naphtho[2,1-e]thiazolo[2,3-c][1,2,4]triazinium perchlorate | 1298087-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphtho[2,1-e]thiazolo[2,3-c][1,2,4]triazinium perchlorate
• 英文别名: 14-Thia-16,17-diaza-11-azoniatetracyclo[8.7.0.02,7.011,15]heptadeca-1(10),2,4,6,8,11(15),12,16-octaene;perchlorate
• CAS: 1298087-36-1
• 化学式: C₁₃H₈N₃S*ClO₄
• 分子量: 337.743
• InChiKey: RIETVAQPMMEDHR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.17
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(2-噻唑基偶氮)-2-萘酚 在 oxovanadium(IV) sulfate 、 calcium perchlorate tetrahydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以85%的产率得到naphtho[2,1-e]thiazolo[2,3-c][1,2,4]triazinium perchlorate
  参考文献：
  名称：

  Planar triazinium cations from VO2+-assisted ring cyclizations: a remarkably efficient thiazole species for nuclear staining, PDT and anaerobic photocleavage of DNA

  摘要：

  来自 VO2+ 辅助环化 1-(2-thiazolylazo)-2-naphthol 的平面三嗪鎓阳离子物种，在 HeLa 和 MCF-7 癌细胞中显示出有效的 DNA 嵌入结合、可见光诱导的厌氧质粒 DNA 光裂解活性和光细胞毒性。细胞核染色和共聚焦成像证明了化合物在细胞核中选择性定位的凋亡途径。

  DOI：

  10.1039/c0cc05386d

文献信息

• Planar triazinium cations from vanadyl-mediated ring cyclizations: the thiazole species for efficient nuclear staining and photocytotoxicity
  作者：Puja Prasad、Imran Khan、Pijus K. Sasmal、Debasis Koley、Paturu Kondaiah、Akhil R. Chakravarty

  DOI：10.1039/c2dt32810k

  日期：——

  Planar triazinium cationic species from vanadyl-assisted cyclization of 1-(2-thiazolylazo)-2-naphthol (H-TAN, 1), 1-(2-pyridylazo)-2-naphthol (H-PAN, 2), 2-(2′-thiazolylazo)-p-cresol (H-TAC, 3) and 6-(2′-thiazolylazo)-resorcinol (H-TAR, 5) were prepared and characterized. A dioxovanadium(V) species [VO2(TAR)] (4) was also isolated. Compounds 1, 2 and 4 were structurally characterized. Both 1 and 2 have planar structures. Complex 4 has VVO3N2 coordination geometry. The cyclised triazinium compound forms a radical species within −0.06 to −0.29 V vs. SCE in DMF–0.1 M tetrabutylammonium perchlorate with a second response due to formation of an anionic species. A confocal microscopic study showed higher nuclear uptake for 1 having a fused thiazole moiety than 2 with a fused pyridine ring. The compounds showed a partial intercalative mode of binding to calf thymus DNA. Compound 1 showed plasmid DNA photo-cleavage activity under argon and photocytotoxicity in HeLa and MCF-7 cells with IC50 values of 15.1 and 3.4 μM respectively in visible light of 400–700 nm, while being essentially non-toxic in the dark with IC50 values of 90.4 and 21.9 μM. A TDDFT study was done to rationalize the experimental data.

  通过1-(2-噻唑偶氮)-2-萘酚（H-TAN，1）、1-(2-吡啶偶氮)-2-萘酚（H-PAN，2）、2-(2'-噻唑偶氮)-对甲酚（H-TAC，3）和6-(2'-噻唑偶氮)-间苯二酚（H-TAR，5）的钒辅助环化反应，制备并表征了平面三嗪阳离子物种。还分离得到了一种二氧钒(V)物种[VO2(TAR)]（4）。化合物1、2和4进行了结构表征。1和2均具有平面结构，复合物4具有VVO3N2配位几何结构。环化的三嗪化合物在DMF-0.1 M四丁基高氯酸铵中形成自由基物种，电位范围为-0.06至-0.29 V vs. SCE，并由于阴离子物种的形成而产生第二个响应。共聚焦显微镜研究表明，与具有 fused 吡啶环的2相比，具有 fused 噻唑基团的1具有更高的细胞核摄取。这些化合物显示出与小牛胸腺DNA的部分嵌插结合模式。在氩气气氛下，化合物1在波长400-700 nm的可见光下表现出质粒DNA光裂解活性，对HeLa和MCF-7细胞分别具有15.1和3.4 μM的IC50值，而在暗处基本无毒，IC50值分别为90.4和21.9 μM。通过TDDFT研究合理化了实验数据。
• Planar triazinium cations from VO2+-assisted ring cyclizations: a remarkably efficient thiazole species for nuclear staining, PDT and anaerobic photocleavage of DNA
  作者：Puja Prasad、Imran Khan、Pijus K. Sasmal、Debasis Koley、Paturu Kondaiah、Akhil R. Chakravarty

  DOI：10.1039/c0cc05386d

  日期：——

  Planar triazinium cationic species, from VO2+-assisted cyclization of 1-(2-thiazolylazo)-2-naphthol, shows efficient DNA intercalative binding, visible light-induced anaerobic plasmid DNA photocleavage activity and photocytotoxicity in HeLa and MCF-7 cancer cells by an apoptotic pathway with selective localization of the compound in the nucleus as evidenced from the nuclear staining and confocal imaging.

  来自 VO2+ 辅助环化 1-(2-thiazolylazo)-2-naphthol 的平面三嗪鎓阳离子物种，在 HeLa 和 MCF-7 癌细胞中显示出有效的 DNA 嵌入结合、可见光诱导的厌氧质粒 DNA 光裂解活性和光细胞毒性。细胞核染色和共聚焦成像证明了化合物在细胞核中选择性定位的凋亡途径。
• Formation of Azolo[1,2,4]triazinium Salts by Reaction of Heterocyclicsubstituted 1-Azo-naphthalen-2-ols with Strong Acids
  作者：Xiuling Yu、Horst Hartmann

  DOI：10.5560/znb.2014-4001

  日期：2014.5.1

  By reaction of heterocyclic-substituted 1-azo-naphth-2-ols with the Vilsmeier reagent or with strong acids polycyclic azolo[1,2,4]triazinium salts are formed in good yields. The azolo[1,2,4] triazinium salts exhibit similar UV=Vis absorption properties as the starting azo compounds, but in contrast to those the fluorescence appears in the visible range.

  杂环取代的 1-偶氮萘-2-醇与 Vilsmeier 试剂或强酸反应后，可生成多环唑并[1,2,4]三嗪盐，产量很高。偶氮并[1,2,4]三嗪盐具有与起始偶氮化合物相似的紫外=可见吸收特性，但与之不同的是，荧光出现在可见光范围内。