9-(4-bromophenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one | 681471-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 9-(4-bromophenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one
• 英文别名: 9-(4-bromophenyl)-6,6-dimethyl-4,5,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8-one
• CAS: 681471-48-7
• 化学式: C₁₆H₁₆BrN₅O
• 分子量: 374.24
• InChiKey: ZMTVFALWDGQGHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(4-bromophenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one 在 盐酸羟胺 作用下， 反应 5.5h， 生成
  参考文献：
  名称：

  新型 5,7,8,9-四氢四唑并[5,1-b]喹唑啉类似物的设计、合成、计算和体外细胞毒性潜力

  摘要：

  摘要 目的：喹唑啉类和缩合喹唑啉类作为药效团核心，通过作用于选定的靶点而发挥重要作用，癌症治疗就是其中之一。考虑到这种特殊支架的重要性，设计了一些新型四唑并[5,1- b ]喹唑啉（Va-Vh）和（VIa-VIh），并通过计算筛选药物相似特性。方法：合成所选化合物，并通过MTT法评价其对人宫颈癌细胞系的体外抗癌活性。随后将化合物对基质金属蛋白酶9（PDB ID：1GKC）和二氢乳清酶（PDB ID：2EG7）进行分子对接分析。结果与讨论：这些化合物具有良好的抗癌特性，IC 50值为1.21±0.10至6.32±0.32μM，其中一些化合物比标准药物甲氨蝶呤更具活性。结论：在对接研究中也观察到了相同的模式，其中化合物与所研究的两种蛋白质有效结合。

  DOI：

  10.1134/s1068162024020043
• 作为产物：
  描述：

  4-(4-bromophenyl)-7,7-dimethyl-2-thioxo-2,3,4,6,7,8-hexahydroquinazolin-5(1H)-one 在 sodium azide 、 mercury(II) diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以69%的产率得到9-(4-bromophenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one
  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。
• Sustainable design and novel synthesis of highly recyclable magnetic carbon containing aromatic sulfonic acid: Fe ₃ O ₄ @C/Ph—SO ₃ H as green solid acid promoted regioselective synthesis of tetrazoloquinazolines
  作者：Asadollah Hassankhani、Behnam Gholipour、Sadegh Rostamnia、Elham Zarenezhad、Nasrin Nouruzi、Taras Kavetskyy、Rovshan Khalilov、Mohammadreza Shokouhimehr

  DOI：10.1002/aoc.6346

  日期：2021.10

  Fe3O4@meso-C immobilized with activated 4-aminobenzenesulfonic acid to achieve Fe3O4@C/Ph—SO3H. Structural, physico-chemical, and magnetic properties of synthesized Fe3O4@C/Ph—SO3H catalyst using various analyses such as FT-IR spectroscopy, TGA, XRD, SEM, TEM. EDX, and VSM were investigated. Fe3O4@C/Ph—SO3H was used as a stable and recoverable acid catalyst for regioselective three-component synthesis of

  制备了封装在多孔碳壳中的绿色且稳定的磁性 Fe 3 O 4核。然后，合成的 Fe 3 O 4 @meso-C 表面固定有活化的 4-氨基苯磺酸以获得 Fe 3 O 4 @C/Ph-SO 3 H。合成 Fe 的结构、物理化学和磁性3 O 4 @C/Ph-SO 3 H 催化剂使用各种分析，如 FT-IR 光谱、TGA、XRD、SEM、TEM。研究了 EDX 和 VSM。Fe 3 O 4 @C/Ph—SO 3H 用作稳定且可回收的酸催化剂，用于在温和条件下区域选择性三组分合成四唑并喹唑啉。由于具有活性 SO 3 H 基团，该催化剂提供了一种一次性的绿色方案，在温和条件下反应，产率高，并且能够回收和再利用而不会显着降低活性。
• An efficient regioselective three-component synthesis of tetrazoloquinazolines using g-C3N4 covalently bonded sulfamic acid
  作者：Asadollah Hassankhani、Behnam Gholipour、Sadegh Rostamnia

  DOI：10.1016/j.poly.2019.114217

  日期：2020.1

  A green and cost-effective protocol developed using covalently bonded sulfamic acid graphitic carbon nitride (g-C3N4/NHSO3H) for the synthesis of quinazoline derivatives using three-component condensation reaction of benzaldehyde, 2-aminotetrazole and dimedone. The XRD, TEM, SEM, EDX and FT-IR techniques were used to identify the physical and chemical properties of g-C3N4/NHSO3H. The -NHSO3H solid catalyst, was reused eight times without significant decrease in activity. This catalyst acts as a benign acid catalyst, a green protocol of a one-pot due to having significant advantages such as active sites containing SO3H groups, reacting under mild conditions with high efficiency as well as the ability to recover and reuse without decreasing activity. (C) 2019 Elsevier Ltd. All rights reserved.
• 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.
• Design, Synthesis, Computational, and In Vitro Cytotoxic Potential of Novel 5,7,8,9-Tetrahydrotetrazolo[5,1-b]quinazolines Analogs
  作者：Asief Mohammed、Shiva Kumar Gubbiyappa、Rajasekhar Reddy Alavala

  DOI：10.1134/s1068162024020043

  日期：2024.4

  treated as the pharmacophore nucleus for various diseases by acting on selected targets, cancer therapeutics is one of such ailments. By considering the importance of this privileged scaffold, some novel tetrazolo [5,1-b]quinazolines (Va–Vh) and (VIa–VIh) were designed and screened computationally for drug likeness properties. Methods: The selected compounds were synthesized and later were evaluated

  摘要 目的：喹唑啉类和缩合喹唑啉类作为药效团核心，通过作用于选定的靶点而发挥重要作用，癌症治疗就是其中之一。考虑到这种特殊支架的重要性，设计了一些新型四唑并[5,1- b ]喹唑啉（Va-Vh）和（VIa-VIh），并通过计算筛选药物相似特性。方法：合成所选化合物，并通过MTT法评价其对人宫颈癌细胞系的体外抗癌活性。随后将化合物对基质金属蛋白酶9（PDB ID：1GKC）和二氢乳清酶（PDB ID：2EG7）进行分子对接分析。结果与讨论：这些化合物具有良好的抗癌特性，IC 50值为1.21±0.10至6.32±0.32μM，其中一些化合物比标准药物甲氨蝶呤更具活性。结论：在对接研究中也观察到了相同的模式，其中化合物与所研究的两种蛋白质有效结合。