3,6-Dibenzyl-1,2-dihydro-[1,2,4,5]tetrazin | 53460-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,6-Dibenzyl-1,2-dihydro-[1,2,4,5]tetrazin
• 英文别名: 3,6-dibenzyl-1,4-dihydro-1,2,4,5-tetrazine
• CAS: 53460-57-4
• 化学式: C₁₆H₁₆N₄
• 分子量: 264.33
• InChiKey: JOCZFBNLJSBBIL-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C
• 沸点：
  416.3±48.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 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-Dibenzyl-1,2-dihydro-[1,2,4,5]tetrazin 在 盐酸 作用下， 反应 0.08h， 生成 3,5-二苄基-1,2,4-三唑-4-胺
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 3,5-Dibenzyl-4-amino-1,2,4-triazole and its Diazo Ligand, Metal Complexes Along with Anticancer Activity

  摘要：

  通过传统方法和微波辐射方法合成了3,5-二苄基-4-氨基-1,2,4-三唑，然后进行重氮化和与2,4-戊二酮的偶联反应。得到了双核配体，并与Ni(II)、Cu(II)和Ru(III)氯化物形成络合物。对Jurkat、Raji和PBMC细胞系进行筛选，以评估这些配合物的抗癌活性。其中，铑配合物表现出潜在的抗癌活性。

  DOI：

  10.1155/2010/569605
• 作为产物：
  描述：

  2-苯基硫代乙酰胺 在 乙醇 、 水 、 肼 作用下， 生成 3,6-Dibenzyl-1,2-dihydro-[1,2,4,5]tetrazin
  参考文献：
  名称：

  Junghahn, Chemische Berichte, 1898, vol. 31, p. 312

  摘要：

  DOI：

文献信息

• First representatives of <i>C</i>-glycosyl 1,2,4,5-tetrazines: synthesis of 3-β-<scp>d</scp>-glucopyranosyl 1,2,4,5-tetrazines and their transformation into 3-β-<scp>d</scp>-glucopyranosyl pyridazines
  作者：Éva Bokor、Dóra T. Kecskés、Ferenc Gombás、Alexandra Fehér、Eszter Kardos、Akram Dabian、Zsófia Vonza、Eszter Szennyes、László Somsák

  DOI：10.1039/d2nj03920f

  日期：——

  applications e.g. in heterocyclic syntheses and recently in bioorthogonal chemistry. C-Glycopyranosyl tetrazines are unknown in the literature, therefore, we have started to study their synthesis. In this paper ring closing reactions leading to s-tetrazines have been investigated with suitable β-D-glucopyranosyl precursors and the feasible transformations have been identified. In addition, the obtained

  1,2,4,5-四嗪（s-四嗪）是一类早已为人所知的化合物，具有许多应用，例如杂环合成和最近的生物正交化学。C- Glycopyranosyl四嗪在文献中是未知的，因此，我们已经开始研究它们的合成。在本文中，已经用合适的 β- D-吡喃葡萄糖基前体研究了导致s-四嗪的闭环反应，并确定了可行的转化。此外，获得的C-吡喃葡萄糖基四嗪的基本保护基相容性及其在反电子需求 Diels-Alder 环加成对各种C-吡喃葡萄糖基哒嗪已被证实。
• 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.
• Pinner, Chemische Berichte, 1897, vol. 30, p. 1885
  作者：Pinner

  DOI：——

  日期：——
• Junghahn, Chemische Berichte, 1898, vol. 31, p. 312
  作者：Junghahn

  DOI：——

  日期：——
• Microwave-Assisted Synthesis of 3,5-Dibenzyl-4-amino-1,2,4-triazole and its Diazo Ligand, Metal Complexes Along with Anticancer Activity
  作者：Anjali Jha、Y. L. N. Murthy、G. Durga、T. T. Sundari

  DOI：10.1155/2010/569605

  日期：——

  Synthesis of 3,5-dibenzyl-4-amino-1,2,4-triazole was accomplished via a conventional method as well as microwave irradiation method, followed by diazotization and coupling with 2,4-pentanedione. The dinucleating ligand was isolated and complexed with Ni(II), Cu(II) and Ru(III) chlorides. These complexes were screened on Jurkat, Raji & PBMC cell lines for anticancer activity. Ruthenium complexes showed potential anticancer activities.

  通过传统方法和微波辐射方法合成了3,5-二苄基-4-氨基-1,2,4-三唑，然后进行重氮化和与2,4-戊二酮的偶联反应。得到了双核配体，并与Ni(II)、Cu(II)和Ru(III)氯化物形成络合物。对Jurkat、Raji和PBMC细胞系进行筛选，以评估这些配合物的抗癌活性。其中，铑配合物表现出潜在的抗癌活性。