3,6-bis(3-methylpyridin-2-yl)-1,2,4,5-tetrazine | 628732-65-0

• 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: 3,6-bis(3-methylpyridin-2-yl)-1,2,4,5-tetrazine
• 英文别名: 1,2,4,5-Tetrazine, 3,6-bis(3-methyl-2-pyridinyl)-
• CAS: 628732-65-0
• 化学式: C₁₄H₁₂N₆
• 分子量: 264.289
• InChiKey: NNEXMQHFVWHKPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [Ru(acac)₂(MeCN)_2] 、 3,6-bis(3-methylpyridin-2-yl)-1,2,4,5-tetrazine 以 二氯甲烷 为溶剂， 反应 24.0h， 以23%的产率得到[[Ru(acetylacetonate)₂]₂(1)]
  参考文献：
  名称：

  桥接两个 [Ru(acac)2] 片段的四嗪螯合物配体：混合价态和自由基络合物形成

  摘要：

  使用 bis(3-methyl-2-pyridyl)-1,2,4,5-tetrazine 1 , 3-(2-pyrimidyl)-6-methyl-1,2,4,5-tetrazine 2和 bis(2-嘧啶基)-1,2,4,5-四嗪=bmtz作为配体，配合物3 =[Ru(acac) 2 ( 1 )], 4 ={[Ru(acac) 2 ] 2 ( 1 )], 5 =制备了{[Ru(acac) 2 ] 2 (bmtz)] 和6 ={[Ru(acac) 2 ] 2 ( 2 )] 并通过结晶材料的结构分析进行了鉴定。单电子氧化型6 (PF 6) 也在结构上进行了研究，表明 II 类混合价情况。中性双核系统表现出两个可逆氧化过程，其歧化常数为 10 9.2 < K c <10 14.1和一个还原过程，通过 UV/vis/NIR 和 EPR 光谱分析。氧化主要产生基于金属的混合价阳离子，在近红外区具有

  DOI：

  10.1002/zaac.202200152
• 作为产物：
  描述：

  2-氰基-3-甲基吡啶 在 盐酸 、 hydrazine hydrate 、 sulfur 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以31%的产率得到3,6-bis(3-methylpyridin-2-yl)-1,2,4,5-tetrazine
  参考文献：
  名称：

  桥接两个 [Ru(acac)2] 片段的四嗪螯合物配体：混合价态和自由基络合物形成

  摘要：

  使用 bis(3-methyl-2-pyridyl)-1,2,4,5-tetrazine 1 , 3-(2-pyrimidyl)-6-methyl-1,2,4,5-tetrazine 2和 bis(2-嘧啶基)-1,2,4,5-四嗪=bmtz作为配体，配合物3 =[Ru(acac) 2 ( 1 )], 4 ={[Ru(acac) 2 ] 2 ( 1 )], 5 =制备了{[Ru(acac) 2 ] 2 (bmtz)] 和6 ={[Ru(acac) 2 ] 2 ( 2 )] 并通过结晶材料的结构分析进行了鉴定。单电子氧化型6 (PF 6) 也在结构上进行了研究，表明 II 类混合价情况。中性双核系统表现出两个可逆氧化过程，其歧化常数为 10 9.2 < K c <10 14.1和一个还原过程，通过 UV/vis/NIR 和 EPR 光谱分析。氧化主要产生基于金属的混合价阳离子，在近红外区具有

  DOI：

  10.1002/zaac.202200152

文献信息

• Synthesis and antitumor activity of s -tetrazine derivatives
  作者：Wei-Xiao Hu、Guo-Wu Rao、Ya-Quan Sun

  DOI：10.1016/j.bmcl.2003.12.056

  日期：2004.3

  Fifty-five compounds of s-tetrazine derivative including hexahydro-, 1,6-dihydro, 1,4-dihydro-, 1,2-dihydro- and aromatic s-tetrazine were prepared. Their antitumor activities were evaluated in vitro by MTT method for P-388 cell and SRB method for A-549 cell. The results show that there are 9 compounds which in 10(-6) muM have more than 50% inhibition rate to A-549 cancer cell growth, and 7 compounds in 10(-6) muM have more than 50% inhibition rate to P-388 cancer cell growth. The IC50 of compound 3q for P-388, Bel-7402, MCF-7 and A-549 are 0.6 muM, 0.6 muM, 0.5 muM and 0.7 muM, respectively. So s-tetrazine derivative is a kind of compound which possesses potential antitumor activities and is worth to research further. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives
  作者：Guo-Wu Rao、Wei-Xiao Hu

  DOI：10.1016/j.bmcl.2006.04.066

  日期：2006.7

  Fourteen compounds of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives were prepared and their structures were confirmed by single-crystal X-ray diffraction and the semi-empirical calculation of PM3 method. This reaction yields the 1,4-dihydro derivatives rather than the 1,2.-dihydro derivatives. The central six-membered ring of 1,4-dihydro-1,2,4,5-tetrazine has a chair conformation and therefore is not homoaromatic. Their antitumor activities were evaluated in vitro by SRB method for A-549 and BEL-7402 cells, and MTT method for P-388 and HL-60 cells. The results show that there is one compound which is highly effective against P-388 cells and one compound which is highly effective against HL-60 cells. So it is a kind of compound which possesses potential antitumor activities and is worth to research further. (c) 2006 Elsevier Ltd. All rights reserved.
• Tetrazine Chelate Ligands Bridging Two [Ru(acac) ₂ ] Fragments: Mixed Valency and Radical Complex Formation
  作者：Wolfgang Kaim、Isabell Löw、Mark R. Ringenberg、Brigitte Schwederski、Vasileios Filippou、Jan Fiedler

  DOI：10.1002/zaac.202200152

  日期：2022.12.13

  Using bis(3-methyl-2-pyridyl)-1,2,4,5-tetrazine 1, 3-(2-pyrimidyl)-6-methyl-1,2,4,5-tetrazine 2 and bis(2-pyrimidyl)-1,2,4,5-tetrazine=bmtz as ligands, the complexes 3=[Ru(acac)2(1)], 4=[Ru(acac)2]2(1)], 5=[Ru(acac)2]2(bmtz)], and 6=[Ru(acac)2]2(2)] were prepared and identified by structure analysis of crystallized material. The one-electron oxidized form 6(PF6) was also studied structurally, suggesting

  使用 bis(3-methyl-2-pyridyl)-1,2,4,5-tetrazine 1 , 3-(2-pyrimidyl)-6-methyl-1,2,4,5-tetrazine 2和 bis(2-嘧啶基)-1,2,4,5-四嗪=bmtz作为配体，配合物3 =[Ru(acac) 2 ( 1 )], 4 =[Ru(acac) 2 ] 2 ( 1 )], 5 =制备了[Ru(acac) 2 ] 2 (bmtz)] 和6 =[Ru(acac) 2 ] 2 ( 2 )] 并通过结晶材料的结构分析进行了鉴定。单电子氧化型6 (PF 6) 也在结构上进行了研究，表明 II 类混合价情况。中性双核系统表现出两个可逆氧化过程，其歧化常数为 10 9.2 < K c <10 14.1和一个还原过程，通过 UV/vis/NIR 和 EPR 光谱分析。氧化主要产生基于金属的混合价阳离子，在近红外区具有