2-iodo-6-methoxyphenylacetate thiosemicarbazone | 358734-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-iodo-6-methoxyphenylacetate thiosemicarbazone
• 英文别名: 4-(carbamothioylhydrazinylidene)methyl-6-methoxy-2-iodophenyl acetate；[4-[(Carbamothioylhydrazinylidene)methyl]-2-iodo-6-methoxyphenyl] acetate
• CAS: 358734-84-6
• 化学式: C₁₁H₁₂IN₃O₃S
• 分子量: 393.205
• InChiKey: NMZYIODNPNUAOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-iodo-6-methoxyphenylacetate thiosemicarbazone 在 吡啶 、 iron(III) chloride 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Design and synthesis of conformationally restricted capsaicin analogues based in the 1, 3, 4-thiadiazole heterocycle reveal a novel family of transient receptor potential vanilloid 1 (TRPV1) antagonists

  摘要：

  4-hydroxy-3-methoxybenzaldehyde was used as starting material to obtain a number of I, 3, 4-thiadiazole alkylamide derivatives. The pharmacological properties of these conformationally restricted capsaicin analogues were evaluated on HEK-293T cells transiently expressing TRPV1 receptor. By means of a highthroughput calcium imaging assay we find that 1, 3, 4-thiadiazoles (compounds 8-15) act as potent antagonists of the capsaicin receptor, inhibiting both, the capsaicin- and temperature-dependent activation. Docking studies suggested a different binding orientation on the vanilloid binding site when compared with capsaicin analogues, such as 5-iodononivamide. Overall, our studies suggest that 1, 3, 4-thiadiazoles interact with capsaicin's binding region of the receptor, although using a different set of interactions within the vanilloid binding pocket. (C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.05.001
• 作为产物：
  描述：

  5-碘香兰素 在 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 生成 2-iodo-6-methoxyphenylacetate thiosemicarbazone
  参考文献：
  名称：

  EP2924028

  摘要：

  公开号：