1-(2-azidoethyl)-5-nitro-1H-indole | 1365478-38-1

• 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: 1-(2-azidoethyl)-5-nitro-1H-indole
• 英文别名: 1-(2-Azidoethyl)-5-nitroindole
• CAS: 1365478-38-1
• 化学式: C₁₀H₉N₅O₂
• 分子量: 231.214
• InChiKey: LHCBHDIUHNQWCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-azidoethyl)-5-nitro-1H-indole 、 (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 以85%的产率得到(1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-(4-{1-[2-(6-nitro-1H-indol-3-yl)ethyl]-1H-1,2,3-triazol-4-yl}butyl)cyclohexanecarb
  参考文献：
  名称：

  Nanomolar E-Selectin Antagonists with Prolonged Half-Lives by a Fragment-Based Approach

  摘要：

  Selectins, a family of C-type lectins, play a key role in inflammatory diseases (e.g., asthma and arthritis). However, the only millimolar affinity of sialyl Lewis(x) (sLe(x)), which is the common tetrasaccharide epitope of all physiological selectin ligands, has been a major obstacle to the development of selectin antagonists for therapeutic applications. In a fragment-based approach guided by NMR, ligands binding to a second site in close proximity to a sLe(x) mimic were identified. A library of antagonists obtained by connecting the sLe(x) mimic to the best second-site ligand via triazole linkers of different lengths was evaluated by surface plasmon resonance. Detailed analysis of the five most promising candidates revealed antagonists with K-D values ranging from 30 to 89 nM. In contrast to carbohydratelectin complexes with typical half-lives (t(1/2)) in the range of one second or even less, these fragment-based selectin antagonists show t(1/2) of several minutes. They exhibit a promising starting point for the development of novel anti-inflammatory drugs.

  DOI：

  10.1021/ja4029582
• 作为产物：
  描述：

  5-硝基吲哚 在 sodium azide 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 1-(2-azidoethyl)-5-nitro-1H-indole
  参考文献：
  名称：

  [EN] E-SELECTIN ANTAGONISTS
  [FR] ANTAGONISTES DE L'E-SÉLECTINE

  摘要：

  提供了抑制E-选择素结合介导的体内外过程的化合物、组合物和方法。更具体地，描述了特定的糖类拟态化合物，其中这些化合物是E-选择素拮抗剂。

  公开号：

  WO2012037034A1

文献信息

• Exploiting translational stalling peptides in an effort to extend azithromycin interaction within the prokaryotic ribosome nascent peptide exit tunnel
  作者：Arren Z. Washington、Subhasish Tapadar、Alex George、Adegboyega K. Oyelere

  DOI：10.1016/j.bmc.2015.04.078

  日期：2015.8

  The ribosome is the primary protein synthesis machine in the cell and is a target for treatment of a variety of diseases including bacterial infection and cancer. The ribosomal peptide exit tunnel, the route of egress for the nascent peptide, is an inviting site for drug design. Toward a rational engagement of the nascent peptide components for the design of small molecule inhibitors of ribosome function, we designed and disclosed herein a set of N-10 indole functionalized azithromycin analogs. The indole moiety of these compounds is designed to mimic the translation stalling interaction of SecM W155 side-chain with the prokaryotic (Escherichia coli) ribosome A751 residue. Many of these N-10 functionalized compounds have enhanced translation inhibition activities against E. coli ribosome relative to azithromycin while a subset inhibited the growth of representative susceptible bacteria strains to about the same extent as azithromycin. Moreover, the inclusion of bovine serum in the bacterial growth media enhanced the anti-bacterial potency of the N-10 functionalized azithromycin analogs by as high as 10-fold. Published by Elsevier Ltd.