N-(N',N'-diethylamino-1'-methyl)butyl 6-fluoroquinol-4(1H)-one-3-carboxamide

• 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: N-(N',N'-diethylamino-1'-methyl)butyl 6-fluoroquinol-4(1H)-one-3-carboxamide
• 英文别名: N-[5-(diethylamino)pentan-2-yl]-6-fluoro-4-oxo-1H-quinoline-3-carboxamide
• 化学式: C₁₉H₂₆FN₃O₂
• 分子量: 347.433
• InChiKey: KXPGSNXIZZLIRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6-氟-4-氧代-1,4-二氢-3-喹啉羧酸乙酯 、 2-氨基-5-二乙基氨基戊烷 在 吡啶 作用下， 生成 N-(N',N'-diethylamino-1'-methyl)butyl 6-fluoroquinol-4(1H)-one-3-carboxamide
  参考文献：
  名称：

  Synthesis and methemoglobin toxicity of the amides of mono or disubstituted quinolone

  摘要：

  A series of 6/7-mono and disubstituted quinolone-3-carboxamide derivatives (1-12) were synthesized and their in vitro methemoglobin producing capacity have been delineated. The compounds 5, 6, 9 and 10 showed minimum methemoglobin toxicity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00688-x

文献信息

• Synthesis and methemoglobin toxicity of the amides of mono or disubstituted quinolone
  作者：Sandhya Srivastava、Sanjay K. Srivastava、Anita Shukla、P.M.S. Chauhan、S.K. Puri、A.P. Bhaduri、V.C. Pandey

  DOI：10.1016/s0960-894x(98)00688-x

  日期：1999.1

  A series of 6/7-mono and disubstituted quinolone-3-carboxamide derivatives (1-12) were synthesized and their in vitro methemoglobin producing capacity have been delineated. The compounds 5, 6, 9 and 10 showed minimum methemoglobin toxicity. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Quinolones:  Novel Probes in Antifilarial Chemotheraphy^,
  作者：Sanjay K. Srivastava、Prem M. S. Chauhan、Amiya P. Bhaduri、Nigar Fatima、Ranjit K. Chatterjee

  DOI：10.1021/jm990438d

  日期：2000.6.1

  Quinolones have been discovered in our laboratory as a new class of antifilarial agents. This has led to the design, synthesis, and antifilarial evaluation of a number of N-substituted quinol-4(1H)-one-3-carboxamide derivatives 4-6. The macrofilaricidal activity of the target compounds was initially evaluated in vivo against Acanthoeilonema viteae by oral administration of 200 mg/kg x 5 days. Among all the synthesized compounds, 13 displayed activity,with the most potent compound (4a) exhibiting 100% macrofilaricidal and 90% microfilaricidal activities. Compound 4e elicited significant macrofilaricidal (80%) response while compound 5c showed 100% sterilization of female worms. Finally, the two most potent macrofilaricidal compounds, namely 4a and 4e, have been screened for their potency against DNA topoisomerase II, and it has been observed that both have the capability to interfere with this enzyme at 10 mu mol/mL concentration. The structure-activity relationship (SAR) associated with position-3 and aryl ring substituents is discussed.