[125I]-(E)-5-(2-Iodovinyl)-2'-fluoro-2'-deoxyuridine | 87782-48-7

• 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: [125I]-(E)-5-(2-Iodovinyl)-2'-fluoro-2'-deoxyuridine
• 英文别名: Ivfru；1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(E)-2-iodoethenyl]pyrimidine-2,4-dione
• CAS: 87782-48-7
• 化学式: C₁₁H₁₂FIN₂O₅
• 分子量: 398.13
• InChiKey: PZPQPNSQTAMTEX-TUSGKMHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  [125I]-(E)-5-(2-Iodovinyl)-2'-fluoro-2'-deoxyuridine 生成 1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(E)-2-(131I)iodanylethenyl]pyrimidine-2,4-dione
  参考文献：
  名称：

  IWASHINA T.; KNAUS E. E.; WIEBE L. I., J. LABELLED COMPOUNDS AND RADIOPHARM., 23,(1986) N 10-12, 1271-1272

  摘要：

  DOI：
• 作为产物：
  描述：

  非阿尿苷 在 bis-triphenylphosphine-palladium(II) chloride 、 一氯化碘 作用下， 以 乙腈 为溶剂， 反应 16.5h， 生成 [125I]-(E)-5-(2-Iodovinyl)-2'-fluoro-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis and Cellular Uptake of 2‘-Substituted Analogues of (E)-5-(2-[¹²⁵I]Iodovinyl)-2‘-deoxyuridine in Tumor Cells Transduced with the Herpes Simplex Type-1 Thymidine Kinase Gene. Evaluation as Probes for Monitoring Gene Therapy

  摘要：

  A useful synthetic methodology was developed to synthesize and radiolabel a series of (E)-5-(2-[I-125]iodovinyl)uracil nucleoside substrates for herpes simplex virus type-1 thymidine kinase (HSV-1 TK). (E)-5-(2-[I-125]Iodovinyl)-2'-deoxyuridine ([I-125]IVDU, 10), (E)-5-(2-[I-125]iodovinyl)-2'-fluoro-2'-deoxyuridine ([I-125]IVFRU, 11), (E)-5-(2-[I-125]iodovinyl)-2'-fluoro-2'-deoxyarabinouridine ([I-125]IVFAU, 12), and (E)-5-(2-[I-125]iodovinyl)arabinouridine ([I-125]IVAU, 13) were synthesized in 63-83% radiochemical yield by reaction of the unprotected (E)-5-(2-(trimethylsilyl)vinyl) precursors (6-9) with [I-125]ICl. Cellular uptake of these labeled compounds (10-13) was evaluated in vitro. All compounds showed minimal uptake in the KBALB cell line. However, increased uptake was observed for all compounds in KBALB-STK cells which are transduced with a replication incompetent Moloney murine leukemia virus vector encoding the HSV-1 TK gene. The results indicate that uptake of these compounds in KBALB-STK cells is variable and highly dependent on the nature of the sugar 2'-substituent. When a fluoro (12) or a hydroxy (13) substituent is present in the arabinofuranosyl (up) configuration at the 2'-position, there is diminished cellular uptake in KBALB-STK cells relative to hydrogen (10) or fluorine (11) in the ribofuranosyl (down) configuration at the 2'-position. Our results indicate that radiolabeled IVFRU (11) is most promising for further in vivo studies.

  DOI：

  10.1021/jm9606406

文献信息

• Nucleosides. 129. Synthesis of antiviral nucleosides: 5-alkenyl-1-(2-deoxy-2-fluoro-.beta.-D-arabinofuranosyl)uracils
  作者：Kyoichi A. Watanabe、Tsann Long Su、Uri Reichman、Nancy Greenberg、Carlos Lopez、Jack J. Fox

  DOI：10.1021/jm00367a020

  日期：1984.1

  Synthesis of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracils containing a vinyl (4a), 2-halovinyl (4b-d), or ethyl substituent at C-5 was achieved. These nucleosides were found to be about a log order less active than 2'-fluoro-5-iodo-ara-C (FIAC) against HSV-1, but they are much less cytotoxic against normal human lymphocytes than FIAC. Nucleosides 4a and 4e showed good activity against HSV-1

  合成了在C-5处含有乙烯基（4a），2-卤代戊基（4b-d）或乙基取代基的1-（2-脱氧-2-氟-β-D-阿拉伯呋喃糖基）尿嘧啶。发现这些核苷对HSV-1的活性比2'-氟-5-碘-ara-C（FIAC）的对数活性低，但与FIAC相比，它们对正常人淋巴细胞的细胞毒性小得多。核苷4a和4e对HSV-1（分别为ED50 = 0.16和0.24 microM）和HSV-2（ED50 = 0.69和0.65 microM）表现出良好的活性，几乎没有细胞毒性（ID50大于100 microM）。
• Synthesis and Cellular Uptake of 2‘-Substituted Analogues of (<i>E</i>)-5-(2-[¹²⁵I]Iodovinyl)-2‘-deoxyuridine in Tumor Cells Transduced with the Herpes Simplex Type-1 Thymidine Kinase Gene. Evaluation as Probes for Monitoring Gene Therapy
  作者：Kevin W. Morin、Elena D. Atrazheva、Edward E. Knaus、Leonard I. Wiebe

  DOI：10.1021/jm9606406

  日期：1997.7.1

  A useful synthetic methodology was developed to synthesize and radiolabel a series of (E)-5-(2-[I-125]iodovinyl)uracil nucleoside substrates for herpes simplex virus type-1 thymidine kinase (HSV-1 TK). (E)-5-(2-[I-125]Iodovinyl)-2'-deoxyuridine ([I-125]IVDU, 10), (E)-5-(2-[I-125]iodovinyl)-2'-fluoro-2'-deoxyuridine ([I-125]IVFRU, 11), (E)-5-(2-[I-125]iodovinyl)-2'-fluoro-2'-deoxyarabinouridine ([I-125]IVFAU, 12), and (E)-5-(2-[I-125]iodovinyl)arabinouridine ([I-125]IVAU, 13) were synthesized in 63-83% radiochemical yield by reaction of the unprotected (E)-5-(2-(trimethylsilyl)vinyl) precursors (6-9) with [I-125]ICl. Cellular uptake of these labeled compounds (10-13) was evaluated in vitro. All compounds showed minimal uptake in the KBALB cell line. However, increased uptake was observed for all compounds in KBALB-STK cells which are transduced with a replication incompetent Moloney murine leukemia virus vector encoding the HSV-1 TK gene. The results indicate that uptake of these compounds in KBALB-STK cells is variable and highly dependent on the nature of the sugar 2'-substituent. When a fluoro (12) or a hydroxy (13) substituent is present in the arabinofuranosyl (up) configuration at the 2'-position, there is diminished cellular uptake in KBALB-STK cells relative to hydrogen (10) or fluorine (11) in the ribofuranosyl (down) configuration at the 2'-position. Our results indicate that radiolabeled IVFRU (11) is most promising for further in vivo studies.
• IWASHINA T.; KNAUS E. E.; WIEBE L. I., J. LABELLED COMPOUNDS AND RADIOPHARM., 23,(1986) N 10-12, 1271-1272
  作者：IWASHINA T.、 KNAUS E. E.、 WIEBE L. I.

  DOI：——

  日期：——