9-(2-O-propionyl-β-D-arabinofuranosyl)adenine | 65174-99-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-(2-O-propionyl-β-D-arabinofuranosyl)adenine
• 英文别名: Propionic acid 2-(6-amino-purin-9-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yl ester；[(2R,3S,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] propanoate
• CAS: 65174-99-4
• 化学式: C₁₃H₁₇N₅O₅
• 分子量: 323.308
• InChiKey: ZJGJHHKPRTUHSO-FAYBLGNRSA-N

物化性质

• 沸点：
  461.79°C (rough estimate)
• 密度：
  1.2703 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  阿糖腺苷 在 吡啶 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 84.0h， 生成 9-(2-O-propionyl-β-D-arabinofuranosyl)adenine
  参考文献：
  名称：

  Synthesis and evaluation of a series of 2'-O-acyl derivatives of 9-.beta.-D-arabinofuranosyladenine as antiherpes agents

  摘要：

  A series of four 9-(2-O-acyl-beta-D-arabinofuranosyl)adenines (5a-d) was synthesized by acylation of 9-[3,5-bis-O-(tert-butyldimethylsilyl)-beta-D-arabinofuranosyl]adenine (2), followed by removal of the tert-butyldimethylsilyl groups under conditions (HOAc, tetra-n-butylammonium fluoride) that prevented acyl migration. The four 2'-O-acyl derivatives 5a-d showed activity in vitro against herpes type 1 viruses [virus ratings = 1.5-2.6; MIC50 = 26-72 micrograms/mL (8.48-21.3 X 10(-5) M)]. The 2'-O-acetyl (5a) and 2'-O-valeryl (5d) derivatives were evaluated in a guinea pig model for genital herpes (herpes type 2); only 5a showed potent activity when given 6 or 24 h postinfection.

  DOI：

  10.1021/jm00369a007

文献信息

• Use of 9-(beta-D-arabinofuranosyl) adenine derivatives for the preparation of pharmaceutical compositions for the treatment of aids
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0317728A2

  公开（公告）日：1989-05-31

  9-(β-D-arabinofuranosyl)adenine, also commonly known as Ara-A or vidarabine, esters thereof, or a pharmaceutically acceptable salt thereof, possess antiviral activity against the HTLV-III/LAV virus implicated in acquired immune deficiency syndrome (AIDS). The invention is related to the use of compounds of formula I for the preparation of pharmaceutical compositions useful in the treatment of infections of the HTLV-III/LAV virus in patients.

  9-(β-D-阿拉伯呋喃糖基)腺嘌呤，通常称为Ara-A或vidarabine，其酯类，或其药用可接受的盐，对HTLV-III/LAV病毒具有抗病毒活性，该病毒与获得性免疫缺陷综合征（AIDS）有关。本发明涉及使用式I化合物制备用于治疗患有HTLV-III/LAV病毒感染的患者的药物组合物。
• US4055718A
  申请人：——

  公开号：US4055718A

  公开（公告）日：1977-10-25
• US4212941A
  申请人：——

  公开号：US4212941A

  公开（公告）日：1980-07-15
• Synthesis and evaluation of a series of 2'-O-acyl derivatives of 9-.beta.-D-arabinofuranosyladenine as antiherpes agents
  作者：David C. Baker、S. D. Kumar、William J. Waites、Gussie Arnett、William M. Shannon、William I. Higuchi、W. J. Lambert

  DOI：10.1021/jm00369a007

  日期：1984.3

  A series of four 9-(2-O-acyl-beta-D-arabinofuranosyl)adenines (5a-d) was synthesized by acylation of 9-[3,5-bis-O-(tert-butyldimethylsilyl)-beta-D-arabinofuranosyl]adenine (2), followed by removal of the tert-butyldimethylsilyl groups under conditions (HOAc, tetra-n-butylammonium fluoride) that prevented acyl migration. The four 2'-O-acyl derivatives 5a-d showed activity in vitro against herpes type 1 viruses [virus ratings = 1.5-2.6; MIC50 = 26-72 micrograms/mL (8.48-21.3 X 10(-5) M)]. The 2'-O-acetyl (5a) and 2'-O-valeryl (5d) derivatives were evaluated in a guinea pig model for genital herpes (herpes type 2); only 5a showed potent activity when given 6 or 24 h postinfection.