葡聚糖凝胶 | 859171-97-4

• 物质功能分类: 生物化工 - 糖类化合物 - 多糖
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 葡聚糖凝胶
• 英文名称: 6'-Iodononivamide
• 英文别名: 6-iodo-nor-6,7-dihydrocapsaicin；6-iodonordihydrocapsaicin；N-[(4-hydroxy-2-iodo-5-methoxyphenyl)methyl]nonanamide
• CAS: 859171-97-4
• 化学式: C₁₇H₂₆INO₃
• 分子量: 419.303
• InChiKey: AAORACFZMYMFCG-UHFFFAOYSA-N

物化性质

• 熔点：
  106-107 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  552.9±50.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)
• 溶解度：
  不溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  3822009000
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  葡聚糖凝胶 、 alpha-溴-4-甲氧基苯乙酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以33%的产率得到6-iodo-3-methoxy-4-(4'-methoxyacetophenone-2-oxy)-N-nonanoylbenzylamine
  参考文献：
  名称：

  Synthesis, photolysis studies and in vitro photorelease of caged TRPV1 agonists and antagonists

  摘要：

  报告了一系列笼型 TRPV1 激动剂和拮抗剂的合成。我们研究了这些化合物在 355 纳米激光照射下的光解特性，在所有情况下都产生了所需的化合物。笼型 TRPV1 激动剂在培养的三叉神经元中光解产生的反应与激活 TRPV1 受体一致。

  DOI：

  10.1039/b914981c
• 作为产物：
  描述：

  香草壬酰胺 在 碘 、 silver trifluoroacetate 、 四氯化锡 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 为溶剂， 反应 72.0h， 生成 葡聚糖凝胶
  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".
• Synthesis, photolysis studies and in vitro photorelease of caged TRPV1 agonists and antagonists
  作者：Michael P. Van Ryssen、Nicolaos Avlonitis、Rashid Giniatullin、Craig McDougall、James L. Carr、Megan N. Stanton-Humphreys、Emma L. A. Borgström、C. Tom A. Brown、Dmitriy Fayuk、Alexander Surin、Minna Niittykoski、Leonard Khiroug、Stuart J. Conway

  DOI：10.1039/b914981c

  日期：——

  The synthesis of a range of caged TRPV1 agonists and antagonists is reported. The photolysis characteristics of these compounds, when irradiated with a 355 nm laser, have been studied and in all cases the desired compound was produced. Photolysis of a caged TRPV1 agonist in cultured trigeminal neurons produced responses that were consistent with the activation of TRPV1 receptors.

  报告了一系列笼型 TRPV1 激动剂和拮抗剂的合成。我们研究了这些化合物在 355 纳米激光照射下的光解特性，在所有情况下都产生了所需的化合物。笼型 TRPV1 激动剂在培养的三叉神经元中光解产生的反应与激活 TRPV1 受体一致。