7-fluoro-2-(4-methoxyphenyl)-4H-benzo[d][1,3]oxazin-4-one | 1323873-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 7-fluoro-2-(4-methoxyphenyl)-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 7-Fluoro-2-(4-methoxyphenyl)-3,1-benzoxazin-4-one
• CAS: 1323873-13-7
• 化学式: C₁₅H₁₀FNO₃
• 分子量: 271.248
• InChiKey: ANPBPLMRARFRNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：
  47.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-fluoro-2-(4-methoxyphenyl)-4H-benzo[d][1,3]oxazin-4-one 、 4-氨基茴香硫醚 在 对甲苯磺酸 、 溶剂黄146 作用下， 以69%的产率得到7-fluoro-2-(4-methoxy-phenyl)-3-(4-methylsulfanylphenyl)-3H-quinazolin-4-one
  参考文献：
  名称：

  Analogue-based design, synthesis and molecular docking analysis of 2,3-diaryl quinazolinones as non-ulcerogenic anti-inflammatory agents

  摘要：

  In our effort to identify potent gastric sparing anti-inflammatory agents, a series of methyl sulfanyl/methyl sulfonyl substituted 2,3-diaryl quinazolinones were designed by analogue-based design strategy and synthesized for biological evaluation. Subsequently, the compounds were evaluated for both cyclooxygenase inhibitions by ovine COX assay and carrageenan-induced rat paw edema assay. All the methyl sulfonyl substituted quinazolinones were exhibited promising anti-inflammatory activity. In particular, 6-bromo-3-(4-methanesulfonyl-phenyl)-2-phenyl-3H-quinazolin-4-one (18), 7-chloro-3-(4-methanesulfonyl-phenyl)-2-phenyl-3H-quinazolin-4-one (19), 3-(4-methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-3H-quinazolin-4-one (21) and 6-bromo-3-(4-methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-3H-quinazolin-4-one (22) emerged as the most active compounds in the series. The results of ulcerogenic activity assay suggest that these compounds are gastric safe compared to indomethacin. The molecular docking analysis was performed to understand the binding interactions of these compounds to COX-2 enzyme. The results from the present investigation suggests that 2,3-diaryl quinazolinones as a promising template for the design of new gastric safe anti-inflammatory agents, which can be further explored for potential anti-inflammatory activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.019
• 作为产物：
  描述：

  2-氨基-4-氟苯甲酸 、 对甲氧基苯甲酰氯 在 吡啶 作用下， 生成 7-fluoro-2-(4-methoxyphenyl)-4H-benzo[d][1,3]oxazin-4-one
  参考文献：
  名称：

  Analogue-based design, synthesis and molecular docking analysis of 2,3-diaryl quinazolinones as non-ulcerogenic anti-inflammatory agents

  摘要：

  In our effort to identify potent gastric sparing anti-inflammatory agents, a series of methyl sulfanyl/methyl sulfonyl substituted 2,3-diaryl quinazolinones were designed by analogue-based design strategy and synthesized for biological evaluation. Subsequently, the compounds were evaluated for both cyclooxygenase inhibitions by ovine COX assay and carrageenan-induced rat paw edema assay. All the methyl sulfonyl substituted quinazolinones were exhibited promising anti-inflammatory activity. In particular, 6-bromo-3-(4-methanesulfonyl-phenyl)-2-phenyl-3H-quinazolin-4-one (18), 7-chloro-3-(4-methanesulfonyl-phenyl)-2-phenyl-3H-quinazolin-4-one (19), 3-(4-methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-3H-quinazolin-4-one (21) and 6-bromo-3-(4-methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-3H-quinazolin-4-one (22) emerged as the most active compounds in the series. The results of ulcerogenic activity assay suggest that these compounds are gastric safe compared to indomethacin. The molecular docking analysis was performed to understand the binding interactions of these compounds to COX-2 enzyme. The results from the present investigation suggests that 2,3-diaryl quinazolinones as a promising template for the design of new gastric safe anti-inflammatory agents, which can be further explored for potential anti-inflammatory activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.019

文献信息

• Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones
  作者：Zhaotao Xu、Bin Huang、Zebiao Zhou、Mingzhong Cai

  DOI：10.1055/s-0039-1690265

  日期：2020.2

  A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N,N-diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional

  已经开发了2-碘苯胺与芳基碘化物的高效且实用的钯催化的羰基化偶联。该反应在一氧化碳（5 bar）下以N，N-二异丙基乙胺为碱在110°C的甲苯中顺利进行，它为构建具有优异原子经济性，高官能团的各种有价值的2-芳基苯并恶嗪酮提供了一个通用而有力的工具钯催化剂具有良好的耐受性，良好的高收率和易于回收利用的特点。该反应是从市售易得的2-碘苯胺和碘代芳基制备各种2-芳基苯并恶嗪酮的异相钯催化羰基化偶联的第一个实例。
• BCL-3 inhibitors
  申请人：University College Cardiff Consultants Limited

  公开号：US10273218B2

  公开（公告）日：2019-04-30

  The present application relates to compounds of any one of Formulae I, Ia, Ib, Ic, Id, Ie, and If. Compounds of Formula (I) have the structure: wherein A, B, W, Y, Z, R2, R4, R5, R6, Rq and q are as defined herein. The compounds can be used as inhibitors of Bcl-3 and can be used for the treatment of cancer, particularly metastatic cancer.

  本申请涉及式 I、Ia、Ib、Ic、Id、Ie 和 If 中任何一种的化合物。式 (I) 的化合物具有如下结构： 其中 A、B、W、Y、Z、R2、R4、R5、R6、Rq 和 q 如本文所定义。这些化合物可用作 Bcl-3 的抑制剂，并可用于治疗癌症，特别是转移性癌症。
• BCL-3 INHIBITORS
  申请人：University College Cardiff Consultants Limited

  公开号：EP3174602A2

  公开（公告）日：2017-06-07
• [EN] BCL-3 INHIBITORS<br/>[FR] INHIBITEURS DE BCL-3
  申请人：UNIV CARDIFF

  公开号：WO2016016728A2

  公开（公告）日：2016-02-04

  The present application relates to compounds of any one of Formulae I, Ia, Ib, Ic, Id, Ie, and If. Compounds of Formula (I) have the structure, wherein A, B, Y, Z, R2, R4, R5, R6, Rq and q are as defined herein. The compounds can be used as inhibitors of Bcl-3 and can be used for the treatment of cancer, particularly metastatic cancer.