3-methoxy-1-(4-methoxy-phenyl)-4-phenylethynyl-azetidin-2-one | 216366-72-2

• 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: 3-methoxy-1-(4-methoxy-phenyl)-4-phenylethynyl-azetidin-2-one
• 英文别名: 3-Methoxy-4-(2-phenylethynyl)azetidin-2-one
• CAS: 216366-72-2
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: ZHPHEXRMBSDLGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-1-(4-methoxy-phenyl)-4-phenylethynyl-azetidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 以18%的产率得到(3R,4S)-3-Methoxy-4-((E)-styryl)-azetidin-2-one
  参考文献：
  名称：

  N-Thiolated β-Lactam Antibacterials: Defining the Role of Unsaturation in the C4 Side Chain

  摘要：

  N-Methylthio beta-lactams represent a novel family of antibacterial agents for methicillin-resistant Staphylococcus aureus (MRSA). The structure-activity functions and mechanism of action of these compounds, although still largely undefined, differ dramatically from those of all previously reported beta-lactam antibiotics. Prior work has established that the N-alkylthio moiety is required for antibacterial activity, and that a variety of unsaturated groups can be tolerated at C-4 of the lactam ring. This report describes the effect that unsaturation within the C-4 substituent has on antibacterial activity of these interesting new N-thiolated beta-lactams. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00383-8
• 作为产物：
  描述：

  3-methoxy-1-(4-methoxy-phenyl)-4-phenylethynyl-azetidin-2-one 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以89%的产率得到3-methoxy-1-(4-methoxy-phenyl)-4-phenylethynyl-azetidin-2-one
  参考文献：
  名称：

  Methods for preventing and treating cancer using N-thiolated beta-lactam compounds and analogs thereof

  摘要：

  本发明涉及N-硫代-β-内酰胺化合物及其类似物和药学上可接受的盐、酯和酰胺。本发明还涉及诱导肿瘤细胞死亡或抑制肿瘤细胞增殖的方法，诱导DNA损伤、抑制DNA复制、激活p38 MAP激酶或激活caspase级联激活，或将细胞色素C从线粒体释放到肿瘤细胞的细胞质中的方法。本发明还揭示了使用N-硫代-β-内酰胺化合物治疗癌症的方法，以及包含它们的制药组合物。

  公开号：

  US20040167115A1

文献信息

• Methods for preventing and treating cancer using N-thiolated beta-lactam compounds and analogs thereof
  申请人：——

  公开号：US20040167115A1

  公开（公告）日：2004-08-26

  The subject invention concerns N-thiolated &bgr;-lactam compounds, their analogs and pharmaceutically acceptable salts, esters and amides thereof. The subject invention also concerns methods for inducing tumor cell death or inhibiting tumor cell proliferation, and methods for inducing DNA damage, inhibiting DNA replication, activating p38 MAP kinase, or activating caspase cascade activation, or releasing cytochrome C from mitochondria into the cytoplasm in a tumor cell. Methods for treating cancer using N-thiolated &bgr;-lactam compounds, as well as pharmaceutical compositions comprising the same are further disclosed.

  本发明涉及N-硫代-β-内酰胺化合物及其类似物和药学上可接受的盐、酯和酰胺。本发明还涉及诱导肿瘤细胞死亡或抑制肿瘤细胞增殖的方法，诱导DNA损伤、抑制DNA复制、激活p38 MAP激酶或激活caspase级联激活，或将细胞色素C从线粒体释放到肿瘤细胞的细胞质中的方法。本发明还揭示了使用N-硫代-β-内酰胺化合物治疗癌症的方法，以及包含它们的制药组合物。
• N-Thiolated β-Lactam Antibacterials: Defining the Role of Unsaturation in the C4 Side Chain
  作者：Cristina Coates、Timothy E Long、Edward Turos、Sonja Dickey、Daniel V Lim

  DOI：10.1016/s0968-0896(02)00383-8

  日期：2003.1

  N-Methylthio beta-lactams represent a novel family of antibacterial agents for methicillin-resistant Staphylococcus aureus (MRSA). The structure-activity functions and mechanism of action of these compounds, although still largely undefined, differ dramatically from those of all previously reported beta-lactam antibiotics. Prior work has established that the N-alkylthio moiety is required for antibacterial activity, and that a variety of unsaturated groups can be tolerated at C-4 of the lactam ring. This report describes the effect that unsaturation within the C-4 substituent has on antibacterial activity of these interesting new N-thiolated beta-lactams. (C) 2002 Elsevier Science Ltd. All rights reserved.