ethyl 1-phenyl-3-methylpyrazolo<3,4-b>pyridin-6(7H)-one-5-carboxylate | 81933-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-phenyl-3-methylpyrazolo<3,4-b>pyridin-6(7H)-one-5-carboxylate
• 英文别名: ethyl 3-methyl-6-oxo-1-phenyl-6,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate；pyrazolo[3,4-b]pyridine-5-carboxylate；ethyl 3-methyl-6-oxo-1-phenyl-7H-pyrazolo[3,4-b]pyridine-5-carboxylate
• CAS: 81933-79-1
• 化学式: C₁₆H₁₅N₃O₃
• 分子量: 297.313
• InChiKey: VTEXTWQCSDWGKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 1-phenyl-3-methylpyrazolo<3,4-b>pyridin-6(7H)-one-5-carboxylate 在 lithium aluminium tetrahydride 、 三溴化磷 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 2-((6-methoxy-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methyl)-7-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Discovery of Pyrazolopyridones as a Novel Class of Noncovalent DprE1 Inhibitor with Potent Anti-Mycobacterial Activity

  摘要：

  A novel pyrazolopyridone class of inhibitors was identified from whole cell screening against Mycobacterium tuberculosis (Mtb). The series exhibits excellent bactericidality in vitro, resulting in a 4 log reduction in colony forming units following compound exposure. The significant modulation of minimum inhibitory concentration (MIC) against a Mtb strain overexpressing the Rv3790 gene suggested the target of pyrazolopyridones to be decaprenylphosphoryl-beta-D-ribose-2'-epimerase (DprE1). Genetic mapping of resistance mutation coupled with potent enzyme inhibition activity confirmed the molecular target. Detailed biochemical characterization revealed the series to be a noncovalent inhibitor of DprE1. Docking studies at the active site suggest that the series can be further diversified to improve the physicochemical properties without compromising the antimycobacterial activity. The pyrazolopyridone class of inhibitors offers an attractive non-nitro lead series targeting the essential and vulnerable DprE1 enzyme for the discovery of novel antimycobacterial agents to treat both drug susceptible and drug resistant strains of Mtb.

  DOI：

  10.1021/jm5002937
• 作为产物：
  描述：

  5-叠氮基-3-甲基-1-苯基吡唑-4-甲醛 在 sodium dithionite 作用下， 以 甲醇 为溶剂， 反应 9.5h， 生成 ethyl 1-phenyl-3-methylpyrazolo<3,4-b>pyridin-6(7H)-one-5-carboxylate
  参考文献：
  名称：

  吡唑并[3,4-b]吡啶的简便合成

  摘要：

  摘要 3-(烷基/芳基)-5-氨基-1-苯基-1H-吡唑-4-甲醛缩合得到了吡唑并[3,4-b]吡啶(4)和(5) (3)与活性亚甲基化合物，即：丙二酸二乙酯和丙二腈。

  DOI：

  10.1080/00397919608003494

文献信息

• Synthesis of New Heterocycles from Reactions of 1‐Phenyl‐1 <i>H</i> ‐pyrazolo[3,4‐ <i>b</i> ]pyridine‐5‐carbonyl Azides
  作者：Ashraf A. Aly、Talaat I. El‐Emary、Aboul‐Fetouh E. Mourad、Zainab Khallaf Alyan、Stefan Bräse、Martin Nieger

  DOI：10.1002/jhet.3511

  日期：2019.4

  Two individual examples of pyrazolo[3,4‐b]pyridine‐5‐carbonyl azides and hydrazides were reacted with various nucleophilic reagents. Different unexpected behaviors was observed. NMR, IR, mass spectra together with elemental analyses and X‐ray structure analyses, were used to prove the structure of the obtained products.

  吡唑并[3,4- b ]吡啶-5-羰基叠氮化物和酰肼的两个单独实例与各种亲核试剂反应。观察到了不同的意外行为。NMR，IR，质谱以及元素分析和X射线结构分析被用来证明所得产物的结构。
• Simay, A.; Takacs, K.; Toth, L., Acta Chimica Academiae Scientiarum Hungaricae, 1982, vol. 109, # 2, p. 175 - 188
  作者：Simay, A.、Takacs, K.、Toth, L.

  DOI：——

  日期：——
• SIMAY, A.;TAKACS, K.;TOTH, L., ACTA CHIM. ACAD. SCI. HUNG., 1982, 109, N 2, 175-187
  作者：SIMAY, A.、TAKACS, K.、TOTH, L.

  DOI：——

  日期：——