ethyl 1,4-dihydro-6-methyl-8-nitro-4-oxoquinoline-3-carboxylate | 94110-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 1,4-dihydro-6-methyl-8-nitro-4-oxoquinoline-3-carboxylate
• 英文别名: Ethyl 4-hydroxy-6-methyl-8-nitro-3-quinolinecarboxylate；ethyl 6-methyl-8-nitro-4-oxo-1H-quinoline-3-carboxylate
• CAS: 94110-94-8
• 化学式: C₁₃H₁₂N₂O₅
• 分子量: 276.249
• InChiKey: AXEVDGVJEIOLKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1,4-dihydro-6-methyl-8-nitro-4-oxoquinoline-3-carboxylate 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以70%的产率得到8-Amino-6-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and antiallergic activity of some quinolinones and imidazoquinolinones

  摘要：

  A group of 1,4-dihydro-4-oxoquinoline-2- and -3-carboxylic acid esters with nitrogen functionality at the 8-position was synthesized, and 6-oxo-6H-imidazo[4,5,1-ij]quinoline-4- and -5-carboxylic acid esters were elaborated from these. Several of the compounds displayed activity in the rat passive cutaneous anaphylaxis (PCA) test for antiallergic activity. However, PCA activity in this series was accompanied by rat toxicity, as measured by a decrease in percent of normal weight gain over a 2-week period, following a single oral dose.

  DOI：

  10.1021/jm00381a007
• 作为产物：
  描述：

  4-甲基-2-硝基苯胺 以 various solvent(s) 为溶剂， 反应 7.5h， 生成 ethyl 1,4-dihydro-6-methyl-8-nitro-4-oxoquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and antiallergic activity of some quinolinones and imidazoquinolinones

  摘要：

  A group of 1,4-dihydro-4-oxoquinoline-2- and -3-carboxylic acid esters with nitrogen functionality at the 8-position was synthesized, and 6-oxo-6H-imidazo[4,5,1-ij]quinoline-4- and -5-carboxylic acid esters were elaborated from these. Several of the compounds displayed activity in the rat passive cutaneous anaphylaxis (PCA) test for antiallergic activity. However, PCA activity in this series was accompanied by rat toxicity, as measured by a decrease in percent of normal weight gain over a 2-week period, following a single oral dose.

  DOI：

  10.1021/jm00381a007

文献信息

• Heterocycle carboxamides as antiviral agents
  申请人：——

  公开号：US20020025959A1

  公开（公告）日：2002-02-28

  The present invention provides a compound of formula I 1 which is useful as antiviral agents, in particular, as agents against viruses of the herpes family.

  本发明提供了一种化合物，其化学式为I1，可作为抗病毒药物，特别是用作抗疱疹病毒家族的药物。
• Regiocontrolled Nitration of 4-Quinolones at Ambient Conditions
  作者：Sonali Sarkar、Prasanjit Ghosh、Anirban Misra、Sajal Das

  DOI：10.1080/00397911.2015.1085576

  日期：2015.10.18

  Regiocontrolled nitration of 4-quinolone, the highly privileged scaffold, has been developed at ambient conditions. The nitro group can selectively be introduced at diverse positions simply by tuning the reactivity of the moiety. Discrimination is being achieved through the selective functionalization of the free N-H group. The functional group has been screened theoretically with the help of Fukui function and local softness calculation. Theoretical predictions are synchronized well with the experimental findings. Finally, this nitration technique allows quick access to the structurally diverse 4-quinolones.
• PEET, N. P.;BAUGH, L. E.;SUNDER, SHYAM;LEWIS, J. E., J. MED. CHEM., 1985, 28, N 3, 298-302
  作者：PEET, N. P.、BAUGH, L. E.、SUNDER, SHYAM、LEWIS, J. E.

  DOI：——

  日期：——
• HETEROCYCLE CARBOXAMIDES AS ANTIVIRAL AGENTS
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1299387A1

  公开（公告）日：2003-04-09
• US6624159B2
  申请人：——

  公开号：US6624159B2

  公开（公告）日：2003-09-23