5-bromo-nor-6,7-dihyrocapsaicin

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-bromo-nor-6,7-dihyrocapsaicin
• 英文别名: Nonanoic acid 3-bromo-4-hydroxy-5-methoxy-benzylamide；N-[(3-bromo-4-hydroxy-5-methoxyphenyl)methyl]nonanamide
• 化学式: C₁₇H₂₆BrNO₃
• 分子量: 372.302
• InChiKey: XPWLKWZLMZEKPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴香兰素 在 sodium tetrahydroborate 、 二苯基磷酸 、 水 、 四氯化锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 73.5h， 生成 5-bromo-nor-6,7-dihyrocapsaicin
  参考文献：
  名称：

  The Taming of Capsaicin. Reversal of the Vanilloid Activity of N-Acylvanillamines by Aromatic Iodination

  摘要：

  Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5'-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6', (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6'-iodo derivatives bind to TRPV1".

  DOI：

  10.1021/jm050139q

文献信息

• The Taming of Capsaicin. Reversal of the Vanilloid Activity of <i>N</i>-Acylvanillamines by Aromatic Iodination
  作者：Giovanni Appendino、Nives Daddario、Alberto Minassi、Aniello Schiano Moriello、Luciano De Petrocellis、Vincenzo Di Marzo

  DOI：10.1021/jm050139q

  日期：2005.7.1

  Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5'-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6', (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6'-iodo derivatives bind to TRPV1".