(+/-)-N-[[3-[4-(4-methoxy-3-oxo-1,4,6-cycloheptatrien-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide | 178384-83-3

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: (+/-)-N-[[3-[4-(4-methoxy-3-oxo-1,4,6-cycloheptatrien-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
• 英文别名: N-[[3-[4-(4-methoxy-3-oxocyclohepta-1,4,6-trien-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 178384-83-3
• 化学式: C₂₀H₂₀N₂O₅
• 分子量: 368.389
• InChiKey: DJMIUCKLXPTAJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-N-[[3-[4-(4-methoxy-3-oxo-1,4,6-cycloheptatrien-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide 、 炔丙胺 生成 N-{2-Oxo-3-[4-(3-oxo-4-prop-2-ynylamino-cyclohepta-1,4,6-trienyl)-phenyl]-oxazolidin-5-ylmethyl}-acetamide
  参考文献：
  名称：

  Synthesis and antibacterial activity of new tropone-substituted phenyloxazolidinone antibacterial agents 1. Identification of leads and importance of the tropone substitution pattern

  摘要：

  Incorporation of a substituted tropone moiety into the para position of suitably functionalized 3-phenyl-2-oxazolidinones affords novel and potent antibacterial agents. The effect of the tropone regioisomer and its attendant substituents on antibacterial activity is discussed. Analogues such as 11c and 13b display in vitro and in vivo activity approaching that of the current clinical benchmark, vancomycin. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00154-0
• 作为产物：
  描述：

  6-bromo-2-methoxycyclohepta-2,4,6-trien-1-one 、 (l)-N-[3-(4-iodophenyl)-2-oxooxazolidin-5-ylmethyl]acetamide 在 bis-triphenylphosphine-palladium(II) chloride 六甲基二锡 作用下， 生成 (+/-)-N-[[3-[4-(4-methoxy-3-oxo-1,4,6-cycloheptatrien-1-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
  参考文献：
  名称：

  Synthesis and antibacterial activity of new tropone-substituted phenyloxazolidinone antibacterial agents 1. Identification of leads and importance of the tropone substitution pattern

  摘要：

  Incorporation of a substituted tropone moiety into the para position of suitably functionalized 3-phenyl-2-oxazolidinones affords novel and potent antibacterial agents. The effect of the tropone regioisomer and its attendant substituents on antibacterial activity is discussed. Analogues such as 11c and 13b display in vitro and in vivo activity approaching that of the current clinical benchmark, vancomycin. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/0960-894x(96)00154-0

文献信息

• TROPONE-SUBSTITUTED PHENYLOXAZOLIDINONE ANTIBACTERIAL AGENTS
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0673370B1

  公开（公告）日：1998-01-07
• JP3558088B2
  申请人：——

  公开号：JP3558088B2

  公开（公告）日：2004-08-25
• US5523403A
  申请人：——

  公开号：US5523403A

  公开（公告）日：1996-06-04
• [EN] TROPONE-SUBSTITUTED PHENYLOXAZOLIDINONE ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTERIENS A BASE DE PHENYLOXAZOLIDINONE SUBSTITUEE PAR TROPONE
  申请人：——

  公开号：WO1994013649A1

  公开（公告）日：1994-06-23

  [EN] A novel class of phenyloxazolidinone antibacterial agents which have, as their salient structural feature, an appended substituted tropone moiety, are described. Intermediates and processes for the preparation of these antibiotics are also disclosed. These compounds are useful antibacterial agents to eradicate or control suceptible organisms. In formula (I), R<1>, R<2> and R<3> are the same as in claim 1 and R<4> is selected from the group consisting of (a), (b), (c) and (d), wherein R and Ra are the same or different and are selected from the group consisting of (C1-C8) alkyl optionally substituted with chloro, fluoro, hydroxy, (C1-C8) alkoxy, amino, (C1-C8) alkylamino, (C1-C8) dialkylamino.
  [FR] Nouvelle catégorie d'agents antibactériens à base de phényloxazolidinone comprenant, comme élément structural saillant, une fraction de tropone substitué annexée. Des intermédiaires et des procédés destinés à leur préparation sont également décrits. Ces composés peuvent être utilisés comme agents antibactériens pour éliminer ou lutter contre des organismes sensibles. Dans la formule (I), R1, R2 et R3 sont tels que décrits dans la revendication 1 et R4 est choisi dans le groupe composé de (a), (b), (c) et (d) où R et Ra sont identiques ou différents et sont choisis dans le groupe composé de (C1-C8) alkyle éventuellement substitué par chloro, fluoro, hydroxy, (C1-C8) alcoxy, amino, (C1-C8) alkylamino, et (C1-C8) dialkylamino.
• Synthesis and antibacterial activity of new tropone-substituted phenyloxazolidinone antibacterial agents 1. Identification of leads and importance of the tropone substitution pattern
  作者：Michael R. Barbachyn、Dana S. Toops、Debra A. Ulanowicz、Kevin C. Grega、Steven J. Brickner、Charles W. Ford、Gary E. Zurenko、Judith C. Hamel、Ronda D. Schaadt、Douglas Stapert、Betty H. Yagi、Jerry M. Buysse、William F. Demyan、James O. Kilburn、Suzanne E. Glickman

  DOI：10.1016/0960-894x(96)00154-0

  日期：1996.5

  Incorporation of a substituted tropone moiety into the para position of suitably functionalized 3-phenyl-2-oxazolidinones affords novel and potent antibacterial agents. The effect of the tropone regioisomer and its attendant substituents on antibacterial activity is discussed. Analogues such as 11c and 13b display in vitro and in vivo activity approaching that of the current clinical benchmark, vancomycin. (C) 1996 Elsevier Science Ltd.