5-iodouracil-2,3-di-O-benzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid | 231619-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-iodouracil-2,3-di-O-benzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid
• CAS: 231619-85-5
• 化学式: C₂₄H₁₉IN₂O₆
• 分子量: 558.329
• InChiKey: RGHGJHIODOIVDB-UHFFFAOYSA-N

物化性质

• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  99.62
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-iodouracil-2,3-di-O-benzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid 在 bis-triphenylphosphine-palladium(II) chloride 三氯化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-{2-[3,4-Dihydroxy-5-oxo-5H-furan-(2Z)-ylidene]-ethyl}-5-furan-2-yl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of l-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations

  摘要：

  The novel C-5 substituted uracil derivatives Of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4,5-didehydro-5,6-dideoxy-L-ascorbic acid with unsaturated stannanes under Stille reaction conditions. The new compounds were evaluated for their antitumoral and antiviral activities. Among all compounds evaluated the 5-propynyl substituted uracil derivative of L-ascorbic acid (7) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50: 0.2-0.78 PM). However, this compound was also cytotoxic to human normal fibroblasts WI 38. The 5-(phenylethynyl)uracil-2,3-di-O-benzylated L-ascorbic acid derivative (4) exhibited an albeit slight (IC50: 55-108 mu M), but selective inhibitory effect toward all tumor cell lines except for cervical carcinoma (HeLa), pancreatic carcinoma (MiaPaCa-2), laryngeal carcinoma (Hep-2), and colon carcinoma (SW 620), and no cytotoxicity to normal human fibroblast (WI 38). Compound 7 showed some, not highly specific, inhibitory potential against vesicular stomatitis virus, Coxsackie 134 virus, and Sindbis viruses (EC50: 1.6 mu M). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.046
• 作为产物：
  描述：

  5-碘尿嘧啶 、 5,6-di-O-acetyl-2,3-di-O-benzyl-L-ascorbic acid 在 ammonium sulfate 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 生成 5-iodouracil-2,3-di-O-benzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid
  参考文献：
  名称：

  The novel C-5 aryl, alkenyl, and alkynyl substituted uracil derivatives of l-ascorbic acid: Synthesis, cytostatic, and antiviral activity evaluations

  摘要：

  The novel C-5 substituted uracil derivatives Of L-ascorbic acid were synthesized by coupling of 5-iodouracil-4,5-didehydro-5,6-dideoxy-L-ascorbic acid with unsaturated stannanes under Stille reaction conditions. The new compounds were evaluated for their antitumoral and antiviral activities. Among all compounds evaluated the 5-propynyl substituted uracil derivative of L-ascorbic acid (7) exhibited the most pronounced cytostatic activities against all examined tumor cell lines (IC50: 0.2-0.78 PM). However, this compound was also cytotoxic to human normal fibroblasts WI 38. The 5-(phenylethynyl)uracil-2,3-di-O-benzylated L-ascorbic acid derivative (4) exhibited an albeit slight (IC50: 55-108 mu M), but selective inhibitory effect toward all tumor cell lines except for cervical carcinoma (HeLa), pancreatic carcinoma (MiaPaCa-2), laryngeal carcinoma (Hep-2), and colon carcinoma (SW 620), and no cytotoxicity to normal human fibroblast (WI 38). Compound 7 showed some, not highly specific, inhibitory potential against vesicular stomatitis virus, Coxsackie 134 virus, and Sindbis viruses (EC50: 1.6 mu M). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.046

文献信息

• The novel pyrimidine and purine derivatives of l-ascorbic acid: synthesis, one- and two-dimensional 1H and 13C NMR study, cytostatic and antiviral evaluation
  作者：Tatjana Gazivoda、Miha Plevnik、Janez Plavec、Sandra Kraljević、Marijeta Kralj、Krešimir Pavelić、Jan Balzarini、Erik De Clercq、Mladen Mintas、Silvana Raić-Malić

  DOI：10.1016/j.bmc.2004.09.052

  日期：2005.1

  E-configuration of the C4'C5' double bond and position of the lactone ring of the compounds 6-9 were deduced from their one- and two-dimensional (1)H and (13)C NMR spectra and connectivities in NOESY and HMBC spectra. Compounds 15 and 18 showed the best inhibitory activities of all evaluated compounds in the series. The compound 15 containing 5-(trifluoromethyl)uracil showed marked inhibitory activity against

  内酯环的C-2'（6-10）或C-2'和C-3'（11-15）位置含有游离羟基的1-抗坏血酸的新型C-5取代的嘧啶衍生物的合成被描述。2,3-O，O-二苄基-1-抗坏血酸的16-氯-和6-（N-吡咯基）嘌呤衍生物的脱苄基作用（16和17）得到了在C-2'处含有羟基的新化合物（ 18）和C-2'和C-3'（19和20）。从它们的一维和二维（1）H和（13）C NMR谱图和连接性，推导出C4'C5'双键的Z和E构型以及化合物6-9的内酯环的位置。 NOESY和HMBC光谱。在该系列所有评估的化合物中，化合物15和18表现出最佳的抑制活性。含有5-（三氟甲基）尿嘧啶的化合物15显示出对所有人类恶性细胞系（IC（50）：5.6-12.8 microM）的显着抑制活性，除了对人类T淋巴细胞。此外，该化合物还通过增加G2 / M期的细胞数量影响细胞周期，并诱导SW 620和MiaPaCa-2细胞凋亡。