N,N'-(2,6-diethynylpyridine-3,5-diyl)dimethanesulfonamide | 1159200-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N,N'-(2,6-diethynylpyridine-3,5-diyl)dimethanesulfonamide
• 英文别名: N-[2,6-diethynyl-5-(methanesulfonamido)pyridin-3-yl]methanesulfonamide
• CAS: 1159200-35-7
• 化学式: C₁₁H₁₁N₃O₄S₂
• 分子量: 313.358
• InChiKey: QJBZAENGCSEJTG-UHFFFAOYSA-N

物化性质

• 熔点：
  265-266 °C (decomp)(Solvent: Acetone; Hexane)
• 沸点：
  486.3±55.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N'-(2,6-diethynylpyridine-3,5-diyl)dimethanesulfonamide 在 potassium phosphate 、 copper(l) iodide 、 caesium carbonate 、 (1R,2R)-(-)-N,N'-二甲基-1,2-环己二胺 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 67.08h， 生成 ammonium 2-{dipyrrolo[3,2-b:2',3'-e]pyridin-1(7H)-yl}nicotinate
  参考文献：
  名称：

  Design and synthesis of a novel class of CK2 inhibitors: application of copper- and gold-catalysed cascade reactions for fused nitrogen heterocycles

  摘要：

  在以往结构-活性关系（SAR）研究的基础上，我们设计了两类融合氮杂环作为候选的 CK2 抑制剂。利用过渡金属催化的级联反应和/或多组分反应制备了各种二吡咯并[3,2-b:2′,3′-e]吡啶和苯并[g]吲唑衍生物。对这些候选化合物进行的生物学评估显示，苯并[g]吲唑是一种很有前途的强效 CK2 抑制剂支架。本文还介绍了这些强效 CK2 抑制剂对细胞增殖的抑制活性。

  DOI：

  10.1039/c2ob25298h
• 作为产物：
  描述：

  N3,N3,N5,N5-tetrakis(methylsulfonyl)-2,6-bis[(trimethylsilyl)ethynyl]pyridine-3,5-diamine 在 sodium hydroxide 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以90%的产率得到N,N'-(2,6-diethynylpyridine-3,5-diyl)dimethanesulfonamide
  参考文献：
  名称：

  Efficient Synthesis of Aminomethylated Pyrroloindoles and Dipyrrolopyridines via Controlled Copper-Catalyzed Domino Multicomponent Coupling and Bis-cyclization

  摘要：

  Efficient methods for the synthesis of pyrrole-fused indole derivatives via domino copper-catalyzed multicomponent coupling and bis-cyclization have been developed. The mono- or bis-aminomethylated pyrroloindoles and dipyrrolopyridines were selectively obtained in moderate to excellent yields by a controlled Mannich-type reaction-cyclization of 4,6-diethynyl-1,3-phenylenediamine or its pyridine congener with paraformaldehyde and a secondary amine. The high-yielding bis-cyclization of terminal alkynes without using Mannich-type reactions is also presented.

  DOI：

  10.1021/jo900681p

文献信息

• Efficient Synthesis of Aminomethylated Pyrroloindoles and Dipyrrolopyridines via Controlled Copper-Catalyzed Domino Multicomponent Coupling and Bis-cyclization
  作者：Yamato Suzuki、Yusuke Ohta、Shinya Oishi、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1021/jo900681p

  日期：2009.6.5

  Efficient methods for the synthesis of pyrrole-fused indole derivatives via domino copper-catalyzed multicomponent coupling and bis-cyclization have been developed. The mono- or bis-aminomethylated pyrroloindoles and dipyrrolopyridines were selectively obtained in moderate to excellent yields by a controlled Mannich-type reaction-cyclization of 4,6-diethynyl-1,3-phenylenediamine or its pyridine congener with paraformaldehyde and a secondary amine. The high-yielding bis-cyclization of terminal alkynes without using Mannich-type reactions is also presented.
• Design and synthesis of a novel class of CK2 inhibitors: application of copper- and gold-catalysed cascade reactions for fused nitrogen heterocycles
  作者：Yamato Suzuki、Shinya Oishi、Yoshinori Takei、Misato Yasue、Ryosuke Misu、Saori Naoe、Zengye Hou、Tatsuhide Kure、Isao Nakanishi、Hiroaki Ohno、Akira Hirasawa、Gozoh Tsujimoto、Nobutaka Fujii

  DOI：10.1039/c2ob25298h

  日期：——

  Two classes of fused nitrogen heterocycles were designed as CK2 inhibitor candidates on the basis of previous structure–activity relationship (SAR) studies. Various dipyrrolo[3,2-b:2′,3′-e]pyridine and benzo[g]indazole derivatives were prepared using transition-metal-catalysed cascade and/or multicomponent reactions. Biological evaluation of these candidates revealed that benzo[g]indazole is a promising scaffold for potent CK2 inhibitors. The inhibitory activities on cell proliferation of these potent CK2 inhibitors are also presented.

  在以往结构-活性关系（SAR）研究的基础上，我们设计了两类融合氮杂环作为候选的 CK2 抑制剂。利用过渡金属催化的级联反应和/或多组分反应制备了各种二吡咯并[3,2-b:2′,3′-e]吡啶和苯并[g]吲唑衍生物。对这些候选化合物进行的生物学评估显示，苯并[g]吲唑是一种很有前途的强效 CK2 抑制剂支架。本文还介绍了这些强效 CK2 抑制剂对细胞增殖的抑制活性。