armeniaspirol C | 1206881-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: armeniaspirol C
• 英文别名: (2R)-3',4'-dichloro-6-hydroxy-1'-methyl-7-[(4S)-4-methylhexyl]spiro[1-benzofuran-2,5'-pyrrole]-2',3-dione
• CAS: 1206881-49-3
• 化学式: C₁₉H₂₁Cl₂NO₄
• 分子量: 398.286
• InChiKey: WMKWPEBMZCUXQG-OVWNDWIMSA-N

物化性质

• 沸点：
  608.3±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  armeniaspirol C 在 溴 、 溶剂黄146 作用下， 反应 12.0h， 以68%的产率得到(2R)-5-bromo-3',4'-dichloro-6-hydroxy-1'-methyl-7-[(4S)-4-methylhexyl]spiro[1-benzofuran-2,5'-pyrrole]-2',3-dione
  参考文献：
  名称：

  Armeniaspiroles, a new class of antibacterials: antibacterial activities and total synthesis of 5-chloro-Armeniaspirole A

  摘要：

  Armeniaspiroles, a novel class of natural products isolated from Streptomyces armeniacus, are characterized by a novel spiro[4.4]non-8-ene scaffold. Various derivatives of Armeniaspiroles could be obtained by halogenation, alkylation, addition/elimination or reductions. A total synthesis of the 5-chloro analog of Armeniaspirole A has been accomplished in a linear six-step sequence. 5-Chloro-Armeniaspirole A exhibits good activity against a range of multidrug-resistant, Gram-positive bacterial pathogens. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.107

文献信息

• [EN] STREPTOSPIROLE DERIVATIVES<br/>[FR] DÉRIVÉS STREPTOSPIROLE
  申请人：SANOFI AVENTIS

  公开号：WO2010012381A8

  公开（公告）日：2010-05-06
• STREPTOSPIROLE DERIVATIVES
  申请人：Dufour-Schroif Cosima

  公开号：US20110295009A1

  公开（公告）日：2011-12-01

  The invention relates to streptospirole derivatives of the general formula (I), wherein R 1 , R 2 , R 3 , X 1 , X 2 , Y 1 and Y 2 are as defined herein, a process for the preparation of said compounds by fermenting the microorganism Streptomyces sp. ST 108140 (DSM 19369) and optionally derivatizing the compounds produced by said microorganism, a pharmaceutical composition comprising at least one compound of the formula (I), and the use of a compound of the formula (I) for the preparation of a medicament for the treatment and/or prophylaxis of bacterial infections.
• US8765799B2
  申请人：——

  公开号：US8765799B2

  公开（公告）日：2014-07-01
• Armeniaspiroles, a new class of antibacterials: antibacterial activities and total synthesis of 5-chloro-Armeniaspirole A
  作者：Cédric Couturier、Armin Bauer、Astrid Rey、Cosima Schroif-Dufour、Mark Broenstrup

  DOI：10.1016/j.bmcl.2012.06.107

  日期：2012.10

  Armeniaspiroles, a novel class of natural products isolated from Streptomyces armeniacus, are characterized by a novel spiro[4.4]non-8-ene scaffold. Various derivatives of Armeniaspiroles could be obtained by halogenation, alkylation, addition/elimination or reductions. A total synthesis of the 5-chloro analog of Armeniaspirole A has been accomplished in a linear six-step sequence. 5-Chloro-Armeniaspirole A exhibits good activity against a range of multidrug-resistant, Gram-positive bacterial pathogens. (C) 2012 Elsevier Ltd. All rights reserved.