1-(4-chlorophenyl)-4-(1-methyl-1H-indol-3-yl)-3,3-di-p-tolylazetidin-2-one | 1396320-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-(4-chlorophenyl)-4-(1-methyl-1H-indol-3-yl)-3,3-di-p-tolylazetidin-2-one
• 英文别名: 1-(4-Chlorophenyl)-4-(1-methylindol-3-yl)-3,3-bis(4-methylphenyl)azetidin-2-one
• CAS: 1396320-60-7
• 化学式: C₃₂H₂₇ClN₂O
• 分子量: 491.032
• InChiKey: LOHXUFHOORCNHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-甲基吲哚-3-甲醛 以 乙醇 、 苯 为溶剂， 生成 1-(4-chlorophenyl)-4-(1-methyl-1H-indol-3-yl)-3,3-di-p-tolylazetidin-2-one
  参考文献：
  名称：

  Synthesis of N-(1-methyl-1H-indol-3-yl)methyleneamines and 3,3-diaryl-4-(1-methyl-1H-indol-3-yl)azetidin-2-ones as potential antileishmanial agents

  摘要：

  A series of N-(1-methyl-1H-indol-3-yl)methyleneamines and eight new 3,3-diaryl-4-(1-methyl-1H-indol-3-yl)azetidin-2-ones have been synthesized and screened for their antileishmanial activity against Leishmania major. 3,3-Diaryl-4-(1-methyl-1H-indol-3-yl)azetidin-2-ones have been synthesized by the Staudinger's ketene-imine cycloaddition employing two 2-diazo-1,2-diarylethanones as the precursors of diarylketenes. A marked improvement in anti-parasitic activity is observed by transformation of the methyleneamines to azetidin-2-ones in seven out of eight compounds. Two compounds displayed antileishmanial activity comparable to that of the clinically used antileshmanial drug, amphotericine B. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.081

文献信息

• Synthesis, Antimicrobial, and Brine Shrimps Lethality Assays of 3,3-Diaryl-4-(1-methyl-1<i>H</i>-indol-3-yl)azetidin-2-ones
  作者：Girija S. Singh、Yasser M. S. A. Al-kahraman、Disah Mpadi、Masoom Yasinzai

  DOI：10.1002/jhet.2057

  日期：2015.3

  The paper describes the synthesis, characterization data, and biological activity (antibacterial, antifungal, and brine shrimps lethality) of new azetidin‐2‐ones. The compounds have been synthesized by the reaction of diarylketenes, generated in situ from thermal decomposition of the 2‐diazo‐1,2‐diarylethanones, with N‐(1‐methyl‐1H‐indol‐3‐yl)methyleneamines. The compounds have been characterized by

  本文描述了新的azetidin-2-one的合成，表征数据和生物学活性（抗菌，抗真菌和盐水虾致死性）。这些化合物是由二芳基酮与2- N-（1-甲基-1 H-吲哚-3-基）亚甲基胺热分解而合成的，这些化合物是由二芳基1,2-二芳基酮的热分解而原位生成的。该化合物已通过元素分析和光谱（IR，1 H和13 C NMR和MS）数据进行了表征。该论文还报告了这些化合物的抗菌，抗真菌和盐水虾杀伤力测定结果。一些化合物表现出显着的生物学活性。
• Synthesis of N-(1-methyl-1H-indol-3-yl)methyleneamines and 3,3-diaryl-4-(1-methyl-1H-indol-3-yl)azetidin-2-ones as potential antileishmanial agents
  作者：Girija S. Singh、Yasser M.S.A. Al-kahraman、Disah Mpadi、Masoom Yasinzai

  DOI：10.1016/j.bmcl.2012.06.081

  日期：2012.9

  A series of N-(1-methyl-1H-indol-3-yl)methyleneamines and eight new 3,3-diaryl-4-(1-methyl-1H-indol-3-yl)azetidin-2-ones have been synthesized and screened for their antileishmanial activity against Leishmania major. 3,3-Diaryl-4-(1-methyl-1H-indol-3-yl)azetidin-2-ones have been synthesized by the Staudinger's ketene-imine cycloaddition employing two 2-diazo-1,2-diarylethanones as the precursors of diarylketenes. A marked improvement in anti-parasitic activity is observed by transformation of the methyleneamines to azetidin-2-ones in seven out of eight compounds. Two compounds displayed antileishmanial activity comparable to that of the clinically used antileshmanial drug, amphotericine B. (C) 2012 Elsevier Ltd. All rights reserved.