1-(4'-chlorophenylamino)-4-methyl-5-phenyl-2-(β-D-ribofuranosyl)sulfanyl-1H-imidazole | 302919-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4'-chlorophenylamino)-4-methyl-5-phenyl-2-(β-D-ribofuranosyl)sulfanyl-1H-imidazole
• 英文别名: 1-(4-Chloroanilino)-4-methyl-5-phenyl-2-[(β-D-ribofuranosyl)sulfanyl]imidazole；(2S,3R,4S,5R)-2-[1-(4-chloroanilino)-4-methyl-5-phenylimidazol-2-yl]sulfanyl-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 302919-27-3
• 化学式: C₂₁H₂₂ClN₃O₄S
• 分子量: 447.942
• InChiKey: FXLSAFSNJNPYDS-AFYVEPGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(4'-chlorophenylamino)-4-methyl-5-phenyl-2-(β-D-ribofuranosyl)sulfanyl-1H-imidazole 在 碘 作用下， 以18%的产率得到1-(4'-chlorophenylamino)-4-methyl-5-phenyl-3-(β-D-ribofuranosyl)-1H-imidazole-2-thione
  参考文献：
  名称：

  Synthesis ofN-Substituted 1-Amino-2,3-dihydro-1H-imidazole-2-thione-N-nucleosides andS-Glycosylated Derivatives

  摘要：

  Fusion of the N-substituted 1-amino-2,3-dihydro-1H-imidazole-2-thiones 1-4 with the peracylated ribose 5 in the presence of iodine afforded the N-nucleosides 6-9 in moderate yields. Deblocking with NaOMe/MeOH gave the free nucleosides 10-13. Alternatively, silylation of 4 followed by ribosylation with 5 in the presence of TMSOTf as catalyst afforded 9 in moderate yield. Ribosylation of 4 with the chlorodeoxyribose derivative 15 as well as 5 in the presence of NaH in DMF afforded the thioglycosides 16 and 18, respectively. Deblocking of 16 and 18 with NaOMe/MeOH gave the free S-thioglycosides 17 and 19, respectively. Thermal rearrangement of 19 at high temperature in the presence of iodine furnished 13 in low yield. The new free nucleosides and thioglycosides were inactive against HIV-1 and HIV-2 induced cytopathicity in human MT-4 lymphocyte cells.

  DOI：

  10.1081/ncn-120021429
• 作为产物：
  描述：

  1-[(4-氯苯基)氨基]-1,3-二氢-4-甲基-5-苯基-2H-咪唑-2-硫酮 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4'-chlorophenylamino)-4-methyl-5-phenyl-2-(β-D-ribofuranosyl)sulfanyl-1H-imidazole
  参考文献：
  名称：

  Synthesis ofN-Substituted 1-Amino-2,3-dihydro-1H-imidazole-2-thione-N-nucleosides andS-Glycosylated Derivatives

  摘要：

  Fusion of the N-substituted 1-amino-2,3-dihydro-1H-imidazole-2-thiones 1-4 with the peracylated ribose 5 in the presence of iodine afforded the N-nucleosides 6-9 in moderate yields. Deblocking with NaOMe/MeOH gave the free nucleosides 10-13. Alternatively, silylation of 4 followed by ribosylation with 5 in the presence of TMSOTf as catalyst afforded 9 in moderate yield. Ribosylation of 4 with the chlorodeoxyribose derivative 15 as well as 5 in the presence of NaH in DMF afforded the thioglycosides 16 and 18, respectively. Deblocking of 16 and 18 with NaOMe/MeOH gave the free S-thioglycosides 17 and 19, respectively. Thermal rearrangement of 19 at high temperature in the presence of iodine furnished 13 in low yield. The new free nucleosides and thioglycosides were inactive against HIV-1 and HIV-2 induced cytopathicity in human MT-4 lymphocyte cells.

  DOI：

  10.1081/ncn-120021429

文献信息

• Glycosylation of 1-Aminoimidazole-2(3H)-thiones
  作者：Irene M. Lagoja、Arthur Van Aerschot、Chris Hendrix、Piet Herdewijn

  DOI：10.1135/cccc20001145

  日期：——

  The selectivity of the glycosylation of 1-aminoimidazole-2(3H)-thiones can be controlled. Depending on the chosen conditions, either the kinetically favored S-glycosides or the thermodynamically more stable N-glycosylated compounds are obtained in only one anomeric configuration (β-anomer).

  1-氨基咪唑-2(3H)-硫酮的糖基化的选择性可以被控制。根据选择的条件，可以获得动力学上更有利的S-糖苷或热力学上更稳定的N-糖基化化合物，仅以一种异构构型（β-异构体）获得。