ethyl 5-methyl-7-(phenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 5-methyl-7-(phenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
• 英文别名: ethyl 4,7-dihydro-5-methyl-7-phenyltetrazolo[1,5-a]pyrimidine-6-carboxylate；ethyl 5-methyl-7-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate；ethyl 7-methyl-5-phenyl-1,5-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate；6-ethoxycarbonyl-5-methyl-7-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine；ethyl 5-methyl-7-phenyl-1,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
• 化学式: C₁₄H₁₅N₅O₂
• 分子量: 285.305
• InChiKey: SNYKFSWOVGKZTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 ethyl 5-methyl-7-(phenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate 在 吡啶 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  DNA profiling and in vitro cytotoxicity studies of tetrazolo[1,5-a]pyrimidine-based copper(II) complexes

  摘要：

  A series of N-benzoylated mononuclear copper(II) complexes of the type [Cu(L1-6)Cl-2] (1-6), where L-1=ethyl 4-benzoyl-5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, L-2=ethyl 4-(4-nitrobenzoyl)-5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, L-3=ethyl 4-benzoyl-5-methyl-7-(4-methoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, L-4=ethyl 4-(4-nitrobenzoyl)-5-methyl-7-(4-methoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, L-5=ethyl 4-benzoyl-5-methyl-7-(4-chlorophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate and L-6=ethyl 4-(4-nitrobenzoyl)-5-methyl-7-(4-chlorophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate have been synthesized and characterized by spectral methods. Electron paramagnetic resonance spectra of complexes show four lines, characteristic of square planar geometry. The binding studies of the complexes with calf thymus DNA (CT-DNA) revealed groove mode of binding, which were further supported by molecular docking studies. Gel electrophoresis experiments demonstrated the ability of the complexes to cleave plasmid DNA in the absence of activators. Further, the cytotoxicity activity of the complexes were examined on three cancerous cell lines (lung (A549), cervical (HeLa) and colon (HCT-15)), and on two normal cells (human embryonic kidney (HEK) and peripheral blood mononuclear cells (PBMC)) by MTT assay.

  DOI：

  10.1007/s10534-019-00196-2
• 作为产物：
  描述：

  6-甲基-4-苯基-2-硫代-1,2,3,4-四氢嘧啶-5-羧酸乙酯 在 sodium azide 、 mercury(II) diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以92%的产率得到ethyl 5-methyl-7-(phenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  One-Step Synthesis of Tetrazolo[1,5-a]pyrimidines by Cyclization Reaction of Dihydropyrimidine-2-thiones with Sodium Azide

  摘要：

  An novel, versatile and cost-effective approach for tetrazolo[1,5-a]pyrimidines and tetrazolo[1,5-a]quinazolines from cyclization reaction of dihydropyrimidinethiones with sodium azide in the presence of mercuric acetate is described. To compare this procedure with the conventional method, we carried out the cyclization reactions through direct functionalization of the pyrimidinethione core, which obtained from Biginelli 3,4-dihydropyrimidine-2-thiones or 4-aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones.

  DOI：

  10.3987/com-11-12351

文献信息

• Al(III) chloride catalyzed multi-component domino strategy: Synthesis of library of dihydrotetrazolo[1,5- a ]pyrimidines and tetrahydrotetrazolo[1,5- a ]quinazolinones
  作者：Parteek Kour、Varun P. Singh、Brijmohan Khajuria、Tajinder Singh、Anil Kumar

  DOI：10.1016/j.tetlet.2017.09.052

  日期：2017.11

  Tetrazolo[1,5-a]pyrimidines are well recognized and valuable scaffolds in drug discovery. In the current manuscript, we demonstrated AlCl3 catalyzed synthesis of series of dihydrotetrazolo[1,5-a]pyrimidines and tetrahydrotetrazolo[1,5-a]quinazolinones via a modified Biginelli type multi-component reaction of 5-aminotetrazole, aldehyde and diverse active methylene components such as acetophenone/al

  Tetrazolo [1,5- a ]嘧啶是药物发现中公认的有价值的支架。在当前的手稿中，我们证明了AlCl 3通过5-氨基四唑，醛和多种多样的修饰的Biginelli型多组分反应，催化合成一系列二氢四唑并[1,5- a ]嘧啶和四氢四唑并[1,5- a ]喹唑啉酮。活性亚甲基组分，如苯乙酮/乙酰乙酸烷基酯/二甲酮。这提供了直接从容易获得的起始原料直接构建高度官能化的二氢四唑并[1,5- a ]嘧啶和四氢四唑并[1,5- a ]喹唑啉酮的有效途径。
• Iodine Catalyzed One-Pot Multicomponent Synthesis of a Library of Compounds Containing Tetrazolo[1,5-<i>a</i>]pyrimidine Core
  作者：Li-Yan Zeng、Chun Cai

  DOI：10.1021/cc9000983

  日期：2010.1.11

  blocks with active methylene catalyzed by iodine were investigated in a multicomponent one-pot protocol. A series of 5,7-diaryl-4,7-dihydrotetrazolo[1,5-a]pyrimidines C and 5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylates D were obtained in moderate to good yields. Further exploration rapidly afforded various E in good to excellent yields; in addition, compound F was also obtained under

  在多组分一锅法中研究了5-氨基四唑与结构上不同的芳基醛和碘催化的具有活性亚甲基的结构单元的多功能和新型反应。一系列5,7-二芳基-4,7-二氢四唑[1,5-a]嘧啶C和5-甲基-7-芳基-4,7-二氢四唑[1,5-a]嘧啶-6-羧酸酯D以中等至良好的产量获得。进一步的勘探迅速提供了各种优良至优良产量的E。另外，在相同条件下也获得了化合物F。产物的结构通过LC-MS，（1）H NMR，（13）C NMR和元素分析来表征。
• Solvent-free synthesis of 5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-<i>a</i>]pyrimidine-6-carboxylic esters catalyzed by sulfamic acid
  作者：Changsheng Yao、Song Lei、Cuihua Wang、Chenxia Yu、Shujiang Tu

  DOI：10.1002/jhet.5570450609

  日期：2008.11

  The solvent-free synthesis of 5-methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic esters was performed and effectively catalyzed by sulfamic acid. Compared with conventional methods, this protocol features mild reaction conditions and high yields. Furthermore, it is solvent-free and thus eco-friendly.

  进行了无溶剂的5-甲基-7-芳基-4,7-二氢四唑并[1,5 - a ]嘧啶-6-羧酸酯的合成，并被氨基磺酸有效地催化。与常规方法相比，该方案具有温和的反应条件和高收率。此外，它不含溶剂，因此对环境无害。
• 四氮唑并[1,5-a]嘧啶衍生物的溶剂热合成法
  申请人：江苏建筑职业技术学院

  公开号：CN110229161A

  公开（公告）日：2019-09-13

  本发明公开了一种四氮唑并[1,5‑a]嘧啶衍生物的溶剂热合成法，以脂肪醛或芳香醛，乙酰乙酸乙酯或乙酰丙酮，5‑氨基四唑为原料，以1,2‑丙二醇的水溶液为溶剂，在溶剂热条件下，高产率的得到了一系列的四氮唑并[1,5‑a]嘧啶类化合物。本反应方法不使用催化剂，辅助试剂便宜，无毒或低毒，且可以重复使用，后处理简单，产品收率大于90%，尤其适用于易挥发的脂肪醛类，为四氮唑并[1,5‑a]嘧啶衍生物的大规模生产创造良好条件。
• A novel magnetically recyclable silver-loaded cellulose-based bionanocomposite catalyst for green synthesis of tetrazolo[1,5-a]pyrimidines
  作者：Ali Maleki、Parisa Ravaghi、Morteza Aghaei、Hamed Movahed

  DOI：10.1007/s11164-017-2941-4

  日期：2017.10

  5-Methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic ester derivatives were efficiently synthesized by reaction of methyl or ethyl acetoacetate, 5-aminotetrazole (produced from 2-cyanoguanidine and sodium azide), and various aromatic aldehydes in presence of a new cellulose-based Ag-loaded magnetic bionanostructure. This protocol offers many advantages such as short reaction time, high

  通过乙酰乙酸甲酯或乙酸乙酯，5-氨基四唑（由2-氰基胍和叠氮化钠制得）有效合成5-甲基-7-芳基-4,7-二氢四唑[1,5- a ]嘧啶-6-羧酸酯衍生物）和各种芳族醛，并存在新的基于纤维素的银负载磁性生物纳米结构。该方案具有许多优点，例如反应时间短，收率高，纳米复合材料具有显着的磁性，并且易于从反应混合物中分离出纳米催化剂，而不会显着降低催化活性。此外，X射线衍射分析，场发射扫描电子显微镜和能量色散X射线（EDX）分析被用来表征制备的纳米催化剂。