cyclopropavir monophosphate | 841275-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: cyclopropavir monophosphate
• 英文别名: [(2Z)-2-[(2-amino-6-oxo-1H-purin-9-yl)methylene]-1-(hydroxymethyl)cyclopropyl]methyl dihydrogen phosphate；[(2Z)-2-[(2-amino-6-oxo-1H-purin-9-yl)methylidene]-1-(hydroxymethyl)cyclopropyl]methyl dihydrogen phosphate
• CAS: 841275-74-9
• 化学式: C₁₁H₁₄N₅O₆P
• 分子量: 343.236
• InChiKey: SQZGLGQWGAQMCL-KXFIGUGUSA-N

物化性质

• 沸点：
  758.2±70.0 °C(Predicted)
• 密度：
  2.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cyclopropavir monophosphate 在 吡啶 、 N,N'-二环己基-4-吗啉脒 、 N,N'-二环己基碳二亚胺 作用下， 反应 10.0h， 以93%的产率得到Cyclovir monophosphate
  参考文献：
  名称：

  Nucleotides and Pronucleotides of 2,2-Bis(hydroxymethyl)methylenecyclopropane Analogues of Purine Nucleosides:  Synthesis and Antiviral Activity

  摘要：

  Phenylmethylphosphor-L-alaninate pronucleotides 7a, 7b, 8a, and 8b, cyclic phosphates 10a and 10b, and phosphates 11a and 11b derived from 2,2-bis(hydroxymethyl)methylenecyclopropane analogues 1a, 1b, 2a, and 2b were synthesized and evaluated for their antiviral activity. An improved protocol for the synthesis of analogues 1a, 1b, 2a, and 2b is also described. Phosphate 11a was the most effective agent against human and murine cytomegalovirus (EC50 0.25-1.1 muM). The Z-pronucleotides 7a and 7b had EC50 3.6-25.2 and 3-18.4 muM, respectively. The EC50 of cyclic phosphate 10a was 6.0-20 muM. The activity against Epstein-Barr (EBV) was assay-dependent. Pronucleotides 7a and 7b and phosphate 11a had EC50 2.3-3.4 muM against EBV/H-1, but 7b was cytotoxic (CC50 3.8 muM). Cyclic phosphate 10a was the only compound effective against EBV/Daudi (EC50 0.96 muM). but it was inactive in H-1 cells. Pronucleotide 7a was active against varicella zoster virus with EC50 6.3 and 7.3 muM, respectively. and hepatitis B virus (HBV, EC50 4.1 muM). Cyclic phosphate 10a was the most effective analogue against HBV (EC50 0.8 muM).

  DOI：

  10.1021/jm040149b
• 作为产物：
  描述：

  cyclopropavir 在 碘 吡啶 、 咪唑 、 三甲基氯硅烷 、 甲烷磺酸 、 diphenyl phosphite 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.17h， 生成 cyclopropavir monophosphate
  参考文献：
  名称：

  Nucleotides and Pronucleotides of 2,2-Bis(hydroxymethyl)methylenecyclopropane Analogues of Purine Nucleosides:  Synthesis and Antiviral Activity

  摘要：

  Phenylmethylphosphor-L-alaninate pronucleotides 7a, 7b, 8a, and 8b, cyclic phosphates 10a and 10b, and phosphates 11a and 11b derived from 2,2-bis(hydroxymethyl)methylenecyclopropane analogues 1a, 1b, 2a, and 2b were synthesized and evaluated for their antiviral activity. An improved protocol for the synthesis of analogues 1a, 1b, 2a, and 2b is also described. Phosphate 11a was the most effective agent against human and murine cytomegalovirus (EC50 0.25-1.1 muM). The Z-pronucleotides 7a and 7b had EC50 3.6-25.2 and 3-18.4 muM, respectively. The EC50 of cyclic phosphate 10a was 6.0-20 muM. The activity against Epstein-Barr (EBV) was assay-dependent. Pronucleotides 7a and 7b and phosphate 11a had EC50 2.3-3.4 muM against EBV/H-1, but 7b was cytotoxic (CC50 3.8 muM). Cyclic phosphate 10a was the only compound effective against EBV/Daudi (EC50 0.96 muM). but it was inactive in H-1 cells. Pronucleotide 7a was active against varicella zoster virus with EC50 6.3 and 7.3 muM, respectively. and hepatitis B virus (HBV, EC50 4.1 muM). Cyclic phosphate 10a was the most effective analogue against HBV (EC50 0.8 muM).

  DOI：

  10.1021/jm040149b

文献信息

• Nucleotides and Pronucleotides of 2,2-Bis(hydroxymethyl)methylenecyclopropane Analogues of Purine Nucleosides:  Synthesis and Antiviral Activity
  作者：Zhaohua Yan、Earl R. Kern、Elizabeth Gullen、Yung-Chi Cheng、John C. Drach、Jiri Zemlicka

  DOI：10.1021/jm040149b

  日期：2005.1.1

  Phenylmethylphosphor-L-alaninate pronucleotides 7a, 7b, 8a, and 8b, cyclic phosphates 10a and 10b, and phosphates 11a and 11b derived from 2,2-bis(hydroxymethyl)methylenecyclopropane analogues 1a, 1b, 2a, and 2b were synthesized and evaluated for their antiviral activity. An improved protocol for the synthesis of analogues 1a, 1b, 2a, and 2b is also described. Phosphate 11a was the most effective agent against human and murine cytomegalovirus (EC50 0.25-1.1 muM). The Z-pronucleotides 7a and 7b had EC50 3.6-25.2 and 3-18.4 muM, respectively. The EC50 of cyclic phosphate 10a was 6.0-20 muM. The activity against Epstein-Barr (EBV) was assay-dependent. Pronucleotides 7a and 7b and phosphate 11a had EC50 2.3-3.4 muM against EBV/H-1, but 7b was cytotoxic (CC50 3.8 muM). Cyclic phosphate 10a was the only compound effective against EBV/Daudi (EC50 0.96 muM). but it was inactive in H-1 cells. Pronucleotide 7a was active against varicella zoster virus with EC50 6.3 and 7.3 muM, respectively. and hepatitis B virus (HBV, EC50 4.1 muM). Cyclic phosphate 10a was the most effective analogue against HBV (EC50 0.8 muM).