orthidine F | 1042101-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: orthidine F
• 英文别名: 1,14-Sperminedihomovanillamide；2-(4-hydroxy-3-methoxyphenyl)-N-[3-[4-[3-[[2-(4-hydroxy-3-methoxyphenyl)acetyl]amino]propylamino]butylamino]propyl]acetamide
• CAS: 1042101-33-6
• 化学式: C₂₈H₄₂N₄O₆
• 分子量: 530.665
• InChiKey: XKQYVDZNXRMQNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  38
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  141
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  精胺 、 高香草酸 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以39%的产率得到orthidine F
  参考文献：
  名称：

  Orthidines A–E, tubastrine, 3,4-dimethoxyphenethyl-β-guanidine, and 1,14-sperminedihomovanillamide: potential anti-inflammatory alkaloids isolated from the New Zealand ascidian Aplidium orthium that act as inhibitors of neutrophil respiratory burst

  摘要：

  In addition to the known dihydroxystyrylguanidine alkaloid tubastrine (1), five new dinners, orthidines A-E (2-6) and the biosynthetically unrelated 1,14-sperminedihomovanillamide (orthidine F, 7) were isolated from the New Zealand ascidian Aplidium orthium. The structures of the new compounds, elucidated by interpretation of spectroscopic data, encompass benzodioxane neolignan-type scaffolds (2-5) and a 1,2,3,4-tetrasubstituted cyclobutane (6), the latter likely having arisen via [(pi)2(s)+(pi)2(s)] dimerization of tubastrine. The subunit head-to-tail orientation of dimer 6 was established unambiguously by interpretation of data from a (2)J,(3)J-HMBC NMR experiment. The structure of 7 was also confirmed by facile synthesis. Compounds 1-4, 6, and 7 inhibited the in vitro production of superoxide by PMA-stimulated human neutrophils in a dose-dependent manner with IC(50)s of 10-36 mu M and this was associated with inhibition of superoxide production by neutrophils in vivo in a murine model of gouty inflammation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.012

文献信息

• Orthidines A–E, tubastrine, 3,4-dimethoxyphenethyl-β-guanidine, and 1,14-sperminedihomovanillamide: potential anti-inflammatory alkaloids isolated from the New Zealand ascidian Aplidium orthium that act as inhibitors of neutrophil respiratory burst
  作者：A. Norrie Pearce、Elizabeth W. Chia、Michael V. Berridge、Elizabeth W. Maas、Michael J. Page、Jacquie L. Harper、Victoria L. Webb、Brent R. Copp

  DOI：10.1016/j.tet.2008.04.012

  日期：2008.6

  In addition to the known dihydroxystyrylguanidine alkaloid tubastrine (1), five new dinners, orthidines A-E (2-6) and the biosynthetically unrelated 1,14-sperminedihomovanillamide (orthidine F, 7) were isolated from the New Zealand ascidian Aplidium orthium. The structures of the new compounds, elucidated by interpretation of spectroscopic data, encompass benzodioxane neolignan-type scaffolds (2-5) and a 1,2,3,4-tetrasubstituted cyclobutane (6), the latter likely having arisen via [(pi)2(s)+(pi)2(s)] dimerization of tubastrine. The subunit head-to-tail orientation of dimer 6 was established unambiguously by interpretation of data from a (2)J,(3)J-HMBC NMR experiment. The structure of 7 was also confirmed by facile synthesis. Compounds 1-4, 6, and 7 inhibited the in vitro production of superoxide by PMA-stimulated human neutrophils in a dose-dependent manner with IC(50)s of 10-36 mu M and this was associated with inhibition of superoxide production by neutrophils in vivo in a murine model of gouty inflammation. (C) 2008 Elsevier Ltd. All rights reserved.