2,5,6-trichloro-1-(α-L-arabinofuranosyl)benzimidazole | 219674-96-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 苯并咪唑核糖核苷和核糖核苷酸
• 英文名称: 2,5,6-trichloro-1-(α-L-arabinofuranosyl)benzimidazole
• 英文别名: (2S,3R,4R,5R)-2-(hydroxymethyl)-5-(2,5,6-trichlorobenzimidazol-1-yl)tetrahydrofuran-3,4-diol；(2S,3R,4R,5R)-2-(hydroxymethyl)-5-(2,5,6-trichlorobenzimidazol-1-yl)oxolane-3,4-diol
• CAS: 219674-96-1
• 化学式: C₁₂H₁₁Cl₃N₂O₄
• 分子量: 353.589
• InChiKey: BSDCIRGNJKZPFV-UKKRHICBSA-N

物化性质

• 沸点：
  638.8±65.0 °C(Predicted)
• 密度：
  1.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  环庚胺 、 2,5,6-trichloro-1-(α-L-arabinofuranosyl)benzimidazole 以 乙醇 为溶剂， 反应 48.0h， 以69%的产率得到2-cycloheptylamino-5,6-dichloro-1-(α-L-arabinofuranosyl)benzimidazole
  参考文献：
  名称：

  Design, Synthesis and Antiviral Activity of α-L-Arabinofuranosyl Derivatives of 2-Substituted-5,6-dichlorobenzimidazoles

  摘要：

  A number of 2-substituted-5,6-dichloro-1-(alpha-L-arabinofuranosyl)benzimidazoles have been prepared by condensation of 2-bromo-5,6-dichlorobenzimidazole or 2,5,6-trichlorobenzimidazole with tetra-O-acetyl-L-arabinofuranose. 2-Alkylamino derivatives were prepared by a substitution of the 2-chloro group with the appropriate amines. All target compounds were evaluated for activity against HCMV and HSV-1. The 2-chloro and 2-bromo derivatives showed moderate activity against HCMV at non-cytotoxic concentrations.

  DOI：

  10.1080/07328319808004326
• 作为产物：
  描述：

  2,5,6-trichloro-1-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)benzimidazole 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以60%的产率得到2,5,6-trichloro-1-(α-L-arabinofuranosyl)benzimidazole
  参考文献：
  名称：

  Design, Synthesis and Antiviral Activity of α-L-Arabinofuranosyl Derivatives of 2-Substituted-5,6-dichlorobenzimidazoles

  摘要：

  A number of 2-substituted-5,6-dichloro-1-(alpha-L-arabinofuranosyl)benzimidazoles have been prepared by condensation of 2-bromo-5,6-dichlorobenzimidazole or 2,5,6-trichlorobenzimidazole with tetra-O-acetyl-L-arabinofuranose. 2-Alkylamino derivatives were prepared by a substitution of the 2-chloro group with the appropriate amines. All target compounds were evaluated for activity against HCMV and HSV-1. The 2-chloro and 2-bromo derivatives showed moderate activity against HCMV at non-cytotoxic concentrations.

  DOI：

  10.1080/07328319808004326

文献信息

• [EN] ARABINOFURANOSYL BENZIMIDAZOLES AS ANTIVIRAL AGENTS<br/>[FR] ARABINOFURANOSYL BENZIMIDAZOLES COMME AGENTS ANTIVIRAUX
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：WO1999051619A1

  公开（公告）日：1999-10-14

  (EN) The present invention pertains to arabinofuranosyl benzimidazole compounds, specifically, $g(b)-D-arabinofuranosylbenzimidazole of structure (I) and its $g(b)-L, $g(a)-D-, and $g(a)-L analogs, wherein R2, R4, R5, R6, and R7 are independently selected from the group consisting of: -H, halo, -NO2, -NH2, -NHR8, -N(R8)2, -OR8, -SR8, and -CF3; wherein R8 is -H or an alkyl group of 1-8 carbon atoms; R10, R11, and R12 are independently selected from -H, -OH or a hydroxyl protecting group; and pharmaceutically acceptable salts thereof, with the provisos that: a) when each of R4, R5, R6, and R7 is a hydrogen, R2 is a group other than hydrogen; b) when R10 is -H, R11 is not -H, and the compound is not a $g(b)-compound; and c) the compound is not 2,5,6-trichloro-1-($g(b)-D-arabinofuranosyl)benzimidazole. Methods for using the compounds of this invention to prevent, inhibit or treat viral replication and/or propagation are provided. Additionally methods for using such compounds to prepare an antiviral medicament are provided.(FR) La présente invention a trait à des composés d'arabinofuranosyl benzimidazole, spécifiquement à un $g(b)-D-arabinofuranosylbenzimidazole représenté par la structure (I) et à ses analogues $g(b)-L, $g(a)-D et $g(a)-L. Dans la formule, R2, R4, R5, R6 et R7 sont sélectionnés indépendamment dans le groupe constitué par: -H, halo, -NO2, -NH2, -NHR8, -N(R8)2, -OR8, -SR8, et -CF3; R8 est -H ou un groupe alkyle de 1-8 atomes de carbone; R10, R11 et R12 sont sélectionnés indépendamment dans le groupe comprenant -H, -OH et un groupe protecteur hydroxyle; l'invention concerne également des sels pharmaceutiquement acceptables de ces composés, à condition que: a) lorsque chaque R4, R5, R6 et R7 est hydrogène, R2 est un groupe autre qu'hydrogène; b) lorsque R10 est -H, R11 n'est pas -H, et le composé n'est pas un composé $g(b); et c) le composé n'est pas 2,5,6-trichloro-1-($g(b)-D-arabinofuranosyl)benzimidazole. L'invention concerne des procédés d'utilisation des composés pour prévenir, inhiber ou traiter une réplication et/ou une propagation virale. De plus, l'invention concerne des procédés d'utilisation de ces composés pour préparer un médicament antiviral.
• Design, Synthesis and Antiviral Activity of α-L-Arabinofuranosyl Derivatives of 2-Substituted-5,6-dichlorobenzimidazoles
  作者：Jean-Luc Girardet、John C. Drach、Stanley D. Chamberlain、George W. KosLzalka、Leroy B. Townsend

  DOI：10.1080/07328319808004326

  日期：1998.12

  A number of 2-substituted-5,6-dichloro-1-(alpha-L-arabinofuranosyl)benzimidazoles have been prepared by condensation of 2-bromo-5,6-dichlorobenzimidazole or 2,5,6-trichlorobenzimidazole with tetra-O-acetyl-L-arabinofuranose. 2-Alkylamino derivatives were prepared by a substitution of the 2-chloro group with the appropriate amines. All target compounds were evaluated for activity against HCMV and HSV-1. The 2-chloro and 2-bromo derivatives showed moderate activity against HCMV at non-cytotoxic concentrations.