ethyl 5-phenyl-2-ureidothiophene-3-carboxylate | 106666-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ethyl 5-phenyl-2-ureidothiophene-3-carboxylate
• 英文别名: Ethyl 2-(carbamoylamino)-5-phenylthiophene-3-carboxylate
• CAS: 106666-40-4
• 化学式: C₁₄H₁₄N₂O₃S
• 分子量: 290.343
• InChiKey: ADNROFCMRHNNQE-UHFFFAOYSA-N

物化性质

• 沸点：
  464.2±45.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 5-phenyl-2-ureidothiophene-3-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以95%的产率得到6-phenylthieno<2,3-d>pyrimidine-2,4-dione
  参考文献：
  名称：

  2,4-Diaminothienopyrimidines as Orally Active Antimalarial Agents

  摘要：

  A novel series of 2,4-diaminothienopyrimidines with potential as antimalarials was identified from whole-cell high-throughput screening of a SoftFocus ion channel library. Synthesis and structure activity relationship studies identified compounds with potent antiplasmodial activity and low in vitro cytotoxicity. Several of these analogues exhibited in vivo activity in the Plasmodium berghei mouse model when administered orally. However, inhibition of the hERG potassium channel was identified as a liability for this series.

  DOI：

  10.1021/jm401760c
• 作为产物：
  描述：

  ethyl 5-phenyl-2-(3-(2,2,2-trichloroacetyl)ureido)thiophene-3-carboxylate 在 甲醇 、 氨 作用下， 反应 0.5h， 以98%的产率得到ethyl 5-phenyl-2-ureidothiophene-3-carboxylate
  参考文献：
  名称：

  2,4-Diaminothienopyrimidines as Orally Active Antimalarial Agents

  摘要：

  A novel series of 2,4-diaminothienopyrimidines with potential as antimalarials was identified from whole-cell high-throughput screening of a SoftFocus ion channel library. Synthesis and structure activity relationship studies identified compounds with potent antiplasmodial activity and low in vitro cytotoxicity. Several of these analogues exhibited in vivo activity in the Plasmodium berghei mouse model when administered orally. However, inhibition of the hERG potassium channel was identified as a liability for this series.

  DOI：

  10.1021/jm401760c

文献信息

• Synthesis and evaluation of thiophene based small molecules as potent inhibitors of Mycobacterium tuberculosis
  作者：Chhuttan L. Meena、Padam Singh、Ravi P. Shaliwal、Varun Kumar、Arun Kumar、Anoop Kumar Tiwari、Shailendra Asthana、Ramandeep Singh、Dinesh Mahajan

  DOI：10.1016/j.ejmech.2020.112772

  日期：2020.12

  Herein, we report the synthesis and anti-tubercular studies of novel molecules based on thiophene scaffold. We identified two novel small molecules 4a and 4b, which demonstrated 2-fold higher in vitro activity (MIC99: 0.195 μM) compared to first line TB drug, isoniazid (0.39 μM). The identified leads demonstrated additive effect with front line TB drugs (isoniazid, rifampicin and levofloxacin) and

  在这里，我们报告基于噻吩支架的新型分子的合成和抗结核研究。我们确定了两个新的小分子图4a和4b中，这表明高2倍的体外（MIC活动99：0.195  μ相比第一线TB药物，异烟肼（0.39 M）  μ M）。鉴定出的线索证明与一线结核病药物（异烟肼，利福平和左氧氟沙星）具有加合作用，与最近获得FDA批准的药物bedaquiline具有协同作用。机理研究（i）否定了Pks13的作用，并且（ii）建议KatG参与这些已鉴定导线的抗结核活性。