(2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(4-nitrophenyl)methanone | 247206-90-2

• 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-nitrophenyl)methanone
• 英文别名: (2-Amino-4,5,6,7-tetrahydrobenzo[b]thien-3-yl)(4-nitrophenyl)methanone；(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)-(4-nitrophenyl)methanone
• CAS: 247206-90-2
• 化学式: C₁₅H₁₄N₂O₃S
• 分子量: 302.354
• InChiKey: YYNZJDLJGYZNKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(4-nitrophenyl)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)(4-nitrophenyl)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：

  4-硝基苯甲酰乙腈 、 环己酮 在 sulfur 、 二乙胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以15%的产率得到(2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(4-nitrophenyl)methanone
  参考文献：
  名称：

  Allosteric Modulation of the Adenosine A₁ Receptor. Synthesis and Biological Evaluation of Novel 2-Amino-3-benzoylthiophenes as Allosteric Enhancers of Agonist Binding

  摘要：

  Novel allosteric enhancers of agonist binding to the rat adenosine Al receptor are described. The lead compound for the new series was PD 81,723 ((2-amino-4,5-dimethyl-3-thienyl)[3(trifluoromethyl)phenyl]methanone), a compound previously reported by Bruns and co-workers (Mol. Pharmacol. 1990, 38, 950-958). The 4,5-dimethyl group and the benzoyl moiety were targets for further modifications, leading to series of 4,5-dialkyl (12a-g), of tetrahydrobenzo (12h-u), and of tetrahydropyridine (13a-g) derivatives. A number of compounds, in particular 12b, 12e, 12j, 12n, and 12u, proved superior to PD 81,723, Their EC50 values for enhancing the binding of the adenosine Al receptor agonist N-6-cyclopentyladenosine to the receptor were lower, and/or their antagonistic activity on the adenosine Al receptor was shown to be diminished.

  DOI：

  10.1021/jm991051d

文献信息

• SPHINGOSINE-1-PHOSPHATE (S1P) RECEPTOR COMPOUNDS
  申请人：Brussee Johannes

  公开号：US20100317709A1

  公开（公告）日：2010-12-16

  The invention relates to compounds, in particular 2-amino-3,4,5,-trisubstituted thiophenes, pharmaceutical compositions containing them and the uses of said compounds and compositions for diseases related to sphingosine-1-phosphate (S1P) receptors, predominantly S1P3 receptors. The diseases include cardiovascular diseases, atherosclerosis, cancer, pulmonary oedema, autoimmune disorders and Adult Respiratory Distress Syndrome.
• Allosteric Modulation of the Adenosine A₁ Receptor. Synthesis and Biological Evaluation of Novel 2-Amino-3-benzoylthiophenes as Allosteric Enhancers of Agonist Binding
  作者：Pieter A. M. van der Klein、Angeliki P. Kourounakis、Ad P. IJzerman

  DOI：10.1021/jm991051d

  日期：1999.9.1

  Novel allosteric enhancers of agonist binding to the rat adenosine Al receptor are described. The lead compound for the new series was PD 81,723 ((2-amino-4,5-dimethyl-3-thienyl)[3(trifluoromethyl)phenyl]methanone), a compound previously reported by Bruns and co-workers (Mol. Pharmacol. 1990, 38, 950-958). The 4,5-dimethyl group and the benzoyl moiety were targets for further modifications, leading to series of 4,5-dialkyl (12a-g), of tetrahydrobenzo (12h-u), and of tetrahydropyridine (13a-g) derivatives. A number of compounds, in particular 12b, 12e, 12j, 12n, and 12u, proved superior to PD 81,723, Their EC50 values for enhancing the binding of the adenosine Al receptor agonist N-6-cyclopentyladenosine to the receptor were lower, and/or their antagonistic activity on the adenosine Al receptor was shown to be diminished.
• 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。