ethyl 2-(1,3-dioxolanyl)-5-nitro-4-pyridinepyruvate | 119694-71-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: ethyl 2-(1,3-dioxolanyl)-5-nitro-4-pyridinepyruvate
• 英文别名: ethyl 2-(1,3-dioxolan)-5-nitro-4-pyridinylpyruvate；4-Pyridinepropanoic acid,2-(1,3-dioxolan-2-yl)-5-nitro-a-oxo-,ethyl ester；ethyl 3-[2-(1,3-dioxolan-2-yl)-5-nitropyridin-4-yl]-2-oxopropanoate
• CAS: 119694-71-2
• 化学式: C₁₃H₁₄N₂O₇
• 分子量: 310.263
• InChiKey: OJZFKHWTCIANAD-UHFFFAOYSA-N

物化性质

• 熔点：
  86-87 °C(Solv: ethanol (64-17-5))
• 沸点：
  488.2±45.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-(1,3-dioxolanyl)-5-nitro-4-pyridinepyruvate 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 7.0h， 生成 2-(ethoxycarbonyl)-1H-pyrrolo<2,3-c>pyridine-5-carboxaldehyde thiosemicarbazone
  参考文献：
  名称：

  Hybrid molecules: growth inhibition of Leishmania donovani promastigotes by thiosemicarbazones of 3-carboxy-.beta.-carbolines

  摘要：

  The thiosemicarbazones of beta-carboline-3-carboxaldehyde (compound 2) and 3-acetyl-beta-carboline (compound 3) were found to effectively inhibit the in vitro growth of the promastigote form of Leishmania donovani, 50% inhibition being obtained at concentrations of 5.0 and 2.5 microM, respectively, while irreversible growth inhibition was achieved at 40 (compound 2) and 17.5 microM (compound 3). The thiosemicarbazone of pyridine-2-carboxyaldehyde (compound 4) was considerably less active while both methyl beta-carboline-3-carboxylate (compound 1) and the thiosemicarbazone of ethyl 5-formyl-6-azaindole-2-carboxylate (compound 5) were inactive at the highest concentrations tested. At concentrations provoking approximately 50% growth inhibition of promastigotes, compound 2 was observed to preferentially block DNA rather than RNA synthesis, but for compound 3, the reverse was true. Compound 3, the most active analogue studied, may thus act, at least partially, via a novel, though as yet unelucidated, mechanism.

  DOI：

  10.1021/jm00126a021
• 作为产物：
  描述：

  2,4-二甲基-5-硝基吡啶 在 selenium(IV) oxide 、 乙醇 、 氢化钾 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 5.0h， 生成 ethyl 2-(1,3-dioxolanyl)-5-nitro-4-pyridinepyruvate
  参考文献：
  名称：

  Hybrid molecules: growth inhibition of Leishmania donovani promastigotes by thiosemicarbazones of 3-carboxy-.beta.-carbolines

  摘要：

  The thiosemicarbazones of beta-carboline-3-carboxaldehyde (compound 2) and 3-acetyl-beta-carboline (compound 3) were found to effectively inhibit the in vitro growth of the promastigote form of Leishmania donovani, 50% inhibition being obtained at concentrations of 5.0 and 2.5 microM, respectively, while irreversible growth inhibition was achieved at 40 (compound 2) and 17.5 microM (compound 3). The thiosemicarbazone of pyridine-2-carboxyaldehyde (compound 4) was considerably less active while both methyl beta-carboline-3-carboxylate (compound 1) and the thiosemicarbazone of ethyl 5-formyl-6-azaindole-2-carboxylate (compound 5) were inactive at the highest concentrations tested. At concentrations provoking approximately 50% growth inhibition of promastigotes, compound 2 was observed to preferentially block DNA rather than RNA synthesis, but for compound 3, the reverse was true. Compound 3, the most active analogue studied, may thus act, at least partially, via a novel, though as yet unelucidated, mechanism.

  DOI：

  10.1021/jm00126a021

文献信息

• Dodd, Robert H.; Doisy, Xavier; Potier, Pierre, Heterocycles, 1989, vol. 28, # 2, p. 1101 - 1113
  作者：Dodd, Robert H.、Doisy, Xavier、Potier, Pierre、Potier, Marie-Claude、Rossier, Jean

  DOI：——

  日期：——
• DODD, ROBERT H.;OUANNES, CATHERINE;ROBERT-GERO, MALKA;POTIER, PIERRE, J. MED. CHEM., 32,(1989) N, C. 1272-1276
  作者：DODD, ROBERT H.、OUANNES, CATHERINE、ROBERT-GERO, MALKA、POTIER, PIERRE

  DOI：——

  日期：——
• Hybrid molecules: growth inhibition of Leishmania donovani promastigotes by thiosemicarbazones of 3-carboxy-.beta.-carbolines
  作者：Robert H. Dodd、Catherine Ouannes、Malka Robert-Gero、Pierre Potier

  DOI：10.1021/jm00126a021

  日期：1989.6

  The thiosemicarbazones of beta-carboline-3-carboxaldehyde (compound 2) and 3-acetyl-beta-carboline (compound 3) were found to effectively inhibit the in vitro growth of the promastigote form of Leishmania donovani, 50% inhibition being obtained at concentrations of 5.0 and 2.5 microM, respectively, while irreversible growth inhibition was achieved at 40 (compound 2) and 17.5 microM (compound 3). The thiosemicarbazone of pyridine-2-carboxyaldehyde (compound 4) was considerably less active while both methyl beta-carboline-3-carboxylate (compound 1) and the thiosemicarbazone of ethyl 5-formyl-6-azaindole-2-carboxylate (compound 5) were inactive at the highest concentrations tested. At concentrations provoking approximately 50% growth inhibition of promastigotes, compound 2 was observed to preferentially block DNA rather than RNA synthesis, but for compound 3, the reverse was true. Compound 3, the most active analogue studied, may thus act, at least partially, via a novel, though as yet unelucidated, mechanism.