(5-aminobenzo[b]thiophen-2-yl)(3,4,5-trimethoxyphenyl)methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5-aminobenzo[b]thiophen-2-yl)(3,4,5-trimethoxyphenyl)methanone
• 英文别名: (5-Amino-1-benzothiophen-2-yl)-(3,4,5-trimethoxyphenyl)methanone；(5-amino-1-benzothiophen-2-yl)-(3,4,5-trimethoxyphenyl)methanone
• 化学式: C₁₈H₁₇NO₄S
• 分子量: 343.403
• InChiKey: VLKRUYISSBQNBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  99
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5-aminobenzo[b]thiophen-2-yl)(3,4,5-trimethoxyphenyl)methanone 在 吡啶 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 2-iodo-N-[2-(3,4,5-trimethoxybenzoyl)-1-benzo[b]thien-5-yl]acetamide
  参考文献：
  名称：

  Concise Synthesis and Biological Evaluation of 2-Aroyl-5-Amino Benzo[b]thiophene Derivatives As a Novel Class of Potent Antimitotic Agents

  摘要：

  The biological importance of microtubules make them an interesting target for the synthesis of antitumor agents. The 2(3',4',5'-trimethoxybenzoyl)-5-aminobenzo[b]thiophene moiety was identified as a novel scaffold for the preparation of potent inhibitors of microtubule polymerization acting through the colchicine site of tubulin. The position of the methoxy group on the benzo[b]thiophene was important for maximal antiproliferative activity. Structure-activity relationship analysis established that the best activities were obtained with amino and methoxy groups placed at the C-5 and C-7 positions, respectively. Compounds 3c-e showed more potent inhibition of tubulin polymerization than combretastatin A-4 and strong binding to the colchicine site. These compounds also demonstrated substantial antiproliferative activity, with IC50 values ranging from 2.6 to 18 nM in a variety of cancer cell lines. Importantly, compound 3c (50 mg/kg), significantly inhibited the growth of the human osteosarcoma MNNG/HOS xenograft in nude mice.

  DOI：

  10.1021/jm4013938
• 作为产物：
  描述：

  2-mercapto-5-nitrobenzaldehyde 在 tin(II) chloride dihdyrate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 19.0h， 生成 (5-aminobenzo[b]thiophen-2-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Concise Synthesis and Biological Evaluation of 2-Aroyl-5-Amino Benzo[b]thiophene Derivatives As a Novel Class of Potent Antimitotic Agents

  摘要：

  The biological importance of microtubules make them an interesting target for the synthesis of antitumor agents. The 2(3',4',5'-trimethoxybenzoyl)-5-aminobenzo[b]thiophene moiety was identified as a novel scaffold for the preparation of potent inhibitors of microtubule polymerization acting through the colchicine site of tubulin. The position of the methoxy group on the benzo[b]thiophene was important for maximal antiproliferative activity. Structure-activity relationship analysis established that the best activities were obtained with amino and methoxy groups placed at the C-5 and C-7 positions, respectively. Compounds 3c-e showed more potent inhibition of tubulin polymerization than combretastatin A-4 and strong binding to the colchicine site. These compounds also demonstrated substantial antiproliferative activity, with IC50 values ranging from 2.6 to 18 nM in a variety of cancer cell lines. Importantly, compound 3c (50 mg/kg), significantly inhibited the growth of the human osteosarcoma MNNG/HOS xenograft in nude mice.

  DOI：

  10.1021/jm4013938