2-Propenoic acid,3-[4-[[[2-[(4-aminophenyl)amino]-2-oxoethyl]propylamino]sulfonyl]phenyl]-, methyl ester | 916336-22-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-Propenoic acid,3-[4-[[[2-[(4-aminophenyl)amino]-2-oxoethyl]propylamino]sulfonyl]phenyl]-, methyl ester
• 英文别名: (E)-3-(4-{[(4-Amino-phenylcarbamoyl)-methyl]-propyl-sulfamoyl}-phenyl)-acrylic acid methyl ester
• CAS: 916336-22-6
• 化学式: C₂₁H₂₅N₃O₅S
• 分子量: 431.513
• InChiKey: SPDCBNHGAAWYPV-UHFFFAOYSA-N

物化性质

• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  118.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-氯-8-硝基喹唑啉-4-醇 、 2-Propenoic acid,3-[4-[[[2-[(4-aminophenyl)amino]-2-oxoethyl]propylamino]sulfonyl]phenyl]-, methyl ester 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-3-[4-({[4-(4-Hydroxy-8-nitro-quinazolin-5-ylamino)-phenylcarbamoyl]-methyl}-propyl-sulfamoyl)-phenyl]-acrylic acid methyl ester
  参考文献：
  名称：

  4′-Alkoxyl substitution enhancing the anti-mitotic effect of 5-(3′,4′,5′-substituted)anilino-4-hydroxy-8-nitroquinazolines as a novel class of anti-microtubule agents

  摘要：

  Mitosis inhibitors are powerful anticancer drugs. Based on a novel anti-microtubule agent of 5-(4'-methoxy)anilino-4-hydroxy-8-nitroquinazoline, a series of 5-(3',4',5'-substituted)anilino-4-hydroxy-8- nitroquinazolines were designed and synthesized to investigate the effect of the substitution on the inhibitory activity against mitotic progression of tumor cells. The large alkoxyl substitution on the 4'-position of 5-anilino ring is beneficial for the potency. The 5-(3',4,5'-trimethoxy)anilino-8-nitroquinazoline (1h) displays an overwhelming activity in arresting the cells at the G2/M phase, providing a promising new template for further development of potent microtubule-targeted anti-mitotic drugs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.058
• 作为产物：
  描述：

  2-氯-4’-硝基乙酰苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 铁粉 、 氯化铵 、 N,N-二异丙基乙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-Propenoic acid,3-[4-[[[2-[(4-aminophenyl)amino]-2-oxoethyl]propylamino]sulfonyl]phenyl]-, methyl ester
  参考文献：
  名称：

  4′-Alkoxyl substitution enhancing the anti-mitotic effect of 5-(3′,4′,5′-substituted)anilino-4-hydroxy-8-nitroquinazolines as a novel class of anti-microtubule agents

  摘要：

  Mitosis inhibitors are powerful anticancer drugs. Based on a novel anti-microtubule agent of 5-(4'-methoxy)anilino-4-hydroxy-8-nitroquinazoline, a series of 5-(3',4',5'-substituted)anilino-4-hydroxy-8- nitroquinazolines were designed and synthesized to investigate the effect of the substitution on the inhibitory activity against mitotic progression of tumor cells. The large alkoxyl substitution on the 4'-position of 5-anilino ring is beneficial for the potency. The 5-(3',4,5'-trimethoxy)anilino-8-nitroquinazoline (1h) displays an overwhelming activity in arresting the cells at the G2/M phase, providing a promising new template for further development of potent microtubule-targeted anti-mitotic drugs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.058