2-nitro-1-pentyl-1H-imidazole | 20358-62-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-nitro-1-pentyl-1H-imidazole
• 英文别名: N-Amyl-2-nitro-imidazol；2-Nitro-1-pentylimidazole；2-nitro-1-pentylimidazole
• CAS: 20358-62-7
• 化学式: C₈H₁₃N₃O₂
• 分子量: 183.21
• InChiKey: GFJHZKIOXGMXBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-nitro-1-pentyl-1H-imidazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以75%的产率得到4-bromo-2-nitro-1-pentyl-1H-imidazole
  参考文献：
  名称：

  Identification of a Human Toll-Like Receptor (TLR) 8-Specific Agonist and a Functional Pan-TLR Inhibitor in 2-Aminoimidazoles

  摘要：

  Activation of human toll-like receptor-8 (TLR8), expressed in myeloid dendritic cells, monocytes, and monocyte-derived dendritic cells, evokes a distinct cytokine profile which favors the development of Type 1 helper T cells. Part structures of the 2-aminobenzimidazole scaffold were examined with a-view to identifying structural requisites corresponding to the smallest possible fragment of the benzimidazole core that would allow for retention of TLR8-agonistic activity. TLR8-specific agonistic activity was retained in 1-penty1-4-phenyl-1H-imidazol-2-amine. The crystal structure of this compound bound to the TLR8 ectodomain displayed binding interactions that are common to other TLR8 agonists. This compound showed markedly attenuated proinflammatory properties in ex vivo human blood models. SAP. studies revealed that 4-(2-(benzyloxy)pheny1)-1-pentyl-1H-imidazol-2-amine inhibited TLR signaling in a variety of TLR reporter cell lines, as well as in pharmacologically relevant human blood model systems. A kinase screen of this compound showed relative specificity for calmodulin kinases.

  DOI：

  10.1021/acs.jmedchem.6b00023
• 作为产物：
  描述：

  2-硝基咪唑 、 1-碘戊烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以82%的产率得到2-nitro-1-pentyl-1H-imidazole
  参考文献：
  名称：

  Identification of a Human Toll-Like Receptor (TLR) 8-Specific Agonist and a Functional Pan-TLR Inhibitor in 2-Aminoimidazoles

  摘要：

  Activation of human toll-like receptor-8 (TLR8), expressed in myeloid dendritic cells, monocytes, and monocyte-derived dendritic cells, evokes a distinct cytokine profile which favors the development of Type 1 helper T cells. Part structures of the 2-aminobenzimidazole scaffold were examined with a-view to identifying structural requisites corresponding to the smallest possible fragment of the benzimidazole core that would allow for retention of TLR8-agonistic activity. TLR8-specific agonistic activity was retained in 1-penty1-4-phenyl-1H-imidazol-2-amine. The crystal structure of this compound bound to the TLR8 ectodomain displayed binding interactions that are common to other TLR8 agonists. This compound showed markedly attenuated proinflammatory properties in ex vivo human blood models. SAP. studies revealed that 4-(2-(benzyloxy)pheny1)-1-pentyl-1H-imidazol-2-amine inhibited TLR signaling in a variety of TLR reporter cell lines, as well as in pharmacologically relevant human blood model systems. A kinase screen of this compound showed relative specificity for calmodulin kinases.

  DOI：

  10.1021/acs.jmedchem.6b00023

文献信息

• [EN] HYPOXIA ACTIVATED PRODRUGS OF ANTHRACYCLINES<br/>[FR] PROMÉDICAMENTS D'ANTHRACYCLINES ACTIVÉS PAR UNE HYPOXIE
  申请人：THRESHOLD PHARMACEUTICALS INC

  公开号：WO2009018163A1

  公开（公告）日：2009-02-05

  Hypoxia activated prodrug compounds of anthracyclines are useful in the treatment of cancer and other hyperproliferative diseases. Certain compounds contain a 2-nitroimidazole moiety covalently bonded via the 1-N nitrogen atom to an alkylene and/or a heterolalyene linker; the alkylene and/or a heterolalyene linker is covalently bonded to the anthracycline.
• Identification of a Human Toll-Like Receptor (TLR) 8-Specific Agonist and a Functional Pan-TLR Inhibitor in 2-Aminoimidazoles
  作者：Mallesh Beesu、Giuseppe Caruso、Alex C. D. Salyer、Nijunj M. Shukla、Karishma K. Khetani、Luke J. Smith、Lauren M. Fox、Hiromi Tanji、Umeharu Ohto、Toshiyuki Shimizu、Sunil A. David

  DOI：10.1021/acs.jmedchem.6b00023

  日期：2016.4.14

  Activation of human toll-like receptor-8 (TLR8), expressed in myeloid dendritic cells, monocytes, and monocyte-derived dendritic cells, evokes a distinct cytokine profile which favors the development of Type 1 helper T cells. Part structures of the 2-aminobenzimidazole scaffold were examined with a-view to identifying structural requisites corresponding to the smallest possible fragment of the benzimidazole core that would allow for retention of TLR8-agonistic activity. TLR8-specific agonistic activity was retained in 1-penty1-4-phenyl-1H-imidazol-2-amine. The crystal structure of this compound bound to the TLR8 ectodomain displayed binding interactions that are common to other TLR8 agonists. This compound showed markedly attenuated proinflammatory properties in ex vivo human blood models. SAP. studies revealed that 4-(2-(benzyloxy)pheny1)-1-pentyl-1H-imidazol-2-amine inhibited TLR signaling in a variety of TLR reporter cell lines, as well as in pharmacologically relevant human blood model systems. A kinase screen of this compound showed relative specificity for calmodulin kinases.