Methyl 6-methoxy-3-(3,4,5-trimethoxyanilino)-1-benzothiophene-2-carboxylate | 1427420-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Methyl 6-methoxy-3-(3,4,5-trimethoxyanilino)-1-benzothiophene-2-carboxylate
• 英文别名: methyl 6-methoxy-3-(3,4,5-trimethoxyanilino)-1-benzothiophene-2-carboxylate
• CAS: 1427420-65-2
• 化学式: C₂₀H₂₁NO₆S
• 分子量: 403.456
• InChiKey: NLNGAPHYPPKMFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-氨基-6-甲氧基-1-苯并[b]噻吩-2-羧酸甲酯 在 亚硝酸特丁酯 、 cesium bicarbonate 、 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 copper(ll) bromide 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 20.0h， 生成 Methyl 6-methoxy-3-(3,4,5-trimethoxyanilino)-1-benzothiophene-2-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-(Alkoxycarbonyl)-3-Anilinobenzo[b]thiophenes and Thieno[2,3-b]pyridines as New Potent Anticancer Agents

  摘要：

  Two new series of inhibitors of tubulin polymerization based on the 2-(alkoxycarbonyl)-3-(3',4',5'-trimethoxyanilino)benzo[b]thiophene and thieno[2,3-b]pyridine molecular skeletons were synthesized and evaluated for antiproliferative activity on a panel of cancer cell lines, inhibition of tubulin polymerization, cell cycle effects, and in vivo potency. Antiproliferative activity was strongly dependent on the position of the methyl group on the benzene portion of the benzo[b]thiophene nucleus, with the greatest activity observed when the methyl was located at the C-6 position. Also, in the smaller thieno[2,3-b]pyridine series, the introduction of the methyl group at the C-6 position resulted in improvement of antiproliferative activity to the nanomolar level. The most active compounds (4i and 4n) did not induce cell death in normal human lymphocytes, suggesting that the compounds may be selective against cancer cells. Compound 4i significantly inhibited in vivo the growth of a syngeneic hepatocellular carcinoma in Balb/c mice.

  DOI：

  10.1021/jm400043d

文献信息

• Synthesis and Biological Evaluation of 2-(Alkoxycarbonyl)-3-Anilinobenzo[<i>b</i>]thiophenes and Thieno[2,3-<i>b</i>]pyridines as New Potent Anticancer Agents
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Kimatrai Salvador、Delia Preti、Mojgan Aghazadeh Tabrizi、Marcella Bassetto、Andrea Brancale、Ernest Hamel、Ignazio Castagliuolo、Roberta Bortolozzi、Giuseppe Basso、Giampietro Viola

  DOI：10.1021/jm400043d

  日期：2013.3.28

  Two new series of inhibitors of tubulin polymerization based on the 2-(alkoxycarbonyl)-3-(3',4',5'-trimethoxyanilino)benzo[b]thiophene and thieno[2,3-b]pyridine molecular skeletons were synthesized and evaluated for antiproliferative activity on a panel of cancer cell lines, inhibition of tubulin polymerization, cell cycle effects, and in vivo potency. Antiproliferative activity was strongly dependent on the position of the methyl group on the benzene portion of the benzo[b]thiophene nucleus, with the greatest activity observed when the methyl was located at the C-6 position. Also, in the smaller thieno[2,3-b]pyridine series, the introduction of the methyl group at the C-6 position resulted in improvement of antiproliferative activity to the nanomolar level. The most active compounds (4i and 4n) did not induce cell death in normal human lymphocytes, suggesting that the compounds may be selective against cancer cells. Compound 4i significantly inhibited in vivo the growth of a syngeneic hepatocellular carcinoma in Balb/c mice.