N-[3-[2-[2-[3-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]propoxy]ethoxy]ethoxy]propyl]-1-fluorocyclooct-2-yne-1-carboxamide | 1227407-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: N-[3-[2-[2-[3-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]propoxy]ethoxy]ethoxy]propyl]-1-fluorocyclooct-2-yne-1-carboxamide
• CAS: 1227407-75-1
• 化学式: C₂₉H₄₇FN₄O₆S
• 分子量: 598.78
• InChiKey: IYLZLLGTYWLOJB-SZMZOMNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  41
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4,7,10-四氮杂环十二烷-1,4,7-三(乙酸)-10-(叠异丙基乙基乙酰胺) 、 N-[3-[2-[2-[3-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]propoxy]ethoxy]ethoxy]propyl]-1-fluorocyclooct-2-yne-1-carboxamide 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以44%的产率得到2-[4-[2-[3-[4-[3-[2-[2-[3-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]propoxy]ethoxy]ethoxy]propylcarbamoyl]-4-fluoro-6,7,8,9-tetrahydro-5H-cycloocta[d]triazol-1-yl]propylamino]-2-oxoethyl]-7,10-bis(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetic acid
  参考文献：
  名称：

  Synthesis of a DOTA−Biotin Conjugate for Radionuclide Chelation via Cu-Free Click Chemistry

  摘要：

  A strain-induced copper-free click reaction mediated by a new and easily prepared cyclooctyne derivative was used to efficiently assemble a DOTA biotin adduct capable of radionuclide ((68)Ga) uptake. This synthetic strategy offers a potentially general and convenient means of preparing targeted radiolabeling and radiotherapeutic agents.

  DOI：

  10.1021/ol100774p
• 作为产物：
  描述：

  1-fluoro-2-cyclooctyne-1-carboxylic acid pentafluorophenyl ester 、 N-(3-(2-(2-(3-氨基丙氧基)乙氧基)乙氧基)丙基)-5-((3AS,4S,6AR)-2-氧代六氢-1H-噻吩并[3,4-D]咪唑哌啶-4-基)戊酰胺 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84 mg的产率得到N-[3-[2-[2-[3-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]propoxy]ethoxy]ethoxy]propyl]-1-fluorocyclooct-2-yne-1-carboxamide
  参考文献：
  名称：

  Synthesis of a DOTA−Biotin Conjugate for Radionuclide Chelation via Cu-Free Click Chemistry

  摘要：

  A strain-induced copper-free click reaction mediated by a new and easily prepared cyclooctyne derivative was used to efficiently assemble a DOTA biotin adduct capable of radionuclide ((68)Ga) uptake. This synthetic strategy offers a potentially general and convenient means of preparing targeted radiolabeling and radiotherapeutic agents.

  DOI：

  10.1021/ol100774p

文献信息

• Synthesis of a DOTA−Biotin Conjugate for Radionuclide Chelation via Cu-Free Click Chemistry
  作者：Michael K. Schultz、Sharavathi G. Parameswarappa、F. Christopher Pigge

  DOI：10.1021/ol100774p

  日期：2010.5.21

  A strain-induced copper-free click reaction mediated by a new and easily prepared cyclooctyne derivative was used to efficiently assemble a DOTA biotin adduct capable of radionuclide ((68)Ga) uptake. This synthetic strategy offers a potentially general and convenient means of preparing targeted radiolabeling and radiotherapeutic agents.