3,5-bis-[2-chlorophenyl]-1,4,2-dioxazole | 1144046-52-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-bis-[2-chlorophenyl]-1,4,2-dioxazole
• 英文别名: 3,5-Bis-(2-chlorophenyl)-1,4,2-dioxazole；3,5-bis(2-chlorophenyl)-1,4,2-dioxazole
• CAS: 1144046-52-5
• 化学式: C₁₄H₉Cl₂NO₂
• 分子量: 294.137
• InChiKey: WPWVCBNHFGAQIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻氯苯甲醛肟 、 2-氯苯甲醛 在 sodium hypochlorite 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 49.0h， 以34%的产率得到3,5-bis-[2-chlorophenyl]-1,4,2-dioxazole
  参考文献：
  名称：

  New derivatives of 3,5-substituted-1,4,2-dioxazoles: Synthesis and activity against Entamoeba histolytica

  摘要：

  Dioxazole derivatives (1-33) were synthesized in two steps via their corresponding oximes (I-III). All the compounds were characterized using various spectroscopic techniques. A comparative study of in vitro antiamoebic activity of these heterocyclic compounds, viz. 3-o-chloro (1-11), 3-m-chloro (12-22) and 3-p-chloro (23-33) dioxazoles having same substituents at 5-position of dioxazole ring, was performed against HM1:IMSS strain of Entamoeba histolytica. The results showed a regular pattern in the activity and out of 33 compounds assayed 15 compounds showed better antiamoebic activity than metronidazole with IC50 values in the range 0.41-1.73 mu M and 1.80 mu M. Dioxazoles having o-chloro, m-chloro, p-chloro, dichloro and pyridine substituents at 5-position were more active than the standard drug metronidazole. The toxicity studies against human kidney epithelial cell line showed that all the compounds were non-toxic. 3,5-Bis-[2-chlorophenyl]-1,4,2-dioxazole (10) was most active and least toxic among all the compounds. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.001

文献信息

• New derivatives of 3,5-substituted-1,4,2-dioxazoles: Synthesis and activity against Entamoeba histolytica
  作者：Abdul R. Bhat、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejmech.2008.02.001

  日期：2009.2

  Dioxazole derivatives (1-33) were synthesized in two steps via their corresponding oximes (I-III). All the compounds were characterized using various spectroscopic techniques. A comparative study of in vitro antiamoebic activity of these heterocyclic compounds, viz. 3-o-chloro (1-11), 3-m-chloro (12-22) and 3-p-chloro (23-33) dioxazoles having same substituents at 5-position of dioxazole ring, was performed against HM1:IMSS strain of Entamoeba histolytica. The results showed a regular pattern in the activity and out of 33 compounds assayed 15 compounds showed better antiamoebic activity than metronidazole with IC50 values in the range 0.41-1.73 mu M and 1.80 mu M. Dioxazoles having o-chloro, m-chloro, p-chloro, dichloro and pyridine substituents at 5-position were more active than the standard drug metronidazole. The toxicity studies against human kidney epithelial cell line showed that all the compounds were non-toxic. 3,5-Bis-[2-chlorophenyl]-1,4,2-dioxazole (10) was most active and least toxic among all the compounds. (C) 2008 Elsevier Masson SAS. All rights reserved.