4-(N-tert-butoxycarbonyl)methylazetidin-2-one | 1428654-55-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: 4-(N-tert-butoxycarbonyl)methylazetidin-2-one
• 英文别名: tert-butyl N-[(4-oxoazetidin-2-yl)methyl]carbamate
• CAS: 1428654-55-0
• 化学式: C₉H₁₆N₂O₃
• 分子量: 200.238
• InChiKey: GQJJGJOSSIGSLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(N-tert-butoxycarbonyl)methylazetidin-2-one 在 lithium hexamethyldisilazane 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Structure–Activity Relationships among Antifungal Nylon-3 Polymers: Identification of Materials Active against Drug-Resistant Strains of Candida albicans

  摘要：

  Fungal infections are a major challenge to human health that is heightened by pathogen resistance to current therapeutic agents. Previously, we were inspired by host-defense peptides to develop nylon-3 polymers (poly-β-peptides) that are toxic toward the fungal pathogen Candida albicans but exert little effect on mammalian cells. Based on subsequent analysis of structure-activity relationships among antifungal nylon-3 polymers, we have now identified readily prepared cationic homopolymers active against strains of C. albicans that are resistant to the antifungal drugs fluconazole and amphotericin B. These nylon-3 polymers are nonhemolytic. In addition, we have identified cationic-hydrophobic copolymers that are highly active against a second fungal pathogen, Cryptococcus neoformans, and moderately active against a third pathogen, Aspergillus fumigatus.

  DOI：

  10.1021/ja500036r
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 2-吖丁啶酮,4-(氨基甲基)- 以 甲醇 为溶剂， 生成 4-(N-tert-butoxycarbonyl)methylazetidin-2-one
  参考文献：
  名称：

  Nylon-3 Polymers with Selective Antifungal Activity

  摘要：

  Host-defense peptides inhibit bacterial growth but show little toxicity toward mammalian cells. A variety of synthetic polymers have been reported to mimic this antibacterial selectivity; however, achieving comparable selectivity for fungi is more difficult because these pathogens are eukaryotes. Here we report nylon-3 polymers based on a novel subunit that display potent antifungal activity (MIC = 3.1 mu g/mL for Candida albicans) and favorable selectivity (IC10 > 400 mu g/mL for 3T3 fibroblast toxicity; HC10 > 400 mu g/mL for hemolysis).

  DOI：

  10.1021/ja4006404

文献信息

• NYLON-3 POLYMERS ACTIVE AGAINST CLOSTRIDIUM DIFFICILE
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20170000818A1

  公开（公告）日：2017-01-05

  A method and corresponding composition to inhibit outgrowth of C. difficile spores and/or to inhibit growth of C. difficile vegetative cells in a mammal in which an amount of a nylon-3 polymer or nylon-3 copolymer or a pharmaceutically suitable salt thereof is administered to the subject.
• Structure–Activity Relationships among Antifungal Nylon-3 Polymers: Identification of Materials Active against Drug-Resistant Strains of <i>Candida albicans</i>
  作者：Runhui Liu、Xinyu Chen、Shaun P. Falk、Brendan P. Mowery、Amy J. Karlsson、Bernard Weisblum、Sean P. Palecek、Kristyn S. Masters、Samuel H. Gellman

  DOI：10.1021/ja500036r

  日期：2014.3.19

  Fungal infections are a major challenge to human health that is heightened by pathogen resistance to current therapeutic agents. Previously, we were inspired by host-defense peptides to develop nylon-3 polymers (poly-β-peptides) that are toxic toward the fungal pathogen Candida albicans but exert little effect on mammalian cells. Based on subsequent analysis of structure-activity relationships among antifungal nylon-3 polymers, we have now identified readily prepared cationic homopolymers active against strains of C. albicans that are resistant to the antifungal drugs fluconazole and amphotericin B. These nylon-3 polymers are nonhemolytic. In addition, we have identified cationic-hydrophobic copolymers that are highly active against a second fungal pathogen, Cryptococcus neoformans, and moderately active against a third pathogen, Aspergillus fumigatus.
• Nylon-3 Polymers with Selective Antifungal Activity
  作者：Runhui Liu、Xinyu Chen、Zvi Hayouka、Saswata Chakraborty、Shaun P. Falk、Bernard Weisblum、Kristyn S. Masters、Samuel H. Gellman

  DOI：10.1021/ja4006404

  日期：2013.4.10

  Host-defense peptides inhibit bacterial growth but show little toxicity toward mammalian cells. A variety of synthetic polymers have been reported to mimic this antibacterial selectivity; however, achieving comparable selectivity for fungi is more difficult because these pathogens are eukaryotes. Here we report nylon-3 polymers based on a novel subunit that display potent antifungal activity (MIC = 3.1 mu g/mL for Candida albicans) and favorable selectivity (IC10 > 400 mu g/mL for 3T3 fibroblast toxicity; HC10 > 400 mu g/mL for hemolysis).