(2-{2-[2-(7-nitrobenzo[1,2,5]oxadiazol-4-ylamino)ethoxy]ethoxy}ethyl)carbamic acid tert-butyl ester | 1269638-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: (2-{2-[2-(7-nitrobenzo[1,2,5]oxadiazol-4-ylamino)ethoxy]ethoxy}ethyl)carbamic acid tert-butyl ester
• 英文别名: (2-{2-[2-(7-nitrobenzo[c][1,2,5]oxadiazol-4-ylamino)ethoxy]ethoxy}ethyl)carbamic acid tert-butyl ester
• CAS: 1269638-29-0
• 化学式: C₁₇H₂₅N₅O₇
• 分子量: 411.415
• InChiKey: JUQWMVPDOJRSMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  150.88
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2-{2-[2-(7-nitrobenzo[1,2,5]oxadiazol-4-ylamino)ethoxy]ethoxy}ethyl)carbamic acid tert-butyl ester 在 sodium sulfate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(2-{2-[2-(7-nitrobenzo[1,2,5]oxadiazol-4-ylamino)ethoxy]ethoxy}ethyl)succinamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Fluorescent Probes Based on the Pyochelin Siderophore Scaffold

  摘要：

  Pyochelin is a siderophore common to several pathogenic bacterial strains. Two conjugates, 1 and 2, between the NBD (4-nitro-benzo[1,2,5]oxadiazole) fluorophore and an N3 ''-functionalized pyochelin were synthesized. These fluorescent probes unexpectedly increased their fluorescence in an aqueous medium in the presence of iron(III) and were transported into bacterial cells.

  DOI：

  10.1021/ol1028173
• 作为产物：
  描述：

  4-氯-7-硝基苯并-2-氧杂-1,3-二唑 、 2-(2-(2-氨基乙氧基)乙氧基)乙基氨基甲酸叔丁酯 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 以68%的产率得到(2-{2-[2-(7-nitrobenzo[1,2,5]oxadiazol-4-ylamino)ethoxy]ethoxy}ethyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  选择性检测气单胞菌属。通过基于铁载体阿莫那巴汀的荧光探针

  摘要：

  Amonabactins 是由属于气单胞菌属的一些病原菌产生的铁载体，可用于制备通过其特定运输机制导入细胞的结合物。在此，我们报告了一种新的基于 amonabactin 的荧光探针的设计和合成，方法是使用硫醇-马来酰亚胺点击反应将适当的 amonabactin 类似物与 sulforhodamine B (AMB-SRB) 结合。生长促进测定和荧光显微镜研究表明，AMB-SRB 荧光探针能够标记鱼类病原细菌A. salamicida subsp。鲑鱼通过其外膜转运 (OMT) 蛋白 FstC。其他气单胞菌的标签物种，例如人类病原体A.hydrophila，表明该探针可以成为研究阿莫纳巴汀依赖性铁摄取机制的非常有用的分子工具。此外，在存在其他鱼类病原菌的情况下选择性标记杀鲑鱼和其他气单胞菌，表明该探针可用于通过荧光测定法检测水和其他养鱼样品中的气单胞菌。

  DOI：

  10.1016/j.jinorgbio.2022.111743

文献信息

• Dyeing fungi: amphotericin B based fluorescent probes for multiplexed imaging
  作者：Assel Baibek、Muhammed Üçüncü、Bryn Short、Gordon Ramage、Annamaria Lilienkampf、Mark Bradley

  DOI：10.1039/d0cc08177a

  日期：——

  The clinically used antifungal polyene amphotericin B was conjugated, via the mycosamine and the aglycon moieties, to fluorophores. The Cy5 conjugated probe showed selective labelling of fungi in the presence of bacteria, allowing multiplexed imaging and identification of microbial species in a co-culture of fungi and Gram-positive and Gram-negative bacteria.

  临床上使用的抗真菌多烯两性霉素B通过霉菌胺和糖苷配基与荧光团结合。Cy5共轭探针在存在细菌的情况下显示出对真菌的选择性标记，从而可以在真菌与革兰氏阳性和革兰氏阴性细菌的共培养物中进行多重成像和鉴定微生物物种。
• Lichen butyrolactone derivatives disrupt oral bacterial membrane
  作者：Alaa Sweidan、Imen Smida、Marylène Chollet-Krugler、Aurélie Sauvager、Julien Vallet、Nicolas Gouault、Nolwenn Oliviero、Zohreh Tamanai-Shacoori、Agnès Burel、Pierre van de Weghe、Ali Chokr、Sophie Tomasi、Latifa Bousarghin

  DOI：10.1016/j.fitote.2019.104274

  日期：2019.9

  We have previously demonstrated that out of the butyrolactones series synthesized based on the natural lichen metabolite lichesterinic acid, compound (B-13) was the most effective against oral bacteria. However, its antibacterial mechanism is still unknown. In this study, we have investigated its bacterial localization by synthesizing a fluorescently labeled B-13 with NBD while maintaining its antibacterial activity. We showed that this compound binds to Streptococcus gordonii cell surface, as demonstrated by HPLC analysis. By adhering to cell surface, B-13 induced cell wall disruption leading to the release of bacterial constituents and consequently, the death of S. gordonii, a Gram-positive bacterium. A Gram-negative counterpart, Porphyromanas gingivalis, showed also cracked and ruptured cells in the presence of B-13. Besides, we also demonstrated that the analog of B-13, B-12, has also induced disruption of P. gingivalis and S. gordonii. This study revealed that butyrolactones can be considered as potent antibacterial compounds against oral pathogens causing medical complications.