6-amino-2-chloro-5-iodobenzimidazole | 142356-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 6-amino-2-chloro-5-iodobenzimidazole
• 英文别名: 2-Chloro-5-iodo-1H-benzo[d]imidazol-6-amine；2-chloro-6-iodo-1H-benzimidazol-5-amine
• CAS: 142356-55-6
• 化学式: C₇H₅ClIN₃
• 分子量: 293.494
• InChiKey: SGLZOBHYWCZASX-UHFFFAOYSA-N

物化性质

• 沸点：
  471.8±55.0 °C(Predicted)
• 密度：
  2.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-amino-2-chloro-5-iodobenzimidazole 在 硫酸 、 potassium iodide 、 sodium nitrite 作用下， 生成 2-Chloro-5,6-diiodobenzimidazole
  参考文献：
  名称：

  Design, Synthesis, and Antiviral Evaluation of 2-Chloro-5,6-dihalo-1-β-d-ribofuranosylbenzimidazoles as Potential Agents for Human Cytomegalovirus Infections

  摘要：

  2-Chloro-5,6-difluorobenzimidazole (8) was prepared from 4,5-difluoro-2-nitroaniline (5) via successive reduction, cyclization, and diazotization reactions. 2-Chloro-5,6-dibromobenzimidazole (10) was obtained by a direct bromination of 2-chlorobenzimidazole (9) with bromine-water. 2-Chloro-5,6-diiodobenzimidazole (15) was synthesized by a stepwise transformation of the nitro functions of 2-chloro-5,6-dinitrobenzimidazole (11) into iodo groups via diazotization reactions. Ribosylation of 8, 10, and 15 gave the respective beta nucleosides 16a-c as the major products along with a small amount of the alpha anomers 17a-c. Deprotection of 16a-c afforded the corresponding free beta nucleo sides 2-chloro-5,6-difluoro-1-beta-D-ribofuranosylbenzimidazole (2), 2-chloro-5,D-dibromo-1-beta-D-ribofuranosylbenzimidazole (3), and 2-chloro-5,6-diiodo-1-beta-D-ribofuranosylbenzimidazole (4). Similar deprotection of the alpha anomers (17a-c) resulted in a removal of the acetyl protecting groups and a concomitant cyclization to give the 2,2'-O-cyclonucleosides (18a-c). Most of the benzimidazole heterocycles, but not the difluoro analog, were active against human cytomegalovirus (HCMV) (IC50's = 3-40 mu M) and herpes simplex virus type 1 (HSV-1) (IC50's = 50-90 mu M). This activity, however, was not well separated from cytotoxicity, IC50's = 10-100 mu M. The corresponding unsubstituted, the 5,6-dimethyl, and the 5,6-difluoro ribonucleosides (19, 20, and 2, respectively), were inactive against both viruses. Similar to the previously reported 2,5,6-trichloro analog (TCRB), the 5,6-dibromo ribonucleoside 3 was active against HCMV (IC50 approximate to 4 mu M) but more cytotoxic than TCRB. The 5,6-diiodo analog 4 also was active (IC50 approximate to 2 mu M) but more cytotoxic (IC50 = 10-20 mu M) than either 3 or TCRB. The cyclonucleosides were inactive against both viruses and not cytotoxic, or slightly active with corresponding cytotoxicity. The order of activity against HCMV of the dihalobenzimidazole ribonucleosides was I similar or equal to Br similar or equal to Cl much greater than F > H = CH3. The order of cytotoxicity among the most active compounds, however, was I > Br > Cl, thereby establishing that TCRB had the best antiviral properties.

  DOI：

  10.1021/jm960462g
• 作为产物：
  描述：

  2-chloro-5(6)-iodo-6(5)-nitrobenzimidazole 在 镍 氢气 、 silica 、 chloroform methanol 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、45.96 MPa 条件下， 反应 7.0h， 以gave 0.190 g (62%) of 26a as a foam的产率得到6-amino-2-chloro-5-iodobenzimidazole
  参考文献：
  名称：

  Polysubstituted benzimidazoles as antiviral agents

  摘要：

  本发明涉及新型多取代苯并咪唑及其组合物，以及它们在治疗病毒感染方面的应用。本发明的多取代苯并咪唑和组合物对疱疹病毒家族的病毒，尤其是人类巨细胞病毒（HCMV）和单纯疱疹病毒（HSV）表现出抗病毒特性。

  公开号：

  US05646125A1

文献信息

• POLYSUBSTITUTED BENZIMIDAZOLES AS ANTIVIRAL AGENTS
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：EP0556334A1

  公开（公告）日：1993-08-25
• EP0556334A4
  申请人：——

  公开号：EP0556334A4

  公开（公告）日：1995-03-29
• US5248672A
  申请人：——

  公开号：US5248672A

  公开（公告）日：1993-09-28
• US5360795A
  申请人：——

  公开号：US5360795A

  公开（公告）日：1994-11-01
• US5574058A
  申请人：——

  公开号：US5574058A

  公开（公告）日：1996-11-12