(E)-tert-butyl methyl(4-(4-(prop-2-yn-1-yloxy)styryl)phenyl)carbamate | 1422568-49-7

• 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)-tert-butyl methyl(4-(4-(prop-2-yn-1-yloxy)styryl)phenyl)carbamate
• 英文别名: tert-butyl N-methyl-N-[4-[(E)-2-(4-prop-2-ynoxyphenyl)ethenyl]phenyl]carbamate
• CAS: 1422568-49-7
• 化学式: C₂₃H₂₅NO₃
• 分子量: 363.456
• InChiKey: CRZULMYYEHRWBS-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-tert-butyl methyl(4-(4-(prop-2-yn-1-yloxy)styryl)phenyl)carbamate 在 copper(l) iodide 、 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 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 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
• 作为产物：
  描述：

  (4-氨基-苯基)-磷酸二乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 13.0h， 生成 (E)-tert-butyl methyl(4-(4-(prop-2-yn-1-yloxy)styryl)phenyl)carbamate
  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

• [EN] RADIOLIGANDS FOR MYELIN<br/>[FR] RADIOLIGANDS POUR LA MYÉLINE
  申请人：UNIV CASE WESTERN RESERVE

  公开号：WO2017156303A1

  公开（公告）日：2017-09-14

  A radioligand for labeling myelin includes a fluorescent trans-stilbene derivative.

  用于标记髓鞘的放射性配体包括荧光转-双苯乙烯衍生物。
• Discovery of 1,2,3-Triazole Derivatives for Multimodality PET/CT/Cryoimaging of Myelination in the Central Nervous System
  作者：Chunying Wu、Brendan Eck、Sheng Zhang、Junqing Zhu、Anand Dev Tiwari、Yifan Zhang、Yunjie Zhu、Jinming Zhang、Bin Wang、Xizhen Wang、Xu Wang、Jingqiang You、Jian Wang、Yihui Guan、Xingdang Liu、Xin Yu、Bruce D. Trapp、Robert Miller、Jerry Silver、David Wilson、Yanming Wang

  DOI：10.1021/acs.jmedchem.6b01328

  日期：2017.2.9

  Myelin pathology is present in many neurological conditions such as multiple sclerosis (MS) and traumatic spinal cord injury (SCI): To. facilitate development of novel therapies aimed at myelin repair, we set out to develop imaging agents that permit direct quantification of myelination in vivo. In this work, we designed and synthesized a series of fluorescent fluorinated myelin imaging agents that can be used for in vivo positron emission tomography (PET) imaging combined with subsequent post-mortem fluorescent cryoimaging. Structure-activity relationship (SAR) studies of the newly developed myelin imaging agents led us to identify a lead compound (TAFDAS, 21) that readily enters the brain and spinal cord and selectively binds to myelin. By conducting sequential PET and 3D cryoimaging in an SCI rat model, we demonstrated for the first time that PET and cryoimaging can be combined as a novel technique to image the spinal cord with high sensitivity and spatial resolution.
• 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.