(E)-tri-tert-butyl 2,2′,2″-(10-(2-((3-(4-((4-(4-((tert-butoxycarbonyl)(methyl)amino)styryl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)propyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate | 1422568-51-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-tri-tert-butyl 2,2′,2″-(10-(2-((3-(4-((4-(4-((tert-butoxycarbonyl)(methyl)amino)styryl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)propyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate
• 英文别名: tert-butyl 2-[4-[2-[3-[4-[[4-[(E)-2-[4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]phenyl]ethenyl]phenoxy]methyl]triazol-1-yl]propylamino]-2-oxoethyl]-7,10-bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetate
• CAS: 1422568-51-1
• 化学式: C₅₄H₈₃N₉O₁₀
• 分子量: 1018.31
• InChiKey: YGVCMVPGROXIIX-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  73
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (E)-tri-tert-butyl 2,2′,2″-(10-(2-((3-(4-((4-(4-((tert-butoxycarbonyl)(methyl)amino)styryl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)propyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate 、 三氟乙酸 反应 24.0h， 以0.085 g的产率得到(E)-2,2′,2″-(10-(2-((3-(4-((4-(4-(methylamino)styryl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)propyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid trifluoroacetate
  参考文献：
  名称：

  Synthesis and Characterization of a Novel Gadolinium-Based Contrast Agent for Magnetic Resonance Imaging of Myelination

  摘要：

  Myelin is a membrane system that fosters nervous impulse conduction in the vertebrate nervous system. Myelin sheath disruption is a common characteristic of several neuroodegenerative diseases such as multiple sclerosis (MS) and various leukodystrophies. To date, the diagnosis of MS is obtained using a set of criteria in which MRI observations play a central role. However, because of the lack of specificity for myelin integrity, the use of MRI as the primary diagnostic tool has not yet been accepted. In order to improve MR specificity, we began developing MR probes targeted toward myelin. In this work we describe a new myelin-targeted MR contrast agent, Gd-DODAS, based on a stilbene binding moiety and demonstrate its ability to specifically bind to myelin in vitro and in vivo. We also present evidence that Gd-DODAS generates MR contrast in vivo in T-1-weighed images and in T-1 maps that correlates to the myelin content.

  DOI：

  10.1021/jm301435z
• 作为产物：
  描述：

  (4-氨基-苯基)-磷酸二乙酯 在 copper(l) iodide 、 sodium hydride 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 40.0h， 生成 (E)-tri-tert-butyl 2,2′,2″-(10-(2-((3-(4-((4-(4-((tert-butoxycarbonyl)(methyl)amino)styryl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)propyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate
  参考文献：
  名称：

  Synthesis and Characterization of a Novel Gadolinium-Based Contrast Agent for Magnetic Resonance Imaging of Myelination

  摘要：

  Myelin is a membrane system that fosters nervous impulse conduction in the vertebrate nervous system. Myelin sheath disruption is a common characteristic of several neuroodegenerative diseases such as multiple sclerosis (MS) and various leukodystrophies. To date, the diagnosis of MS is obtained using a set of criteria in which MRI observations play a central role. However, because of the lack of specificity for myelin integrity, the use of MRI as the primary diagnostic tool has not yet been accepted. In order to improve MR specificity, we began developing MR probes targeted toward myelin. In this work we describe a new myelin-targeted MR contrast agent, Gd-DODAS, based on a stilbene binding moiety and demonstrate its ability to specifically bind to myelin in vitro and in vivo. We also present evidence that Gd-DODAS generates MR contrast in vivo in T-1-weighed images and in T-1 maps that correlates to the myelin content.

  DOI：

  10.1021/jm301435z

文献信息

• Synthesis and Characterization of a Novel Gadolinium-Based Contrast Agent for Magnetic Resonance Imaging of Myelination
  作者：Luca Frullano、Junqing Zhu、Robert H. Miller、Yanming Wang

  DOI：10.1021/jm301435z

  日期：2013.2.28

  Myelin is a membrane system that fosters nervous impulse conduction in the vertebrate nervous system. Myelin sheath disruption is a common characteristic of several neuroodegenerative diseases such as multiple sclerosis (MS) and various leukodystrophies. To date, the diagnosis of MS is obtained using a set of criteria in which MRI observations play a central role. However, because of the lack of specificity for myelin integrity, the use of MRI as the primary diagnostic tool has not yet been accepted. In order to improve MR specificity, we began developing MR probes targeted toward myelin. In this work we describe a new myelin-targeted MR contrast agent, Gd-DODAS, based on a stilbene binding moiety and demonstrate its ability to specifically bind to myelin in vitro and in vivo. We also present evidence that Gd-DODAS generates MR contrast in vivo in T-1-weighed images and in T-1 maps that correlates to the myelin content.