phyllostictine A | 1007346-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phyllostictine A
• 英文别名: 4-ethyl-11,15-dihydroxy-12-methoxy-5-methyl-13-oxa-4-aza-tricyclo[10.2.1.0^2,5]-pentadec-1-en-3-one；(1E,5R,11S,12S,15S)-4-ethyl-11,15-dihydroxy-12-methoxy-5-methyl-13-oxa-4-azatricyclo[10.2.1.02,5]pentadec-1-en-3-one
• CAS: 1007346-21-5
• 化学式: C₁₇H₂₇NO₅
• 分子量: 325.405
• InChiKey: SJSPSHPVPXPTPG-WCYNIRFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phyllostictine A 、 甲氧基-三氟甲基苯 在 吡啶 作用下， 反应 1.0h， 以0.7 mg的产率得到
  参考文献：
  名称：

  Phyllostictines A–D, oxazatricycloalkenones produced by Phyllosticta cirsii, a potential mycoherbicide for Cirsium arvense biocontrol

  摘要：

  Phyllosticta cirsii, a fungal pathogen isolated from Cirsium arvense and proposed as biocontrol agent of this noxious perennial weed, produces in liquid cultures different phytotoxic metabolites with potential herbicidal activity. Four new oxazatricycloalkenones, named phyllostictines A-D, were isolated and characterized using essentially spectroscopic and chemical methods. Tested by leaf-puncture assay on the fungal host plant phyllostictine A proved to be highly toxic. The phytotoxicity decreases when both the dimension and the conformational freedom of the macrocyclic ring change, as in phyllostictines B and D, and it is totally lost when also the functionalization of the same ring is modified, as in phyllostictine C. Beside its phytotoxic properties, phyllostictine A has no antifungal activity, an interesting antibiotic activity only against Gram+ bacteria, and a noticeable zootoxic activity when tested at high concentrations. The integrity of the oxazatricycloalkenone system appears to be an important feature to preserve these activities. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.12.010