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9-(2,3,5-tri-Ο-acetyl-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine | 80585-34-8

中文名称
——
中文别名
——
英文名称
9-(2,3,5-tri-Ο-acetyl-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine
英文别名
(-)-2',3',5'-tri-O-acetyl-N6-(piperidin-1-yl)adenosine;[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-piperidin-1-ylpurin-9-yl)oxolan-2-yl]methyl acetate
9-(2,3,5-tri-Ο-acetyl-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine化学式
CAS
80585-34-8
化学式
C21H27N5O7
mdl
——
分子量
461.475
InChiKey
YXTXYFOUWKYOCI-QTQZEZTPSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    626.5±65.0 °C(Predicted)
  • 密度:
    1.50±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    0.9
  • 重原子数:
    33
  • 可旋转键数:
    9
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.62
  • 拓扑面积:
    135
  • 氢给体数:
    0
  • 氢受体数:
    11

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    参考文献:
    名称:
    Discovery of 6-[4-(6-nitroxyhexanoyl)piperazin-1-yl)]-9H-purine, as pharmacological post-conditioning agent
    摘要:
    Novel purine analogues bearing nitrate esters were designed and synthesized in an effort to develop compounds triggering endogenous cardioprotective mechanisms such as ischemic preconditioning (IPC) or postconditioning (PostC). The majority of the compounds reduced infarct size compared to the control group in anesthetized rabbits, whereas administration of the most active analogue 16 at a dose of 3.8 mu mol/kg resulted on a significant reduction of infarct size, compared to PostC group (13.4 +/- 1.9% vs 26.4 +/- 2.3%). These findings introduce a novel class of promising pharmacological compounds that could be used as mimics or enhancers of PostC. (C) 2012 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2012.07.037
  • 作为产物:
    描述:
    6-哌啶嘌呤四乙酰核糖硫酸氢铵六甲基二硅氮烷三氟甲磺酸三甲基硅酯 作用下, 以 1,2-二氯乙烷 为溶剂, 以85%的产率得到9-(2,3,5-tri-Ο-acetyl-1β-D-ribofuranosyl)-6-(piperidin-1-yl)-9H-purine
    参考文献:
    名称:
    Discovery of 6-[4-(6-nitroxyhexanoyl)piperazin-1-yl)]-9H-purine, as pharmacological post-conditioning agent
    摘要:
    Novel purine analogues bearing nitrate esters were designed and synthesized in an effort to develop compounds triggering endogenous cardioprotective mechanisms such as ischemic preconditioning (IPC) or postconditioning (PostC). The majority of the compounds reduced infarct size compared to the control group in anesthetized rabbits, whereas administration of the most active analogue 16 at a dose of 3.8 mu mol/kg resulted on a significant reduction of infarct size, compared to PostC group (13.4 +/- 1.9% vs 26.4 +/- 2.3%). These findings introduce a novel class of promising pharmacological compounds that could be used as mimics or enhancers of PostC. (C) 2012 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2012.07.037
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文献信息

  • A Highly Facile and Efficient One-Step Synthesis of <i>N</i><sup>6</sup>-Adenosine and <i>N</i><sup>6</sup>-2‘-Deoxyadenosine Derivatives
    作者:Zhao-Kui Wan、Eva Binnun、Douglas P. Wilson、Jinbo Lee
    DOI:10.1021/ol052424+
    日期:2005.12.1
    [reaction: see text] A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives has been developed. Treatment of inosine or 2'-deoxyinosine, without protection of sugar hydroxyl groups, with alkyl or arylamines, in the presence of BOP and DIPEA in DMF, led to the formation of N6-adenosine and N6-2'-deoxyadenosine derivatives in good to excellent yields. Carcinogenic
    [反应:见正文]已开发出一种高度容易和高效的一步合成N6-腺苷和N6-2'-脱氧腺苷生物的方法。在DMF中存在BOP和DIPEA的情况下,在没有烷基糖基或芳基胺的情况下用烷基或芳基胺处理肌苷2'-脱氧肌苷,导致形成N6-腺苷和N6-2'-脱氧腺苷生物,优异的产量。因此,由2'-脱氧肌苷直接以98%的产率直接合成了致癌的多环芳烃(PAH)N6-2'-脱氧腺苷加合物10和稀有DNA成分11。
  • Synthesis of N6,N6-Dialkyladenine Nucleosides Using Hexaalkylphosphorus Triamides Produced in Situ
    作者:Mahesh K. Lakshman、Asad Choudhury、Suyeal Bae、Eliezer Rochttis、Padmanava Pradhan、Amit Kumar
    DOI:10.1002/ejoc.200800752
    日期:——
    Reactions between secondary amines and phosphorus trichloride (PCl3) leads to the formation of the corresponding tris(dialkylamino)phosphines or hexaalkylphosphorus triamides [HAPT: (R2N)3P]. Reaction of silyl-protected 2'-deoxyinosine and acetyl-protected inosine with the in situ formed HAPT and iodine (I2) leads to the formation of N6,N6-dialkyl adenosine and 2'-deoxyadenosine. In some cases the
    仲胺与三氯化磷 (PCl3) 之间的反应导致形成相应的三(二烷基基)膦或六烷基三酰胺 [HAPT: (R2N)3P]。甲硅烷基保护的 2'-脱氧肌苷和乙酰基保护的肌苷与原位形成的 HAPT (I2) 的反应导致形成 N6,N6-二烷基腺苷2'-脱氧腺苷。在某些情况下,胺的化学计量与叔胺碱的使用一样重要。通过 31 P1H} NMR 研究了胺化学计量对 HAPT 与 I2 反应的影响。
  • Mild and Efficient Functionalization at C6 of Purine 2‘-Deoxynucleosides and Ribonucleosides<sup>1</sup>
    作者:Xiaoyu Lin、Morris J. Robins
    DOI:10.1021/ol000255h
    日期:2000.11.1
    [reaction: see text] Treatment of sugar-protected inosine and 2'-deoxyinosine derivatives with a cyclic secondary amine or imidazole and I(2)/Ph(3)P/EtN(i-Pr)(2)/(CH(2)Cl(2) or toluene) gave quantitative conversions into 6-N-(substituted)purine nucleosides. S(N)Ar reactions with 6-(imidazol-1-yl) derivatives gave 6-(N, O, or S)-substituted products. The 6-(benzylsulfonyl) group underwent S(N)Ar displacement
    [反应:请参见文本]用环状仲胺或咪唑和I(2)/ Ph(3)P / EtN(i-Pr)(2)/(CH( 2)Cl(2)或甲苯)定量转化为6-N-(取代)嘌呤核苷。与6-(咪唑-1-基)衍生物的S(N)Ar反应得到6-(N,O或S)-取代的产物。在环境温度下用芳基胺对6-(苄基磺酰基)进行S(N)Ar取代。
  • Permanganate oxidation of N6,N6,8-trisubstituted-2′,3′,5′- tri-o-acetyladenosines
    作者:Tetsuo Kato、Shuichi Ogawa、Isoo Ito
    DOI:10.1016/s0040-4039(01)81864-5
    日期:1981.1
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