(2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(3,4,5-trimethoxyphenyl)methanone | 864378-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(3,4,5-trimethoxyphenyl)methanone
• 英文别名: (2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-(3,4,5-trimethoxy-phenyl)-methanone；(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)-(3,4,5-trimethoxyphenyl)methanone
• CAS: 864378-38-1
• 化学式: C₁₈H₂₁NO₄S
• 分子量: 347.435
• InChiKey: UFCXZXHZPWSXTE-UHFFFAOYSA-N

物化性质

• 沸点：
  585.0±50.0 °C(predicted)
• 密度：
  1.249±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(3,4,5-trimethoxyphenyl)methanone 在 对甲苯磺酸 、 sodium nitrite 、 potassium iodide 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 生成 (2-iodo-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  设计和微波辅助合成新型2-苯基/ 2-苯基乙炔基-3-芳酰基噻吩作为有效的抗增殖剂† ‡

  摘要：

  在本研究中，已设计并通过微波辅助方法合成了2-苯基/ 2-苯基乙炔基-3-芳酰基噻吩。评价所有合成的化合物对各种人类癌细胞系的体外抗增殖活性。发现化合物12j和14h是针对所有测试癌细胞系的最有希望的化合物，尤其是针对A-375（分别为IC 50 = 1.07±0.1和0.81±0.1μM）和MIA PaCa-2（IC 50 = 5.35）分别为±0.6和3.00±1.0μM）癌细胞系，与标准紫杉醇相当。此外，最有效的化合物12j和通过钙黄绿素AM和克隆形成测定证实了14h，并且发现其诱导了G 2 / M期的细胞周期停滞，表明细胞暴露于选定的衍生物会产生有丝分裂失败。在计算机模拟中，ADME研究赋予口服药物类似有效化合物的特征。

  DOI：

  10.1039/c6md00256k
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰乙腈 、 环己酮 在 吗啉 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of new anti-tubulin agents containing different benzoheterocycles

  摘要：

  A new series of compounds, in which the 2-amino-4-methoxyphenyl ring of phenstatin analogue 5 was replaced with 2- or 3-amino-benzoheterocycles, was synthesized and evaluated for antiproliferative activity and inhibition of colchicine binding. The lack of activity of 3 ',4 '-dimethoxy- and 4 '-methoxy-benzoyl derivatives (8 and 9, respectively) indicates that the 3 ',4 ',5 '-trimethoxybenzoyl moiety is critical for the activity. Two compounds, 7 and 11, displayed potent antiproliferative activity, with IC50 values ranging from 25 to 100 nM against a variety of cancer cell lines. Derivative 11 was more active than CA-4 as an inhibitor of tubulin polymerization. The results demonstrated that the antiproliferative activity was correlated with inhibition of tubulin polymerization. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.022

文献信息

• Synthesis and preliminary biological evaluation of new anti-tubulin agents containing different benzoheterocycles
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、M. Katherine Jung、Maria Antonietta Iaconinoto、Maria Dora Carrion、Vincent Remusat、Delia Preti、Mojgan Aghazadeh Tabrizi、Fruttarolo Francesca、Erik De Clercq、Jan Balzarini、Ernest Hamel

  DOI：10.1016/j.bmcl.2005.06.022

  日期：2005.9

  A new series of compounds, in which the 2-amino-4-methoxyphenyl ring of phenstatin analogue 5 was replaced with 2- or 3-amino-benzoheterocycles, was synthesized and evaluated for antiproliferative activity and inhibition of colchicine binding. The lack of activity of 3 ',4 '-dimethoxy- and 4 '-methoxy-benzoyl derivatives (8 and 9, respectively) indicates that the 3 ',4 ',5 '-trimethoxybenzoyl moiety is critical for the activity. Two compounds, 7 and 11, displayed potent antiproliferative activity, with IC50 values ranging from 25 to 100 nM against a variety of cancer cell lines. Derivative 11 was more active than CA-4 as an inhibitor of tubulin polymerization. The results demonstrated that the antiproliferative activity was correlated with inhibition of tubulin polymerization. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of 2- and 3-Aminobenzo[<i>b</i>]thiophene Derivatives as Antimitotic Agents and Inhibitors of Tubulin Polymerization
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Carlota Lopez Cara、Delia Preti、Francesca Fruttarolo、Maria Giovanna Pavani、Mojgan Aghazadeh Tabrizi、Manlio Tolomeo、Stefania Grimaudo、Antonella Di Cristina、Jan Balzarini、John A. Hadfield、Andrea Brancale、Ernest Hamel

  DOI：10.1021/jm070050f

  日期：2007.5.1

  Two new series of inhibitors of tubulin polymerization based on the 2-amino-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene molecular skeleton and its 3-amino positional isomer were synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. Although many more 3-amino derivatives have been synthesized so far, the most promising compound in this series was 2-amino-6-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene, which inhibits cancer cell growth at subnanomolar concentrations and interacts strongly with tubulin by binding to the colchicine site.
• Design and microwave assisted synthesis of novel 2-phenyl/2-phenylethynyl-3-aroyl thiophenes as potent antiproliferative agents
  作者：Rupinder Kaur Gill、Ramandeep Kaur、Virender Kumar、Vivek Gupta、Gagandeep Singh、Jitender Bariwal

  DOI：10.1039/c6md00256k

  日期：——

  study, 2-phenyl/2-phenylethynyl-3-aroyl thiophenes have been designed and synthesized via microwave assisted methods. All the synthesized compounds were evaluated for in vitro antiproliferative activity against various human cancer cell lines. Compounds 12j and 14h were found to be the most promising compounds against all the tested cancer cell lines, particularly against A-375 (IC50 = 1.07 ± 0.1 and

  在本研究中，已设计并通过微波辅助方法合成了2-苯基/ 2-苯基乙炔基-3-芳酰基噻吩。评价所有合成的化合物对各种人类癌细胞系的体外抗增殖活性。发现化合物12j和14h是针对所有测试癌细胞系的最有希望的化合物，尤其是针对A-375（分别为IC 50 = 1.07±0.1和0.81±0.1μM）和MIA PaCa-2（IC 50 = 5.35）分别为±0.6和3.00±1.0μM）癌细胞系，与标准紫杉醇相当。此外，最有效的化合物12j和通过钙黄绿素AM和克隆形成测定证实了14h，并且发现其诱导了G 2 / M期的细胞周期停滞，表明细胞暴露于选定的衍生物会产生有丝分裂失败。在计算机模拟中，ADME研究赋予口服药物类似有效化合物的特征。