2-氨基-9-[(3S,4S)-3,4-二羟基环戊基]-3H-嘌呤-6-酮 | 140438-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-氨基-9-[(3S,4S)-3,4-二羟基环戊基]-3H-嘌呤-6-酮
• 中文别名: 2-脱氧-2-((3R)-3-羟基-十四烷酰氨基)-3-O-(3-羟基十四烷基)-4-O-磷羧基葡萄吡喃糖
• 英文名称: (+/-)-2-amino-1,9-dihydro-9-<(1'α,3'β,4'β)-(3',4'dihydroxy-1'cyclopentyl)>-6H-purin-6-one
• 英文别名: Carbocyclic 5'-nor-2'-deoxyguanosine；2-amino-9-[(3S,4S)-3,4-dihydroxycyclopentyl]-1H-purin-6-one
• CAS: 140438-62-6
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 251.245
• InChiKey: LDYHQWURHCKRLK-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+/-)-(1α,2β,4β)-4-<(2-amino-6-chloropyrimidin-4-yl)amino>-1,2-cyclopentanediol 在 盐酸 、 sodium acetate 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 33.5h， 生成 2-氨基-9-[(3S,4S)-3,4-二羟基环戊基]-3H-嘌呤-6-酮
  参考文献：
  名称：

  (.+-.)-Carbocyclic 5'-nor-2'-deoxyguanosine and related purine derivatives: synthesis and antiviral properties

  摘要：

  Beginning with 3-cyclopenten-1-ylamine hydrochloride, the 5'-nor derivatives of carbocyclic 2'-deoxyguanosine (2), 2'-deoxyadenosine (3), and 2,6-diaminopurine 2'-deoxyribofuranoside (4) have been prepared. These compounds were evaluated for antiviral potential versus herpes simplex virus, varicella-zoster virus, cytomegalovirus, vaccinia virus, vesicular stomatitis virus, and human immunodeficiency virus and found to lack activity. Also, compounds 2-4 were virtually nontoxic toward the host (human diploid fibroblast ESM and HEL) cells. These biological properties may be due to the inability of 2-4 to be phosphorylated to the requisite nucleotide level that is likely to be necessary for biological activity by correlation to carbocyclic 2'-deoxyguanosine (1), which possesses significant antiviral properties as a result of conversion to its 5'-triphosphate derivative.

  DOI：

  10.1021/jm00090a007

文献信息

• (.+-.)-Carbocyclic 5'-nor-2'-deoxyguanosine and related purine derivatives: synthesis and antiviral properties
  作者：Sharadbala D. Patil、Masakazu Koga、Stewart W. Schneller、Robert Snoeck、Erik De Clercq

  DOI：10.1021/jm00090a007

  日期：1992.6

  Beginning with 3-cyclopenten-1-ylamine hydrochloride, the 5'-nor derivatives of carbocyclic 2'-deoxyguanosine (2), 2'-deoxyadenosine (3), and 2,6-diaminopurine 2'-deoxyribofuranoside (4) have been prepared. These compounds were evaluated for antiviral potential versus herpes simplex virus, varicella-zoster virus, cytomegalovirus, vaccinia virus, vesicular stomatitis virus, and human immunodeficiency virus and found to lack activity. Also, compounds 2-4 were virtually nontoxic toward the host (human diploid fibroblast ESM and HEL) cells. These biological properties may be due to the inability of 2-4 to be phosphorylated to the requisite nucleotide level that is likely to be necessary for biological activity by correlation to carbocyclic 2'-deoxyguanosine (1), which possesses significant antiviral properties as a result of conversion to its 5'-triphosphate derivative.