ethyl 5-methyl-7-(4-methoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate | 361481-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 5-methyl-7-(4-methoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
• 英文别名: ethyl 7-(4-methoxyphenyl)-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate；ethyl 7-(4-methoxyphenyl)-5-methyl-1,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
• CAS: 361481-38-1
• 化学式: C₁₅H₁₇N₅O₃
• 分子量: 315.332
• InChiKey: DPKKANSRYAZVMF-UHFFFAOYSA-N

物化性质

• 沸点：
  421.7±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  91.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-methyl-7-(4-methoxyphenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate 、 苯甲酰氯 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：

  2-巯基-4-(4-甲氧基苯基)-6-甲基-1,4-二氢嘧啶-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86%的产率得到ethyl 5-methyl-7-(4-methoxyphenyl)-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

• 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。
• Bhagare, Arun M.; Gaware, Manoj R.; Lokhande, Dnyaneshwar. D., Indian Journal of Heterocyclic Chemistry, 2020, vol. 30, # 4, p. 621 - 624
  作者：Bhagare, Arun M.、Gaware, Manoj R.、Lokhande, Dnyaneshwar. D.

  DOI：——

  日期：——
• Theoretical, single crystal and molecular docking analysis of tetrazolo[1,5-a]pyrimidine-6-carboxylate derivatives
  作者：Azees Khan Haleel、Ummer Muhammed Rafi、Mugamathu Ali Jayathuna、Aziz Kalilur Rahiman

  DOI：10.1016/j.molstruc.2021.131706

  日期：2022.2
• One-Step Synthesis of Tetrazolo[1,5-a]pyrimidines by Cyclization Reaction of Dihydropyrimidine-2-thiones with Sodium Azide
  作者：Xi-Cun Wang、Ying Wei、Yu-Xia Da、Zhang Zhang、Zheng-Jun Quan

  DOI：10.3987/com-11-12351

  日期：——

  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.
• DNA profiling and in vitro cytotoxicity studies of tetrazolo[1,5-a]pyrimidine-based copper(II) complexes
  作者：Azees Khan Haleel、Ummer Muhammed Rafi、Dharmasivam Mahendiran、Liviu Mitu、Vijaykumar Veena、Aziz Kalilur Rahiman

  DOI：10.1007/s10534-019-00196-2

  日期：2019.8

  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.