1-(4-Chloroanilino)-4-methyl-5-phenyl-2-[(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)sulfanyl]imidazole-2(3H)-thione | 302919-25-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 1-(4-Chloroanilino)-4-methyl-5-phenyl-2-[(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)sulfanyl]imidazole-2(3H)-thione
• 英文别名: 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1-(4'-methoxyphenylamino)-4-methyl-5-phenyl-1H-imidazole-2-thione；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-[3-(4-chloroanilino)-5-methyl-4-phenyl-2-sulfanylideneimidazol-1-yl]oxolan-2-yl]methyl benzoate
• CAS: 302919-25-1
• 化学式: C₄₂H₃₄ClN₃O₇S
• 分子量: 760.267
• InChiKey: ACYAYEWNOPNQBX-DOVDTPAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  54.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  110.02
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-(4-Chloroanilino)-4-methyl-5-phenyl-2-[(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)sulfanyl]imidazole-2(3H)-thione 在 氨 作用下， 以 甲醇 为溶剂， 以95%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：

  Glycosylation of 1-Aminoimidazole-2(3H)-thiones

  摘要：

  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。

  DOI：

  10.1135/cccc20001145
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 1-[(4-氯苯基)氨基]-1,3-二氢-4-甲基-5-苯基-2H-咪唑-2-硫酮 在 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以72%的产率得到1-(4-Chloroanilino)-4-methyl-5-phenyl-2-[(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)sulfanyl]imidazole-2(3H)-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