1-[2-N-[2-(trimethylsilyl)ethoxycarbonyl]pteroyl]imidazole | 292045-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 1-[2-N-[2-(trimethylsilyl)ethoxycarbonyl]pteroyl]imidazole
• 英文别名: (6-([4-(imidazol-1-ylcarbonyl)phenylamino]methyl)-4-oxo-3,4-dihydro-pteridin-2-yl)-carbamic acid 2-trimethylsilylethyl ester；1-[2-[2-(trimethylsilyl)ethoxycarbonyl]pteroyl]-imidazole；1-[2-N-[2-(trimethylsilyl)ethoxycarbonyl]pteroyl]-imidazole；2-trimethylsilylethyl N-[6-[[4-(imidazole-1-carbonyl)anilino]methyl]-4-oxo-3H-pteridin-2-yl]carbamate
• CAS: 292045-48-8
• 化学式: C₂₃H₂₆N₈O₄Si
• 分子量: 506.596
• InChiKey: NCXWLNDBFDXSBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  153
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-[2-N-[2-(trimethylsilyl)ethoxycarbonyl]pteroyl]imidazole 在 三乙胺 、 7-甲基-1,5,7-三氮杂二环[4.4.0]癸-5-烯 、 氯甲酸异丁酯 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 1-(2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)-4-N-[γ-[α-[2-(trimethylsilyl)ethoxy]-2-N-[2-(trimethylsilyl)ethoxycarbonyl]folyl]]cytosine
  参考文献：
  名称：

  开发一种有效的中间体α-[2-（三甲基甲硅烷基）乙氧基] -2-N- [2-（三甲基甲硅烷基）乙氧基羰基]叶酸，用于合成叶酸（γ）-共轭物，并将其用于合成叶酸（γ）叶酸-核苷结合物。

  摘要：

  DOI：

  10.1021/jo000132a
• 作为产物：
  描述：

  folate 在 carboxypeptidase G 、 三乙胺 、 zinc(II) chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 130.0h， 生成 1-[2-N-[2-(trimethylsilyl)ethoxycarbonyl]pteroyl]imidazole
  参考文献：
  名称：

  A step-wise synthetic approach is necessary to access γ-conjugates of folate: folate-conjugated prodigiosenes

  摘要：

  尽管有大量的文献描述了将叶酸与药效团反应，但这种方法无法有效地提供所需的共轭物的正确位置异构体。

  DOI：

  10.1039/c9ra01435g

文献信息

• Process for producing folic acid derivatives
  申请人：Kataoka Kazunori

  公开号：US20070142387A1

  公开（公告）日：2007-06-21

  This invention provides a process for efficient production of folic acid derivatives suitable for forming conjugates of anticancer drug with folic acid. It discloses a process comprising a step of reacting 2-amino-protected pteroylimidazole with γ-lower alkyl glutamate; and a step of reacting the resulting product with an amino compound having a reactive group which is readily reactable with a functional group of the drug.

  该发明提供了一种高效生产适合与叶酸形成抗癌药物偶联物的叶酸衍生物的方法。其中包括反应2-氨基保护的叶酸咪唑与γ-低烷基谷氨酸的步骤，以及反应所得产物与具有与药物的功能基易于反应的反应性基团的氨基化合物的步骤。
• Folic acid functionalization for targeting self-assembled paclitaxel-based nanoparticles
  作者：Eleonora Colombo、Davide Andrea Coppini、Simone Maculan、Pierfausto Seneci、Benedetta Santini、Filippo Testa、Lucia Salvioni、Giovanni Maria Vanacore、Miriam Colombo、Daniele Passarella

  DOI：10.1039/d2ra06306a

  日期：——

  Hetero-nanoparticles self-assembled from a conjugate bearing folic acid as the targeting agent, and another bearing paclitaxel as the active agent are reported. Hetero-nanoparticles containing varying percentages of folic acid conjugates are characterised, and their biological activity is determined.

  报道了由以叶酸为靶向剂的缀合物和另一种以紫杉醇为活性剂的缀合物自组装的杂纳米颗粒。表征了含有不同百分比的叶酸缀合物的杂纳米颗粒，并确定了它们的生物活性。
• Cryptophane-Folate Biosensor for ¹²⁹Xe NMR
  作者：Najat S. Khan、Brittany A. Riggle、Garry K. Seward、Yubin Bai、Ivan J. Dmochowski

  DOI：10.1021/bc5005526

  日期：2015.1.21

  Folate-conjugated cryptophane was developed for targeting cryptophane to membrane-bound folate receptors that are overexpressed in many human cancers. The cryptophane biosensor was synthesized in 20 nonlinear steps, which included functionalization with folate recognition moiety, solubilizing peptide, and Cy3 fluorophore. Hyperpolarized Xe-129 NMR studies confirmed xenon binding to the folate-conjugated cryptophane. Cellular internalization of biosensor was monitored by confocal laser scanning microscopy and quantified by flow cytometry. Competitive blocking studies confirmed cryptophane endocytosis through a folate receptor-mediated pathway. Flow cytometry revealed 10-fold higher cellular internalization in KB cancer cells overexpressing folate receptors compared to HT-1080 cells with normal folate receptor expression. The biosensor was determined to be nontoxic in HT-1080 and KB cells by MTT assay at low micromolar concentrations typically used for hyperpolarized Xe-129 NMR experiments.
• EP1734044
  申请人：——

  公开号：——

  公开（公告）日：——
• Regioselective synthesis of folic acid conjugates from diether-type archaeal lipid analogues
  作者：Céline Lainé、Clémence Mocquet、Loïc Lemiègre、Thierry Benvegnu

  DOI：10.1016/j.tet.2008.12.013

  日期：2009.2

  A regioselective access to both alpha- and gamma-folic acid conjugates derived from archaeal lipid analogues is described. The synthetic approach is based on conveniently protected glutamates that led first to alpha- and gamma-glutamate derivatives. The final reconstruction of the folic acid moiety was achieved through the reaction of a protected/activated pteroate followed by a simple deprotection step. These alpha- and gamma-folic acid conjugates Would permit to establish the importance of a regiocontrolled introduction of folic acid on the folic acid/folate receptor interaction in the case of a targeted drug/gene delivery. (C) 2008 Elsevier Ltd. All rights reserved.