2,2,2-trifluoro-N-(2-oxotetrahydrothiophen-3-yl)acetamide | 78829-05-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2,2-trifluoro-N-(2-oxotetrahydrothiophen-3-yl)acetamide
• 英文别名: TFA-tHcy；N-trifluoroacetylhomocysteine thiolactone；2,2,2-trifluoro-N-(2-oxothiolan-3-yl)acetamide
• CAS: 78829-05-7
• 化学式: C₆H₆F₃NO₂S
• 分子量: 213.18
• InChiKey: QDHMJEONPBNKOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  三氟乙酸酐 、 高半胱氨酸硫内酯 以 乙腈 为溶剂， 反应 0.67h， 以96%的产率得到2,2,2-trifluoro-N-(2-oxotetrahydrothiophen-3-yl)acetamide
  参考文献：
  名称：

  Synthesis and characterization of fluorinated homocysteine derivatives as potential molecular probes for 19 F magnetic resonance spectroscopy and imaging

  摘要：

  A N-trifluoroacetyl-protected amino acid containing a thioester function, 2,2,2-trifluoro-N-(2-oxo-tetrahydrothiophen-3-yl)acetamide (TFA-tHcy), has been synthesized and characterized. It was then used to prepare a fluorine-labeled N-homocysteinylated protein, F-19-Hcy-epsilon N-Lys-albumin, that was characterized by SDS-PAGE, MALDI-TOF-MS, UV-vis and F-19 NMR spectroscopy. On average, four N-trifluoroacetylhomocysteine residues were covalently conjugated to human serum albumin through the N-substituted homocysteine thiolactone. The in situ homocysteinylation of human plasma proteins with TFA-tHcy has also been performed and has led to the formation of N-homocysteinylated proteins, with albumin modification accounting for ca. 75% of all fluorine-labeled human plasma proteins. The synthesized fluorinated molecular probes can be potentially used as informative molecular probes for in vivo F-19 magnetic resonance spectroscopy and imaging. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.119

文献信息

• Homocystamide Conjugates of Human Serum Albumin as a Platform to Prepare Bimodal Multidrug Delivery Systems for Boron Neutron Capture Therapy
  作者：Tatyana Popova、Maya A. Dymova、Ludmila S. Koroleva、Olga D. Zakharova、Vladimir A. Lisitskiy、Valeria I. Raskolupova、Tatiana Sycheva、Sergei Taskaev、Vladimir N. Silnikov、Tatyana S. Godovikova

  DOI：10.3390/molecules26216537

  日期：——

  thenoyltrifluoroacetone were bound to each albumin. Along with its beneficial properties as a chemotherapeutic agent, thenoyltrifluoroacetone is a promising magnetic resonance imaging agent. The conjugation of bimodal HSA with undecahydro-closo-dodecaborate only slightly reduced human glioma cell line viability in the absence of irradiation (~30 μM of boronated albumin) but allowed for neutron capture and

  硼中子俘获疗法是一种独特的癌症辅助疗法，可用于治疗包括恶性神经胶质瘤在内的各种恶性肿瘤。硼化合物与人血清白蛋白 (HSA)（一种血浆半衰期长的载体蛋白）的结合有望延长硼化合物的全身循环并增加它们在人神经胶质瘤细胞中的积累。我们报告了人血清白蛋白的荧光团标记的同型半胱酰胺缀合物的合成及其在硫醇-“点击”化学中的用途，以制备可在肿瘤细胞中积累的新型多模式硼化白蛋白基治疗诊断剂。这项工作的新颖之处在于开发了用于成像引导的硼中子俘获疗法组合的白蛋白偶联物的合成方法。在此处，我们建议使用苯酰三氟丙酮作为抗癌治疗诊断结构的一部分：大约 5.4 分子的苯酰三氟丙酮与每个白蛋白结合。除了作为化学治疗剂的有益特性外，三氟丙酮是一种很有前途的磁共振成像剂。双峰 HSA 与十一氢-闭合碳-dodecaborate仅略微降低人胶质瘤细胞存活力在没有照射的（〜硼化白蛋白的30μM），但允许中子俘获和下超热中子通量降