3-amino-2-(phenoxymethyl)quinazolin-4(3H)-one | 276687-49-1

• 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: 3-amino-2-(phenoxymethyl)quinazolin-4(3H)-one
• 英文别名: 3-amino-2-(phenoxymethyl)quinazolin-4-one
• CAS: 276687-49-1
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: YEZWAJDLKMDLJK-UHFFFAOYSA-N

物化性质

• 沸点：
  479.5±47.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-2-(phenoxymethyl)quinazolin-4(3H)-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2–(4-(4-methoxyphenyl)piperazin-1-yl)-N-(4-oxo-2-(phenoxymethyl)quinazolin-3(4H)-yl)acetamide
  参考文献：
  名称：

  Development of newly synthesised quinazolinone-based CDK2 inhibitors with potent efficacy against melanoma

  摘要：

  DOI：

  10.1080/14756366.2022.2036985
• 作为产物：
  描述：

  N-[2-(hydrazinecarbonyl)phenyl]-2-phenoxyacetamide 以 乙醇 为溶剂， 生成 3-amino-2-(phenoxymethyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Design, synthesis and antihistaminic (H1) activity of some condensed 3-aminopyrimidin-4(3H)-ones

  摘要：

  A novel series of condensed 3-amino-2-(substituted)methylpyrimidin-4(3H)-ones is reported with potential H-1 receptor antagonistic activity. The IC50 values for 23 compounds were found to be in the micromolar range. Five lead compounds (10c, e, g, r and t), when evaluated by the in vivo method were found to protect guinea-pigs from the histamine induced asphyxia and antagonized histamine in a competitive and reversible manner. With a pA(2) value of 8.7 and protection time of 9.5 min (in vivo test), compound 10g was the most active amongst these five compounds. The isosteric replacement of the side chain -NH- in series 1, by oxygen and -NHSO2- functions, was undertaken to investigate the role of two amino functions in the receptor binding. This isosteric replacement with -O- does not affect thr antihistaminic activity and the sedative potential of the series. Preliminary molecular modelling studies indicate that the compounds with -NHSO2- in the side chain exhibit a closer fit with temelastine than their -O- isosteres. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00128-8

文献信息

• Synthesis and Anticonvulsant Activity of Some Quinazolin-4-(3H)-one Derivatives
  作者：Hanan Georgey、Nagwa Abdel-Gawad、Safinaz Abbas

  DOI：10.3390/molecules13102557

  日期：——

  ) quinazolin-4(3H)-one derivatives 4a,b, 5a-c, 6, 7a-f, 8a-e and 9a,b have been synthesized. Their structures have been elucidated on the basis of elemental analyses and spectroscopic studies (IR, 1H-NMR, MS). A preliminary evaluation of the anticonvulsant activity of the prepared compounds has indicated that compounds 4b, 7b-f, 8a and 9b exhibit significant anticonvulsant activity, while compounds

  已经合成了许多3-取代的-2-（取代的苯氧基甲基）喹唑啉-4（3H）-一衍生物4a，b，5a-c，6，7a-f，8a-e和9a，b。在元素分析和光谱研究（IR，1H-NMR，MS）的基础上阐明了它们的结构。对制备的化合物的抗惊厥活性的初步评估表明，化合物4b，7b-f，8a和9b表现出显着的抗惊厥活性，而化合物6、8b和8d表现出轻度至中度活性。
• Potassium channel modulators
  申请人：Scanio Marc J.

  公开号：US08962639B2

  公开（公告）日：2015-02-24

  Disclosed herein are KCNQ potassium channels modulators of formula (I) wherein ring G1, X, R1, and R2 are as defined in the specification. Compositions comprising such compounds; and methods for treating conditions and disorders using such compounds and compositions are also described.

  本文公开了式(I)的KCNQ钾通道调节剂，其中环G1、X、R1和R2如规范中定义。还描述了包含这些化合物的组合物；以及使用这些化合物和组合物治疗疾病和疾病的方法。
• POTASSIUM CHANNEL MODULATORS
  申请人：Scanio Marc J.

  公开号：US20100305109A1

  公开（公告）日：2010-12-02

  Disclosed herein are KCNQ potassium channels modulators of formula (I) wherein ring G 1 , X, R 1 , and R 2 are as defined in the specification. Compositions comprising such compounds; and methods for treating conditions and disorders using such compounds and compositions are also described.

  本文披露了公式（I）中的KCNQ钾通道调节剂，其中环G1、X、R1和R2如规范所定义。还描述了包含这些化合物的组合物；以及使用这些化合物和组合物治疗疾病和疾病的方法。
• US8962639B2
  申请人：——

  公开号：US8962639B2

  公开（公告）日：2015-02-24
• Exploring new quinazolin‐4(3<i>H</i>)‐one derivatives as CDK2 inhibitors: Design, synthesis, and anticancer evaluation
  作者：Basant T. Ibrahim、Heba Abdelrasheed Allam、Nehad M. El‐Dydamony、Marwa A. Fouad、Eman R. Mohammed

  DOI：10.1002/ddr.22163

  日期：2024.4

  In the present work, five series of new 2,3‐disubstituted quinazolin‐4(3H)‐ones 4a–c, 5a–d, 6a–g, 7a,b, and 9a–c were designed, synthesized, and screened in vitro for their cytotoxic activity against 60 cancer cell lines by the National Cancer Institute, USA. Five candidates 4c, 6a, 6b, 6d, and 6g revealed promising cytotoxicity with significant percentage growth inhibition in the range of 81.98%–96.45% against the central nervous system (CNS) (SNB‐19), melanoma (MDA‐MB‐435), and non‐small cell lung cancer (HOP‐62) cell lines. The in vitro cytotoxic half maximal inhibitory concentration (IC₅₀) values for the most active compounds 4c, 6a, 6b, 6d, and 6g against the most sensitive cell lines were evaluated. Additionally, screening their cyclin‐dependent kinase 2 (CDK2) inhibitory activity was performed. Ortho‐chloro‐benzylideneamino derivative 6b emerged as the most potent compound with IC₅₀ = 0.67 µM compared to Roscovitine (IC₅₀ = 0.64 µM). The most active candidates arrested the cell cycle at G1, S phases, or both, leading to cell death and inducing apoptosis against CNS (SNB‐19), melanoma (MDA‐MB‐435), and non‐small cell lung cancer (HOP‐62) cell lines. The molecular docking study verified the resulting outcomes for the most active candidates in the CDK2‐binding pocket. Finally, physicochemical, and pharmacokinetic properties deduced that compounds 4c, 6a, 6b, 6d, and 6g displayed significant drug‐likeness properties. According to the obtained results, the newly targeted compounds are regarded as promising scaffolds for the continued development of novel CDK2 inhibitors.