3,6-二(4-氯苯基)-1,2-二氢-1,2,4,5-四嗪 | 53876-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,6-二(4-氯苯基)-1,2-二氢-1,2,4,5-四嗪
• 英文名称: 3,6-bis-(4-chloro-phenyl)-1,4-dihydro-[1,2,4,5]tetrazine
• 英文别名: 3,6-bis(4-chlorophenyl)-1,4-dihydro-1,2,4,5-tetrazine；3,6-Bis-(p-Chlorphenyl)-1,4-dihydro-1,2,4,5-tetrazin
• CAS: 53876-70-3
• 化学式: C₁₄H₁₀Cl₂N₄
• 分子量: 305.166
• InChiKey: ZWCXJQUMYHNLFW-UHFFFAOYSA-N

物化性质

• 熔点：
  252 °C(Solv: 1-butanol (71-36-3))
• 沸点：
  413.0±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.8
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3,6-二(4-氯苯基)-1,2-二氢-1,2,4,5-四嗪 在 溶剂黄146 、 sodium nitrite 作用下， 以87%的产率得到3,6-bis-(4-chloro-phenyl)-[1,2,4,5]tetrazine
  参考文献：
  名称：

  Synthesis and antitumor activity of s -tetrazine derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2003.12.056
• 作为产物：
  描述：

  对氯苯甲腈 在 sulfur 、 一水合肼 作用下， 以 乙醇 为溶剂， 以71.1%的产率得到3,6-二(4-氯苯基)-1,2-二氢-1,2,4,5-四嗪
  参考文献：
  名称：

  Synthesis and Structure of bis(cyclohexylmethyl) 3,6-bis(4-chlorophenyl)-1,2,4,5-tetrazine-1,2-dicarboxylate

  摘要：

  双(环己基甲基) 3,6-双(4-氯苯基)-1,2,4,5-四嗪-1,2-二甲酸酯由氯甲酸环己基甲基酯和 3,6-双(4-氯苯基)-1,2(或 1,4)-二氢-1,2,4,5-四嗪制备而成，并通过 X 射线衍射测定了其结构。该反应生成的是标题化合物，而不是 3,6-双（4-氯苯基）-1,2,4,5-四嗪-1,4-二甲酸双（环己基甲基）酯。四嗪中央六元环中的 2,3-二氮杂丁二烯基团不是平面的，四嗪环呈扭曲构象。

  DOI：

  10.3184/174751911x13043532722967

文献信息

• Synthesis, structure analysis, antitumor evaluation and 3D-QSAR studies of 3,6-disubstituted-dihydro-1,2,4,5-tetrazine derivatives
  作者：Guo-Wu Rao、Cui Wang、Jian Wang、Zhen-Guo Zhao、Wei-Xiao Hu

  DOI：10.1016/j.bmcl.2013.09.036

  日期：2013.12

  3,6-Diaryl-dihydro-1,2,4,5-tetrazine derivatives were synthesized and their structures were confirmed by single-crystal X-ray diffraction. Monosubstituted dihydrotetrazines are the 1,4-dihydro structure, but disubstituted dihydrotetrazines are the 1,2-dihydro structure. The results of further research indicated there may be a rearrangement during the synthesis process of disubstituted dihydrotetrazines. Their antitumor activities were evaluated against A-549 and P388 cells in vitro. The results showed several compounds to be endowed with cytotoxicity in the low micromolar range. Two compounds were highly effective against A-549 cell and IC50 values were 0.575 and 2.08 mu M, respectively. Three-dimensional quantitative structure-activity relationship (3D-QSAR) studies of comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were carried out on 37 1,2,4,5-tetrazine derivatives with antitumor activity against A-549 cell. Models with good predictive abilities were generated with the cross validated q(2) values for CoMFA and CoMSIA being 0.744 and 0.757, respectively. Conventional r(2) values were 0.978 and 0.988, respectively, the predicted R-2 values were 0.916 and 0.898, respectively. The results provide the tool for guiding the design and synthesis of novel and more potent tetrazine derivatives. (C) 2013 Elsevier Ltd. All rights reserved.
• Hunter, Daniel; Neilson, Douglas G., Journal of the Chemical Society. Perkin transactions I, 1983, # 8, p. 1601 - 1603
  作者：Hunter, Daniel、Neilson, Douglas G.

  DOI：——

  日期：——
• Santus, Maria, Acta Poloniae Pharmaceutica, 1993, vol. 50, # 2.3, p. 183 - 188
  作者：Santus, Maria

  DOI：——

  日期：——
• Stolle; Weindel, Journal fur praktische Chemie (Leipzig 1954), 1906, vol. <2> 74, p. 11
  作者：Stolle、Weindel

  DOI：——

  日期：——
• 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.