2,4,6-tris(3-nitroaniline)-1,3,5-triazine | 2352-35-4

• 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: 2,4,6-tris(3-nitroaniline)-1,3,5-triazine
• 英文别名: N,N',N''-tris-(3-nitro-phenyl)-[1,3,5]triazine-2,4,6-triamine；N²,N⁴,N⁶-tris-(3-nitro-phenyl)-[1,3,5]triazine-2,4,6-triyltriamine；N²,N⁴,N⁶-Tris-(3-nitro-phenyl)-[1,3,5]triazin-2,4,6-triyltriamin；2,4,6-Tris-<3-nitroanilino>-1,3,5-triazin；2,4,6-Tris-(3-nitro-anilino)-1,3,5-triazin；2-N,4-N,6-N-tris(3-nitrophenyl)-1,3,5-triazine-2,4,6-triamine
• CAS: 2352-35-4
• 化学式: C₂₁H₁₅N₉O₆
• 分子量: 489.407
• InChiKey: VJJSAHZVRRMMJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  212
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,4,6-tris(3-nitroaniline)-1,3,5-triazine 在 盐酸 、 tin 、 三溴化硼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  构象选择作为柔性超分子宿主中客体结合的机制

  摘要：

  这项研究提供了对新型酶模拟金属配体宿主中宿主 - 客体封装行为的详细机制研究，并首次观察了超分子系统中的构象选择机制（与诱导匹配相反）。所描述的 Ga4L4 主体具有 C3 对称配体基序和间位取代的苯基间隔基团，这使主体能够最初自组装成 S4 对称结构，然后随后异构化为 T 对称四面体，以便更好地容纳足够大的来宾。选择性反转恢复 1H NMR 研究提供了对该动态系统中主体和客体的自交换行为的结构洞察。封装-异构化事件的动力学分析表明，增加客体浓度会抑制主客体松弛的速率，这是构象选择的一个关键区别特征。对这种简单酶模拟物的综合研究提供了对生物物理学和酶学中类似行为的深入了解，旨在为高效自组装微环境催化剂的设计提供信息。

  DOI：

  10.1021/jacs.7b03812
• 作为产物：
  描述：

  2,4,6-三溴-1,3,5-三嗪 、 间硝基苯胺 在 苯 作用下， 生成 2,4,6-tris(3-nitroaniline)-1,3,5-triazine
  参考文献：
  名称：

  v.Meyer,E.; Naebe, Journal fur praktische Chemie (Leipzig 1954), 1910, vol. <2>82, p. 536

  摘要：

  DOI：

文献信息

• Prodrugs for nitroreductase based cancer therapy-4: Towards prostate cancer targeting: Synthesis of N-heterocyclic nitro prodrugs, Ssap-NtrB enzymatic activation and anticancer evaluation
  作者：Tuğba Güngör、Esra Tokay、Ünzile Güven Gülhan、Nelin Hacıoğlu、Ayhan Çelik、Feray Köçkar、Mehmet Ay

  DOI：10.1016/j.bioorg.2020.104450

  日期：2020.12

  In this study, various N-heterocyclic nitro prodrugs (NHN1-16) containing pyrimidine, triazine and piperazine rings were designed and synthesized. The final compounds were identified using FT-IR, ¹H NMR, ¹³C NMR as well as elemental analyses. Enzymatic activities of compounds were conducted by using HPLC analysis to investigate the interaction of substrates with Ssap-NtrB nitroreductase enzyme. MTT assay was performed to evaluate the toxic effect of compounds against Hep3B and PC3 cancer cell lines and healthy HUVEC cell. It was observed that synthesized compounds NHN1-16 exhibited different cytotoxic profiles. Pyrimidine derivative NHN3 and triazine derivative NHN5 can be good drug candidates for prostate cancer with IC₅₀ values of 54.75 µM and 48.9 µM, respectively. Compounds NHN6, NHN10, NHN12, NHN14 and NHN16 were selected as prodrug candidates because of non-toxic properties against three different cell models. The NHN prodrugs and Ssap-NtrB combinations were applied to SRB assay to reveal the prodrug capabilities of these selected compounds. SRB screening results showed that the metabolites of all selected non-toxic compounds showed remarkable cytotoxicity with IC₅₀ values in the range of 1.71-4.72 nM on prostate cancer. Among the tested compounds, especially piperazine derivatives NHN12 and NHN14 showed significant toxic effect with IC₅₀ values of 1.75 nM and 1.79 nM against PC3 cell compared with standart prodrug CB1954 (IC₅₀: 1.71 nM). Novel compounds NHN12 and NHN14 can be considered as promising prodrug candidates for nitroreductase-prodrug based prostate cancer therapy.