3-Amino-4-(4-ethoxy-phenyl)-thiophene-2-carboxylic acid methyl ester | 723294-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-Amino-4-(4-ethoxy-phenyl)-thiophene-2-carboxylic acid methyl ester
• 英文别名: Methyl 3-amino-4-(4-ethoxyphenyl)thiophene-2-carboxylate
• CAS: 723294-99-3
• 化学式: C₁₄H₁₅NO₃S
• 分子量: 277.344
• InChiKey: LSNNGVGTTKEKLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Amino-4-(4-ethoxy-phenyl)-thiophene-2-carboxylic acid methyl ester 在 4-氯吡啶盐酸盐 作用下， 以 1,4-二氧六环 为溶剂， 生成 [4-(4-Ethoxy-phenyl)-3-pyrrol-1-yl-thiophen-2-yl]-pyrrolidin-1-yl-methanone
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents

  摘要：

  Structure-activity relationship studies of a new series of tripentones (thieno[2.3-h]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2.3-b]pyrrolizin-8-one 20 (leukemia L1210. IC50= 15 nM) was shown to be a potent inhibitor of tubulin polymerization. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00403-6
• 作为产物：
  描述：

  4-乙氧基苯甲醛 在 sodium tetrahydroborate 、 氯化亚砜 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 3-Amino-4-(4-ethoxy-phenyl)-thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents

  摘要：

  Structure-activity relationship studies of a new series of tripentones (thieno[2.3-h]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2.3-b]pyrrolizin-8-one 20 (leukemia L1210. IC50= 15 nM) was shown to be a potent inhibitor of tubulin polymerization. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00403-6

文献信息

• Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents
  作者：Vincent Lisowski、Cécile Enguehard、Jean-Charles Lancelot、Daniel-Henri Caignard、Stéphanie Lambel、Stéphane Leonce、Alain Pierre、Ghanem Atassi、Pierre Renard、Sylvain Rault

  DOI：10.1016/s0960-894x(01)00403-6

  日期：2001.8

  Structure-activity relationship studies of a new series of tripentones (thieno[2.3-h]pyrrolizin-8-ones), led us to prepare several derivatives with antiproliferative activities. The most promising 3-(3-hydroxy-4-methoxyphenyl)thieno[2.3-b]pyrrolizin-8-one 20 (leukemia L1210. IC50= 15 nM) was shown to be a potent inhibitor of tubulin polymerization. (C) 2001 Elsevier Science Ltd. All rights reserved.