4-Methyl-2-methylsulfanyl-1,4-dihydroquinazoline | 790170-53-5

• 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: 4-Methyl-2-methylsulfanyl-1,4-dihydroquinazoline
• CAS: 790170-53-5
• 化学式: C₁₀H₁₂N₂S
• 分子量: 192.285
• InChiKey: JVVMQMVEJCQORB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Methyl-2-methylsulfanyl-1,4-dihydroquinazoline 在 ammonium hydroxide 作用下， 生成 4-Methyl-1,4-dihydroquinazolin-2-amine
  参考文献：
  名称：

  Cyclic guanidines as dual 5-HT5A/5-HT7 receptor ligands: Structure–activity relationship elucidation

  摘要：

  The optimisation of affinity and selectivity in a novel series of dual 5-HT5A/5-HT7 receptor ligands is described. Brain penetrant 2-aminodihydroquinazolines with low nanomolar affinities were identified. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.080
• 作为产物：
  描述：

  4-Methyl-3,4-dihydro-1H-chinazolin-2-thion 、 碘甲烷 生成 4-Methyl-2-methylsulfanyl-1,4-dihydroquinazoline
  参考文献：
  名称：

  Cyclic guanidines as dual 5-HT5A/5-HT7 receptor ligands: Structure–activity relationship elucidation

  摘要：

  The optimisation of affinity and selectivity in a novel series of dual 5-HT5A/5-HT7 receptor ligands is described. Brain penetrant 2-aminodihydroquinazolines with low nanomolar affinities were identified. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.080

文献信息

• New cyclic arylguanidine scaffolds as a platform for development of antimicrobial and antiviral agents
  作者：Przemysław Zaręba、Anna K. Drabczyk、Sylwia Wnorowska、Artur Wnorowski、Jolanta Jaśkowska

  DOI：10.1016/j.bioorg.2023.106730

  日期：2023.10

  resistance, immunopressure, and mutations within the bacterial and viral genomes necessitates the search for new molecules exhibiting antimicrobial and antiviral activities. Such molecules often contain cyclic guanidine moiety. As part of this work, we investigated the selected antimicrobial and antiviral activity of compounds from the cyclic arylguanidine group. Molecules were designed using molecular modeling

  世界卫生组织表示，传染病仍然对公众健康构成重大威胁。抗生素耐药性、免疫压力以及细菌和病毒基因组内突变的综合影响使得需要寻找具有抗菌和抗病毒活性的新分子。此类分子通常含有环状胍部分。作为这项工作的一部分，我们研究了环状芳基胍基团化合物的选定抗菌和抗病毒活性。根据先前开发的途径，使用分子建模设计分子，并使用微波辐射 ( MW ) 和声化学 ( ))) ) 方法获得分子。筛选了所得化合物对大肠杆菌、鲍曼不动杆菌、铜绿假单胞菌、金黄色葡萄球菌、白色念珠菌和新型隐球菌生长的抑制能力。使用生物发光免疫测定法探讨了阻止严重急性呼吸综合征冠状病毒 2 (SARS-CoV-2) 进入宿主细胞的能力。还评估了最活跃分子的细胞毒性和溶血特性。N -[2-(萘-1-基)乙基]-5-苯基-1,4,5,6-四氢-1,3,5-三嗪-2-胺12j对金黄色葡萄球菌具有高度抑制作用新型隐球菌(MIC ≤ 0.25 µg/mL)，无细胞毒性或溶血作用
• Cyclic guanidines as dual 5-HT5A/5-HT7 receptor ligands: Structure–activity relationship elucidation
  作者：Jens-Uwe Peters、Thomas Lübbers、Alexander Alanine、Sabine Kolczewski、Francesca Blasco、Lucinda Steward

  DOI：10.1016/j.bmcl.2007.10.080

  日期：2008.1

  The optimisation of affinity and selectivity in a novel series of dual 5-HT5A/5-HT7 receptor ligands is described. Brain penetrant 2-aminodihydroquinazolines with low nanomolar affinities were identified. (C) 2007 Elsevier Ltd. All rights reserved.
• SPINDLER, JURGEN;KEMPTER, GERHARD;SCHROEDER, CHRISTINE;JUMAR, ALFRED
  作者：SPINDLER, JURGEN、KEMPTER, GERHARD、SCHROEDER, CHRISTINE、JUMAR, ALFRED

  DOI：——

  日期：——
• Cyclic guanidines as dual 5-HT5A/5-HT7 receptor ligands: Optimising brain penetration
  作者：Jens-Uwe Peters、Thomas Lübbers、Alexander Alanine、Sabine Kolczewski、Francesca Blasco、Lucinda Steward

  DOI：10.1016/j.bmcl.2007.10.078

  日期：2008.1

  The optimisation of molecular properties within a series of 2-amino dihydroquinazoline 5-HT5A/5-HT7 receptor ligands resulted in a significantly improved brain-to-plasma ratio, enhancing the pharmacological utility of these compounds. By modulating the lipophilicity and pK(a), 20-fold increase in brain-to-plasma ratio could be achieved, leading to micromolar brain concentrations after oral administration. The enantiomers of one representative of this series of improved compounds were separated, and the configuration of the eutomer was determined by X-ray crystallography. (C) 2067 Elsevier Ltd. All rights reserved.