1-甲基-4-氧代-1,4-二氢-3-吡啶甲酰氯 | 60219-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 1-甲基-4-氧代-1,4-二氢-3-吡啶甲酰氯
• 英文名称: 1-Methyl-4-oxo-1,4-dihydropyridine-3-carbonyl chloride
• 英文别名: 1-methyl-4-oxopyridine-3-carbonyl chloride
• CAS: 60219-04-7
• 化学式: C₇H₆ClNO₂
• 分子量: 171.583
• InChiKey: BMBZUDOQGVJXEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-甲基-4-氧代-1,4-二氢-3-吡啶甲酰氯 、 3-氨基-5-硝基苯并异噻唑 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80 mg的产率得到1-methyl-N-(5-nitrobenzo[d]isothiazol-3-yl)-4-oxo-1,4-dihydropyridine-3-carboxamide
  参考文献：
  名称：

  A Parallel Synthesis Approach to the Identification of Novel Diheteroarylamide-Based Compounds Blocking HIV Replication: Potential Inhibitors of HIV-1 Pre-mRNA Alternative Splicing

  摘要：

  A 256-compound library was evaluated in an anti-HIV screen to identify structural "mimics" of the fused tetracyclic indole compound 1 (IDC16) that conserve its anti-HIV activity without associated cytotoxicity. Four diheteroarylamide-type compounds, containing a common 5-nitroisobenzothiazole motif, were identified as active. In subsequent screens, the most potent compound 9 (1C8) was active against wild-type HIV-1(IIIB) (subtype B, X4-tropic) and HIV-1 97USSN54 (subtype A, R5-tropic) with EC50's of 0.6 and 0.9 mu M, respectively. Compound 9 also inhibited HIV strains resistant to drugs targeting HIV reverse transcriptase, protease, integrase, and coreceptor CCRS with EC50's ranging from 0.9 to 1.5 mu M. The CC50 value obtained in a cytotoxicity assay for compound 9 was >100 mu M, corresponding to a therapeutic index (CC50/EC50) of approximately 100. Further comparison studies revealed that, whereas the anti-HIV activity for compound 9 and the parent molecule 1 are similar, the cytotoxic effect for compound 9 was, as planned, markedly suppressed.

  DOI：

  10.1021/acs.jmedchem.5b01357
• 作为产物：
  描述：

  4-氯吡啶 在 氯化亚砜 、 水 、 potassium hydrogencarbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-甲基-4-氧代-1,4-二氢-3-吡啶甲酰氯
  参考文献：
  名称：

  A Parallel Synthesis Approach to the Identification of Novel Diheteroarylamide-Based Compounds Blocking HIV Replication: Potential Inhibitors of HIV-1 Pre-mRNA Alternative Splicing

  摘要：

  A 256-compound library was evaluated in an anti-HIV screen to identify structural "mimics" of the fused tetracyclic indole compound 1 (IDC16) that conserve its anti-HIV activity without associated cytotoxicity. Four diheteroarylamide-type compounds, containing a common 5-nitroisobenzothiazole motif, were identified as active. In subsequent screens, the most potent compound 9 (1C8) was active against wild-type HIV-1(IIIB) (subtype B, X4-tropic) and HIV-1 97USSN54 (subtype A, R5-tropic) with EC50's of 0.6 and 0.9 mu M, respectively. Compound 9 also inhibited HIV strains resistant to drugs targeting HIV reverse transcriptase, protease, integrase, and coreceptor CCRS with EC50's ranging from 0.9 to 1.5 mu M. The CC50 value obtained in a cytotoxicity assay for compound 9 was >100 mu M, corresponding to a therapeutic index (CC50/EC50) of approximately 100. Further comparison studies revealed that, whereas the anti-HIV activity for compound 9 and the parent molecule 1 are similar, the cytotoxic effect for compound 9 was, as planned, markedly suppressed.

  DOI：

  10.1021/acs.jmedchem.5b01357

文献信息

• A Parallel Synthesis Approach to the Identification of Novel Diheteroarylamide-Based Compounds Blocking HIV Replication: Potential Inhibitors of HIV-1 Pre-mRNA Alternative Splicing
  作者：Peter K. Cheung、David Horhant、Laura E. Bandy、Maryam Zamiri、Safwat M. Rabea、Stoyan K. Karagiosov、Mitra Matloobi、Steven McArthur、P. Richard Harrigan、Benoit Chabot、David S. Grierson

  DOI：10.1021/acs.jmedchem.5b01357

  日期：2016.3.10

  A 256-compound library was evaluated in an anti-HIV screen to identify structural "mimics" of the fused tetracyclic indole compound 1 (IDC16) that conserve its anti-HIV activity without associated cytotoxicity. Four diheteroarylamide-type compounds, containing a common 5-nitroisobenzothiazole motif, were identified as active. In subsequent screens, the most potent compound 9 (1C8) was active against wild-type HIV-1(IIIB) (subtype B, X4-tropic) and HIV-1 97USSN54 (subtype A, R5-tropic) with EC50's of 0.6 and 0.9 mu M, respectively. Compound 9 also inhibited HIV strains resistant to drugs targeting HIV reverse transcriptase, protease, integrase, and coreceptor CCRS with EC50's ranging from 0.9 to 1.5 mu M. The CC50 value obtained in a cytotoxicity assay for compound 9 was >100 mu M, corresponding to a therapeutic index (CC50/EC50) of approximately 100. Further comparison studies revealed that, whereas the anti-HIV activity for compound 9 and the parent molecule 1 are similar, the cytotoxic effect for compound 9 was, as planned, markedly suppressed.