2-[1-(2,4-Dimethoxyanilino)ethyl]-3-(4-methylpiperazin-1-yl)quinazolin-4-one | 562836-26-4

• 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: 2-[1-(2,4-Dimethoxyanilino)ethyl]-3-(4-methylpiperazin-1-yl)quinazolin-4-one
• CAS: 562836-26-4
• 化学式: C₂₃H₂₉N₅O₃
• 分子量: 423.515
• InChiKey: HHOBUHWAEWBZRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  异氰酸间氰基苯酯 、 2-[1-(2,4-Dimethoxyanilino)ethyl]-3-(4-methylpiperazin-1-yl)quinazolin-4-one 以 1,2-二氯乙烷 为溶剂， 生成 3-(3-Cyanophenyl)-1-(2,4-dimethoxyphenyl)-1-[1-[3-(4-methylpiperazin-1-yl)-4-oxoquinazolin-2-yl]ethyl]urea
  参考文献：
  名称：

  Quinazolinone fungal efflux pump inhibitors. Part 2: In vitro structure–activity relationships of (N-methyl-piperazinyl)-containing derivatives

  摘要：

  Structure-activity relationships of a novel series of fungal efflux pump inhibitors with respect to potentiation of the activity of fluconazole against strains of Candida albicans and Candida glabrata over-expressing ABC-type efflux pumps are systematically explored. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.071
• 作为产物：
  描述：

  2-乙基-苯并[d][1,3]噁嗪-4-酮 在 溴 、 sodium acetate 、 sodium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[1-(2,4-Dimethoxyanilino)ethyl]-3-(4-methylpiperazin-1-yl)quinazolin-4-one
  参考文献：
  名称：

  Quinazolinone-based fungal efflux pump inhibitors. Part 1: Discovery of an (N-methylpiperazine)-containing derivative with activity in clinically relevant Candida spp.

  摘要：

  The discovery of a series of quinazolinone-based fungal efflux pump inhibitors by high-throughput screening for potentiation of fluconazole in C. albicans is described. Attempts to improve the aqueous solubility of screening hits led to the discovery of an analog with greatly improved physical properties and activity against clinically-relevant Candida spp. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.070

文献信息

• Fungal efflux pump inhibitors
  申请人：——

  公开号：US20030229097A1

  公开（公告）日：2003-12-11

  This invention relates to compounds that are efflux pump inhibitors and therefore are useful as potentiators of anti-fungal agents for the treatment of infections caused by fungi that employ an efflux pump resistance mechanism.

  这项发明涉及一种能够抑制外排泵并因此可用作抗真菌药物的增效剂，用于治疗由利用外排泵耐药机制的真菌引起的感染。
• Quinazolinone-based fungal efflux pump inhibitors. Part 1: Discovery of an (N-methylpiperazine)-containing derivative with activity in clinically relevant Candida spp.
  作者：Rémy C. Lemoine、Tomasz W. Glinka、William J. Watkins、Aesop Cho、Jessie Yang、Nadeem Iqbal、Rajeshwar Singh、Deidre Madsen、Karen Lolans、Olga Lomovskaya、Uma Oza、Michael N. Dudley

  DOI：10.1016/j.bmcl.2004.07.070

  日期：2004.10

  The discovery of a series of quinazolinone-based fungal efflux pump inhibitors by high-throughput screening for potentiation of fluconazole in C. albicans is described. Attempts to improve the aqueous solubility of screening hits led to the discovery of an analog with greatly improved physical properties and activity against clinically-relevant Candida spp. (C) 2004 Elsevier Ltd. All rights reserved.
• Quinazolinone fungal efflux pump inhibitors. Part 2: In vitro structure–activity relationships of (N-methyl-piperazinyl)-containing derivatives
  作者：William J. Watkins、Rémy C. Lemoine、Lee Chong、Aesop Cho、Thomas E. Renau、Bonnie Kuo、Vickie Wong、Maria Ludwikow、Negar Garizi、Nadeem Iqbal、John Barnard、Renata Jankowska、Rajeshwar Singh、Deidre Madsen、Karen Lolans、Olga Lomovskaya、Uma Oza、Michael N. Dudley

  DOI：10.1016/j.bmcl.2004.07.071

  日期：2004.10

  Structure-activity relationships of a novel series of fungal efflux pump inhibitors with respect to potentiation of the activity of fluconazole against strains of Candida albicans and Candida glabrata over-expressing ABC-type efflux pumps are systematically explored. (C) 2004 Elsevier Ltd. All rights reserved.