3,6-双(4-氯苄基)-1,4-二氢-1,2,4,5-四嗪 | 82481-31-0

• 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-双(4-氯苄基)-1,4-二氢-1,2,4,5-四嗪
• 英文名称: 3,6-bis(4-chlorobenzyl)-1,4-dihydro-s-tetrazine
• 英文别名: 3,6-bis[(4-chlorophenyl)methyl]-1,4-dihydro-1,2,4,5-tetrazine
• CAS: 82481-31-0
• 化学式: C₁₆H₁₄Cl₂N₄
• 分子量: 333.22
• InChiKey: LYWYRVJEQHGTQG-UHFFFAOYSA-N

物化性质

• 熔点：
  203-204 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  467.1±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  48.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-双(4-氯苄基)-1,4-二氢-1,2,4,5-四嗪 在 溶剂黄146 、 sodium nitrite 作用下， 以57%的产率得到3,6-bis(4-chlorobenzyl)-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：

  对氯苯乙腈 在 sulfur 、 一水合肼 作用下， 以 乙醇 为溶剂， 以32%的产率得到3,6-双(4-氯苄基)-1,4-二氢-1,2,4,5-四嗪
  参考文献：
  名称：

  Synthesis, structure analysis, and antitumor activity of 3,6-disubstituted-1,4-dihydro-1,2,4,5-tetrazine derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2006.04.066

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.
• Hunter, Daniel; Neilson, Douglas G.; Weakley, Timothy J.R., Journal of the Chemical Society. Perkin transactions I, 1982, p. 1165 - 1170
  作者：Hunter, Daniel、Neilson, Douglas G.、Weakley, Timothy J.R.

  DOI：——

  日期：——
• HUNTER, D.;NEILSON, D. G.;WEAKLEY, T. J. R., J. CHEM. SOC. PERKIN TRANS., 1982, N 5, 1165-1170
  作者：HUNTER, D.、NEILSON, D. G.、WEAKLEY, T. J. R.

  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.