homovanilic acid N-hydroxysuccinimide ester | 72072-13-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: homovanilic acid N-hydroxysuccinimide ester
• 英文别名: Homovanillinsaeure-N-hydroxysuccinimidester；N-succinimidyl 4-hydroxy-3-methoxyphenylacetate；(2,5-Dioxopyrrolidin-1-yl) 2-(4-hydroxy-3-methoxyphenyl)acetate
• CAS: 72072-13-0
• 化学式: C₁₃H₁₃NO₆
• 分子量: 279.249
• InChiKey: ILPNXIYWZUDNNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  homovanilic acid N-hydroxysuccinimide ester 、 9,13,14-orthophenylacetylresiniferonylamine 以 二氯甲烷 为溶剂， 反应 18.0h， 以27%的产率得到N-(9,13,14-orthophenylacetylresiniferonyl)-4-hydroxy-3-methoxyphenylacetamide
  参考文献：
  名称：

  Similarities and Differences in the Structure−Activity Relationships of Capsaicin and Resiniferatoxin Analogues

  摘要：

  Structure-activity relationships in analogues of the irritant natural product capsaicin have previously been rationalized by subdivision of the molecule into three structural regions (A, B, and C). The hypothesis that resiniferatoxin (RTX), which is a high-potency ligand for the same receptor and which has superficial structural similarities with capsaicin, could be analogously subdivided has been investigated. The effects of making parallel changes in the two structural series have been studied in a cellular functional assay which is predictive of analgesic activity. Parallel structural changes in the two series lead to markedly different consequences on biological activity; the 3- and 4-position aryl substituents (corresponding to the capsaicin 'A-region') which are strictly required for activity in capsaicin analogues are not important in RTX analogues. The homovanillyl C-20 ester group in RTX (corresponding to the capsaicin 'B-region') is more potent than the corresponding amide, in contrast to the capsaicin analogues. Structural variations to the diterpene moiety suggest that the functionalized 5-membered diterpene ring of RTX is an important structural determinant for high potency. Modeling studies indicate that the 3D position of the alpha-hydroxy ketone moiety in the 5-membered ring is markedly different in the phorbol (inactive) analogues and RTX (active) series. This difference appears to be due to the influence of the strained ortho ester group in RTX, which acts as a local conformational constraint. The reduced activity of an analogue substituted in this region and the inactivity of a simplified analogue in which this unit is entirely removed support this conclusion.

  DOI：

  10.1021/jm960139d

文献信息

• Phenolsäureamide hydroxysubstituierter Benzylamine
  申请人：HAARMANN & REIMER GMBH

  公开号：EP0900781B1

  公开（公告）日：2002-03-20
• US6117365A
  申请人：——

  公开号：US6117365A

  公开（公告）日：2000-09-12