(2R)-3’,4’-dichloro-7-hexyl-6-hydroxy-1'-methyl-spiro[benzofuran-2(3H),2’-[2H]pyrrole]-3,5’-(1’H)-dione | 1206881-47-1

• 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: (2R)-3’,4’-dichloro-7-hexyl-6-hydroxy-1'-methyl-spiro[benzofuran-2(3H),2’-[2H]pyrrole]-3,5’-(1’H)-dione
• 英文别名: armeniaspirol A；streptospirole A；(2R)-3',4'-dichloro-7-hexyl-6-hydroxy-1'-methylspiro[1-benzofuran-2,5'-pyrrole]-2',3-dione
• CAS: 1206881-47-1
• 化学式: C₁₈H₁₉Cl₂NO₄
• 分子量: 384.259
• InChiKey: ZSUZJBBHPTXKIV-SFHVURJKSA-N

物化性质

• 沸点：
  608.8±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (2R)-3’,4’-dichloro-7-hexyl-6-hydroxy-1'-methyl-spiro[benzofuran-2(3H),2’-[2H]pyrrole]-3,5’-(1’H)-dione 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以72%的产率得到5-Chloro Armeniaspirole A
  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

• Isolation and Structural Elucidation of Armeniaspirols A-C: Potent Antibiotics against Gram-Positive Pathogens
  作者：Cosima Dufour、Joachim Wink、Michael Kurz、Herbert Kogler、Helene Olivan、Serge Sablé、Winfried Heyse、Martin Gerlitz、Luigi Toti、Antje Nußer、Astrid Rey、Cedric Couturier、Armin Bauer、Mark Brönstrup

  DOI：10.1002/chem.201201635

  日期：2012.12.7

  malt‐containing medium. The challenging structural elucidation of the isolated compounds was achieved by using three independent methods, that is, chemical degradation followed by NMR spectroscopy, a computer‐assisted structure prediction algorithm, and X‐ray crystallography. The compounds, named armeniaspirol A–C (2–4), exhibit a compact, hitherto unprecedented chlorinated spiro[4.4]non‐8‐ene scaffold. Labeling

  在一项抗生素先导发现计划中，发现已知的亚美尼亚链霉菌DSM19369菌株在含麦芽的培养基上培养时可产生三种新的天然产物。通过使用三种独立的方法，即化学降解后进行NMR光谱分析，计算机辅助结构预测算法和X射线晶体学分析，可以对分离出的化合物进行具有挑战性的结构解析。这些化合物命名为armeniaspirol A–C（2 – 4），具有紧凑，前所未有的氯化螺[4.4] non-8-ene骨架。标记实验用[1- 13 C]乙酸盐，[1,2 13 C2〕乙酸甲酯，和[U- 13C]脯氨酸建议通过罕见的两链机制进行生物合成。亚美尼亚醇在体外对革兰氏阳性病原体（如耐甲氧西林的金黄色葡萄球菌（MRSA）或耐万古霉素的粪肠球菌（VRE））具有中等至较高的体外活性。由于类似物2在MRSA败血症模型中具有体内活性，并且在连续传代实验中未显示出耐药性，因此它代表了一种新的抗生素前导结构。
• [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.