(-)-9-{(Z)-(R)-2-[(S)-1,2-dihydroxyethyl]cyclopropylidenemethyl}adenine | 1153777-78-6

• 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: (-)-9-{(Z)-(R)-2-[(S)-1,2-dihydroxyethyl]cyclopropylidenemethyl}adenine
• 英文别名: (1S)-1-[(1R,2Z)-2-[(6-aminopurin-9-yl)methylidene]cyclopropyl]ethane-1,2-diol
• CAS: 1153777-78-6
• 化学式: C₁₁H₁₃N₅O₂
• 分子量: 247.257
• InChiKey: OQXYWTDDSQPSMF-VFLSYPMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9-{(R)-2-[(S)-1,2-diacetoxyethyl]cyclopropylidenemethyl}adenine 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以51%的产率得到(-)-9-{(Z)-(R)-2-[(S)-1,2-dihydroxyethyl]cyclopropylidenemethyl}adenine
  参考文献：
  名称：

  (Z)- and (E)-2-(1,2-Dihydroxyethyl)methylenecyclopropane Analogues of 2′-Deoxyadenosine and 2′-Deoxyguanosine. Synthesis of All Stereoisomers, Absolute Configuration, and Antiviral Activity

  摘要：

  Chiral Z- and E-stereoisomers of (1,2-dihydroxyethyl)methylenecyclopropane analogues of 2'-deoxyadenosine and 2'-deoxyguanosine were. synthesized, and their antiviral activity was investigated. (S)-Methylenecyclo-propylcarbinol (16) was converted in seven steps to reagents 26 and 27, which were used for alkylation-elimination of adenine and 2-amino-6-chloropurine to get ultimately analogues 12a, 12b, 13a, 13b, 14a, 14b, 15a, and 15b. The enantiomeric series ent-12a, ent-12b, ent-13a, ent-13b, ent-14a, ent-14b, ent-15a, and ent-15b was obtained by similar procedures starting from (R)-methylenecyclopropylcarbinol (ent-16). The Z-isomer ent-12b was an inhibitor of two strains of human cytomegalovirus (HCMV) with EC50 of 6.8 and 7.5 mu M and of murine cytomegalovirus (MCMV) with EC50 of 11.3 mu M. It was less active against HCMV with mutated gene UL97. It inhibited Epstein-Barr virus (EBV) with EC50 of 8 mu M. The E-isomers ent-15a, ent-13a, and 15b were less effective. All adenine analogues with the exception of the Z-isomers ent-12a and ent-14a were moderate substrates for adenosine deaminase.

  DOI：

  10.1021/jm900126v

文献信息

• (<i>Z</i>)- and (<i>E</i>)-2-(1,2-Dihydroxyethyl)methylenecyclopropane Analogues of 2′-Deoxyadenosine and 2′-Deoxyguanosine. Synthesis of All Stereoisomers, Absolute Configuration, and Antiviral Activity
  作者：Shaoman Zhou、John C. Drach、Mark N. Prichard、Jiri Zemlicka

  DOI：10.1021/jm900126v

  日期：2009.5.28

  Chiral Z- and E-stereoisomers of (1,2-dihydroxyethyl)methylenecyclopropane analogues of 2'-deoxyadenosine and 2'-deoxyguanosine were. synthesized, and their antiviral activity was investigated. (S)-Methylenecyclo-propylcarbinol (16) was converted in seven steps to reagents 26 and 27, which were used for alkylation-elimination of adenine and 2-amino-6-chloropurine to get ultimately analogues 12a, 12b, 13a, 13b, 14a, 14b, 15a, and 15b. The enantiomeric series ent-12a, ent-12b, ent-13a, ent-13b, ent-14a, ent-14b, ent-15a, and ent-15b was obtained by similar procedures starting from (R)-methylenecyclopropylcarbinol (ent-16). The Z-isomer ent-12b was an inhibitor of two strains of human cytomegalovirus (HCMV) with EC50 of 6.8 and 7.5 mu M and of murine cytomegalovirus (MCMV) with EC50 of 11.3 mu M. It was less active against HCMV with mutated gene UL97. It inhibited Epstein-Barr virus (EBV) with EC50 of 8 mu M. The E-isomers ent-15a, ent-13a, and 15b were less effective. All adenine analogues with the exception of the Z-isomers ent-12a and ent-14a were moderate substrates for adenosine deaminase.