3-甲氧基噻吩-2-硼酸 | 162607-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-甲氧基噻吩-2-硼酸
• 英文名称: 3-methoxy-thiophene-2-boronic acid
• 英文别名: (3-Methoxythiophen-2-yl)boronic acid
• CAS: 162607-22-9
• 化学式: C₅H₇BO₃S
• mdl: MFCD09952077
• 分子量: 157.986
• InChiKey: TYUQSAPZLQSKPS-UHFFFAOYSA-N

物化性质

• 沸点：
  338.2±52.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲氧基噻吩-2-硼酸 、 3-{[(5-bromo-1,2-oxazol-3-yl)methyl]amino}adamantan-1-ol 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以63%的产率得到3-({[5-(3-methoxythiophen-2-yl)-1,2-oxazol-3-yl]methyl}amino)adamantan-1-ol
  参考文献：
  名称：

  Expeditious Lead Optimization of Isoxazole-Containing Influenza A Virus M2-S31N Inhibitors Using the Suzuki–Miyaura Cross-Coupling Reaction

  摘要：

  The existence of multidrug-resistant influenza viruses, coupled with the continuously antigenic shift and antigenic drift of influenza viruses, necessitates the development of the next-generation of influenza antivirals. As the AM2-S31N mutant persists in more than 95% of current circulating influenza A viruses, targeting the AM2-S31N proton channel appears to be a logical and valid approach to combating drug resistance. Starting from compound 1, an isoxazole compound with potent AM2-S31N channel blockage and antiviral activity, in this study we report an expeditious synthetic strategy that allows us to promptly explore the structure activity relationships of isoxazole-containing AM2-S31N inhibitors. Propelled by the convenient synthesis, the lead optimization effort yielded a number of potent antivirals with submicromolar efficacy against several human clinical isolates of influenza A viruses, including both oseltamivir-sensitive and -resistant strains.

  DOI：

  10.1021/acs.jmedchem.6b01852

文献信息

• 一种吲哚类衍生物及其在糖尿病中的应用
  申请人：北京圣永制药有限公司

  公开号：CN108503632B

  公开（公告）日：2020-07-28

  本发明公开了一种如式Ⅰ所示的吲哚类衍生物或其药学上可接受的盐其中，R1、R2、R3各自独立的选自H或OCH3。体外DPP‑4酶抑制试验中所列化合物对DPP‑4的IC50值均小于omarigliptin和Sitagliptin。表明本发明化合物具有较好的DPP‑4抑制活性，可以作为治疗和/或预防非胰岛素依赖性糖尿病、高血糖或胰岛素抗性的药物进行更加深层次的研究。
• 一种DPP-4抑制剂及其制备和在糖尿病中的 应用
  申请人：中昱医学检验（广州）有限公司

  公开号：CN108707143B

  公开（公告）日：2020-06-26

  本发明公开了一种如式Ⅰ所示的化合物或其药学上可接受的盐其中，R1、R2、R3各自独立的选自H或OCH3。体外DPP‑4酶抑制试验中所列化合物对DPP‑4的IC50值均小于omarigliptin和Sitagliptin。表明本发明化合物具有较好的DPP‑4抑制活性，可以作为治疗和/或预防非胰岛素依赖性糖尿病、高血糖或胰岛素抗性的药物进行更加深层次的研究。
• Expeditious Lead Optimization of Isoxazole-Containing Influenza A Virus M2-S31N Inhibitors Using the Suzuki–Miyaura Cross-Coupling Reaction
  作者：Fang Li、Yanmei Hu、Yuanxiang Wang、Chunlong Ma、Jun Wang

  DOI：10.1021/acs.jmedchem.6b01852

  日期：2017.2.23

  The existence of multidrug-resistant influenza viruses, coupled with the continuously antigenic shift and antigenic drift of influenza viruses, necessitates the development of the next-generation of influenza antivirals. As the AM2-S31N mutant persists in more than 95% of current circulating influenza A viruses, targeting the AM2-S31N proton channel appears to be a logical and valid approach to combating drug resistance. Starting from compound 1, an isoxazole compound with potent AM2-S31N channel blockage and antiviral activity, in this study we report an expeditious synthetic strategy that allows us to promptly explore the structure activity relationships of isoxazole-containing AM2-S31N inhibitors. Propelled by the convenient synthesis, the lead optimization effort yielded a number of potent antivirals with submicromolar efficacy against several human clinical isolates of influenza A viruses, including both oseltamivir-sensitive and -resistant strains.