4-((2-chloro-9H-purin-6-yl)amino)benzenesulfonamide | 1236432-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 4-((2-chloro-9H-purin-6-yl)amino)benzenesulfonamide
• 英文别名: 4-[(2-chloro-7H-purin-6-yl)amino]benzenesulfonamide
• CAS: 1236432-59-9
• 化学式: C₁₁H₉ClN₆O₂S
• 分子量: 324.75
• InChiKey: HAKQIKNLEZYQIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-羟乙基哌嗪 、 4-((2-chloro-9H-purin-6-yl)amino)benzenesulfonamide 在 sodium tetrahydroborate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 生成 4-((2-(4-(2-hydroxyethyl)piperazin-1-yl)-9H-purin-6-yl)amino)benzenesulfonamide
  参考文献：
  名称：

  Discovery of novel purine derivatives with potent and selective inhibitory activity against c-Src tyrosine kinase

  摘要：

  We report here the discovery of novel purine derivatives with potent and selective inhibitory activity against c-Src tyrosine kinase by adopting a strategy integrating focused combinatorial library design, virtual screening, chemical synthesis, and bioassay. Thirty two compounds were selected and synthesized. All compounds showed potent inhibitory activity against c-Src kinase with IC50 values ranging from 3.14 mu M to 0.02 mu M. Compound 5i was identified as one of the most potent agent with an IC50 120 times lower than those of the hits. The high hit rate (100%) and the potency of the new Src kinase inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening. The novel active chemical entities reported here should be good leads for further development of purine-based anticancer drugs targeting Src tyrosine kinase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.032
• 作为产物：
  描述：

  磺胺 、 2,6-二氯嘌呤 在 三乙胺 作用下， 以 正丁醇 为溶剂， 70.0 ℃ 、1.79 MPa 条件下， 反应 0.17h， 以75%的产率得到4-((2-chloro-9H-purin-6-yl)amino)benzenesulfonamide
  参考文献：
  名称：

  Discovery of Multitarget Antivirals Acting on Both the Dengue Virus NS5-NS3 Interaction and the Host Src/Fyn Kinases

  摘要：

  This study describes the discovery of novel dengue virus inhibitors targeting both a crucial viral protein protein interaction and an essential host cell factor as a strategy to reduce the emergence of drug resistance. Starting from known c-Src inhibitors, a virtual screening was performed to identify molecules able to interact with a recently discovered allosteric pocket on the dengue virus NS5 polymerase. The selection of cheap-to-produce scaffolds and the exploration of the biologically relevant chemical space around them suggested promising candidates for chemical synthesis. A series of purines emerged as the most interesting candidates able to inhibit virus replication at low micromolar concentrations with no Significant toxicity to the host cell. Among the identified antivirals, compound 16i proved to be 10 times More potent than ribavirin, showed a better selectivity index and represents the first-in-class DENV-NS5 allosteric inhibitor able to target both the virus NS5-NS3 interaction and the host kinases c-Src/Fyn.

  DOI：

  10.1021/acs.jmedchem.5b00108