(3R-cis)-1,9-dihydro-9--6H-purin-6-one (Iso-ddI) | 143191-81-5

• 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: (3R-cis)-1,9-dihydro-9--6H-purin-6-one (Iso-ddI)
• 英文别名: 1,4-Anhydro-2,3-dideoxy-2-(1,6-dihydro-6-oxo-9H-purin-9-yl)-D-arabinitol；(3R-cis)-1,9-dihydro-9-[tetrahydro-5-(hydroxymethyl)-3-furanyl]-6H-purin-6-one (Iso-ddI)；9-[(3S,5S)-5-(hydroxymethyl)oxolan-3-yl]-1H-purin-6-one
• CAS: 143191-81-5
• 化学式: C₁₀H₁₂N₄O₃
• 分子量: 236.23
• InChiKey: OENKSAWKKLMVEL-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  [(3aR,5S,6aR)-2,2-dimethyltetrhydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate 在 盐酸 、 三乙基硅烷 、 sodium hydroxide 、 三甲基氯硅烷 、 18-冠醚-6 、 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 89.0h， 生成 (3R-cis)-1,9-dihydro-9--6H-purin-6-one (Iso-ddI)
  参考文献：
  名称：

  Novel isomeric dideoxynucleosides as potential antiviral agents

  摘要：

  Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.

  DOI：

  10.1016/s0040-4020(01)85259-5

文献信息

• Synthesis and anti-HIV activity of isonucleosides
  作者：Donna M. Huryn、Barbara C. Sluboski、Steve Y. Tam、Manfred Weigele、Iain Sim、Barry D. Anderson、Hiroaki Mitsuya、Samuel Broder

  DOI：10.1021/jm00091a001

  日期：1992.6

  A series of isomeric 2',3'-dideoxynucleosides which contains a modified carbohydrate moiety has been prepared. This class of compounds was designed to mimic the activity of known anti-HIV dideoxynucleosides, while imparting enhanced chemical and enzymatic stability. Isonucleosides containing the standard heterocyclic bases (A, C, G, T) were synthesized via nucleophilic addition of the base to an isomeric sugar unit. Modified derivatives were generated by manipulation of the intact isonucleoside. Two of the compounds prepared, iso-ddA (1) and iso-ddG (6), exhibit significant and selective anti-HIV activity, as well as beneficial hydrolytic stability.
• US5231174A
  申请人：——

  公开号：US5231174A

  公开（公告）日：1993-07-27
• [EN] 2'ISODIDEOXY-(BETA)-D-NUCLEOSIDES AS STABLE ANTIVIRAL AGENTS
  申请人：UNIVERSITY OF IOWA RESEARCH FOUNDATION

  公开号：WO1993017035A1

  公开（公告）日：1993-09-02

  (EN) The present invention is concerned with new 2'-isomeric 2', 3'-dideoxy-2'$g(b)-D-nucleosides and their derivatives where the base moiety has $g(b)-stereo-chemistry but is transposed from the normal 1'-position to the 2'-position and the carbohydrate moiety has the D-configuration at the 4'-position. These compounds are resistant towards hydrolytic cleavage of the glycosidic bond and are resistant to enzymatic deamination. They have potential in the treatment or prophylaxis of viral infections, particularly retroviral infections and especialy AIDS.(FR) La présente invention concerne de nouveaux 3'-didésoxy-2'$g(b)-D nucléosides 2'-isomère 2' et leurs dérivés. La fraction de base possède une stéréochimie $g(b), mais est transposée de la position normale 1'- à la position 2'- et la fraction de glucide possède la configuration D à la position 4'-. Ces composés sont résistants au clivage hydrolytique de la liaison glycosidique et sont également résistants à la désamination enzymatique. Ils sont puissants dans le traitement ou la prophylaxie d'infections virales, notamment des infections rétrovirales et en particulier du SIDA.
• Novel isomeric dideoxynucleosides as potential antiviral agents
  作者：Pascal J. Bolon、Todd B. Sells、Zoraida M. Nuesca、David F. Purdy、Vasu Nair

  DOI：10.1016/s0040-4020(01)85259-5

  日期：1994.1

  Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.