1,4,7-tris(tert-butoxycarbonylmethyl)-10-[4-((triphenylmethylthio)methyl)phenyl]methyl-1,4,7,10-tetraazacyclododecane | 1245403-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,4,7-tris(tert-butoxycarbonylmethyl)-10-[4-((triphenylmethylthio)methyl)phenyl]methyl-1,4,7,10-tetraazacyclododecane
• 英文别名: Tert-butyl 2-[4,7-bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-10-[[4-(tritylsulfanylmethyl)phenyl]methyl]-1,4,7,10-tetrazacyclododec-1-yl]acetate
• CAS: 1245403-45-5
• 化学式: C₅₃H₇₂N₄O₆S
• 分子量: 893.244
• InChiKey: KTIWDYPQHFPKMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  64
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,4,7-tris(tert-butoxycarbonylmethyl)-10-[4-((triphenylmethylthio)methyl)phenyl]methyl-1,4,7,10-tetraazacyclododecane 在 三乙基硅烷 、 丁硫醇 、 三氟乙酸 作用下， 以80%的产率得到1,4,7-tris(carboxymethyl)-10-[4-(thiomethyl)phenyl]methyl-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetic Acid Derived, Redox-Sensitive Contrast Agents for Magnetic Resonance Imaging

  摘要：

  The design and synthesis of three 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid (DO3A) derivatives bearing linkers with terminal thiol groups and a preliminary evaluation of their potential for use in assembling redox-sensitive magnetic resonance imaging contrast agents are reported. The linkers were selected on the basis of computational docking with a crystal structure of human serum albumin (HSA). Gd(III)-DO3A and EU(III)-DOA complexes were synthesized, and the structure of one complex was established by X-ray crystallographic analysis. The binding to HSA of a Gd(III)-DO3A complex bearing a thiol-terminated 3,6-dioxanonyl chain was competitively inhibited by homocysteine and by the corresponding Eu chelate. Binding, to HSA was abolished when the terminal thiol group of this complex was absent. The longitudinal water-proton relaxivities (r(1)) of the three Gd(III)-DO3A complexes and of two Gd(III)-1,4,7,10-tetraazacyclododecane-,4,7,10-tetraacetic acid (DOTA) complexes were measured in saline at 7 T. The DO3A complexes exhibited smaller r(t) values, in both bound and free states, than the DOTA complexes.

  DOI：

  10.1021/jm100592u
• 作为产物：
  描述：

  1-bromomethyl-4-(triphenylmethylthio)methylbenzene 、 1,4,7,10-四氮杂环十二烷-1,4,7-三乙酸三叔丁酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以80%的产率得到1,4,7-tris(tert-butoxycarbonylmethyl)-10-[4-((triphenylmethylthio)methyl)phenyl]methyl-1,4,7,10-tetraazacyclododecane
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetic Acid Derived, Redox-Sensitive Contrast Agents for Magnetic Resonance Imaging

  摘要：

  The design and synthesis of three 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid (DO3A) derivatives bearing linkers with terminal thiol groups and a preliminary evaluation of their potential for use in assembling redox-sensitive magnetic resonance imaging contrast agents are reported. The linkers were selected on the basis of computational docking with a crystal structure of human serum albumin (HSA). Gd(III)-DO3A and EU(III)-DOA complexes were synthesized, and the structure of one complex was established by X-ray crystallographic analysis. The binding to HSA of a Gd(III)-DO3A complex bearing a thiol-terminated 3,6-dioxanonyl chain was competitively inhibited by homocysteine and by the corresponding Eu chelate. Binding, to HSA was abolished when the terminal thiol group of this complex was absent. The longitudinal water-proton relaxivities (r(1)) of the three Gd(III)-DO3A complexes and of two Gd(III)-1,4,7,10-tetraazacyclododecane-,4,7,10-tetraacetic acid (DOTA) complexes were measured in saline at 7 T. The DO3A complexes exhibited smaller r(t) values, in both bound and free states, than the DOTA complexes.

  DOI：

  10.1021/jm100592u

文献信息

• Design, Synthesis, and Evaluation of 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetic Acid Derived, Redox-Sensitive Contrast Agents for Magnetic Resonance Imaging
  作者：Natarajan Raghunand、Gerald P. Guntle、Vijay Gokhale、Gary S. Nichol、Eugene A. Mash、Bhumasamudram Jagadish

  DOI：10.1021/jm100592u

  日期：2010.9.23

  The design and synthesis of three 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid (DO3A) derivatives bearing linkers with terminal thiol groups and a preliminary evaluation of their potential for use in assembling redox-sensitive magnetic resonance imaging contrast agents are reported. The linkers were selected on the basis of computational docking with a crystal structure of human serum albumin (HSA). Gd(III)-DO3A and EU(III)-DOA complexes were synthesized, and the structure of one complex was established by X-ray crystallographic analysis. The binding to HSA of a Gd(III)-DO3A complex bearing a thiol-terminated 3,6-dioxanonyl chain was competitively inhibited by homocysteine and by the corresponding Eu chelate. Binding, to HSA was abolished when the terminal thiol group of this complex was absent. The longitudinal water-proton relaxivities (r(1)) of the three Gd(III)-DO3A complexes and of two Gd(III)-1,4,7,10-tetraazacyclododecane-,4,7,10-tetraacetic acid (DOTA) complexes were measured in saline at 7 T. The DO3A complexes exhibited smaller r(t) values, in both bound and free states, than the DOTA complexes.