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N6-(3-Aminopropyl)adenosine | 34436-52-7

中文名称
——
中文别名
——
英文名称
N6-(3-Aminopropyl)adenosine
英文别名
N-(3-Aminopropyl)adenosine;(2R,3R,4S,5R)-2-[6-(3-aminopropylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
N6-(3-Aminopropyl)adenosine化学式
CAS
34436-52-7
化学式
C13H20N6O4
mdl
——
分子量
324.34
InChiKey
PQJLAZRZUFGWPG-QYVSTXNMSA-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:
    698.7±65.0 °C(Predicted)
  • 密度:
    1.79±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    -0.4
  • 重原子数:
    23
  • 可旋转键数:
    6
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.62
  • 拓扑面积:
    152
  • 氢给体数:
    5
  • 氢受体数:
    9

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

反应信息

  • 作为反应物:
    参考文献:
    名称:
    霉酚酸的新缀合物及其抗增殖活性。
    摘要:
    在EDCI作为偶联剂的存在下,N 6-(ω-氨基烷基)腺苷与MPA的反应获得了新的霉酚酸(MPA)共轭物。在健康捐献者的白血病细胞系(Jurkat)和PBMC上评估了新化合物4a–h。接头的长度影响观察到的活性。具有1,3-二胺间隔基的化合物4b显示出最有希望的结果,可以考虑用于进一步的研究。
    DOI:
    10.1080/10286020.2016.1184653
  • 作为产物:
    描述:
    6-氯嘌呤核苷1,3-丙二胺三乙胺 作用下, 以 乙醇 为溶剂, 反应 18.0h, 生成 N6-(3-Aminopropyl)adenosine
    参考文献:
    名称:
    霉酚酸的新缀合物及其抗增殖活性。
    摘要:
    在EDCI作为偶联剂的存在下,N 6-(ω-氨基烷基)腺苷与MPA的反应获得了新的霉酚酸(MPA)共轭物。在健康捐献者的白血病细胞系(Jurkat)和PBMC上评估了新化合物4a–h。接头的长度影响观察到的活性。具有1,3-二胺间隔基的化合物4b显示出最有希望的结果,可以考虑用于进一步的研究。
    DOI:
    10.1080/10286020.2016.1184653
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文献信息

  • Adenosine Analogues as Inhibitors of <i>Trypanosoma </i><i>b</i><i>rucei </i>Phosphoglycerate Kinase:  Elucidation of a Novel Binding Mode for a 2-Amino-N<sup>6</sup>-Substituted Adenosine
    作者:Jerome C. Bressi、Jungwoo Choe、Melinda T. Hough、Frederick S. Buckner、Wesley C. Van Voorhis、Christophe L. M. J. Verlinde、Wim G. J. Hol、Michael H. Gelb
    DOI:10.1021/jm000287a
    日期:2000.11.1
    As part of a project aimed at structure-based design of adenosine analogues as drugs against African trypanosomiasis, N-6-, 2-amino-N-6-, and N-2-substituted adenosine analogues were synthesized and tested to establish structure-activity relationships for inhibiting Trypanosoma brucei glycosomal phosphoglycerate kinase (PGK), glyceraldehyde-3-phosphate dehydrogenase (GAPDH), and glycerol-3-phosphate dehydrogenase (GPDH). Evaluation of X-ray structures of parasite PGK, GAPDH, and GPDH complexed with their adenosyl-bearing substrates led us to generate a series of adenosine analogues which would target all three enzymes simultaneously. There was a modest preference by PGK for NG-substituted analogues bearing the 2-amino group. The best compound in this series, 2-amino-N-6-[2 "-(p-hydroxyphenyl)ethyl]adenosine (46b), displayed a 23-fold improvement over adenosine with an IC50 of 130 muM. 2-[[2 "-(p-Hydroxyphenyl)ethyl]amino]adenosine (46c) was a weak inhibitor of T. brucei PGK with an IC50 of 500 muM. To explore the potential of an additive effect that having the N-6 and N-2 substitutions in one molecule might provide, the best ligands from the two series were incorporated into N-6,N-2-disubstituted adenosine analogues to yield N-6-(2 " -phenylethyl)-2-[(2 " -phenylethyl)amino]adenosine (69) as a 30 muM inhibitor of T. brucei PGK which is 100-fold more potent than the adenosine template. In contrast, these series gave no compounds that inhibited parasitic GAPDH or GPDH more than 10-20% when tested at 1.0 mM. A 3.0 Angstrom X-ray structure of a T, brucei PGK/46b complex revealed a binding mode in which the nucleoside analogue was flipped and the ribosyl moiety adopted a syn conformation as compared with the previously determined binding mode of ADP. Molecular docking experiments using QXP and SAS program suites reproduced this "flipped and rotated" binding mode.
  • ITIKAVA, MASATSUNEH;FUDZIYAMA, KADZUO;SIBUYA, SUSUMU;IKEHDA, TAKAO
    作者:ITIKAVA, MASATSUNEH、FUDZIYAMA, KADZUO、SIBUYA, SUSUMU、IKEHDA, TAKAO
    DOI:——
    日期:——
  • New conjugates of mycophenolic acid and their antiproliferative activity
    作者:Michał Prejs、Grzegorz Cholewinski、Agnieszka Siebert、Piotr Trzonkowski、Krystyna Dzierzbicka
    DOI:10.1080/10286020.2016.1184653
    日期:2016.11.1
    The new conjugates of mycophenolic acid (MPA) were obtained in the reaction of N6-(ω-aminoalkyl)adenosines with MPA in the presence of EDCI as a coupling reagent. New compounds 4a–h were evaluated on leukemia cell line (Jurkat) and PBMC from healthy donors. Length of the linker influenced observed activity. The compound 4b possessing 1,3-diamine spacer exhibited the most promising results and can be
    在EDCI作为偶联剂的存在下,N 6-(ω-氨基烷基)腺苷与MPA的反应获得了新的霉酚酸(MPA)共轭物。在健康捐献者的白血病细胞系(Jurkat)和PBMC上评估了新化合物4a–h。接头的长度影响观察到的活性。具有1,3-二胺间隔基的化合物4b显示出最有希望的结果,可以考虑用于进一步的研究。
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