5,7-diethyl-1,2,4-triazolo[1,5-a]pyrimidine | 65267-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 5,7-diethyl-1,2,4-triazolo[1,5-a]pyrimidine
• 英文别名: 5,7-Diethyl[1,2,4]triazolo[1,5-a]pyrimidine；5,7-diethyl-[1,2,4]triazolo[1,5-a]pyrimidine
• CAS: 65267-58-5
• 化学式: C₉H₁₂N₄
• 分子量: 176.221
• InChiKey: JCUFRHRRSPEXOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,7-diethyl-1,2,4-triazolo[1,5-a]pyrimidine 、 cis-dichlorobis(dimethylsulfoxide)platinum(II) 以 乙醇 、 水 为溶剂， 反应 96.0h， 以48%的产率得到cis-[PtCl₂(5,7-diethyl-1,2,4-triazolo[1,5-a]pyrimidine)(dimethyl sulfoxide)]
  参考文献：
  名称：

  Synthesis, characterization and in vitro cytotoxicity of three types of platinum(II) complexes containing 5,7-diethyl-1,2,4-triazolo[1,5-a]pyrimidine

  摘要：

  Three structurally different mononuclear dichlorido platinum(II) complexes with 5,7-diethyl-1,2,4triazolo[1,5-a]pyrimidine (detp) were synthesized and characterized through multinuclear magnetic resonance (H-1, C-13, N-15, Pt-195) and infrared spectroscopy. The X-ray structure of cis-[PtCl2(detp)(dmso)] (2) was determined using the single-crystal X-ray diffraction technique. The molecular structure of (2) exhibits a square planar geometry surrounding the Pt(II) ion with a unique placement of two chlorido ligands in the cis position in the presence of a S-dmso molecule in the coordination sphere.All NMR data obtained in solution unambiguously confirmed the square planar geometry of Pt(II) with monodentate N3-bonded detp, a monodentate second ligand (detp or NH3 or dmso) and two chlorido ligands in the cis geometry.Cytotoxicity tests using human carcinoma cell lines, specifically the T47D (breast cancer), A549 (non small cell lung carcinoma), and LoVo (colon cancer) cell lines, and the healthy cell line BALB/3T3 (mouse embryonic fibroblast), indicated that only cis-[PtCl2(detp)(2)] (1) possesses similar in vitro cytotoxicity against T47D and sevenfold lower toxicity than cisplatin. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2016.09.010
• 作为产物：
  描述：

  3-氨基-1,2,4-三氮唑 、 3,5-庚烷二酮 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以57%的产率得到5,7-diethyl-1,2,4-triazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  具有桥头氮的嘌呤类似物的二烷基双环杂环具有明显的心脏正性肌力活动

  摘要：

  一些5,7-二烷基小号-三唑并[1,5-一个]嘧啶和5,7- dialkylpyrazolo [1,5-一个]嘧啶类和含有桥头氮相关杂环已经制备和研究作为在心血管药剂麻醉的狗。这些化合物中的许多已显示出显着的正性肌力活性，而对心率的影响很小。尤其是活性5,7-二烷基-2-氨基或2-烷硫基小号-三唑并[1,5-一个]嘧啶。相反，这些环系化合物中的高极性嘌呤类似物，例如5,7-二-正丙基-2-苄硫基-1,3,4-噻二唑并[3,2- a ]嘧啶溴化物45桥头上含氮的电荷不活泼。讨论了相关环系统的二烷基衍生物的详细的结构活性关系。某些环氮原子的存在对于有效的体内活性至关重要，大概是由于这些位点上的特定酶结合所致。研究的几种化合物具有口服活性，是优良的候选食品，可进一步在人体中进行评估。

  DOI：

  10.1002/jhet.5570200345

文献信息

• Nanoencapsulation of a ruthenium(<scp>ii</scp>) complex with triazolopyrimidine in liposomes as a tool for improving its anticancer activity against melanoma cell lines
  作者：Marzena Fandzloch、Anna Jaromin、Magdalena Zaremba-Czogalla、Andrzej Wojtczak、Agnieszka Lewińska、Jerzy Sitkowski、Joanna Wiśniewska、Iwona Łakomska、Jerzy Gubernator

  DOI：10.1039/c9dt03464a

  日期：——

  One of the six new Ru(ii) complexes synthesized using purine analogues, such as triazolopyrimidines, encapsulated in PEG-modified liposomes, representing an effective alternative for enhanced selective cytotoxicity against melanoma cell lines.

  使用嘌呤类似物（如三唑嘧啶）合成的六个新Ru（II）配合物，封装在PEG修饰的脂质体中，代表了一种有效的选择性细胞毒性增强的替代方案，可针对黑色素瘤细胞系。
• New organometallic ruthenium(<scp>ii</scp>) complexes with purine analogs – a wide perspective on their biological application
  作者：Marzena Fandzloch、Tomasz Jędrzejewski、Liliana Dobrzańska、Ginés M. Esteban-Parra、Joanna Wiśniewska、Agata Paneth、Piotr Paneth、Jerzy Sitkowski

  DOI：10.1039/d0dt03974h

  日期：——

  than cisplatin. At the same time, 3 has shown antimetastatic activity comparable to NAMI-A against HeLa cells both after 24 and 48 h of treatment in a wound healing assay. In order to better understand the mechanism of anticancer action and differences in the cytotoxic activity of 1–3, the studies were expanded to determining their lipophilicity, the kinetic stability at pH 6.5–8, the effect on reactive

  含有嘌呤类似物的三个半夹心有机金属钌( II )配合物，例如通式为[(η 6 - p -cym)Ru(L)Cl 2 ]的三唑并嘧啶，其中p -cym代表p -伞花烃，L为5,6 ,7-三甲基-1,2,4-三唑并[1,5- a ]嘧啶（ 1的tmtp），5,7-二乙基-1,2,4-三唑并[1,5 -a ]嘧啶（1的detp） 2 ) 和 5-甲基-1,2,4-三唑并[1,5- a ]嘧啶-7(4 H )-酮 (HmtpO for 3 ) 已被合成并通过元素分析、红外、多核磁共振进行表征光谱技术（ 1 H、 13 C、 15 N）和单晶 X 射线衍射（ 1和2 ）。所有这些复合物均已针对 MCF-7 和 HeLa 细胞系以及 L929 小鼠成纤维细胞的体外细胞毒性进行了彻底筛选，表明 [(η 6 - p -cym)Ru(HmtpO)Cl 2 ] ( 3 ) 作为对抗 HeLa 细胞系最活跃的代表，同时对正常
• Synthesis, structure and biological evaluation of ruthenium(III) complexes of triazolopyrimidines with anticancer properties
  作者：Marzena Fandzloch、Liliana Dobrzańska、Tomasz Jędrzejewski、Julia Jezierska、Joanna Wiśniewska、Iwona Łakomska

  DOI：10.1007/s00775-019-01743-5

  日期：2020.2

  have been carried out to reveal the mechanism by which complexes 1–6 interact with DNA, albumin, and apotransferrin. The biological studies were complemented by detailed kinetic studies of the hydrolysis of the complexes in the pH range 5–8, to determine the stability of the complexes in solution. Graphic abstractSix novel ruthenium(III) complexes with triazolopyrimidine derivatives demonstrated the

  摘要六个新颖钌（III）通式的配合物将[RuCl 3（L）3 ]（1，3，5）和将[RuCl 3（H 2 O）（L）2 ]（2，4，6），其中L代表报道了三个不同的三唑并嘧啶衍生的配体。这些化合物已进行了结构表征（IR，EPR，SCXRD），并确定了它们的磁矩。单晶X射线衍射研究表明，Ru（III）配合物的mer构型分别为1和5，fac的八面体几何形状略有扭曲。配置3。在2和4中，三个氯离子处于mer构型，并且两个三唑并嘧啶与水分子相互反式取向，起到第六配体的作用。已对所有复合物针对人乳腺癌细胞系MCF-7，人宫颈癌细胞系HeLa和L929鼠成纤维细胞的体外细胞毒性进行了彻底筛选，发现其中大多数亲脂性复合物5和6都含有庞大的配体dptp（5,7-二苯基-1,2,4-三唑[1,5- a]嘧啶）对MCF-7和HeLa细胞显示出高细胞毒活性。此外，也有人揭示了复合物的相互作用期间1 - 6与癌症
• First dinuclear rhodium(II) complexes with triazolopyrimidines and the prospect of their potential biological use
  作者：Marzena Fandzloch、Adam W. Augustyniak、Liliana Dobrzańska、Tomasz Jędrzejewski、Jerzy Sitkowski、Magdalena Wypij、Patrycja Golińska

  DOI：10.1016/j.jinorgbio.2020.111072

  日期：2020.9

  triazolopyrimidine derivative, in particular dimethyl-1,2,4-triazolo[1,5-a]pyrimidine (dmtp) for (1), 5,7-diethyl-1,2,4-triazolo[1,5-a]pyrimidine (detp) for (2), 7-isobutyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine (ibmtp) for (3), 7-hydroxy-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine (HmtpO) for (4) and 5,7-ditertbutyl-1,2,4-triazolo[1,5-a]pyrimidine (dbtp) for (5) are reported. These first representatives of paddle-wheel

  五个新颖铑（II）通式的配合物的[Rh 2（μ-OOCCH 3）4大号2 ]，其中L为三唑并嘧啶衍生物，特别是二甲基-1,2,4-三唑并[1,5一]嘧啶（dmtp）对于（1），5,7-二乙基-1,2,4-三唑[1,5- a ]嘧啶（detp）对于（2），7-异丁基-5-甲基-1,2,4 -三唑并[1,5-一个]嘧啶（ibmtp）对于（3），7-羟基-5-甲基-1,2,4-三唑并[1,5一]嘧啶（HmtpO）为（4）和5 ，7-二叔丁基-1,2,4-三唑并[1,5-一个]嘧啶（dbtp）为（5）报告。这些具有三唑并嘧啶的叶轮吡啶鎓络合物的第一批代表物已通过IR和NMR光谱以及单晶X射线衍射研究进行了表征。在体外彻底筛选了三种新复合物（1），（2）和（5）对人乳腺癌细胞系MCF-7和L929鼠成纤维细胞的细胞毒性。有利地，在相同条件下，它们对L929细胞生长的抑制作用明显小于顺铂。配合物（1）和（5）显示中等的细胞毒活性（IC
• Coordination chemistry of substituted [1,2,4]triazolo[1,5-a]pyrimidines with first-row transition-metal ions: Synthesis, spectroscopy and single-crystal structure analysis
  作者：Jeral M. Balkaran、Stein C.P. van Bezouw、John van Bruchem、Joeri Verasdonck、Peter C. Verkerk、Anne Geert Volbeda、Ilpo Mutikainen、Urho Turpeinen、Gerard A. van Albada、Patrick Gamez、Jaap G. Haasnoot、Jan Reedijk

  DOI：10.1016/j.ica.2008.02.020

  日期：2009.2

  A number of new coordination compounds with transition-metal salts and triazole-based heterocyclic ligands is described. The ligands used are disubstituted [1,2,4] triazolo[1,5-a] pyrimidines, with as substituents: ethyl, methyl and phenyl, and in addition a 2-methylthio-dimethyl ligand was used (sdmtp). To determine the structures of the coordination compounds in a number of cases 3D crystal structure determinations have been carried out, i.e. for [Fe(NCS)(2)(detp)(3)(H2O)], [Co(NCS)(2)(sdmtp)(2)(H2O)], [ZnBr2(fmtp)(2)], [Ni(NCS)(2)(detp)(3)(CH3OH)] and [Fe(NCS)(2)(fmtp)(2)(H2O)(2)](fmtp). The latter compound is quite unusual as it contains an uncoordinated fmtp ligand in the crystal lattice with special packing features. The ligands and the coordination compounds have been further characterized by NMR, IR and LF spectra, as well as by C, H, N element analyses. The coordination around the metal varies from 4 (Zn), via 5 (Co) to 6 (for Ni and Fe). (C) 2008 Elsevier B. V. All rights reserved.