2-(benzoimidazol-1-yl)-ethyliodide | 861784-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(benzoimidazol-1-yl)-ethyliodide
• 英文别名: 1-(2-iodoethyl)-1H-benzimidazole；1-(2-iodo-ethyl)-1H-benzimidazole；1-(2-Jod-aethyl)-1H-benzimidazol；benzoimidazol-1-yl-ethyliodide；1-(2-Iodoethyl)benzimidazole
• CAS: 861784-06-7
• 化学式: C₉H₉IN₂
• 分子量: 272.088
• InChiKey: NPKIKRVQQQFXKT-UHFFFAOYSA-N

物化性质

• 沸点：
  347.2±44.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(benzoimidazol-1-yl)-ethyliodide 在 氨 、 caesium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3"-(benzoimidazole-1"-yl)ethyloxy)adenosine
  参考文献：
  名称：

  Structure−Activity Relationships of 2,N⁶,5‘-Substituted Adenosine Derivatives with Potent Activity at the A_2B Adenosine Receptor

  摘要：

  2, N-6, and 5'-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A(2B)AR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N-6-ethyl or N-6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-( 3-( indolyl)ethyloxy) adenosine series. Indole 5 ''- or 6 ''-halo substitution was favored at the A(2B)AR, but a 5'-N-ethylcarboxyamide did not further enhance potency. 2-(3 ''-(6 ''-Bromoindolyl)ethyloxy)adenosine 28 displayed an A(2B)AR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5'-N-ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A(2B) and A(2A)ARs and a low efficacy partial agonist at A(1) and A(3)ARs. Thus, we have identified and optimized 2-(2-arylethyl) oxo moieties in AR agonists that enhance A(2B)AR potency and selectivity.

  DOI：

  10.1021/jm061278q
• 作为产物：
  描述：

  2-(1H-苯并咪唑-1-基)乙醇 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 2.0h， 以88%的产率得到2-(benzoimidazol-1-yl)-ethyliodide
  参考文献：
  名称：

  Structure−Activity Relationships of 2,N⁶,5‘-Substituted Adenosine Derivatives with Potent Activity at the A_2B Adenosine Receptor

  摘要：

  2, N-6, and 5'-substituted adenosine derivatives were synthesized via alkylation of 2-oxypurine nucleosides leading to 2-arylalkylether derivatives. 2-(3-(Indolyl)ethyloxy)adenosine 17 was examined in both binding and cAMP assays and found to be a potent agonist of the human A(2B)AR. Simplification, altered connectivity, and mimicking of the indole ring of 17 failed to maintain A2BAR potency. Introduction of N-6-ethyl or N-6-guanidino substitution, shown to favor A2BAR potency, failed to enhance potency in the 2-( 3-( indolyl)ethyloxy) adenosine series. Indole 5 ''- or 6 ''-halo substitution was favored at the A(2B)AR, but a 5'-N-ethylcarboxyamide did not further enhance potency. 2-(3 ''-(6 ''-Bromoindolyl)ethyloxy)adenosine 28 displayed an A(2B)AR EC50 value of 128 nM, that is, more potent than the parent 17 (299 nM) and similar to 5'-N-ethylcarboxamidoadenosine (140 nM). Compound 28 was a full agonist at A(2B) and A(2A)ARs and a low efficacy partial agonist at A(1) and A(3)ARs. Thus, we have identified and optimized 2-(2-arylethyl) oxo moieties in AR agonists that enhance A(2B)AR potency and selectivity.

  DOI：

  10.1021/jm061278q

文献信息

• Ligand-promoted intramolecular dehydrogenative cross-coupling using a Cu catalyst: direct access to polycyclic heteroarenes
  作者：Devalina Ray、T. Manikandan、Arup Roy、Krishna N. Tripathi、Ravi P. Singh

  DOI：10.1039/c5cc01817j

  日期：——

  A copper(ii)-promoted intramolecular C–H coupling reaction between indole-2 and imidazole-2 moieties, which provides direct access to biheteroaryl incorporated polycyclic frameworks.

  一种铜（II）促进的间分子C-H偶联反应，介导了吲哚-2和咪唑-2基团之间的反应，直接获得了双杂环芳基多环骨架。
• Meisenheimer; Wieger, Journal fur praktische Chemie (Leipzig 1954), 1921, vol. <2> 102, p. 46,51, 53
  作者：Meisenheimer、Wieger

  DOI：——

  日期：——
• [EN] A2 ADENOSINE RECEPTOR AGONISTS<br/>[FR] AGONISTES DES RÉCEPTEURS D'ADÉNOSINE A2
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2009006089A3

  公开（公告）日：2009-04-09