3-amino-2-(4-methoxyphenyl)-4(3H)-quinazolinone | 55390-99-3

• 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-(4-methoxyphenyl)-4(3H)-quinazolinone
• 英文别名: 2-(4-methoxyphenyl)-3-aminoquinazolin-4(3H)-one；3-amino-2-(4-methoxyphenyl)quinazolin-4(3H)-one；2-(p-Methoxyphenyl)-3-amino-4-chinazolon；3-Amino-2-(4-methoxy-phenyl)-3H-chinazolin-4-on；3-Amino-2-<4-methoxy-phenyl>-chinazolon-(4)；3-amino-2-(4-methoxy-phenyl)-3H-quinazolin-4-one；3-amino-2-(4-methoxyphenyl)-3,4-dihydroquinazolin-4-one；3-amino-2-(4-methoxyphenyl)quinazolin-4-one
• CAS: 55390-99-3
• 化学式: C₁₅H₁₃N₃O₂
• mdl: MFCD03287804
• 分子量: 267.287
• InChiKey: ARZJEBXFTPBYCK-UHFFFAOYSA-N

物化性质

• 熔点：
  171 °C
• 沸点：
  465.6±47.0 °C(Predicted)
• 密度：
  1.31±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：
  2
• 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-(4-methoxyphenyl)-4(3H)-quinazolinone 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 2-(4-甲氧基苯基)-1H-喹唑啉-4-酮
  参考文献：
  名称：

  Dean, William D.; Papadopoulos, Eleftherios P., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1117 - 1124

  摘要：

  DOI：
• 作为产物：
  描述：

  2-异硫氰基苯甲酸甲酯 在 三氯化铝 、 sodium 、 肼 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 3-amino-2-(4-methoxyphenyl)-4(3H)-quinazolinone
  参考文献：
  名称：

  Dean, William D.; Papadopoulos, Eleftherios P., Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1117 - 1124

  摘要：

  DOI：

文献信息

• Asymmetric Synthesis of N–N Axially Chiral Compounds by Phase-Transfer-Catalyzed Alkylations
  作者：Ming Pan、Ying-Bo Shao、Qun Zhao、Xin Li

  DOI：10.1021/acs.orglett.1c04028

  日期：2022.1.14

  N–N axially chiral skeletons are significant structural motifs in natural products, pharmaceuticals, and functional materials. Herein we disclose a method for the asymmetric synthesis of N–N axially chiral compounds by phase-transfer catalysis. A wide range of N–N axially chiral quinazolinone derivatives were prepared in high yields with excellent stereoselectivities. Furthermore, the synthetic utility

  N-N 轴向手性骨架是天然产物、药物和功能材料中的重要结构基序。在此，我们公开了一种通过相转移催化不对称合成 N-N 轴向手性化合物的方法。以高产率制备了多种 N-N 轴向手性喹唑啉酮衍生物，具有优异的立体选择性。此外，该协议的合成效用通过产物的大规模反应和转化得到证明。密度泛函理论计算提供了对该机制的深入了解。
• Quinazolin-4-one derivatives
  申请人：Itai Akiko

  公开号：US20060229324A1

  公开（公告）日：2006-10-12

  A medicament having an inhibitory activity against hematopoietic prostaglandin D2 synthase, which comprises as an active ingredient a compound represented by the following general formula (I) or a salt thereof: wherein X represents a group represented by the formula —N═C(R 5 )— or the formula —NH—CH(R 5 )—, R 1 , R 2 , R 3 , and R 4 represent a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, or a hydroxy group, R 5 represents a C 1 to C 6 alkyl group or a C 6 to C 10 aryl group, and R represents an amino group.

  一种具有对造血前列腺素D2合成酶抑制活性的药物，其包括以下一般式（I）所代表的化合物或其盐作为活性成分： 其中X代表由式—N═C(R5)—或式—NH—CH(R5)—所代表的基团，R1、R2、R3和R4代表氢原子、卤原子、C1到C6烷基或羟基，R5代表C1到C6烷基或C6到C10芳基，R代表氨基。
• Novel quinazoline–chromene hybrids as anticancer agents: Synthesis, biological activity, molecular docking, dynamics and ADME studies
  作者：Feyzi Sinan Tokalı、Halil Şenol、Hande İpek Yetke、Ebru Hacıosmanoğlu‐Aldoğan

  DOI：10.1002/ardp.202300423

  日期：2023.11

  In this study, new quinazoline–chromene hybrid compounds were synthesized. The cytotoxic effects on cell viability of the hybrid compounds were tested against A549 human lung adenocarcinoma and BEAS‐2B healthy bronchial epithelial cell lines in vitro. In addition, the ability of the active compounds to inhibit cell migration was tested. Molecular docking studies were performed to evaluate the ligand–protein interactions, and molecular dynamics simulations were performed to determine the interactions and stability of ligand–protein complexes. In silico absorption, distribution, metabolism, and excretion (ADME) studies were conducted to estimate the drug‐likeness of the compounds. Compounds 4 (IC₅₀ = 51.2 µM) and 5 (IC₅₀ = 44.2 µM) were found to be the most active agents against A549 cells. They are found to be more selective against A549 cells than the reference drug doxorubicin. They also have the ability to significantly inhibit cell migration. They have the best docking scores against epidermal growth factor receptor (EGFR) (−11.300 and −11.226 kcal/mol) and vascular endothelial growth factor receptor 2 (VEGFR2) (−10.987 and −11.247 kcal/mol), respectively. In MD simulations, compounds 4 and 5 have strong hydrogen bond interactions above 80% of simulation times and showed a low ligand root mean square deviation (RMSD) around 2 Å. According to the ADME analysis, compounds 4 and 5 exhibit excellent drug‐likeness and pharmacokinetic characteristics.

  摘要 本研究合成了新的喹唑啉-色烯杂化化合物。在体外测试了混合化合物对 A549 人肺腺癌和 BEAS-2B 健康支气管上皮细胞系细胞活力的细胞毒性作用。此外，还测试了活性化合物抑制细胞迁移的能力。分子对接研究评估了配体与蛋白质之间的相互作用，分子动力学模拟确定了配体与蛋白质复合物的相互作用和稳定性。还进行了吸收、分布、代谢和排泄（ADME）硅学研究，以估计化合物的药物亲和性。研究发现，化合物 4（IC50 = 51.2 µM）和化合物 5（IC50 = 44.2 µM）是对 A549 细胞最有效的药物。与参考药物多柔比星相比，它们对 A549 细胞的选择性更强。它们还能显著抑制细胞迁移。它们与表皮生长因子受体（EGFR）（-11.300 和 -11.226 kcal/mol）和血管内皮生长因子受体 2（VEGFR2）（-10.987 和 -11.247 kcal/mol）的对接得分最高。在 MD 模拟中，化合物 4 和 5 的氢键相互作用强度超过模拟次数的 80%，配体均方根偏差（RMSD）在 2 Å 左右，显示出较低的配体均方根偏差。根据 ADME 分析，化合物 4 和 5 表现出了极佳的药物相似性和药代动力学特征。
• Novel acetic acid derivatives containing quinazolin‐4(3 <i>H</i> )‐one ring: Synthesis, in vitro, and in silico evaluation of potent aldose reductase inhibitors
  作者：Feyzi Sinan Tokalı、Yeliz Demir、Cüneyt Türkeş、Büşra Dinçer、Şükrü Beydemir

  DOI：10.1002/ddr.22031

  日期：——

  Aldose reductase (AR) is a crucial enzyme of the polyol pathway through which glucose is metabolized under conditions of hyperglycemia related to diabetes. A series of novel acetic acid derivatives containing quinazolin-4(3H)-one ring (1–22) was synthesized and tested for in vitro AR inhibitory effect. All the target compounds exhibited nanomolar activity against the target enzyme, and all compounds

  醛糖还原酶（AR）是多元醇途径中的关键酶，在与糖尿病相关的高血糖条件下，葡萄糖通过该途径代谢。合成了一系列含有喹唑啉-4(3 H )-单环( 1-22 )的新型乙酸衍生物，并测试了其体外AR抑制作用。所有目标化合物均表现出针对目标酶的纳摩尔活性，并且与参比药物依帕司他相比，所有化合物均表现出更高的活性。其中，化合物19，命名为2-(4-[(2-[(4-甲基哌嗪-1-基)甲基]-4-氧代喹唑啉-3(4H ) -亚氨基)甲基]苯氧基)乙酸，显示出抑制作用最强，K I值为 61.20 ± 10.18 nM。此外，还使用 ​​MTT 测定研究了这些化合物针对 L929（非肿瘤成纤维细胞）和 MCF-7（乳腺癌细胞）的活性。化合物16和19对正常L929细胞显示出较低的毒性。还评估了合成化合物（1-22）的吸收、分布、代谢和排泄特性。分子对接模拟被用来研究这些抑制剂对抗 AR 的可能结合机制。
• Synthesis of 3-Aminoquinazolinones via a SnCl₂-Mediated ANRORC-like Reductive Rearrangement of 1,3,4-Oxadiazoles
  作者：Mohamed Elagawany、Lingaiah Maram、Bahaa Elgendy

  DOI：10.1021/acs.joc.3c01973

  日期：2023.12.15

  Herein, we developed a new SnCl2-mediated ANRORC (addition of nucleophile, ring-opening, and ring-closure)-like rearrangement for the synthesis of 3-amino-2-substituted-quinazolin-4(3H)-one from 2-(2-nitrophenyl)-5-substituted-1,3,4-oxadiazole. The new method is solvent-dependent and features the use of a green solvent system (i.e., ethanol/water), high yields, and simple workup. The reduced product

  在此，我们开发了一种新的SnCl 2介导的ANRORC（亲核试剂加成、开环和闭环）类重排，用于合成3-氨基-2-取代-喹唑啉-4(3 H )-one 2-(2-硝基苯基)-5-取代-1,3,4-恶二唑。新方法依赖于溶剂，具有使用绿色溶剂系统（即乙醇/水）、高产率和简单后处理的特点。将溶剂改为乙腈即可独家合成还原产物。