methylcarbapenems 1 are described. Most compounds displayed extremely potent antibacterial activity and high renal DHP-1 stability. The best compound in this series, FR21818 (1a) displayed excellent in vivo efficacy against an MRSA infection in mice. (C) 1997 Elsevier Science Ltd.