(4-chlorocarbonylmethylphenyl)carbamic acid benzyl ester | 1258011-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-chlorocarbonylmethylphenyl)carbamic acid benzyl ester
• CAS: 1258011-40-3
• 化学式: C₁₆H₁₄ClNO₃
• 分子量: 303.745
• InChiKey: CYCVIYCUTXOBTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4-chlorocarbonylmethylphenyl)carbamic acid benzyl ester 、 (4-methoxy-3-nitrobenzylidene)-(3,4,5-trimethoxyphenyl) amine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 {4-[2-(4-methoxy-3-nitrophenyl)-4-oxo-1-(3,4,5-trimethoxyphenyl)azetidin-3-yl]phenyl}carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Azetidinone Analogues of Combretastatin A-4 as Tubulin Targeting Agents

  摘要：

  The synthesis and antiproliferative activity of a new series of rigid analogues of combretastatin A-4 are described which contain the 1,4-diaryl-2-azetidinone (beta-lactam) ring system in place of the usual ethylene bridge present in the natural combretastatin stilbene products. These novel compounds are also substituted at position 3 of the beta-lactam ring with an aryl ring. A number of analogues showed potent nanomolar activity in human MCF-7 and MDA-MB-231 breast cancer cell lines, displayed in vitro inhibition of tubulin polymerization, and did not cause significant cytotoxicity in normal murine breast epithelial cells. 4-(4-Methoxyaryl)-substituted compound 32, 4-(3-hydroxy-4-methoxyaryl)-substituted compounds 35 and 41, and the 3-(4-aminoaryl)-substituted compounds 46 and 47 displayed the most potent antiproliferative activity of the series. beta-Lactam 41 in particular showed subnanomolar activity in MCF-7 breast cancer cells (IC50 = 0.8 nM) together with significant in vitro inhibition of tubulin polymerization and has been selected for further biochemical assessment. These novel beta-lactam compounds are identified as potentially useful scaffolds for the further development of antitumor agents that target tubulin.

  DOI：

  10.1021/jm101115u
• 作为产物：
  描述：

  (4-苄基氧基羰基氨基苯基)-乙酸 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 生成 (4-chlorocarbonylmethylphenyl)carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis and Evaluation of Azetidinone Analogues of Combretastatin A-4 as Tubulin Targeting Agents

  摘要：

  The synthesis and antiproliferative activity of a new series of rigid analogues of combretastatin A-4 are described which contain the 1,4-diaryl-2-azetidinone (beta-lactam) ring system in place of the usual ethylene bridge present in the natural combretastatin stilbene products. These novel compounds are also substituted at position 3 of the beta-lactam ring with an aryl ring. A number of analogues showed potent nanomolar activity in human MCF-7 and MDA-MB-231 breast cancer cell lines, displayed in vitro inhibition of tubulin polymerization, and did not cause significant cytotoxicity in normal murine breast epithelial cells. 4-(4-Methoxyaryl)-substituted compound 32, 4-(3-hydroxy-4-methoxyaryl)-substituted compounds 35 and 41, and the 3-(4-aminoaryl)-substituted compounds 46 and 47 displayed the most potent antiproliferative activity of the series. beta-Lactam 41 in particular showed subnanomolar activity in MCF-7 breast cancer cells (IC50 = 0.8 nM) together with significant in vitro inhibition of tubulin polymerization and has been selected for further biochemical assessment. These novel beta-lactam compounds are identified as potentially useful scaffolds for the further development of antitumor agents that target tubulin.

  DOI：

  10.1021/jm101115u