1H-[1,2,4]Triazolo[4,3-a]pyridin-4-ium and 3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium derivatives as new intercalating agents for DNA

MarianHebenbrock; JensMüller

首页> 外文期刊>Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences >1H-[1,2,4]Triazolo[4,3-a]pyridin-4-ium and 3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium derivatives as new intercalating agents for DNA

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1H-[1,2,4]Triazolo[4,3-a]pyridin-4-ium and 3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium derivatives as new intercalating agents for DNA

机译：1H-[1,2,4]三唑唑[4,3-A]吡啶-4-IUM和3H- [1,2,4]三唑唑[4,3-A]喹啉-10-10-Ium衍生物作为新的插入剂对于DNA

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Two new cationic DNA intercalators, 3-phenyl-1-(6-phenylpyridin-2-yl)-1H-[1,2,4]triazolo[4,3-a]pyridin-4-ium (1a)+ and 1-phenyl-3-(6-phenylpyridin-2-yl)-3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium (1b)+, were synthesized from 2-chloropyridine and 2-chloroquinoline, respectively, in a four-step procedure. Generation of the hydrazine, followed by condensation with an aldehyde to give a hydrazone and subsequent Buchwald-Hartwig amination gave a mixture of E- and Z-configured N,N-functionalized hydrazones. Finally, oxidative cyclisation gave rise to the formation of the cationic DNA intercalators, whose molecular structures were determined by single-crystal X-ray diffraction analysis of the hexafluorophosphate and tribromide salt of (1a)+ and (1b)+, respectively. The intercalative binding of (1a)PF6 and (1b)PF6 to ctDNA was confirmed by means of UV, CD and luminescence spectroscopy, determination of the DNA melting temperature and by rheology measurements.

机译：两个新的阳离子DNA嵌入剂，3-苯基-1-（6-苯基吡啶-2-基）-1H-[1,2,4]三唑唑[4,3-A]吡啶-4-Ium（1a）+和1 -phenyl-3-（6-苯基吡啶-2-基）-3H- [1,2,4]三唑唑[4,3-a]喹啉-10uum（1b）+由2-氯吡啶合成，2 - 在四步骤中分别在四步骤中。肼的产生，然后用醛冷凝得到腙，随后的Buchwald-Hartwig胺化得到E和Z构造的N，N-官能化腙的混合物。最后，氧化环化产生阳离子DNA嵌入剂的形成，其分子结构分别通过（1a）+和（1b）+的三溴代盐和三溴盐的单晶X射线衍射分析来确定。通过UV，Cd和发光光谱，通过UV，Cd和发光光谱，测定DNA熔化温度和流变测量来确认（1A）PF6和（1B）PF6至CTDNA的间隔结合。

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《Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences》 |2018年第11期|共9页
作者
MarianHebenbrock; JensMüller;
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作者单位

Westf?lische Wilhelms-Universit?t Münster Institut für Anorganische und Analytische Chemie Corrensstra?e 28/30 48149 Münster Germany;

Westf?lische Wilhelms-Universit?t Münster Institut für Anorganische und Analytische Chemie Corrensstra?e 28/30 48149 Münster Germany Phone: +49 251 83 36006;

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原文格式 PDF
正文语种 eng
中图分类化学;
关键词
DNA; intercalator;

机译：DNA;嵌入师;

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1. 1H-[1,2,4]Triazolo[4,3-a]pyridin-4-ium and 3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium derivatives as new intercalating agents for DNA [J] . MarianHebenbrock, JensMüller Zeitschrift fur Naturforschung, B. A Journal of Chemical Sciences . 2018,第11期

机译：1H-[1,2,4]三唑唑[4,3-A]吡啶-4-IUM和3H- [1,2,4]三唑唑[4,3-A]喹啉-10-10-Ium衍生物作为新的插入剂对于DNA
2. Differentiation between [1,2,4]triazolo[1,5-a] pyrimidine and [1,2,4]triazolo[4,3-a]- Pyrimidine regioisomers by ~1H-~(15)N HMBC experiments [J] . Salgado A., Varela C., Collazo A.M.G., Magnetic Resonance in Chemistry: MRC . 2010,第8期

机译：通过〜1H-〜（15）N HMBC实验区分[1,2,4]三唑并[1,5-a]嘧啶和[1,2,4]三唑并[4,3-a]-嘧啶区域异构体
3. Quinoxaline derivatives. Part II: Synthesis and antimicrobial testing of 1,2,4-triazolo(4,3-a)quinoxalines, 1,2,4-triazino(4,3-a)quinoxalines and 2-pyrazolylquinoxalines. [J] . el Hawash-SA, Habib NS, Fanaki NH Die Pharmazie . 1999,第11期

机译：喹喔啉衍生物。第二部分：1,2,4-三唑（4,3-A）喹喔啉，1,2,4-三唑（4,3-A）喹喔啉和2-吡唑基喹啉的合成和抗微生物检测。
4. Synthesis of the 3,6-dinitro-1,2,4triazolo 4,3-b1,2,4triazolate anion and characterization of its energetic salts [C] . Matthew Gettings, Matthias Zeller, Edward Byrd, Seminar on new trends in research of energetic materials . 2020

机译：3,6-二硝基-1,2,4三唑4,3-b 1,2,4三唑酸根阴离子的合成及其高能盐的表征
5. Antiviral Agents: 3,5-Disubstituted 1,2,4-Oxadiazole Derivatives and Novel Peptidomimetics Containing Hydroxyethyl Isostere and Imidazolidinone Structures. [D] . Krake, Susann H. 2013

机译：抗病毒剂：3,5-二取代的1,2,4-恶二唑衍生物和新型的模拟拟肽，其中含有羟乙基等排酮和咪唑烷酮结构。
6. Pyrido[4,3-e][1,2,4]triazolo[4,3-a]pyrazines as Selective, Brain Penetrant Phosphodiesterase2 (PDE2) Inhibitors [O] . Frederik J. R. Rombouts, *, Gary Tresadern, 2016

机译：Pyrido [4,3-e] [1,2,4]三唑并[4,3-a]吡嗪为选择性的脑渗透性磷酸二酯酶2（PDE2）抑制剂
7. Synthesis and Positive Inotropic Activity of [1,2,4]Triazolo[4,3-a] Quinoxaline Derivatives Bearing Substituted Benzylpiperazine and Benzoylpiperazine Moieties [O] . Xue-Kun Liu, Long-Xu Ma, Zhi-Yu Wei, 2017

机译：具有取代苄基哌嗪和苯甲酰基哌嗪部分的[1,2,4]三唑并[4,3-a]喹喔啉衍生物的合成和正性肌力活性
8. Theoretical Prediction of the Heat of Formation, Density, and Relative Sensitivity for 3,7-dinitro-[1,2,4]triazolo[5,1-c][1,2,4] triazin-4-amine. [R] . Byrd, E. F. 2015

机译：3,7-二硝基 - [1,2,4]三唑并[5,1-c] [1,2,4]三嗪-4-胺的生成热，密度和相对灵敏度的理论预测。

1H-[1,2,4]Triazolo[4,3-a]pyridin-4-ium and 3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium derivatives as new intercalating agents for DNA

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