(5S)-2-imino-5-(1H-indol-3-ylmethyl)-1,3-oxazolidin-4-one | 65954-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (5S)-2-imino-5-(1H-indol-3-ylmethyl)-1,3-oxazolidin-4-one
• CAS: 65954-89-4
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: FGTZCVGIFPOOSE-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 在 甲基溴化镁 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 生成 (5S)-2-imino-5-(1H-indol-3-ylmethyl)-1,3-oxazolidin-4-one
  参考文献：
  名称：

  研究天然产物吲哚霉素和合成改进的抗分枝杆菌药物类似物

  摘要：

  吲哚霉素 (IND) 是一种微生物天然产物，可选择性抑制细菌色氨酸-tRNA 合成酶 (TrpRS)。色氨酸生物合成途径最近被证明是开发针对结核分枝杆菌(Mtb) 的新型抗菌剂的重要目标。我们研究了 IND 对几种分枝杆菌模型菌株的抗菌活性。开发了一种 TrpRS 生化试验来分析合成 IND 类似物的文库。4″-甲基化 IND 化合物 Y-13 显示出改善的抗 Mtb 活性，最小抑制浓度 (MIC) 为 1.88 μM (~0.5 μg/mL)。当在基因工程替代牛分枝杆菌中诱导 TrpRS 过表达时，MIC 显着增加卡介苗。Mtb TrpRS 与 IND 和 ATP 复合的共晶结构表明氨基酸袋处于 apo 蛋白的开放形式和与反应中间体的封闭复合物之间的状态。在基于全细胞的实验中，我们研究了 Y-13 与不同抗菌剂的组合效果。我们通过基因组测序评估了杀伤动力学、对 IND 的抗性频率以及 IND

  DOI：

  10.1021/acschembio.1c00394

文献信息

• Isolated bacterial strain of the genus Burkholderia and pesticidal metabolites therefrom
  申请人：MARRONE BIO INNOVATIONS, INC.

  公开号：US11382331B2

  公开（公告）日：2022-07-12

  A species of Burkholderia sp with no known pathogenicity to vertebrates but with pesticidal activity (e.g., plants, insects, fungi, weeds and nematodes) is provided. Also provided are natural products derived from a culture of said species and methods of controlling pests using said natural products.

  本发明提供了一种Burkholderia属的菌种，其对脊椎动物没有已知的致病性，但具有杀虫活性（例如，针对植物、昆虫、真菌、杂草和线虫）。此外，本发明还提供了由所述菌种培养获得的天然产物，以及利用所述天然产物进行害虫防治的方法。
• ISOLATED BACTERIAL STRAIN OF THE GENUS BURKHOLDERIA AND PESTICIDAL METABOLITES THEREFROM
  申请人：Asolkar Ratnakar

  公开号：US20110207604A1

  公开（公告）日：2011-08-25

  A species of Burkholderia sp with no known pathogenicity to vertebrates but with pesticidal activity (e.g., plants, insects, fungi, weeds and nematodes) is provided. Also provided are natural products derived from a culture of said species and methods of controlling pests using said natural products.
• ISOLATED BACTERIAL STRAIN OF THE GENUS BURKHOLDERIA AND PESTICIDAL METABOLITES THEREFROM- FORMULATIONS AND USES
  申请人：Asolkar Ratnakar

  公开号：US20140221207A1

  公开（公告）日：2014-08-07

  A species of Burkholderia sp with no known pathogenicity to vertebrates but with pesticidal activity (e.g., plants, algae, arachnids, insects, fungi, weeds and nematodes) as well as methods for controlling algae using said species of Burkholderia . Also provided are natural products derived from a culture of said species and methods of controlling algae and/or arachnids using said natural products.
• Isolated Bacterial Strain of the Genus Burkholderia and Pesticidal Metabolites Therefrom
  申请人：Marrone Bio Innovations, Inc.

  公开号：US20160330975A1

  公开（公告）日：2016-11-17

  A species of Burkholderia sp with no known pathogenicity to vertebrates but with pesticidal activity (e.g., plants, insects, fungi, weeds and nematodes) is provided. Also provided are natural products derived from a culture of said species and methods of controlling pests using said natural products.
• Isolated Bacterial Strain of the Genus Burkholderia and Pesticidal Metabolites Therefrom-Formulations and Uses
  申请人：Marrone Bio Innovations, Inc.

  公开号：US20170208817A1

  公开（公告）日：2017-07-27

  The present invention provides a method of the proliferation of pest infestation using a species of Burkholderia. Also provided are natural products derived from a culture of said species and methods of controlling algae and/or arachnids using said natural products.