3-chloro-1-(4-chloro-phenyl)-4-[4-(2-oxo-3H-benzo[h]chromen-1-ylmethoxy)phenyl]azetidin-2-one | 1204663-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3-chloro-1-(4-chloro-phenyl)-4-[4-(2-oxo-3H-benzo[h]chromen-1-ylmethoxy)phenyl]azetidin-2-one
• 英文别名: 3-Chloro-1-(4-chlorophenyl)-4-[4-[(2-oxobenzo[h]chromen-4-yl)methoxy]phenyl]azetidin-2-one
• CAS: 1204663-18-2
• 化学式: C₂₉H₁₉Cl₂NO₄
• 分子量: 516.38
• InChiKey: MKKWMQJTZFKWCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-{(4-[(4-chloro-phenylimino)methyl]phenoxy)methyl}-benzo[h]chromen-2-one 、 氯乙酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 51.0h， 以71.46%的产率得到3-chloro-1-(4-chloro-phenyl)-4-[4-(2-oxo-3H-benzo[h]chromen-1-ylmethoxy)phenyl]azetidin-2-one
  参考文献：
  名称：

  RETRACTED: 2-Azetidinone derivatives: Design, synthesis, in vitro anti-microbial, cytotoxic activities and DNA cleavage study

  摘要：

  A novel series of 3-chloro-4-[4-(2-oxo-2H-chromen-4-ylmethoxy)-phenyl]-1-phenyl-azetidin-2-one derivatives (5a-j) have been synthesized from 4-aryloxymethylcoumarins (la-e) and 4-aryliminomethylphenols (3a-b). The title compounds were screened for their in vitro anti-bacterial and anti-fungal activities. Results revealed that, compounds (5c), (5f), (5h) and (5j) showed excellent anti-microbial activity against a panel of microorganisms. Brine shrimp bioassay was also carried out to study their in vitro cytotoxic properties among which (5h) and (5j) displayed potent cytotoxic activity against Artemia salina. The DNA cleavage activity of some compounds was studied by agarose gel electrophoresis method. All synthesized compounds were characterized using IR, H-1 NMR, C-13 NMR, MS and elemental analysis. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.011

文献信息

• RETRACTED: 2-Azetidinone derivatives: Design, synthesis, in vitro anti-microbial, cytotoxic activities and DNA cleavage study
  作者：Rangappa S. Keri、Kallappa M. Hosamani、Ramya V. Shingalapur、Harisha R. Seetharama Reddy

  DOI：10.1016/j.ejmech.2009.09.011

  日期：2009.12

  A novel series of 3-chloro-4-[4-(2-oxo-2H-chromen-4-ylmethoxy)-phenyl]-1-phenyl-azetidin-2-one derivatives (5a-j) have been synthesized from 4-aryloxymethylcoumarins (la-e) and 4-aryliminomethylphenols (3a-b). The title compounds were screened for their in vitro anti-bacterial and anti-fungal activities. Results revealed that, compounds (5c), (5f), (5h) and (5j) showed excellent anti-microbial activity against a panel of microorganisms. Brine shrimp bioassay was also carried out to study their in vitro cytotoxic properties among which (5h) and (5j) displayed potent cytotoxic activity against Artemia salina. The DNA cleavage activity of some compounds was studied by agarose gel electrophoresis method. All synthesized compounds were characterized using IR, H-1 NMR, C-13 NMR, MS and elemental analysis. (C) 2009 Elsevier Masson SAS. All rights reserved.