[(3aR,4R,6R,6aS)-6-(6-Chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-acetic acid ethyl ester | 828937-26-4

• 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: [(3aR,4R,6R,6aS)-6-(6-Chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-acetic acid ethyl ester
• CAS: 828937-26-4
• 化学式: C₁₇H₂₁ClN₄O₄
• 分子量: 380.831
• InChiKey: YFDSPVYZZFZSLJ-MHWZDGSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  88.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,6R,6aS)-6-(6-Chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-acetic acid ethyl ester 在 氨 、 二异丁基氢化铝 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (3aS,4R,6S,6aR)-9-<4,5,6,6a-tetrahydro-6-(2-hydroxyethyl)-2,2-dimethyl-3aH-cyclopenta-1,3-dioxol-4-yl>-9H-purin-6-amine
  参考文献：
  名称：

  5′-Homoaristeromycin. Synthesis and antiviral activity against orthopox viruses

  摘要：

  An efficient synthesis of 5'-homoaristeromycin has been developed. This permitted an extensive antiviral analysis, which found potent activity toward vaccinia, cowpox, and monkeypox viruses. For comparative purposes, 5'-homoadenosine was made available by a newly designed route and found to be inactive. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.019
• 作为产物：
  描述：

  在 potassium fluoride 、 sodium tetrahydroborate 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 生成 [(3aR,4R,6R,6aS)-6-(6-Chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  5′-Homoaristeromycin. Synthesis and antiviral activity against orthopox viruses

  摘要：

  An efficient synthesis of 5'-homoaristeromycin has been developed. This permitted an extensive antiviral analysis, which found potent activity toward vaccinia, cowpox, and monkeypox viruses. For comparative purposes, 5'-homoadenosine was made available by a newly designed route and found to be inactive. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.019

文献信息

• 6′-Methyl-5′-homoaristeromycin: A structural variation of the anti-orthopox virus candidate 5′-homoaristeromycin
  作者：Minmin Yang、Wei Ye、Stewart W. Schneller

  DOI：10.1016/j.bmc.2013.04.070

  日期：2013.7

  The synthesis of 6'-methyl-5'-homoaristeromycin is described from a known 6'-ethyl ester. Antiviral analysis showed the (S)-6' stereoisomer retained the vaccinia activity of the parent 5'-homoaristeromycin (1) while the (R)-6' isomer was less active. Both were weaker than 1 towards cowpox. The diastereomers were equally active versus Epstein Barr virus while (S)-6' was three times more active toward vesicular stomatitis virus than (R)-6'. The diastereomers were inactive towards numerous other viruses. The CC50 for both diastereomers was >300 mu M. (C) 2013 Elsevier Ltd. All rights reserved.