N,N-dimethyl-2-<(4'-furan-2''-ylpyrimidin-2'-yl)thio>ethylamine | 109628-19-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N,N-dimethyl-2-<(4'-furan-2''-ylpyrimidin-2'-yl)thio>ethylamine
• 英文别名: 2-{[4-(2-furyl)pyrimidin-2-yl]thio}-N,N-dimethylethanamine；2-[4-(furan-2-yl)pyrimidin-2-yl]sulfanyl-N,N-dimethylethanamine
• CAS: 109628-19-5
• 化学式: C₁₂H₁₅N₃OS
• 分子量: 249.337
• InChiKey: OZLNRLGFHZFWLZ-UHFFFAOYSA-N

物化性质

• 沸点：
  376.4±27.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-<(4-bromophenyl)thio>ethylamine 、 N,N-dimethyl-2-<(4'-furan-2''-ylpyrimidin-2'-yl)thio>ethylamine 在 正丁基锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 1.92h， 以72%的产率得到2-({4-[2-{[2-(dimethylamino)ethyl]thio}-6-(2-furyl)pyrimidin-4-yl]phenyl}thio)-N,N-dimethyl-ethanamine
  参考文献：
  名称：

  De Novo Design of Nonpeptidic Compounds Targeting the Interactions between Interferon-α and its Cognate Cell Surface Receptor

  摘要：

  Type 1 interferons (IFN) bind specifically to the corresponding receptor, IFNAR. Agonists and antagonists for IFNAR have potential therapeutic value in the treatment of viral infections and systemic lupus erythematosus, respectively. Specific sequences on the surface of IFN, IFN receptor recognition peptides (IRRPs) mediate the binding and signal transduction when IFN interacts with IFNAR. Structural features of two such IRRPs, IRRP-1 and IRRP-3, were used as templates to design small molecule mimetics. In silico screening was used to identify the molecular structural features mimicking their surface characteristics. A set of 26 compounds were synthesized and their ability to interfere with IFN-IFNAR interactions was investigated. Two compounds exhibited antagonist activity, specifically, blocking IFN-inducible Stat phosphorylation Stat complex-DNA binding. Design principles revealed here pave the way toward a novel series of small molecules as antagonists for IFN-IFNAR interactions.

  DOI：

  10.1021/jm701182y
• 作为产物：
  描述：

  2-甲胺乙硫醇盐酸盐 、 2-氯-4-(2-呋喃基)嘧啶 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以81%的产率得到N,N-dimethyl-2-<(4'-furan-2''-ylpyrimidin-2'-yl)thio>ethylamine
  参考文献：
  名称：

  [EN] SUBSTITUTED PYRIMIDINE COMPOUNDS AND THEIR USE AS IFNAR MEDIATORS
  [FR] COMPOSÉS DE PYRIMIDINE SUBSTITUÉS ET LEURS UTILISATIONS EN TANT QUE MÉDIATEURS D'IFNAR

  摘要：

  本申请涉及公式I的取代嘧啶化合物及其作为IFNAR配体的用途。该申请进一步涉及通过向需要的受试者施用公式(I)的这些化合物的IFNAR有效量来治疗或预防受益于通过调节IFNAR而获益的疾病或紊乱的方法。

  公开号：

  WO2009111893A1

文献信息

• Molecular basis for bleomycin amplification: conformational and stereoelectronic effects in unfused amplifiers
  作者：Lucjan Strekowski、Jerzy L. Mokrosz、Farial A. Tanious、Rebecca A. Watson、Donald Harden、Maria Mokrosz、W. Daniel Edwards、W. David Wilson

  DOI：10.1021/jm00401a027

  日期：1988.6

  biphenyl compounds substituted with an amino side chain (protonated in water) have been tested for (i) binding with DNA and (ii) their effect on the digestion of the DNA double helix by a bleomycin-iron complex. Only the DNA intercalating molecules amplify the digestion of DNA. One 2,2'-bipyridine derivative tested is an inhibitor of the bleomycin reaction because it removes ferrous ion from the bleomycin

  已经测试了16个未融合的杂双芳香族化合物和联苯化合物（被水质子化）的氨基侧链（i）与DNA结合，以及（ii）它们对博来霉素-铁络合物对DNA双螺旋的消化作用。只有DNA插入分子才能扩增DNA的消化。测试的一种2,2'-联吡啶衍生物是博来霉素反应的抑制剂，因为它从博来霉素复合物中去除了亚铁离子。插入的未融合双芳烃系统的极性对于分子与天然DNA的有效结合以及同时对其扩增活性至关重要。具有双芳族系统的分子在侧阳离子链的方向上广泛极化，因此插入位点构成偶极子的正部分，显示出与DNA的强结合力和良好的扩增活性 对于决定扩增活性的强插入力，重要的是分子的两个杂芳族子系统的偶极子的正端都远离侧链。这项工作为合成新型高效博来霉素放大器提供了一般指导。
• [EN] SUBSTITUTED PYRIMIDINE COMPOUNDS AND THEIR USE AS IFNAR MEDIATORS<br/>[FR] COMPOSÉS DE PYRIMIDINE SUBSTITUÉS ET LEURS UTILISATIONS EN TANT QUE MÉDIATEURS D'IFNAR
  申请人：UNIV HEALTH NETWORK

  公开号：WO2009111893A1

  公开（公告）日：2009-09-17

  The present application relates to substituted pyrimidine compounds of Formula I and their use as ligands for IFNAR. The application further relates to methods of treating or preventing diseases or disorders that benefit from the modulation of IFNAR by administering an IFNAR effective amount of said compounds of Formula (I) to a subject need thereof.

  本申请涉及公式I的取代嘧啶化合物及其作为IFNAR配体的用途。该申请进一步涉及通过向需要的受试者施用公式(I)的这些化合物的IFNAR有效量来治疗或预防受益于通过调节IFNAR而获益的疾病或紊乱的方法。
• New approach to conformational analysis of heterobiaryls in solution
  作者：Lucjan Strekowski、Farial A Tanious、Subramanian Chandrasekaran、Rebecca A Watson、W.David Wilson

  DOI：10.1016/s0040-4039(00)85394-0

  日期：1986.1

  Native DNA is used in conformational studies of heterobiaryls. Evidence is presented that the 4-(2′-furyl)pyrimidine and 4-(2′-thienyl)-pyrimidine systems exist in solution in an essentially planar and conformation, respectively. The 5-methy1-4-(2′-thieny1)pyrimidine system is also

  天然DNA用于杂二芳基的构象研究。证据表明4-（2'-呋喃基）嘧啶和4-（2'-噻吩基）-嘧啶体系分别以基本上平面和构象的形式存在于溶液中。5-methy1-4-（2'-thieny1）嘧啶系统也是
• STREKOWSKI, LUCJAN;MOKROSZ, JERZY L.;TANIOUS, FARIAL A.;WATSON, REBECCA A+, J. MED. CHEM., 31,(1988) N 6, 1231-1240
  作者：STREKOWSKI, LUCJAN、MOKROSZ, JERZY L.、TANIOUS, FARIAL A.、WATSON, REBECCA A+

  DOI：——

  日期：——
• De Novo Design of Nonpeptidic Compounds Targeting the Interactions between Interferon-α and its Cognate Cell Surface Receptor
  作者：Angelica M. Bello、Tanushree Bende、Lianhu Wei、Xiaoyang Wang、Beata Majchrzak-Kita、Eleanor N. Fish、Lakshmi P. Kotra

  DOI：10.1021/jm701182y

  日期：2008.5.1

  Type 1 interferons (IFN) bind specifically to the corresponding receptor, IFNAR. Agonists and antagonists for IFNAR have potential therapeutic value in the treatment of viral infections and systemic lupus erythematosus, respectively. Specific sequences on the surface of IFN, IFN receptor recognition peptides (IRRPs) mediate the binding and signal transduction when IFN interacts with IFNAR. Structural features of two such IRRPs, IRRP-1 and IRRP-3, were used as templates to design small molecule mimetics. In silico screening was used to identify the molecular structural features mimicking their surface characteristics. A set of 26 compounds were synthesized and their ability to interfere with IFN-IFNAR interactions was investigated. Two compounds exhibited antagonist activity, specifically, blocking IFN-inducible Stat phosphorylation Stat complex-DNA binding. Design principles revealed here pave the way toward a novel series of small molecules as antagonists for IFN-IFNAR interactions.