3-[(1S,3aR,4S,6S)-1,4,7-trimethyl-6-(2-methylprop-1-enyl)-2,3,3a,4,5,6-hexahydro-1H-phenaleno[2,1-d][1,3]oxazol-9-yl]propanoic acid | 1338442-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3-[(1S,3aR,4S,6S)-1,4,7-trimethyl-6-(2-methylprop-1-enyl)-2,3,3a,4,5,6-hexahydro-1H-phenaleno[2,1-d][1,3]oxazol-9-yl]propanoic acid
• CAS: 1338442-67-3
• 化学式: C₂₄H₃₁NO₃
• 分子量: 381.515
• InChiKey: XUVXGKQNQBLGRU-XJNFMUPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  pseudopterosin Y aglycone 在 ammonium cerium (IV) nitrate 、 水 、 silver(l) oxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 22.0h， 生成 3-[(1S,3aR,4S,6S)-1,4,7-trimethyl-6-(2-methylprop-1-enyl)-2,3,3a,4,5,6-hexahydro-1H-phenaleno[2,1-d][1,3]oxazol-9-yl]propanoic acid
  参考文献：
  名称：

  One-Pot Syntheses of Pseudopteroxazoles from Pseudopterosins: A Rapid Route to Non-natural Congeners with Improved Antimicrobial Activity

  摘要：

  Rapid one-pot methodologies to prepare pseudopteroxazole (1) and novel congeners from abundant natural pseudopterosins have been devised. This is highlighted here with the first synthesis of the marine natural product homopseudopteroxazole (2) utilizing a novel, silver(I)-mediated catechol to benzoxazole transformation. Pseudopteroxazoles and isopseudopteroxazoles exhibit potent activity against a range of important Gram-positive pathogens including Mycobacterium spp. and vancomycin-resistant Enterococcus faecium. Several non-natural pseudopteroxazoles exhibited strong activity against methicillin-resistant Staphylococcus aureus, thereby displaying a broader spectrum of antibiotic activity compared to pseudopteroxazole.

  DOI：

  10.1021/np2006555

文献信息

• [EN] PREPARATION AND USE OF PSEUDOPTEROXAZOLE AND PSEUDOPTEROSIN ANALOGS AND DERIVATIVES<br/>[FR] PRÉPARATION ET UTILISATION D'ANALOGUES ET DE DÉRIVÉS DE PSEUDOPTÉROXAZOLE ET DE PSEUDOPTÉROSINE
  申请人：NAUTILUS BIOSCIENCES CANADA INC

  公开号：WO2012139212A1

  公开（公告）日：2012-10-18

  New methods of converting pseudopterosins to pseudopteroxazoles have been developed and used to make several new non-natural pseudopteroxazole analogs. These as well as pseudopterosins and derivatives thereof and prenylated aromatic structural mimics of pseudopterosins/pseudopteroxazoles are shown to display anti-bacterial activity including that against non-replicating mycobacteria, with some exhibiting no or limited toxicity against mammalian cells.

  已经开发出将伪角藻素转化为伪角藻恶唑的新方法，并用于制造多种新的非天然伪角藻恶唑类似物。这些物质以及伪角藻素及其衍生物和伪角藻素/伪角藻恶唑的异戊二烯基芳香结构模拟物显示出抗细菌活性，包括对非复制分枝杆菌的活性，其中一些对哺乳动物细胞没有或仅有有限的毒性。
• One-Pot Syntheses of Pseudopteroxazoles from Pseudopterosins: A Rapid Route to Non-natural Congeners with Improved Antimicrobial Activity
  作者：Malcolm W. B. McCulloch、Fabrice Berrue、Brad Haltli、Russell G. Kerr

  DOI：10.1021/np2006555

  日期：2011.10.28

  Rapid one-pot methodologies to prepare pseudopteroxazole (1) and novel congeners from abundant natural pseudopterosins have been devised. This is highlighted here with the first synthesis of the marine natural product homopseudopteroxazole (2) utilizing a novel, silver(I)-mediated catechol to benzoxazole transformation. Pseudopteroxazoles and isopseudopteroxazoles exhibit potent activity against a range of important Gram-positive pathogens including Mycobacterium spp. and vancomycin-resistant Enterococcus faecium. Several non-natural pseudopteroxazoles exhibited strong activity against methicillin-resistant Staphylococcus aureus, thereby displaying a broader spectrum of antibiotic activity compared to pseudopteroxazole.