1-碘-5-异丙基-2,4-二甲氧基苯 | 1155371-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-碘-5-异丙基-2,4-二甲氧基苯
• 英文名称: 1-iodo-5-isopropyl-2,4-dimethoxybenzene
• 英文别名: 1-iodo-2,4-dimethoxy-5-propan-2-ylbenzene
• CAS: 1155371-47-3
• 化学式: C₁₁H₁₅IO₂
• 分子量: 306.143
• InChiKey: QBTLWHYKYLZHKG-UHFFFAOYSA-N

物化性质

• 沸点：
  335.3±42.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1-碘-5-异丙基-2,4-二甲氧基苯 在 吗啉 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 67.0h， 生成 methyl 2-(5-iodo-4-(5-isopropyl-2,4-dimethoxyphenyl)-1H-1,2,3-triazol-1-yl)acetate
  参考文献：
  名称：

  Discovery of 2-((4-resorcinolyl)-5-aryl-1,2,3-triazol-1-yl)acetates as potent Hsp90 inhibitors with selectivity over TRAP1

  摘要：

  As the most abundant heat shock protein (HSP), Hsp90 is actively involved in tumor cell growth and various responses to anti-carcinogenic stress. Hsp90 has thus emerged as a potential drug target. A structure-based drug design approach was applied to develop novel resorcinolyltriazole derivatives as Hsp90 inhibitors. Structure-activity relationships (SARs) and molecular docking were investigated to provide a rationale for binding affinity and paralog selectivity. Click chemistry between iodoethynylresorcinol and an azido derivative was used to synthesize a new family of 2-((4-resorcinolyl)-5-aryl-1,2,3-triazol-1-yl) acetates that exhibited Hsp90 binding affinities of 40-100 nM (IC50). Among the synthesized molecules, the triazole alkyl acetates displayed the highest Hsp90 binding affinities. Their potency against Hsp90 was over 100-fold stronger than against TRAP1 and 1-3-fold stronger than against Grp94. In particular, compounds 18, 19, and 30 had Hsp90 inhibitory activities of similar to 45 nM (IC50) and they displayed over 350-fold selectivity for Hsp90 over TRAP1.

  DOI：

  10.1016/j.bmcl.2019.126809
• 作为产物：
  描述：

  2,4-二甲氧基苯乙酮 在 正丁基锂 、 palladium 10% on activated carbon 、 氢气 、 tetra-N-butylammonium tribromide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 氯仿 为溶剂， 反应 37.25h， 生成 1-碘-5-异丙基-2,4-二甲氧基苯
  参考文献：
  名称：

  Discovery of 2-((4-resorcinolyl)-5-aryl-1,2,3-triazol-1-yl)acetates as potent Hsp90 inhibitors with selectivity over TRAP1

  摘要：

  As the most abundant heat shock protein (HSP), Hsp90 is actively involved in tumor cell growth and various responses to anti-carcinogenic stress. Hsp90 has thus emerged as a potential drug target. A structure-based drug design approach was applied to develop novel resorcinolyltriazole derivatives as Hsp90 inhibitors. Structure-activity relationships (SARs) and molecular docking were investigated to provide a rationale for binding affinity and paralog selectivity. Click chemistry between iodoethynylresorcinol and an azido derivative was used to synthesize a new family of 2-((4-resorcinolyl)-5-aryl-1,2,3-triazol-1-yl) acetates that exhibited Hsp90 binding affinities of 40-100 nM (IC50). Among the synthesized molecules, the triazole alkyl acetates displayed the highest Hsp90 binding affinities. Their potency against Hsp90 was over 100-fold stronger than against TRAP1 and 1-3-fold stronger than against Grp94. In particular, compounds 18, 19, and 30 had Hsp90 inhibitory activities of similar to 45 nM (IC50) and they displayed over 350-fold selectivity for Hsp90 over TRAP1.

  DOI：

  10.1016/j.bmcl.2019.126809

文献信息

• [EN] 4-SUBSTITUTED-6-ISOPROPYL-BENZENE-1,3-DIOL COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS 6-ISOPROPYL-BENZÈNE-1,3-DIOLS SUBSTITUÉS EN POSITION 4 ET LEUR UTILISATION
  申请人：TOPOTARGET AS

  公开号：WO2009066060A3

  公开（公告）日：2009-12-23