(5R)-5-((1H-1,2,3-triazol-1-yl)methyl)-3-(3-fluoro-4-(tetrahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]-2(3H)-yl)phenyl)oxazolidin-2-one | 1395322-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (5R)-5-((1H-1,2,3-triazol-1-yl)methyl)-3-(3-fluoro-4-(tetrahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]-2(3H)-yl)phenyl)oxazolidin-2-one
• 英文别名: 2-[2-fluoro-4-[(5R)-5-(1,2,3-triazol-1-ylmethyl)-2-oxo-3-oxazolidinyl]phenyl]hexahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]；2-[2-fluoro-4-[(5R)-5-(1,2,3-triazol-1-ylmethyl)-2-oxo-3-oxazolidinyl]phenyl]hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2'-[1,3]dioxolane]；(5R)-3-(3-fluoro-4-spiro[1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-5,2'-1,3-dioxolane]-2-ylphenyl)-5-(triazol-1-ylmethyl)-1,3-oxazolidin-2-one
• CAS: 1395322-93-6
• 化学式: C₂₁H₂₄FN₅O₄
• 分子量: 429.451
• InChiKey: MJPNHZVSZIOFQW-DQPZFDDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (5R)-5-((1H-1,2,3-triazol-1-yl)methyl)-3-(3-fluoro-4-(tetrahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]-2(3H)-yl)phenyl)oxazolidin-2-one 在 indium(III) bromide 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 26.0h， 生成 (5R)-3-[4-(5-cyano-5-trimethylsilanyloxyhexahydrocyclopenta[c]pyrrol-2-yl)-3-fluorophenyl]-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and In Vitro Antibacterial Activity of Novel 3-Azabicyclo[3.3.0]octanyl Oxazolidinones

  摘要：

  We synthesized a series of oxazolidinone‐type antibacterials in which morpholine C‐ring of linezolid has been modified by substituted 3‐azabicyclo[3.3.0]octanyl rings. Acetamide or 1,2,3‐triazole heterocycle was used as C‐5 side chain of oxazolidinone. The resulting series of compounds was then screened in vitro against panel of susceptible and resistant Gram‐positive, Gram‐negative bacteria, and Mycobacterium tuberculosis (Mtb). Several analogs in this series exhibited potent in vitro antibacterial activity comparable or superior to linezolid against the tested bacteria. Compounds 10a, 10b, 11a, and 15a displayed highly potent activity against M. tuberculosis. Selected compound 10b showed good human microsomal stability and CYP‐profile, and showed low activity against hERG channel.

  DOI：

  10.1111/j.1747-0285.2012.01404.x
• 作为产物：
  描述：

  2-(2-fluoro-4-nitrophenyl)-5-oxohexahydrocyclopenta[c]pyrrole 在 正丁基锂 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 70.25h， 生成 (5R)-5-((1H-1,2,3-triazol-1-yl)methyl)-3-(3-fluoro-4-(tetrahydro-1H-spiro[cyclopenta[c]pyrrole-5,2'-[1,3]dioxolane]-2(3H)-yl)phenyl)oxazolidin-2-one
  参考文献：
  名称：

  OXAZOLIDINONE DERIVATIVES CONTAINING NEW BICYCLIC GROUP, HAVING ANTIBACTERIAL ACTIVITY, AND METHOD FOR TREATING PATHOGENIC BACTERIAL INFECTIONS USING THE SAME

  摘要：

  本发明涉及含有新的双环基团的噁唑烷酮衍生物，具有抗菌活性，或其药学上可接受的盐，以及制备该衍生物的方法，包含噁唑烷酮衍生物或其药学上可接受的盐作为活性成分的抗菌组合物，以及使用该组合物治疗由病原体引起的传染病的方法。噁唑烷酮衍生物或其药学上可接受的盐可能对包括各种耐药菌株在内的革兰氏阳性细菌表现出优秀的抗菌活性。

  公开号：

  US20130012554A1

文献信息

• OXAZOLIDINONE DERIVATIVES CONTAINING NEW BICYCLIC GROUP, HAVING ANTIBACTERIAL ACTIVITY, AND METHOD FOR TREATING PATHOGENIC BACTERIAL INFECTIONS USING THE SAME
  申请人：KEUM Gyo-Chang

  公开号：US20130012554A1

  公开（公告）日：2013-01-10

  The present invention relates to oxazolidinone derivatives containing new bicyclic group, having antibacterial activity, or a pharmaceutically acceptable salt thereof, a method for preparing the same, an antibacterial composition comprising the oxazolidinone derivative or a pharmaceutically acceptable salt thereof as an active ingredient, and a method for treating an infectious disease caused by pathogen using the same. The oxazolidinone derivative or a pharmaceutically acceptable salt thereof may exhibit excellent antibacterial activity against gram positive bacteria including various resistant strains.

  本发明涉及含有新的双环基团的噁唑烷酮衍生物，具有抗菌活性，或其药学上可接受的盐，以及制备该衍生物的方法，包含噁唑烷酮衍生物或其药学上可接受的盐作为活性成分的抗菌组合物，以及使用该组合物治疗由病原体引起的传染病的方法。噁唑烷酮衍生物或其药学上可接受的盐可能对包括各种耐药菌株在内的革兰氏阳性细菌表现出优秀的抗菌活性。
• Oxazolidinone derivatives containing new bicyclic group, having antibacterial activity, and method for treating pathogenic bacterial infections using the same
  申请人：Keum Gyo-Chang

  公开号：US08507540B2

  公开（公告）日：2013-08-13

  The present invention relates to oxazolidinone derivatives containing new bicyclic group, having antibacterial activity, or a pharmaceutically acceptable salt thereof, a method for preparing the same, an antibacterial composition comprising the oxazolidinone derivative or a pharmaceutically acceptable salt thereof as an active ingredient, and a method for treating an infectious disease caused by pathogen using the same. The oxazolidinone derivative or a pharmaceutically acceptable salt thereof may exhibit excellent antibacterial activity against gram positive bacteria including various resistant strains.

  本发明涉及含有新的双环基团的噁唑烷衍生物，具有抗菌活性或其药学上可接受的盐，制备方法，包含噁唑烷衍生物或其药学上可接受的盐作为活性成分的抗菌组合物，以及使用其治疗由病原体引起的传染病的方法。噁唑烷衍生物或其药学上可接受的盐可能对包括各种耐药菌株在内的革兰氏阳性菌表现出极好的抗菌活性。
• US8507540B2
  申请人：——

  公开号：US8507540B2

  公开（公告）日：2013-08-13
• Synthesis and In Vitro Antibacterial Activity of Novel 3-Azabicyclo[3.3.0]octanyl Oxazolidinones
  作者：Deepak Bhattarai、Sun H. Lee、Seon H. Seo、Ghilsoo Nam、Soon B. Kang、Ae N. Pae、Eunice E. Kim、Taegwon Oh、Sang-Nae Cho、Gyochang Keum

  DOI：10.1111/j.1747-0285.2012.01404.x

  日期：2012.9

  We synthesized a series of oxazolidinone‐type antibacterials in which morpholine C‐ring of linezolid has been modified by substituted 3‐azabicyclo[3.3.0]octanyl rings. Acetamide or 1,2,3‐triazole heterocycle was used as C‐5 side chain of oxazolidinone. The resulting series of compounds was then screened in vitro against panel of susceptible and resistant Gram‐positive, Gram‐negative bacteria, and Mycobacterium tuberculosis (Mtb). Several analogs in this series exhibited potent in vitro antibacterial activity comparable or superior to linezolid against the tested bacteria. Compounds 10a, 10b, 11a, and 15a displayed highly potent activity against M. tuberculosis. Selected compound 10b showed good human microsomal stability and CYP‐profile, and showed low activity against hERG channel.