2-(benzotriazol-1-yl)-ethyliodide | 936252-71-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 2-(benzotriazol-1-yl)-ethyliodide
• 英文别名: benzotriazol-1-yl-ethyliodide；1-(2-Iodoethyl)benzotriazole
• CAS: 936252-71-0
• 化学式: C₈H₈IN₃
• 分子量: 273.076
• InChiKey: BCDZGSFTVRUYJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(benzotriazol-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"-(benzotriazole-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-苯并三唑-1-基)乙醇 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 以88%的产率得到2-(benzotriazol-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

• IMPROVED METAL-LIGAND COMPLEX CATALYZED PROCESSES
  申请人：UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY CORPORATION

  公开号：EP0873292A1

  公开（公告）日：1998-10-28
• HYDROFORMYLATION PROVESS USING A HETEREOCYCLIC AGENT AS CATALYTIC STABILIZING AGENT
  申请人：Dow Technology Investments LLC

  公开号：EP2970074B1

  公开（公告）日：2019-04-24
• HETEREOCYCLIC AGENT AS CATALYTIC STABILIZING AGENT IN A HYDROFORMYLATION PROCESS
  申请人：DOW TECHNOLOGY INVESTMENTS LLC

  公开号：US20150376101A1

  公开（公告）日：2015-12-31

  A heterocyclic nitrogen stabilizing agent is employed to reduce the rate of catalyst deactivation in a hydroformylation process.
• US5731472A
  申请人：——

  公开号：US5731472A

  公开（公告）日：1998-03-24
• US9573870B2
  申请人：——

  公开号：US9573870B2

  公开（公告）日：2017-02-21