3-(2-甲氧基苯基)-2-噻吩甲醛 | 666841-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(2-甲氧基苯基)-2-噻吩甲醛
• 英文名称: 3-(2-methoxyphenyl)thiophene-2-carboxaldehyde
• 英文别名: 3-(2-methoxyphenyl)-2-thiophenecarbaldehyde；2-formyl-3-(2-methoxyphenyl)thiophene；3-(2-Methoxyphenyl)thiophene-2-carbaldehyde
• CAS: 666841-73-2
• 化学式: C₁₂H₁₀O₂S
• 分子量: 218.276
• InChiKey: RNQZIEOWPOWZKT-UHFFFAOYSA-N

物化性质

• 沸点：
  315.4±32.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-甲氧基苯基)-2-噻吩甲醛 在 氯化亚砜 、 sodium azide 、 jones reagent 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 21.0h， 生成 3-(2-Methoxy-phenyl)-thiophene-2-carbonyl azide
  参考文献：
  名称：

  Towards new neuroprotective agents: design and synthesis of 4H-thieno[2,3-c] isoquinolin-5-one derivatives as potent PARP-1 inhibitors

  摘要：

  An excessive activation of poly(ADP-ribose) polymerase-1 (PARP-1), a nuclear enzyme able to catalyze the transfer of ADP-ribose from NAD to acceptor proteins, is involved in the progression of neuronal damage after brain insult. Potent and selective PARP-1 inhibitors have neuroprotective properties in experimental models of brain ischemia. As a follow up of our previous structure-activity relationship study and in search for novel potent PARP-1 inhibitors, a series of 4H-thieno[2,3-c]-isoquinolin-5-one derivatives was designed and synthesized. Tested for their ability to inhibit PARP-1, these novel derivatives showed high inhibitory potency. The unsubstituted derivative TIQ was selected for further characterization and found to be endowed with strong neuroprotective properties in models of cerebral ischemia.

  DOI：

  10.1016/s0014-827x(03)00143-5
• 作为产物：
  描述：

  溴苯 、 2-溴苯甲醚 在 四(三苯基膦)钯 碳酸氢钠 作用下， 以 乙二醇二甲醚 为溶剂， 反应 6.0h， 以75%的产率得到3-(2-甲氧基苯基)-2-噻吩甲醛
  参考文献：
  名称：

  Towards new neuroprotective agents: design and synthesis of 4H-thieno[2,3-c] isoquinolin-5-one derivatives as potent PARP-1 inhibitors

  摘要：

  An excessive activation of poly(ADP-ribose) polymerase-1 (PARP-1), a nuclear enzyme able to catalyze the transfer of ADP-ribose from NAD to acceptor proteins, is involved in the progression of neuronal damage after brain insult. Potent and selective PARP-1 inhibitors have neuroprotective properties in experimental models of brain ischemia. As a follow up of our previous structure-activity relationship study and in search for novel potent PARP-1 inhibitors, a series of 4H-thieno[2,3-c]-isoquinolin-5-one derivatives was designed and synthesized. Tested for their ability to inhibit PARP-1, these novel derivatives showed high inhibitory potency. The unsubstituted derivative TIQ was selected for further characterization and found to be endowed with strong neuroprotective properties in models of cerebral ischemia.

  DOI：

  10.1016/s0014-827x(03)00143-5

文献信息

• Palladium/tetraphosphine catalyzed suzuki cross‐coupling of heteroarylboronic acids with aryl halides
  作者：Isabelle Kondolff、Henri Doucet、Maurice Santelli

  DOI：10.1002/jhet.5570450109

  日期：2008.1

  ne/[PdCl(C3H5)]2 efficiently catalyses the Suzuki reaction of heteroarylboronic acids with aryl bromides and also the coupling of arylboronic acids with heteroaryl bromides. The coupling of thiophene- or benzothiopheneboronic acids, furan- or benzofuranboronic acids and 3-pyridineboronic acid with a variety of aryl bromides gave the corresponding coupling products in good yields. However, in most cases

  顺式，顺式，顺式-1,2,3,4-四（二苯基膦甲基）环戊烷/ [PdCl（C 3 H 5）] 2有效催化杂芳基硼酸与芳基溴化物的Suzuki反应，以及芳基硼酸与杂芳基的偶联溴化物。噻吩或苯并噻吩硼酸，呋喃或苯并呋喃硼酸和3-吡啶硼酸与各种芳基溴的偶合得到相应的偶合产物，收率很高。然而，在大多数情况下，使用杂芳基溴化物与芳基硼酸进行的逆反应在底物/催化剂的比例方面获得了更好的结果。
• Design, synthesis, and anticancer activity of novel aryl/heteroaryl chalcone derivatives
  作者：Ananda Mohan Arasavelli、Ganapavarapu Veera Raghava Sharma、Siddaiah Vidavalur

  DOI：10.1515/hc-2015-0271

  日期：2016.2.1

  were synthesized and evaluated for in vitro antiproliferative activity against human colon cancer cell lines. The synthesis of the key intermediate compounds 3a–d was achieved by tetrakis(triphenylphosphine) palladium(II) mediated Suzuki cross coupling reaction. Chalcone 5a shows superior anticancer activity with IC50 value of 21.0 μg/mL compared to the IC50 value of the reference drug doxorubicin at

  摘要 合成了一系列新的查耳酮 5a-l，并评估其对人结肠癌细胞系的体外抗增殖活性。关键中间体化合物 3a-d 的合成是通过四（三苯基膦）钯（II）介导的 Suzuki 交叉偶联反应实现的。与参考药物阿霉素的 IC50 值 21.65 μg/mL 相比，查耳酮 5a 显示出优异的抗癌活性，IC50 值为 21.0 μg/mL。
• THIENYL-AND FURANYL-ISOQUINOLINONES AND METHODS FOR USING THEM
  申请人：Pellicciari Roberto

  公开号：US20090325951A1

  公开（公告）日：2009-12-31

  The present invention relates to substituted thienyl- and furanyl-isoquinolinones that act, for example, as modulators of poly(ADP-ribose) polymerase (PARP). The present invention also relates to processes for the preparation of substituted thienyl and furanyl-isoquinolinones and to their use in treating various diseases and disorders.

  本发明涉及替代噻吩基和呋吩基异喹啉酮，例如作为聚(ADP-核糖)聚合酶(PARP)调节剂。本发明还涉及制备替代噻吩基和呋吩基异喹啉酮的过程，以及它们在治疗各种疾病和疾病方面的用途。