3,6-二苯基-1,2,4,5-四嗪-1,2-二羧酸二丙酯 | 579523-89-0

• 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: 3,6-二苯基-1,2,4,5-四嗪-1,2-二羧酸二丙酯
• 英文名称: dipropyl 3,6-diphenyl-1,2-dihydro-1,2,4,5-tetrazine-1,2-dicarboxylate
• 英文别名: Dipropyl 3,6-diphenyl-1,2,4,5-tetrazine-1,2-dicarboxylate
• CAS: 579523-89-0
• 化学式: C₂₂H₂₄N₄O₄
• 分子量: 408.457
• InChiKey: DJFNJLZNKSZPKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲腈 在 吡啶 、 sulfur 、 一水合肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3,6-二苯基-1,2,4,5-四嗪-1,2-二羧酸二丙酯
  参考文献：
  名称：

  Synthesis, structure analysis, antitumor evaluation and 3D-QSAR studies of 3,6-disubstituted-dihydro-1,2,4,5-tetrazine derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2013.09.036

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.
• Dipropyl 3,6-diphenyl-1,2-dihydro-1,2,4,5-tetrazine-1,2-dicarboxylate
  作者：Guo-Wu Rao、Wei-Xiao Hu

  DOI：10.1107/s0108270103007212

  日期：2003.5.15

  The title compound, C22H24N4O4, was prepared from propyl chloroformate and 3,6-diphenyl-1,2-dihydro-s-tetrazine. This reaction yields the title compound rather than dipropyl 3,6-diphenyl-1,4-dihydro-s-tetrazine-1,4-dicarboxylate. The 2,3-diazabutadiene group in the central six-membered ring is not planar; the C-N double-bond length is 1.285 (2) Angstrom, and the average N-N single-bond length is 1.401 (3) Angstrom, indicating a lack of conjugation. The ring has a twist conformation, in which adjacent N atoms lie +/-0.3268 (17) Angstrom from the plane of the ring. The molecule has twofold crystallographic symmetry.