N*2*,N*2*-dimethylquinoline-2,4-diamine | 102669-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N*2*,N*2*-dimethylquinoline-2,4-diamine
• 英文别名: 2-dimethylamino-4-aminoquinoline；4-Amino-2-dimethylaminochinolin；N2,N2-Dimethylquinoline-2,4-diamine；2-N,2-N-dimethylquinoline-2,4-diamine
• CAS: 102669-54-5
• 化学式: C₁₁H₁₃N₃
• mdl: MFCD00204146
• 分子量: 187.244
• InChiKey: OXLDRPPQCHUJAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险类别：
  8
• 危险性防范说明：
  P301+P330+P331,P303+P361+P353,P363,P304+P340,P310,P321,P260,P264,P280,P305+P351+P338,P405,P501
• 危险品运输编号：
  3259
• 危险性描述：
  H314
• 包装等级：
  III

反应信息

• 作为反应物：
  描述：

  N*2*,N*2*-dimethylquinoline-2,4-diamine 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(2-dimethylaminoquinolin-4-yl)-2-(4-hydroxyphenyl)-acetamide
  参考文献：
  名称：

  Discovery of Aminoglycoside Mimetics by NMR-Based Screening of Escherichia coli A-site RNA

  摘要：

  A method is described for the NMR-based screening for the discovery of aminoglycoside mimetics that bind to Escherichia coli A-site RNA. Although aminoglycosides are clinically useful, they exhibit high nephrotoxicity and ototoxicity, and their overuse has led to the development of resistance to important microbial pathogens. To identify a new series of aminoglycoside mimetics that could potentially overcome the problems associated with toxicities and resistance development observed with the aminoglycosides, we have prepared large quantities of E. coli 16 S A-site RNA and conducted an NMR-based screening of our compound library in search for small-molecule RNA binders against this RNA target. From these studies, several classes of compounds were identified as initial hits with binding affinities in the range of 70 muM to 3 mM. Lead optimization through synthetic modifications of these initial hits led to the discovery of several small-molecule aminoglycoside mimetics that are structurally very different from the known aminoglycosides. Structural models of the A-site RNA/ligand complexes were prepared and compared to the three-dimensional structures of the RNA/aminoglycoside complexes.

  DOI：

  10.1021/ja021354o
• 作为产物：
  描述：

  (E)-N'-(2-cyanophenyl)-N,N-dimethylacetimidamide 在 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以47%的产率得到N*2*,N*2*-dimethylquinoline-2,4-diamine
  参考文献：
  名称：

  乙酰胺缩醛环化，3. Mitt. 杂环稠合 2-氨基吡啶和-喹啉

  摘要：

  许多杂环氨基酮与酰胺缩醛 2 和 4 缩合形成 2-氨基和吡咯并-吡啶和-喹啉衍生物。邻氨基苯甲酸酯和腈也与 2 反应生成氨基喹啉。

  DOI：

  10.1002/ardp.19863190410

文献信息

• Small molecule toll-like receptor (TLR) antagonists
  申请人：Lipford B. Grayson

  公开号：US20070232622A1

  公开（公告）日：2007-10-04

  The invention provides methods and compositions useful for modulating signaling through Toll-like receptors. The methods involve contacting a TLR-expressing cell with a small molecule having a core structure including at least two rings. Certain of the compounds are 4-primary amino quinolines. Many of the compounds and methods are useful specifically for inhibiting immune stimulation involving at least one of TLR9, TLR8, TLR7, and TLR3. The methods may have use in the treatment of autoimmunity, inflammation, allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer, and immunodeficiency.

  本发明提供了用于调节通过Toll样受体信号传导的方法和组合物。该方法涉及使用一个包含至少两个环的核心结构的小分子接触TLR表达的细胞。其中某些化合物是4-主氨基喹啉。许多化合物和方法特别适用于抑制至少一个TLR9、TLR8、TLR7和TLR3的免疫刺激。该方法可能在治疗自身免疫、炎症、过敏、哮喘、移植排斥、移植物抗宿主病、感染、败血症、癌症和免疫缺陷方面有用。
• EIDEN, F.;BERNDL, K., ARCH. PHARM., 1986, 319, N 4, 347-354
  作者：EIDEN, F.、BERNDL, K.

  DOI：——

  日期：——
• PHENYL UREA AND PHENYL THIOUREA DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1150977A1

  公开（公告）日：2001-11-07
• US6699879B1
  申请人：——

  公开号：US6699879B1

  公开（公告）日：2004-03-02
• US7410975B2
  申请人：——

  公开号：US7410975B2

  公开（公告）日：2008-08-12