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9-(6'-deoxy-α-L-talofuranosyl)hypoxanthine | 86527-20-0

中文名称
——
中文别名
——
英文名称
9-(6'-deoxy-α-L-talofuranosyl)hypoxanthine
英文别名
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(1S)-1-hydroxyethyl]oxolan-2-yl]-1H-purin-6-one
9-(6'-deoxy-α-L-talofuranosyl)hypoxanthine化学式
CAS
86527-20-0
化学式
C11H14N4O5
mdl
——
分子量
282.256
InChiKey
GNEUXCLUOVTONK-ZGAAAFHUSA-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:
    759.4±60.0 °C(Predicted)
  • 密度:
    1.96±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    -0.9
  • 重原子数:
    20
  • 可旋转键数:
    2
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.55
  • 拓扑面积:
    129
  • 氢给体数:
    4
  • 氢受体数:
    7

反应信息

  • 作为产物:
    参考文献:
    名称:
    Synthesis and antitumor activity of 7- and 9-(6'-deoxy-.alpha.-L-talofuranosyl)-hypoxanthine and 9-(6'-deoxy-.alpha.-L-talofuranosyl)-6-thiopurine
    摘要:
    Reaction of 6-deoxy-2,3,5-tris-O-(p-nitrobenzoyl)-L-talofuranosyl bromide (1) with the trimethylsilyl derivative of hypoxanthine, followed by removal of blocking groups, afforded 9- (6) and 7-(6'-deoxy-alpha-L-talofuranosyl)hypoxanthine (7). A study of the published optical rotations and circular dichroic (CD) spectra of pentofuranosylpurines and of (6'-deoxy-beta-D-allo- and -alpha-L-talofuranosyl)purines prepared here suggests that the sign of rotation and the sign of the longer wavelength Cotton effect is determined solely by the configuration of C-1' and its position of attachment to the purine ring. For C-1' R nucleosides, the sign is negative for N-9-linked purine nucleosides and positive for the N-7-linked isomers, and vice versa for C-1'S purine nucleosides. Reaction of 1 with the trimethylsilyl derivative of 6-chloropurine afforded 4, which upon treatment with thiourea and deblocking yielded 9-(6'-deoxy-alpha-L-talofuranosyl)-6-thiopurine (8). Unlike the previously prepared 7-(6'-deoxy-beta-D-allofuranosyl) hypoxanthine which strongly inhibited purine nucleoside phosphorylase, compounds 6-8 did not inhibit this enzyme. Compound 8 significantly inhibited the growth of L1210 tumor cells in vitro and in vivo.
    DOI:
    10.1021/jm00364a032
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文献信息

  • Synthesis and antitumor activity of 7- and 9-(6'-deoxy-.alpha.-L-talofuranosyl)-hypoxanthine and 9-(6'-deoxy-.alpha.-L-talofuranosyl)-6-thiopurine
    作者:Victor Nelson、Hassan S. El Khadem
    DOI:10.1021/jm00364a032
    日期:1983.10
    Reaction of 6-deoxy-2,3,5-tris-O-(p-nitrobenzoyl)-L-talofuranosyl bromide (1) with the trimethylsilyl derivative of hypoxanthine, followed by removal of blocking groups, afforded 9- (6) and 7-(6'-deoxy-alpha-L-talofuranosyl)hypoxanthine (7). A study of the published optical rotations and circular dichroic (CD) spectra of pentofuranosylpurines and of (6'-deoxy-beta-D-allo- and -alpha-L-talofuranosyl)purines prepared here suggests that the sign of rotation and the sign of the longer wavelength Cotton effect is determined solely by the configuration of C-1' and its position of attachment to the purine ring. For C-1' R nucleosides, the sign is negative for N-9-linked purine nucleosides and positive for the N-7-linked isomers, and vice versa for C-1'S purine nucleosides. Reaction of 1 with the trimethylsilyl derivative of 6-chloropurine afforded 4, which upon treatment with thiourea and deblocking yielded 9-(6'-deoxy-alpha-L-talofuranosyl)-6-thiopurine (8). Unlike the previously prepared 7-(6'-deoxy-beta-D-allofuranosyl) hypoxanthine which strongly inhibited purine nucleoside phosphorylase, compounds 6-8 did not inhibit this enzyme. Compound 8 significantly inhibited the growth of L1210 tumor cells in vitro and in vivo.
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