(1S,3S,4S)-9-(3,4-Dihydroxycyclopent-1-yl)-9H-adenine | 132065-10-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (1S,3S,4S)-9-(3,4-Dihydroxycyclopent-1-yl)-9H-adenine
• 英文别名: (1S,2S)-4-(6-Amino-9H-purin-9-yl)cyclopentane-1,2-diol；(1S,2S)-4-(6-aminopurin-9-yl)cyclopentane-1,2-diol
• CAS: 132065-10-2
• 化学式: C₁₀H₁₃N₅O₂
• 分子量: 235.246
• InChiKey: HQDRMBMYUFTHKP-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 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：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 吡啶 、 sodium hydroxide 、 四(三苯基膦)钯 、 硼烷四氢呋喃络合物 、 氨 、 双氧水 、 sodium hydride 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 105.0h， 生成 (1S,3S,4S)-9-(3,4-Dihydroxycyclopent-1-yl)-9H-adenine
  参考文献：
  名称：

  Synthesis of (+)-5'-nor-2'-deoxyaristeromycin and (-)-5'-nor-3'-deoxyaristeromycin

  摘要：

  DOI：

  10.1021/jo00075a052

文献信息

• The synthesis of two 2′-deoxy carbocyclic purine nucleosides lacking the 5′-methylene
  作者：Masakazu Koga、Stewart W Schneller

  DOI：10.1016/s0040-4039(00)97979-6

  日期：1990.1

  The synthesis of the adenine derivative (±)-(1α,2β,4α)-4-(6-amino-9H-purin-9-yl)-1,2-cyclopentanediol (2) and its hypoxanthine analogue (3) as carbocyclic nucleosides lacking the 5′-methylene is described in 7 steps from 3-cyclopenten-1-ylamine hydrochloride (4) in on overall yield of 30% for 2 and 27% for 3.

  腺嘌呤衍生物（±）-（1α，2β，4α）-4-（6-氨基-9H-嘌呤-9-基）-1,2-环戊二醇（2）及其次黄嘌呤类似物（3）的合成缺乏5'-亚甲基核苷的碳环在7个步骤由3-环戊烯-1-基胺盐酸盐（描述4）在30％的总产率为2和27％为3。
• (.+-.)-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.