4-nitrothiophene-2-carboxamide | 36050-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4-nitrothiophene-2-carboxamide
• CAS: 36050-08-5
• 化学式: C₅H₄N₂O₃S
• 分子量: 172.164
• InChiKey: WIMGYMPUMRABOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-nitrothiophene-2-carboxamide 在 三氯化磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以92%的产率得到2-硝基噻吩-4-腈
  参考文献：
  名称：

  2-(2-Thienyl)-5,6-dihydroxy-4-carboxypyrimidines as Inhibitors of the Hepatitis C Virus NS5B Polymerase:  Discovery, SAR, Modeling, and Mutagenesis

  摘要：

  Infections caused by hepatitis C virus (HCV) are a significant world health problem for which novel therapies are in urgent demand. The polymerase of HCV is responsible for the replication of viral RNA. We recently disclosed dihydroxypyrimidine carboxylates 2 as novel, reversible inhibitors of the HCV NS5B polymerase. This series was further developed into 5,6-dihydroxy-2-(2-thienyl)pyrimidine-4-carboxylic acids such as 34 (EC50 9.3 mu M), which now show activity in the cell-based HCV replication assay. The structure-activity relationship of these inhibitors is discussed in the context of their physicochemical properties and of the polymerase crystal structure. We also report the results of mutagenesis experiments which support the proposed binding model, which involves pyrophosphate-like chelation of the active site Mg ions.

  DOI：

  10.1021/jm051064t
• 作为产物：
  描述：

  2-噻吩甲酰胺 在 potassium nitrate 作用下， 以 硫酸 为溶剂， 反应 0.5h， 以74%的产率得到4-nitrothiophene-2-carboxamide
  参考文献：
  名称：

  Erba, Carlo Dell'; Sancassan, Fernando; Novi, Marino, Journal of the Chemical Society. Perkin transactions II, 1989, p. 1779 - 1782

  摘要：

  DOI：

文献信息

• Synthesis of thiophenecarboxamides, thieno[3,4- c ]pyridin-4(5 H )-ones and thieno[3,4- d ]pyrimidin-4(3 H )-ones and preliminary evaluation as inhibitors of poly(ADP-ribose)polymerase (PARP)
  作者：Anne E. Shinkwin、William J.D. Whish、Michael D. Threadgill

  DOI：10.1016/s0968-0896(98)00210-7

  日期：1999.2

  Treatment of 3-cyanothiophene with potassium nitrate and concentrated sulphuric acid gave 5-nitrothiophene-3-carboxamide. 4-Nitrothiophene-2-carboxamide and 5-nitrothiophene-2-carboxamide were formed similarly from 2-cyanothiophene. Reduction with tin(II) chloride gave the corresponding aminothiophenecarboxamide salts which were isolated via their N-Cbz derivatives. Lithiation of 3,4-dibromothiophene at

  聚（ADP-核糖）聚合酶（PARP）抑制剂可抑制受损DNA的修复，从而增强癌症的放射治疗和化学疗法。用硝酸钾和浓硫酸处理3-氰基噻吩，得到5-硝基噻吩-3-甲酰胺。由2-氰基噻吩类似地形成4-硝基噻吩-2-甲酰胺和5-硝基噻吩-2-甲酰胺。用氯化锡（II）还原得到相应的氨基噻吩甲酰胺盐，其通过其N-Cbz衍生物分离。3，4-二溴噻吩在-116℃下锂化并用烷基氯甲酸酯淬灭，得到4-溴噻吩-3-羧酸酯，将其水解为4-溴噻吩-3-羧酸。于特利与戊烷-2,4-二酮和1-苯基丁烷-1,3-二酮的烯醇化物发生Hurtley反应，然后进行酰基裂解，分别产生4-（2-氧丙基）噻吩-3-羧酸和4-苯甲酰基噻吩-3-羧酸。与氨在乙酸中缩合得到6-甲基-和6-苯基硫代[3,4-c]吡啶-4-酮，它们在1-和7-位被选择性硝化或被硝化。将4-乙酰氨基-和4-苯甲酰胺基噻吩-3-羧酸乙酯分别环化成2-甲基-和2-苯基-噻吩并[3
• Labelled compounds of interest as antitumour agents - VI 1. Isotopically efficient syntheses of [15N]-nitrothiophenecarboxamides
  作者：Anne E. Shinkwin、Michael D. Threadgill

  DOI：10.1002/(sici)1099-1344(199611)38:11<1015::aid-jlcr917>3.0.co;2-6

  日期：1996.11
• Arnone, Caterina; Consiglio, Giovanni; Spinelli, Domenico, Journal of the Chemical Society. Perkin transactions II, 1989, p. 1609 - 1612
  作者：Arnone, Caterina、Consiglio, Giovanni、Spinelli, Domenico、Dell'Erba, Carlo、Sancassan, Fernando、Terrier, Francois

  DOI：——

  日期：——
• Dell'Erba, Carlo; Sancassan, Fernando; Novi, Marino, Journal of the Chemical Society. Perkin transactions II, 1991, # 10, p. 1631 - 1636
  作者：Dell'Erba, Carlo、Sancassan, Fernando、Novi, Marino、Spinelli, Domenico、Consiglio, Giovanni

  DOI：——

  日期：——