diethyl 4,5-dihydroxy-1,8,9-triazaanthracene-3,6-dicarboxylate | 28733-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: diethyl 4,5-dihydroxy-1,8,9-triazaanthracene-3,6-dicarboxylate
• 英文别名: 3,7-Dicarbethoxy-4,6-dihydroxy-1,9,10-anthyridin；4,6-dioxo-1,4,6,9-tetrahydro-pyrido[2,3-b][1,8]naphthyridine-3,7-dicarboxylic acid diethyl ester；diethyl 4,6-dioxo-1,9-dihydropyrido[2,3-b][1,8]naphthyridine-3,7-dicarboxylate
• CAS: 28733-29-1
• 化学式: C₁₇H₁₅N₃O₆
• 分子量: 357.323
• InChiKey: PZNXZWIQBGBZEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diethyl 4,5-dihydroxy-1,8,9-triazaanthracene-3,6-dicarboxylate 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 1,8-diethyl-4(1H),5(8H)-dioxo-1,8,9-triazaanthracene-3,6-dicarboxylic acid
  参考文献：
  名称：

  Synthesis and biological activity of new quinolone derivatives

  摘要：

  A series of new quinolone derivatives bearing covalent modifications at the piperazine ring was synthesized and investigated for their biological properties. Two different types of substitutions at the level of the nitrogen at the 4' position were considered: introduction of a di- or tri-oxymethylene chain to modify steric hindrance and improve solubility in aqueous media or formation of a tertiary amide ending with a carboxylate group. In the latter case the net charge on the piperazine moiety changes from positive to negative at physiological conditions. In addition, a 'bis-quinolone' compound was examined, which lacks the piperazine ring and is also negatively charged at neutral pH. The new derivatives, except one, exhibited drug uptake, inhibition of DNA-gyrase activity and anti-bacterial potencies comparable to those of norfloxacin, and were modulated by the nature of the N4'-substituent. Besides indicating possible new modifications of the quinolone basic structure, the observation that substantially different substitution patterns at the same position did not cause impairment of biological activity suggests that the steric and electronic properties of this part of the molecule are not crucial for the recognition of DNA-gyrase.

  DOI：

  10.1016/0223-5234(93)90146-6
• 作为产物：
  描述：

  2,6-bis<2,2-di(ethoxycarbonyl)ethylamino>pyridine 以 二苯醚 为溶剂， 反应 1.0h， 以53%的产率得到diethyl 4,5-dihydroxy-1,8,9-triazaanthracene-3,6-dicarboxylate
  参考文献：
  名称：

  Synthesis and biological activity of new quinolone derivatives

  摘要：

  A series of new quinolone derivatives bearing covalent modifications at the piperazine ring was synthesized and investigated for their biological properties. Two different types of substitutions at the level of the nitrogen at the 4' position were considered: introduction of a di- or tri-oxymethylene chain to modify steric hindrance and improve solubility in aqueous media or formation of a tertiary amide ending with a carboxylate group. In the latter case the net charge on the piperazine moiety changes from positive to negative at physiological conditions. In addition, a 'bis-quinolone' compound was examined, which lacks the piperazine ring and is also negatively charged at neutral pH. The new derivatives, except one, exhibited drug uptake, inhibition of DNA-gyrase activity and anti-bacterial potencies comparable to those of norfloxacin, and were modulated by the nature of the N4'-substituent. Besides indicating possible new modifications of the quinolone basic structure, the observation that substantially different substitution patterns at the same position did not cause impairment of biological activity suggests that the steric and electronic properties of this part of the molecule are not crucial for the recognition of DNA-gyrase.

  DOI：

  10.1016/0223-5234(93)90146-6

文献信息

• Synthesis and biological activity of new quinolone derivatives
  作者：C Antonello、E Uriarte、M Palumbo、S Valisena、C Parolin、G Palù

  DOI：10.1016/0223-5234(93)90146-6

  日期：1993.1

  A series of new quinolone derivatives bearing covalent modifications at the piperazine ring was synthesized and investigated for their biological properties. Two different types of substitutions at the level of the nitrogen at the 4' position were considered: introduction of a di- or tri-oxymethylene chain to modify steric hindrance and improve solubility in aqueous media or formation of a tertiary amide ending with a carboxylate group. In the latter case the net charge on the piperazine moiety changes from positive to negative at physiological conditions. In addition, a 'bis-quinolone' compound was examined, which lacks the piperazine ring and is also negatively charged at neutral pH. The new derivatives, except one, exhibited drug uptake, inhibition of DNA-gyrase activity and anti-bacterial potencies comparable to those of norfloxacin, and were modulated by the nature of the N4'-substituent. Besides indicating possible new modifications of the quinolone basic structure, the observation that substantially different substitution patterns at the same position did not cause impairment of biological activity suggests that the steric and electronic properties of this part of the molecule are not crucial for the recognition of DNA-gyrase.