| 1470111-51-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• CAS: 1470111-51-3
• 化学式: C₃₅H₃₅NO₁₀
• 分子量: 629.664
• InChiKey: DYOJQPRVRJBNMR-GERZCMAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  46.0
• 可旋转键数：
  7.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  143.66
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-hydroxy-2-methoxyphenyl)carbamate 、 在 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 (4-amino-3-methoxyphenyl) [(1R,2R,6R,10S,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-prop-1-en-2-yl-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl carbonate
  参考文献：
  名称：

  The carbonate analogues of 5′-halogenated resiniferatoxin as TRPV1 ligands

  摘要：

  A series of carbonate analogues of 5'-halogenated RTX have been investigated in order to examine the effect of the carbonate group as a linker and the role of halogens in the reversal of activity from agonism to antagonism for rat and human TRPV1 heterologously expressed in Chinese hamster ovary cells. The carbonate analogues showed similar activities to the corresponding RTX derivatives in rat TRPV1 but lower potency in human TRPV1. 5-Halogenation converted the agonists to partial agonists or full antagonists and the extent of antagonism reflected the order of I > Br > Cl > F, with a somewhat greater extent of antagonism for the derivatives of the 4-amino RTX surrogates compared to the corresponding derivatives of RTX itself. The carbonate analogues of I-RTX: (60) and 5-bromo-4-amino-RTX (66) were potent and full antagonists with K-i(ant) = 2.23 and 2.46 nM, respectively, for rat TRPV1, which were ca. 5-fold more potent than I-RTX (2) under our conditions. The conformational analysis of the I-RTX-carbonate (60) indicated that its bent conformation was similar to that of I-RTX, consistent with compound 60 and I-RTX showing comparable potent antagonism. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.042
• 作为产物：
  描述：

  对硝基苯基氯甲酸酯 、 6,7-去环氧-6,7-二去氢-5-脱氧-21-去苯基-21-(苯基甲基)瑞香毒素 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  The carbonate analogues of 5′-halogenated resiniferatoxin as TRPV1 ligands

  摘要：

  A series of carbonate analogues of 5'-halogenated RTX have been investigated in order to examine the effect of the carbonate group as a linker and the role of halogens in the reversal of activity from agonism to antagonism for rat and human TRPV1 heterologously expressed in Chinese hamster ovary cells. The carbonate analogues showed similar activities to the corresponding RTX derivatives in rat TRPV1 but lower potency in human TRPV1. 5-Halogenation converted the agonists to partial agonists or full antagonists and the extent of antagonism reflected the order of I > Br > Cl > F, with a somewhat greater extent of antagonism for the derivatives of the 4-amino RTX surrogates compared to the corresponding derivatives of RTX itself. The carbonate analogues of I-RTX: (60) and 5-bromo-4-amino-RTX (66) were potent and full antagonists with K-i(ant) = 2.23 and 2.46 nM, respectively, for rat TRPV1, which were ca. 5-fold more potent than I-RTX (2) under our conditions. The conformational analysis of the I-RTX-carbonate (60) indicated that its bent conformation was similar to that of I-RTX, consistent with compound 60 and I-RTX showing comparable potent antagonism. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.042