3β-(6-amino-9H-purin-9-yl)cyclobutane-1β-methanol | 125962-36-9

• 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: 3β-(6-amino-9H-purin-9-yl)cyclobutane-1β-methanol
• 英文别名: 9-adenine；9-adenine；9-[(1β,3β)-3-hydroxymethylcyclobutan-1-yl]adenine；9-[cis-3(hydroxymethyl)cyclobutyl]adenine
• CAS: 125962-36-9
• 化学式: C₁₀H₁₃N₅O
• 分子量: 219.246
• InChiKey: IFSFFLAFQQYWAX-KNVOCYPGSA-N

物化性质

• 沸点：
  502.0±53.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.85
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3β-(6-amino-9H-purin-9-yl)cyclobutane-1β-methanol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以20%的产率得到8-bromo-9-adenine
  参考文献：
  名称：

  碳环氧杂环丁烷类似物的合成和抗病毒活性。

  摘要：

  由相应的环丁胺制备9-环丁基腺嘌呤（4a），顺式和反式9- [3-（羟甲基）环丁基]腺嘌呤（4b）和9- [3,3-双（羟甲基）环丁基]腺嘌呤（4d）。导数（1a，1b和1d）。还制备了鸟嘌呤同源物（9a，顺式和反式9b和9d）和碳环氧杂环丁霉素G（1'，2'-trans-9f）。我们已经公开了碳氧杂环丁烷素A（1'，2'-trans-4f）和G在体外对单纯疱疹病毒（1型和2型）具有活性，而cis-4b和cis具有活性。 -9b显示了针对人类免疫缺陷病毒（1型）的体外抗逆转录病毒活性。

  DOI：

  10.1248/cpb.38.2719
• 作为产物：
  描述：

  9-adenine 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以68%的产率得到3β-(6-amino-9H-purin-9-yl)cyclobutane-1β-methanol
  参考文献：
  名称：

  Synthesis of 9-[cis-3-(hydroxymethyl)cyclobutyl]-adenine and -guanine

  摘要：

  2,2-Dichloro-3-(benzyloxymethyl)cyclobutanone 15, which was prepared in 50% yield by the cycloaddition of dichloroketene to allyl benzyl ether 14, was converted in four steps and in similar to 40% overall yield into trans-3-(benzyloxymethyl)cyclobutanol 11b. The latter alcohol 11b was coupled under Mitsunobu conditions with 6-(4-chlorophenylsulfanyl)-9H-purine 21b and 6-(4-chlorophenylsulfanyl)-2-(phenylacetamido)-9H-purine 21c to give the 9-cyclobutylpurine derivatives 22 and 24, respectively, in 88 and 60% yield. The former product 22 was converted in three steps and in 39% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl]adenine 6, and the latter product was converted in four steps and in 42% overall yield into 9-[cis-3-(hydroxymethyl)cyclobutyl] guanine 7. X-Ray crystallographic data relating to compounds 22 and 24 are also reported.

  DOI：

  10.1039/p19950002281

文献信息

• Synthesis of 3-Adenyl- and 3-Thyminylcyclobutane-1,1-dimethanols and Their Homo-octameric Phosphodiesters
  作者：Jean-Michel Henlin、Hans Rink、Erich Spieser、Gerhard Baschang

  DOI：10.1002/hlca.19920750216

  日期：1992.3.18

  3-adenylcyclobutane-1,1-dimethanol were synthesized by direct introduction of the heterocycles (Scheme 1). The mono-O-substituted methoxytrityl derivatives were separately converted to octameric phosphodiesters on an aminomethyl-polystyrene carrier by the phosphotriester method. These oligomers of carba-nucleosides were prepared in order to study their annealing behaviour towards ribo- and deoxyribo-nucleic

  从3-（苄氧基）环丁烷-1,1-二甲醇开始，通过直接引入杂环来合成3-胸苷基和3-腺苷基环丁烷-1,1-二甲醇（方案1）。通过磷酸三酯法将单-O-取代的甲氧基三苯甲基衍生物分别在氨基甲基-聚苯乙烯载体上转化为八聚磷酸二酯。制备这些寡糖核苷的低聚物是为了研究它们对核糖核酸和脱氧核糖核酸的退火行为以及其同源杂交的潜力。
• Hydroxymethyl cyclobutyl purines
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05369098A1

  公开（公告）日：1994-11-29

  Antiviral activity is exhibited by compounds having the formula ##STR1## and their pharmaceutically acceptable salts. R.sub.1 is ##STR2## R.sub.2 is hydrogen, --PO.sub.3 H.sub.2, ##STR3## wherein R.sub.3 is hydrogen, alkyl, substituted alkyl, or aryl, and R.sub.4 is alkyl.

  具有以下式子 ##STR1## 及其药学上可接受的盐的化合物表现出抗病毒活性。其中，R.sub.1是 ##STR2## R.sub.2是氢，--PO.sub.3 H.sub.2，##STR3## 其中R.sub.3是氢、烷基、取代烷基或芳基，R.sub.4是烷基。
• 2' and 3'-Substituted Cyclobutyl Nucleoside Analogs for the Treatment Viral Infections and Abnormal Cellular Proliferation
  申请人：Liotta Dennis C.

  公开号：US20090149416A1

  公开（公告）日：2009-06-11

  Provided are cyclobutyl nucleosides and methods for their use in treatment of infections including Retroviridae (including HIV), Hepadnaviridae (including HBV), or Flaviviridae (including BVDV and HCV) infection, or conditions related to abnormal cellular proliferation, in a host, including animals, and especially humans.

  提供了环丁基核苷和它们的使用方法，用于治疗感染，包括逆转录病毒科（包括HIV），乙肝病毒科（包括HBV）或黄病毒科（包括BVDV和HCV）感染，或与异常细胞增殖有关的情况，在宿主中使用，包括动物，尤其是人类。
• Novel cyclobutane Derivatives, processes for their preparation and pharmaceutical compositions comprising them
  申请人：Nippon Kayaku Kabushiki Kaisha

  公开号：EP0330992A2

  公开（公告）日：1989-09-06

  The invention is directed to cyclobutane derivatives represented by general formula (I): wherein A represents a hydrogen atom, a hydroxy group, an azido group or an amino group; and B represents a purine residue or a pyrimidine residue. The cyclobutane derivatives exhibit antiviral and antitumor activities and are thus expected as drugs.

  本发明涉及通式(I)代表的环丁烷衍生物： 其中 A 代表氢原子、羟基、叠氮基团或氨基；B 代表嘌呤残基或嘧啶残基。环丁烷衍生物具有抗病毒和抗肿瘤活性，因此有望成为药物。
• JPH03232818A
  申请人：——

  公开号：JPH03232818A

  公开（公告）日：1991-10-16