3-((2-Chloroquinolin-3-yl)methyl)quinazolin-4(3H)-one

• 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: 3-((2-Chloroquinolin-3-yl)methyl)quinazolin-4(3H)-one
• 英文别名: 3-[(2-Chloroquinolin-3-yl)methyl]quinazolin-4-one
• 化学式: C₁₈H₁₂ClN₃O
• 分子量: 321.766
• InChiKey: MHJMKQWHPRDBPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((2-Chloroquinolin-3-yl)methyl)quinazolin-4(3H)-one 在 palladium diacetate potassium acetate 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 色氨酸A
  参考文献：
  名称：

  Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted luotonin A derivatives

  摘要：

  A series of A-ring and E-ring analogues of the natural product luotonin A, a known topoisomerase I poison, was evaluated for growth inhibition in human carcinoma and leukemia cell lines. Rational design of structures was based on analogues of the related alkaloid camptothecin, which has been demonstrated to exert cytotoxic effects by the same mechanism of action. When compared to luotonin A, several compounds exhibited an improved topoisomerase I-dependent growth inhibition of a human leukemia cell line. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.067
• 作为产物：
  描述：

  4-羟基喹唑啉 、 3-(bromomethyl)-2-chloroquinoline 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-((2-Chloroquinolin-3-yl)methyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and topoisomerase poisoning activity of A-ring and E-ring substituted luotonin A derivatives

  摘要：

  A series of A-ring and E-ring analogues of the natural product luotonin A, a known topoisomerase I poison, was evaluated for growth inhibition in human carcinoma and leukemia cell lines. Rational design of structures was based on analogues of the related alkaloid camptothecin, which has been demonstrated to exert cytotoxic effects by the same mechanism of action. When compared to luotonin A, several compounds exhibited an improved topoisomerase I-dependent growth inhibition of a human leukemia cell line. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.067

文献信息

• Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent
  作者：Selvaraj Roopan、Fazlur-Rahman Khan、Jong Jin

  DOI：10.2478/s11696-011-0018-1

  日期：2011.1.1

  The Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

  三宅信夫反应是一种被广泛应用于有机合成中的基础反应。本文中，在三宅信夫条件下，(2-氯喹啉-3-基)甲醇与喹唑啉酮、嘧啶酮、2-氧喹啉等氮杂环化合物在干燥的THF中，在三乙胺、三苯基膦和双乙基偶氮二甲酸酯的存在下发生脱水反应，生成相应的产物。作为我们最近研究的一部分，我们尝试在三宅信夫反应条件下耦合两种N-杂环化合物，以提供天然产物合成的高效构建块。