1-(Tetra-O-acetyl-β-D-glucopyranosyl)-benzimidazolinthion | 23732-31-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-(Tetra-O-acetyl-β-D-glucopyranosyl)-benzimidazolinthion
• 英文别名: 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranos-1'-yl)benzimidazole-2-thione；1N-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)benzimidazole-2-thione；1-(tetra-O-acetyl-β-D-glucopyranosyl)-1,3-dihydro-benzoimidazole-2-thione；[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(2-thioxo-3H-benzimidazol-1-yl)tetrahydropyran-2-yl]methyl acetate；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2-sulfanylidene-3H-benzimidazol-1-yl)oxan-2-yl]methyl acetate
• CAS: 23732-31-2
• 化学式: C₂₁H₂₄N₂O₉S
• 分子量: 480.496
• InChiKey: LUDJONSOAAVRLR-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(Tetra-O-acetyl-β-D-glucopyranosyl)-benzimidazolinthion 、 对硝基溴化苄 在 ammonium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 18.5h， 以72%的产率得到2-(4'-nitrobenzylthio)-1-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranos-1''-yl) benzimidazole
  参考文献：
  名称：

  Structure−Activity Relationship of New Anti-Hepatitis C Virus Agents: Heterobicycle−Coumarin Conjugates

  摘要：

  For establishment of the structure-activity relationship, 19 heterobicycle-coumarin conjugated compounds with the -SCH2- linker were synthesized and found to possess significant antiviral activities. Prominent examples included imidazopyridine-coumarin 12c, purine-coumarin 12d, and benzoxazole-coumarin 14c, which inhibited HCV replication at an EC50 of 6.8, 2.0, and 12 mu M, respectively. The heteroatoms in bicycles

  DOI：

  10.1021/jm801240d
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 18.25h， 以52%的产率得到1-(Tetra-O-acetyl-β-D-glucopyranosyl)-benzimidazolinthion
  参考文献：
  名称：

  WO2007/128086

  摘要：

  公开号：

文献信息

• Revisit to the Reaction of<i>O</i>-Phenylene Diamine with Thiosemicarbazide to Give Benzimidazole-2-Thione Rather than Benzotriazine-2-Thione and its Glycosylation
  作者：El Sayed H. El Ashry、Aly A. Aly、Mohamed R. Aouad、Mohammed R. Amer

  DOI：10.1080/15257770.2010.501777

  日期：2010.8.13

  Reaction of o-phenylene diamine with thiosemicarbazide did not give benzotriazine-2-thione 2 as reported, although the product was found to be benzimidazole-2-thione 3. Glycosylation of 3 with acetobromo sugars 4a-4b gave the respective thioglycosides 7a-7d in addition to minor products of the nucleosides 8a and 8b, in the case of the gluco- and galacto-analogs, respectively. The regioselectivity of glycosylation reaction has been investigated.
• WO2007/128086
  申请人：——

  公开号：——

  公开（公告）日：——
• Structure−Activity Relationship of New Anti-Hepatitis C Virus Agents: Heterobicycle−Coumarin Conjugates
  作者：Johan Neyts、Erik De Clercq、Raghunath Singha、Yung Hsiung Chang、Asish R. Das、Subhasish K. Chakraborty、Shih Ching Hong、Shwu-Chen Tsay、Ming-Hua Hsu、Jih Ru Hwu

  DOI：10.1021/jm801240d

  日期：2009.3.12

  For establishment of the structure-activity relationship, 19 heterobicycle-coumarin conjugated compounds with the -SCH2- linker were synthesized and found to possess significant antiviral activities. Prominent examples included imidazopyridine-coumarin 12c, purine-coumarin 12d, and benzoxazole-coumarin 14c, which inhibited HCV replication at an EC50 of 6.8, 2.0, and 12 mu M, respectively. The heteroatoms in bicycles