9-(4-nitrophenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one | 951923-60-7

• 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-nitrophenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one
• 英文别名: 6,6-dimethyl-9-(4-nitrophenyl)-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one；6,6-dimethyl-9-(4-nitrophenyl)-4,5,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8-one
• CAS: 951923-60-7
• 化学式: C₁₆H₁₆N₆O₃
• 分子量: 340.341
• InChiKey: MIECPVAJXRZYAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 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：
  119
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 9-(4-nitrophenyl)-6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one 以81 %的产率得到
  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：

  7,7-dimethyl-4-(4-nitrophenyl)-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67%的产率得到9-(4-nitrophenyl)-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

• 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。
• 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, multicomponent, green protocol to access 4, 7-dihydrotetrazolo [1, 5-<i>a</i>] pyrimidines and 5,6,7,9-tetrahydrotetrazolo[5,1-<i>b</i>]quinazolin-8(4H)-ones using PEG-400 under microwave irradiation
  作者：Shaik Firoj Basha、Tangella Nagendra Prasad、Veera Babu Gudise、Vadiga Shanthi Kumar、Naveen Mulakayala、Shaik Anwar

  DOI：10.1080/00397911.2019.1659973

  日期：2019.11.17

  carry out the synthesis of different dihydrotetrazolo[1,5-a]pyrimidines and tetrahydrotetrazolo[1,5-a]quinazolinones. This method has the advantage of green protocol, operational simplicity, high yields, recyclability of the solvent and involves isolation of the final product without column purification. The scope of this reaction tolerates with aromatic, heteroaromatic and alicyclic aldehydes. Graphical

  摘要 5-甲基-4,7-二氢四唑并[1,5-a]嘧啶、5-叔丁基-4,7-二氢四唑并[1,5-a]嘧啶、6,6 -二甲基-5,6,7,9-四氢四唑并[5,1-b]喹唑啉-8(4H)-one和5,6,7,9-四氢四唑并[5,1-b]喹唑啉-8(4H) -一种衍生物是通过醛、5-氨基四唑和二酮在 PEG-400 中在微波照射下在 110°C 下进行 30 分钟的三组分反应来描述的。广泛的二酮如乙酰乙酸乙酯、乙酰乙酸叔丁酯、5,5-二甲基环己烷-1,3-二酮和1,3-环己二酮用于合成不同的二氢四唑并[1,5-a]嘧啶和四氢四唑并[1,5-a]喹唑啉酮。该方法具有协议绿色、操作简单、产量高、溶剂的可回收性，包括无需柱纯化即可分离最终产品。该反应适用于芳香族、杂芳香族和脂环族醛。图形概要
• 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.