3-bromo-2-(3,4,5-trimethoxyphenyl)furan | 1312996-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-bromo-2-(3,4,5-trimethoxyphenyl)furan
• CAS: 1312996-81-8
• 化学式: C₁₃H₁₃BrO₄
• 分子量: 313.148
• InChiKey: UUMXNKCLBDQRIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-羟基-4-甲氧基苯硼酸 、 3-bromo-2-(3,4,5-trimethoxyphenyl)furan 在 四(三苯基膦)钯 、 sodium carbonate decahydrate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以54%的产率得到2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)-3-furyl]phenol
  参考文献：
  名称：

  Regioselective Suzuki Coupling of Dihaloheteroaromatic Compounds as a Rapid Strategy To Synthesize Potent Rigid Combretastatin Analogues

  摘要：

  Combretastatin A-4 (CA-4) is a potent tubulin depolymerizing agent able to inhibit tumor growth and with antivascular effects. Although it is in clinical trials, the search for novel analogues that may display better/different features is still ongoing. In this manuscript we describe the synthesis of novel constrained analogues of CA-4 obtained in only two synthetic steps exploiting a regioselective Suzuki coupling of dihalogenated heteroaromatic and alicyclic compounds. All the compounds synthesized have been evaluated for cytotoxicity and for their ability to inhibit tubulin assembly. One of them, 38, displayed low nanomolar cytotoxicity and proved to have a pharmacodynamic profile similar to that of CA-4 and a better pharmacokinetic profile, but most important of all, this synthetic strategy may pave the way for the easy and rapid generation of novel rigid analogues of combretastatins.

  DOI：

  10.1021/jm200555r
• 作为产物：
  描述：

  2,3-二溴呋喃 、 3,4,5-三甲氧基苯硼酸 在 四(三苯基膦)钯 、 sodium carbonate decahydrate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以66%的产率得到3-bromo-2-(3,4,5-trimethoxyphenyl)furan
  参考文献：
  名称：

  Regioselective Suzuki Coupling of Dihaloheteroaromatic Compounds as a Rapid Strategy To Synthesize Potent Rigid Combretastatin Analogues

  摘要：

  Combretastatin A-4 (CA-4) is a potent tubulin depolymerizing agent able to inhibit tumor growth and with antivascular effects. Although it is in clinical trials, the search for novel analogues that may display better/different features is still ongoing. In this manuscript we describe the synthesis of novel constrained analogues of CA-4 obtained in only two synthetic steps exploiting a regioselective Suzuki coupling of dihalogenated heteroaromatic and alicyclic compounds. All the compounds synthesized have been evaluated for cytotoxicity and for their ability to inhibit tubulin assembly. One of them, 38, displayed low nanomolar cytotoxicity and proved to have a pharmacodynamic profile similar to that of CA-4 and a better pharmacokinetic profile, but most important of all, this synthetic strategy may pave the way for the easy and rapid generation of novel rigid analogues of combretastatins.

  DOI：

  10.1021/jm200555r

文献信息

• Regioselective Suzuki Coupling of Dihaloheteroaromatic Compounds as a Rapid Strategy To Synthesize Potent Rigid Combretastatin Analogues
  作者：Sewan Theeramunkong、Antonio Caldarelli、Alberto Massarotti、Silvio Aprile、Diego Caprioglio、Roberta Zaninetti、Alessia Teruggi、Tracey Pirali、Giorgio Grosa、Gian Cesare Tron、Armando A. Genazzani

  DOI：10.1021/jm200555r

  日期：2011.7.28

  Combretastatin A-4 (CA-4) is a potent tubulin depolymerizing agent able to inhibit tumor growth and with antivascular effects. Although it is in clinical trials, the search for novel analogues that may display better/different features is still ongoing. In this manuscript we describe the synthesis of novel constrained analogues of CA-4 obtained in only two synthetic steps exploiting a regioselective Suzuki coupling of dihalogenated heteroaromatic and alicyclic compounds. All the compounds synthesized have been evaluated for cytotoxicity and for their ability to inhibit tubulin assembly. One of them, 38, displayed low nanomolar cytotoxicity and proved to have a pharmacodynamic profile similar to that of CA-4 and a better pharmacokinetic profile, but most important of all, this synthetic strategy may pave the way for the easy and rapid generation of novel rigid analogues of combretastatins.