(methyl-1 imidazolyl-5)-2 hydroxy-2 nitro-1 ethane | 85198-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (methyl-1 imidazolyl-5)-2 hydroxy-2 nitro-1 ethane
• 英文别名: 1-(3-methylimidazol-4-yl)-2-nitroethanol
• CAS: 85198-85-2
• 化学式: C₆H₉N₃O₃
• 分子量: 171.156
• InChiKey: WDJUXKTXQMCKPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.27
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.19
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (methyl-1 imidazolyl-5)-2 hydroxy-2 nitro-1 ethane 在 4-二甲氨基吡啶 、 乙酸酐 、 三氟乙酸铵 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 3-(1-(1-methyl-1H-imidazol-5-yl)-2-nitroethyl)-2-phenyl-1H-indole
  参考文献：
  名称：

  Focused structure-activity relationship profiling around the 2-phenylindole scaffold of a cannabinoid type-1 receptor agonist-positive allosteric modulator: site-III aromatic-ring congeners with enhanced activity and solubility

  摘要：

  Specific tuning of cannabinoid 1 receptor (CB1R) activity by small-molecule allosteric modulators is a therapeutic modality with multiple properties inherently advantageous to therapeutic applications. We previously generated a library of unique CB1R positive allosteric modulators (PAMs) derived from GAT211, which has three pharmacophoric sites critical to its ago-PAM activity. To elaborate our CB1R PAM library, we report the rational design and molecular-pharmacology profiling of several 2-phenylindole analogs modified at the "site-III" aromatic ring. The comprehensive structure-activity relationship (SAR) investigation demonstrates that attaching small lipophilic functional groups on the ortho-position of the GAT211 site-III phenyl ring could markedly enhance CB1R ago-PAM activity. Select site-III modifications also improved GAT211's water solubility. The SAR reported both extends the structural diversity of this compound class and demonstrates the utility of GAT211's site-III for improving the parent compound's drug-like properties of potency and/or aqueous solubility.

  DOI：

  10.1016/j.bmc.2020.115727
• 作为产物：
  描述：

  1-甲基-1氢-5-醛基-咪唑 、 硝基甲烷 在 1,1,2,3-四甲基胍 作用下， 生成 (methyl-1 imidazolyl-5)-2 hydroxy-2 nitro-1 ethane
  参考文献：
  名称：

  咪唑类生物碱—VI：芦荟的生物碱异构体，结构，合成

  摘要：

  从卢氏丝囊藻中分离出了八种咪唑生物碱：黄嘌呤，去甲红嘌呤，cynometrine，异黄嘌呤，异cynométrine，异辛基定，羟基黄嘌呤和西诺洛酮。从1-甲基-5-甲氧基羰基咪唑开始异丁烷和异氰基萘的合成，而从1-甲基-4-甲氧基羰基咪唑开始黄嘌呤和cynometrine的合成。

  DOI：

  10.1016/0040-4020(82)80023-9