5-[N-(tert-butoxycarbonyl)amino]-N-(4-chloro-β-phenethyl)salicylamide | 327037-19-4

• 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: 5-[N-(tert-butoxycarbonyl)amino]-N-(4-chloro-β-phenethyl)salicylamide
• 英文别名: tert-butyl N-[3-[2-(4-chlorophenyl)ethylcarbamoyl]-4-hydroxyphenyl]carbamate
• CAS: 327037-19-4
• 化学式: C₂₀H₂₃ClN₂O₄
• 分子量: 390.867
• InChiKey: IYCXSYWQNBUHFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[N-(tert-butoxycarbonyl)amino]-N-(4-chloro-β-phenethyl)salicylamide 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 28.5h， 生成 N-[2-(4-Chloro-phenyl)-ethyl]-5-(2,5-dihydroxy-benzylamino)-2-hydroxy-benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of a Series of Lavendustin A Analogues That Inhibit EGFR and Syk Tyrosine Kinases, as Well as Tubulin Polymerization

  摘要：

  A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibition of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several compounds in the series were effective inhibitors of both kinases, it seemed questionable whether their inhibitory effects on these kinases were responsible for the cytotoxic properties observed in a variety of human cancer cell cultures. Accordingly, a COMPARE analysis of the cytotoxicity profile of the most cytotoxic member of the series was performed, and the results indicated that its cytotoxicity profile was similar to that of antitubulin agents. This mechanism of action was supported by demonstrating that most compounds in the series were moderately effective as inhibitors of tubulin polymerization. This suggests that the lavendustin A analogues reported here, as well as some of the previously reported lavendustin A analogues, may be acting as cytotoxic agents by a mechanism involving the inhibition of tubulin polymerization.

  DOI：

  10.1021/jm000387g
• 作为产物：
  描述：

  5-氨基水杨酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 5-[N-(tert-butoxycarbonyl)amino]-N-(4-chloro-β-phenethyl)salicylamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of a Series of Lavendustin A Analogues That Inhibit EGFR and Syk Tyrosine Kinases, as Well as Tubulin Polymerization

  摘要：

  A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibition of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several compounds in the series were effective inhibitors of both kinases, it seemed questionable whether their inhibitory effects on these kinases were responsible for the cytotoxic properties observed in a variety of human cancer cell cultures. Accordingly, a COMPARE analysis of the cytotoxicity profile of the most cytotoxic member of the series was performed, and the results indicated that its cytotoxicity profile was similar to that of antitubulin agents. This mechanism of action was supported by demonstrating that most compounds in the series were moderately effective as inhibitors of tubulin polymerization. This suggests that the lavendustin A analogues reported here, as well as some of the previously reported lavendustin A analogues, may be acting as cytotoxic agents by a mechanism involving the inhibition of tubulin polymerization.

  DOI：

  10.1021/jm000387g

文献信息

• Design, Synthesis, and Biological Evaluation of a Series of Lavendustin A Analogues That Inhibit EGFR and Syk Tyrosine Kinases, as Well as Tubulin Polymerization
  作者：Fanrong Mu、Stephanie L. Coffing、David J. Riese、Robert L. Geahlen、Pascal Verdier-Pinard、Ernest Hamel、Jill Johnson、Mark Cushman

  DOI：10.1021/jm000387g

  日期：2001.2.1

  A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibition of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several compounds in the series were effective inhibitors of both kinases, it seemed questionable whether their inhibitory effects on these kinases were responsible for the cytotoxic properties observed in a variety of human cancer cell cultures. Accordingly, a COMPARE analysis of the cytotoxicity profile of the most cytotoxic member of the series was performed, and the results indicated that its cytotoxicity profile was similar to that of antitubulin agents. This mechanism of action was supported by demonstrating that most compounds in the series were moderately effective as inhibitors of tubulin polymerization. This suggests that the lavendustin A analogues reported here, as well as some of the previously reported lavendustin A analogues, may be acting as cytotoxic agents by a mechanism involving the inhibition of tubulin polymerization.