3-(5-benzimidazolyl)amino-2-ethoxycarbonyl-prop-2-enoic acid ethyl ester | 58842-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 3-(5-benzimidazolyl)amino-2-ethoxycarbonyl-prop-2-enoic acid ethyl ester
• 英文别名: diethyl 2-[(3H-benzimidazol-5-ylamino)methylidene]propanedioate
• CAS: 58842-46-9
• 化学式: C₁₅H₁₇N₃O₄
• 分子量: 303.318
• InChiKey: FIYSOMWNDPRJNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(5-benzimidazolyl)amino-2-ethoxycarbonyl-prop-2-enoic acid ethyl ester 以 various solvent(s) 为溶剂， 反应 0.25h， 以96%的产率得到ethyl 9-oxo-3,6-dihydroimidazo[4,5-f]quinoline-8-carboxylate
  参考文献：
  名称：

  Milata, Viktor; Ilavsky, Dusan, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 12, p. 2918 - 2925

  摘要：

  DOI：
• 作为产物：
  描述：

  6-硝基苯并咪唑 以83%的产率得到
  参考文献：
  名称：

  SPENCER C. F; SNYDER H. R., JR.; ALAIMO R. J., J. HETEROCYCL. CHEM., 1975, 12, NO 6, 1319-1321

  摘要：

  DOI：

文献信息

• Design and Synthesis of Potent Inhibitors of the Malaria Parasite Dihydroorotate Dehydrogenase
  作者：Timo Heikkilä、Christopher Ramsey、Matthew Davies、Christophe Galtier、Andrew M. W. Stead、A. Peter Johnson、Colin W. G. Fishwick、Andrew N. Boa、Glenn A. McConkey

  DOI：10.1021/jm060687j

  日期：2007.1.1

  Pyrimidine biosynthesis presents an attractive drug target in malaria parasites due to the absence of a pyrimidine salvage pathway. A set of compounds designed to inhibit the Plasmodium falciparum pyrimidine biosynthetic enzyme dihydroorotate dehydrogenase (PfDHODH) was synthesized. PfDHODH-specific inhibitors with low nanomolar binding affinities were identified that bind in the N-terminal hydrophobic channel of dihydroorotate dehydrogenase, the presumed site of ubiquinone binding during oxidation of dihydroorotate to orotate. These compounds also prevented growth of cultured parasites at low micromolar concentrations. Models that suggest the mode of inhibitor binding is based on shape complementarity, matching hydrophobic regions of inhibitor and enzyme, and interaction of inhibitors with amino acid residues F188, H185, and R265 are supported by mutagenesis data. These results further highlight PfDHODH as a promising new target for chemotherapeutic intervention in prevention of malaria and provide better understanding of the factors that determine specificity over human dihydroorotate dehydrogenase.
• Milata, Viktor; Ilavsky, Dusan; Goljer, Igor, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 3, p. 713 - 724
  作者：Milata, Viktor、Ilavsky, Dusan、Goljer, Igor

  DOI：——

  日期：——
• MILATA, V.;ILAVSKY, D.;GOLJER, I., CHEM. PAP., 42,(1988) N, C. 801-810
  作者：MILATA, V.、ILAVSKY, D.、GOLJER, I.

  DOI：——

  日期：——
• MILATA, VIKTOR;ILAVSKY, DUSAN;GOLJER, IGOR, COLLECT. CZECHOSL. CHEM. COMMUN., 54,(1989) N, C. 713-724
  作者：MILATA, VIKTOR、ILAVSKY, DUSAN、GOLJER, IGOR

  DOI：——

  日期：——
• SPENCER C. F; SNYDER H. R., JR.; ALAIMO R. J., J. HETEROCYCL. CHEM., 1975, 12, NO 6, 1319-1321
  作者：SPENCER C. F、 SNYDER H. R., JR.、 ALAIMO R. J.

  DOI：——

  日期：——