7-bromo-2-cyanoimidazo[1,2-a]pyridine | 1525387-68-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 7-bromo-2-cyanoimidazo[1,2-a]pyridine
• 英文别名: 7-Bromoimidazo[1,2-a]pyridine-2-carbonitrile
• CAS: 1525387-68-1
• 化学式: C₈H₄BrN₃
• mdl: MFCD22077087
• 分子量: 222.044
• InChiKey: IRNDAJAYWYYKGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(N-Boc-6-cyanoindol-2-yl)phenylboronic acid pinacol ester 、 7-bromo-2-cyanoimidazo[1,2-a]pyridine 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 3.5h， 以70%的产率得到N-Boc-6-cyano-2-[4-(2-cyanoimidazo[1,2-a]pyridin-6-yl)phenyl]indole
  参考文献：
  名称：

  [EN] ANTIMICROBIAL COMPOUNDS
  [FR] COMPOSÉS ANTIMICROBIENS

  摘要：

  这项发明提供了抗微生物有机化合物及其组合物，可以杀灭或抑制一种或多种微生物病原体细胞的生长。

  公开号：

  WO2013040528A1

文献信息

• Synthesis and antifungal evaluation of head-to-head and head-to-tail bisamidine compounds
  作者：Son T. Nguyen、Steven M. Kwasny、Xiaoyuan Ding、John D. Williams、Norton P. Peet、Terry L. Bowlin、Timothy J. Opperman

  DOI：10.1016/j.bmc.2015.07.006

  日期：2015.9

  Herein, we describe the antifungal evaluation of 43 bisamidine compounds, of which 26 are new, having the scaffold [Am]-[HetAr]-[linker]-[HetAr]-[Am], in which [Am] is a cyclic or acyclic amidine group, [linker] is a benzene, pyridine, pyrimidine, pyrazine ring, or an aliphatic chain of two to four carbon, and [HetAr] is a 5,6-bicyclic heterocycle such as indole, benzimidazole, imidazopyridine, benzofuran, or benzothiophene. In the head-to-head series the two [HetAr] units are oriented such that the 5-membered rings are connected through the linker, and in the head-to-tail series, one of the [HetAr] systems is connected through the 6-membered ring; additionally, in some of the head-to-tail compounds, the [linker] is omitted. Many of these compounds exhibited significant antifungal activity against Candida albicans, Candida krusei, Candida glabrata, Candida parapsilosis, and Cryptococcus neoformans (MIC <= 4 mu g/ml). The most potent compounds, for example, P10, P19 and P34, are comparable in antifungal activities to amphotericin B (MIC 0.125 mu g/ml). They exhibited rapid fungicidal activity (>3 log(10) decrease in cfu/ml in 4 h) at concentrations equivalent to 4x the MIC in time kill experiments. The bisamidines strongly inhibited DNA, RNA and cell wall biosynthesis in C. albicans in macromolecular synthesis assays. However, the half-maximal inhibitory concentration for DNA synthesis was approximately 30-fold lower than those for RNA and cell wall biosynthesis. Fluorescence microscopy of intact cells of C. albicans treated with a bisamidine exhibited enhanced fluorescence in the presence of DNA, demonstrating that the bisamidine was localized to the nucleus. The results of this study show that bisamidines are potent antifungal agents with rapid fungicidal activity, which is likely to be the result of their DNA-binding activity. Although it was difficult to obtain a broad-spectrum antifungal compound with low cytotoxicity, some of the compounds (e.g., P9, P14 and P43) exhibited favorable CC50 values against HeLa cells and maintained considerable antifungal activity. (C) 2015 Elsevier Ltd. All rights reserved.