1-(6-methoxypyridin-3-yl)-1H-benzimidazol-5-amine | 860301-34-4

• 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: 1-(6-methoxypyridin-3-yl)-1H-benzimidazol-5-amine
• 英文别名: 1-(6-Methoxypyridin-3-yl)benzimidazol-5-amine
• CAS: 860301-34-4
• 化学式: C₁₃H₁₂N₄O
• 分子量: 240.264
• InChiKey: SJJDJUUKRAVPBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(6-methoxypyridin-3-yl)-1H-benzimidazol-5-amine 、 乙醛 在 三乙酰氧基硼氢化钠 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole

  摘要：

  A chemically diverse library of about 400,000 small molecules was screened for antiviral activity against lentiviral pseudotypes with the Lassa virus envelope glycoprotein (LASV GP) gene incorporated. High-throughput screening resulted in discovery of a hit compound (ST-37) possessing a benzimidazole core which led to a potent compound series. Herein, we report SAR studies which involved structural modifications to the phenyl rings and methylamino linker portion attached to the benzimidazole core. Many analogs in this study possessed single digit nanomolar potency against LASV pseudotypes. Compounds in this benzimidazole series also exhibited nanomolar antiviral activity against pseudotypes generated from other arenavirus envelopes indicating the potential for development of a broad-spectrum inhibitor. Ultimately, lead compound ST-193 was identified and later found to be efficacious in a lethal LASV guinea pig model showing superior protection compared to ribavirin treatment. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.095
• 作为产物：
  描述：

  5-氨基-2-甲氧基吡啶 在 盐酸 、 palladium on activated charcoal 、 氢气 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 生成 1-(6-methoxypyridin-3-yl)-1H-benzimidazol-5-amine
  参考文献：
  名称：

  Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole

  摘要：

  A chemically diverse library of about 400,000 small molecules was screened for antiviral activity against lentiviral pseudotypes with the Lassa virus envelope glycoprotein (LASV GP) gene incorporated. High-throughput screening resulted in discovery of a hit compound (ST-37) possessing a benzimidazole core which led to a potent compound series. Herein, we report SAR studies which involved structural modifications to the phenyl rings and methylamino linker portion attached to the benzimidazole core. Many analogs in this study possessed single digit nanomolar potency against LASV pseudotypes. Compounds in this benzimidazole series also exhibited nanomolar antiviral activity against pseudotypes generated from other arenavirus envelopes indicating the potential for development of a broad-spectrum inhibitor. Ultimately, lead compound ST-193 was identified and later found to be efficacious in a lethal LASV guinea pig model showing superior protection compared to ribavirin treatment. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.095

文献信息

• Selective Kinase Inhibitors
  申请人：Styles Michelle Leanne

  公开号：US20080207613A1

  公开（公告）日：2008-08-28

  A compound of the general formula (I) or pharmaceutically acceptable prodrugs, salts, hydrates, solvates, crystal forms or diastereomers thereof, wherein A represents a variety of six membered nitrogen containing heterocyclic rings, Q is a bond, halogen, C 1-4 alkyl, O, S, SO 2 , CO or CS and X 1 , X 2 , X 3 and X 4 are optionally substituted by 9 specific substituents or one can be nitrogen. Compositions comprising a carrier and at least one compound of formula (I) are also provided. Further provided are methods of treating tyrosine kinase-associated disease states by administering a compound of formula (I) and methods of suppressing the immune system of a subject by administering a compound of formula (I).

  本发明涉及一种具有一般式(I)的化合物或药物可接受的前药、盐、水合物、溶剂合物、晶体形式或对映体，其中A代表多种六元杂环氮含杂环，Q为键，卤素，C1-4烷基，O，S，SO2，CO或CS，X1、X2、X3和X4可选地被9种特定取代基取代，或者其中一个可以是氮。还提供包含载体和至少一种式(I)的化合物的组合物。此外，本发明还提供了通过给予式(I)的化合物治疗酪氨酸激酶相关疾病状态的方法，以及通过给予式(I)的化合物抑制主体的免疫系统的方法。
• SELECTIVE KINASE INHIBITORS
  申请人：STYLES MICHELLE LEANNE

  公开号：US20110082142A1

  公开（公告）日：2011-04-07

  A compound of the general formula (I) or pharmaceutically acceptable prodrugs, salts, hydrates, solvates, crystal forms or diastereomers thereof, wherein A represents a variety of six membered nitrogen containing heterocyclic rings, Q is a bond, halogen, C 1-4 alkyl, O, S, SO 2 , CO or CS and X 1 , X 2 , X 3 and X 4 are optionally substituted by 9 specific substituents or one can be nitrogen. Compositions comprising a carrier and at least one compound of formula (I) are also provided. Further provided are methods of treating tyrosine kinase-associated disease states by administering a compound of formula (I) and methods of suppressing the immune system of a subject by administering a compound of formula (I).

  通式（I）或其药学上可接受的前药、盐、水合物、溶剂合物、晶体形式或对映体的化合物，其中A代表多种含六元杂环氮的杂环，Q是键、卤素、C1-4烷基、O、S、SO2、CO或CS，X1、X2、X3和X4可以选择性地被9个特定的取代基或一个可以是氮原子的取代基所取代。还提供包含载体和至少一种通式（I）化合物的组合物。此外，还提供了通过给予通式（I）化合物治疗酪氨酸激酶相关疾病状态的方法，以及通过给予通式（I）化合物抑制受试者的免疫系统的方法。
• US8329737B2
  申请人：——

  公开号：US8329737B2

  公开（公告）日：2012-12-11
• Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole
  作者：Dongcheng Dai、James R. Burgeson、Dima N. Gharaibeh、Amy L. Moore、Ryan A. Larson、Natasha R. Cerruti、Sean M. Amberg、Tove’ C. Bolken、Dennis E. Hruby

  DOI：10.1016/j.bmcl.2012.11.095

  日期：2013.2

  A chemically diverse library of about 400,000 small molecules was screened for antiviral activity against lentiviral pseudotypes with the Lassa virus envelope glycoprotein (LASV GP) gene incorporated. High-throughput screening resulted in discovery of a hit compound (ST-37) possessing a benzimidazole core which led to a potent compound series. Herein, we report SAR studies which involved structural modifications to the phenyl rings and methylamino linker portion attached to the benzimidazole core. Many analogs in this study possessed single digit nanomolar potency against LASV pseudotypes. Compounds in this benzimidazole series also exhibited nanomolar antiviral activity against pseudotypes generated from other arenavirus envelopes indicating the potential for development of a broad-spectrum inhibitor. Ultimately, lead compound ST-193 was identified and later found to be efficacious in a lethal LASV guinea pig model showing superior protection compared to ribavirin treatment. (c) 2012 Elsevier Ltd. All rights reserved.