(2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-methoxyphenyl)methanone | 40312-30-9

• 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)-(4-methoxyphenyl)methanone
• 英文别名: (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(4-methoxyphenyl)methanone；(2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanone；(2-Amino-4,5,6,7-tetrahydro-1-benzothien-3-yl)(4-methoxyphenyl)methanone；(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)-(4-methoxyphenyl)methanone
• CAS: 40312-30-9
• 化学式: C₁₆H₁₇NO₂S
• mdl: MFCD00427061
• 分子量: 287.382
• InChiKey: IQHWZRXYZAPXKD-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  529.5±50.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.312
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-methoxyphenyl)methanone 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 (2-Amino-benzo[b]thiophen-3-yl)-(4-methoxy-phenyl)-methanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2- and 3-Aminobenzo[b]thiophene Derivatives as Antimitotic Agents and Inhibitors of Tubulin Polymerization

  摘要：

  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.

  DOI：

  10.1021/jm070050f
• 作为产物：
  描述：

  环己酮 、 4-甲氧基苯甲酰基乙腈 在 吗啉 、 sulfur 作用下， 以 乙醇 为溶剂， 以85%的产率得到(2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-methoxyphenyl)methanone
  参考文献：
  名称：

  WO2006/63732

  摘要：

  公开号：

文献信息

• Synthesis and antimicrobial evaluation of 3-(4-arylthieno[2,3-<i>d</i>]pyrimidin-2-yl)- 2<i>H</i>-chromen-2-ones
  作者：Sergiy V. Vlasov、Sergiy M. Kovalenko、Pavlo E. Shynkarenko、Konstantin Yu. Krolenko、Vitaliy S. Vlasov

  DOI：10.1515/hc-2018-0013

  日期：2018.8.28

  Abstract Syntheses of 3-(4-arylthieno[2,3-d]pyrimidin-2-yl)-2H-chromen-2-ones 5 by the reaction of 2-iminocoumarin-3-carboxamides 1 with (2-aminothiophen-3-yl)(aryl)methanones 2 and by the alternative Suzuki coupling of 4-chlorothieno[2,3-d]pyrimidin-2-yl-2H-chromen-2-one 7 with arylboronic acids were developed. Compound 5d showed higher antimicrobial activity against Staphylococcus aureus than the

  摘要 2-亚氨基香豆素-3-甲酰胺1与(2-氨基噻吩-3)反应合成3-(4-芳基噻吩并[2,3-d]嘧啶-2-基)-2H-色烯-2-酮5 -yl)(aryl)methanones 2 和 4-chlorothieno[2,3-d]pyrimidin-2-yl-2H-chromen-2-one 7 与芳基硼酸的交替 Suzuki 偶联被开发出来。化合物 5d 对金黄色葡萄球菌的抗菌活性高于参考药物链霉素。
• 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。
• Thieno-pyridine derivatives as allosteric enhancers of the GABAB receptors
  申请人：Malherbe Parichehr

  公开号：US20060135552A1

  公开（公告）日：2006-06-22

  The present invention relates to compounds of formula I wherein R 1 , R 2 , R 3 , R 4 , and R 5 are as defined in the specification. Compounds of the invention are active on the GABAB receptor and are useful for treating a variety of CNS disorders, including anxiety, depression, epilepsy, schizophrenia, cognitive disorders, spasticity-and skeletal muscle rigidity, spinal cord injury, multiple sclerosis, amyotrophic lateral sclerosis, cerebral palsy, neuropathic pain and craving associated with cocaine and nicotine, psychosis, panic disorder, posttraumatic stress disorders and gastrointestinal disorders.

  本发明涉及式I化合物，其中R1、R2、R3、R4和R5如规范中所定义。本发明的化合物在GABAB受体上具有活性，并可用于治疗多种中枢神经系统疾病，包括焦虑、抑郁、癫痫、精神分裂症、认知障碍、痉挛和骨骼肌强直、脊髓损伤、多发性硬化症、肌萎缩性侧索硬化、脑瘫、神经病性疼痛和与可卡因和尼古丁有关的渴望、精神病、惊恐障碍、创伤后应激障碍和胃肠疾病。
• 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.
• CORRAL C.; MADRONERO R.; ULECIA N., AFINIDAD, 1978, 35, NO 354, 129-133,
  作者：CORRAL C.、 MADRONERO R.、 ULECIA N.

  DOI：——

  日期：——