5-tributylstannyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil | 732298-75-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-tributylstannyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil
• 英文别名: 5-Tributylstannyl-1-(2-deoxy-2-fluoro-beta-d-arabinofuranosyl)uracil；1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-tributylstannylpyrimidine-2,4-dione
• CAS: 732298-75-8
• 化学式: C₂₁H₃₇FN₂O₅Sn
• 分子量: 535.244
• InChiKey: BJDDDTXKWAIWSX-FNDYBIIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-tributylstannyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil 在 sodium hydroxide 、 sodium iodide 、 双氧水 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 [125I]-Fialuridine
  参考文献：
  名称：

  Synthesis and in Vitro Evaluation of 5-[¹⁸F]Fluoroalkyl Pyrimidine Nucleosides for Molecular Imaging of Herpes Simplex Virus Type 1 Thymidine Kinase Reporter Gene Expression

  摘要：

  Two novel series of 5-fluoroalkyl-2'-deoxyuridines (FPrDU, FBuDU, FPeDU) and 2'-fluoro-2'-deoxy-5-fluoroalkylarabinouridines (FFPrAU, FFBuAU, FFPeAU) that have three, four, or five methylene units (propyl, butyl, or pentyl) at C-5 were prepared and tested as reporter probes for imaging herpes simplex virus type I thymidine kinase (HSV1-tk) gene expression. The Negishi coupling methodology was employed in efficiently synthesizing the radiolabeling precursors. All six 5-[F-18]fluoroalkyl pyrimidines were readily prepared from 3-N-benzoyl-3',5'-di-O-benzoyl-protected 5-O-mesylate Precursors in 17-35% radiochemical yield (decay-corrected). In vitro studies highlighted that all six [F-18]-labeled nucleosides selectively accumulated in cells expressing the HSV1-TK protein and there was negligible uptake in control cells. [F-18]FPrDU, [F-18]FBuDU, [F-18]FPeDU, and [F-18]FFBuAU had the best uptake profiles. Despite their selective accumulation in HSV1-tk-expressing cells, all 5-fluoroalkyl pyrimidine nucleosides had low-to-negligible cytotoxic activity (CC50 > 1000-1209 mu M). Ultimately, the results demonstrated that 5-[F-18]fluoropropyl, [F-18]fluorobutyl, and [F-18]fluoropentyl pyrimidine nucleosides have the potential to be in vivo HSV1-TK PET reporter probes over a dynamic range of reporter gene expression levels.

  DOI：

  10.1021/jm800501d
• 作为产物：
  描述：

  C₇H₅O₂Pol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 5-tributylstannyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  Structure and Configuration of Phosphoeleganin, a Protein Tyrosine Phosphatase 1B Inhibitor from the Mediterranean Ascidian Sidnyum elegans

  摘要：

  A new phosphorylated polyketide, phosphoeleganin (1), has been isolated from the Mediterranean ascidian Sidnyum elegans. Its structure and configuration have been determined by extensive use of 2D NMR and microscale chemical degradation and/or derivatization. Phosphoeleganin (1) inhibited the protein tyrosine phosphatase 1B (PTP1B) activity.

  DOI：

  10.1021/acs.jnatprod.6b00063
• 作为试剂：
  描述：

  、 N4,2',3'-O,O-tribenzoylcytidin-5'-yl hydrogenophosphonate, triethylammonium salt 在 吡啶 、 5-tributylstannyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 O-(N4,2',3'-O,O-tribenzoylcytidin-5'-yl)-O-{N2-isobutyryl-2'-O-methyl-5'-O-[bis-(2-cyanoethyl)phosphoryl]guanosin-3'-yl} hydrogenphosphonate diester
  参考文献：
  名称：

  磷酰胺二核苷作为丙型肝炎病毒聚合酶抑制剂。

  摘要：

  合成了表现出与中性、两亲性、带正电或带负电的侧链的氨基磷酸酯核苷间键合的GC二核苷。在体外和在含有 HCV 复制子的细胞中评估了它们对丙型肝炎病毒 (HCV) NS5B 聚合酶的潜在抑制作用。虽然发现两亲物和带正电的类似物是无活性的，但当作为非对映异构体混合物进行测试时，中性 (1) 和带负电 (4) 的类似物会抑制酶活性。最有效的抑制剂被证明是带有羧基侧链的 5'-硫代磷酸化二核苷酸的 Sp 异构体 (8)（体外 IC 50 为 25 microM，在 HCV 亚基因组复制子中 EC 50 为 9 microM）。

  DOI：

  10.1021/jm800617c

文献信息

• TW2018/3885
  申请人：——

  公开号：——

  公开（公告）日：——
• Solid phase synthesis of 2-aminobenzothiazoles
  作者：Francesco Piscitelli、Carlo Ballatore、Amos B. Smith

  DOI：10.1016/j.bmcl.2009.11.055

  日期：2010.1

  A traceless solid supported protocol for the synthesis of 2-aminobenzothiazoles is described, employing resin-bound acyl-isothiocyanate and a series of anilines. Cyclization of the resulting N-acyl, N'-phenylthioureas generates the 2-aminobenzothiazole scaffold, which can be further elaborated prior to hydrazine-mediated cleavage of the final products from the carboxy-polystyrene resin. A small, focused library of 2-aminobenzothiazoles was prepared. (C) 2009 Elsevier Ltd. All rights reserved.