7-chloro-3,4-dihydro-9-phenyl-2-[(pyridine-2yl)methylene]acridin-1(2H)-one | 1384192-83-9

• 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: 7-chloro-3,4-dihydro-9-phenyl-2-[(pyridine-2yl)methylene]acridin-1(2H)-one
• 英文别名: 7-Chloro-3,4-dihydro-9-phenyl-2-[(pyridin-2-yl)methylidene]acridin-1(2h)-one；7-chloro-9-phenyl-2-(pyridin-2-ylmethylidene)-3,4-dihydroacridin-1-one
• CAS: 1384192-83-9
• 化学式: C₂₅H₁₇ClN₂O
• 分子量: 396.876
• InChiKey: NDCVEFKCWPCEPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡啶-2-甲醛 、 7-chloro-3,4-dihydro-9-phenylacridin-1(2H)-one 在 potassium hydroxide 作用下， 反应 5.0h， 以92%的产率得到7-chloro-3,4-dihydro-9-phenyl-2-[(pyridine-2yl)methylene]acridin-1(2H)-one
  参考文献：
  名称：

  Synthesis, spectral characterization and larvicidal activity of acridin-1(2H)-one analogues

  摘要：

  Acridin-1(2H)-one analogue of 7-chloro-3,4-dihydro-9-phenyl-2-[(pyridine-2yl) methylene] acridin-1(2H)-one, 5 was prepared by using 7-chloro-3,4-dihydro-9-phenylacridin-1(2H)-one, 3 and picolinaldehyde, 4 in the presence of KOH at room temperature. These compounds were characterized by analytical and spectral analyses. The purpose of the present study was to assess the efficacy of larvicidal and repellent activity of synthesized 7-chloro-3,4-dihydro-9-phenyl-acridin-1(2H)-one analogues such as compounds 3 and 5 against the early fourth instar larvae of filariasis vector, Culex quinquefasciatus and Japanese encephalitis vector, Culex gelidus (Diptera: Culicidae). The compound exhibited high larvicidal effects at 50 mg/L against both the mosquitoes with LC50 values of 25.02 mg/L (r(2) = 0.998) and 26.40 mg/L (r(2) = 0.988) against C. quinquefasciatus and C. gelidus, respectively. The 7-chloro-3,4-dihydro-9-phenyl-acridin-1(2H)-one analogues that are reported for the first time to our best of knowledge can be better explored for the control of mosquito population. This is an ideal ecofriendly approach for the control of Japanese encephalitis vectors, C. quinquefasciatus and C. gelidus. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.04.015