4-(4-Bromophenyl)-2-[(4-methoxyphenyl)methyl]phthalazin-1-one | 1318877-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(4-Bromophenyl)-2-[(4-methoxyphenyl)methyl]phthalazin-1-one
• CAS: 1318877-18-7
• 化学式: C₂₂H₁₇BrN₂O₂
• 分子量: 421.293
• InChiKey: HPAVAGUZDRPGMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-Bromophenyl)-2-[(4-methoxyphenyl)methyl]phthalazin-1-one 、 联硼酸频那醇酯 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium acetate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以65%的产率得到2-[(4-Methoxyphenyl)methyl]-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phthalazin-1-one
  参考文献：
  名称：

  Design and synthesis of boron containing 2,4-disubstituted-phthalazin-1(2H)-one and 3,7-disubstituted-2H-benzo[b][1,4] oxazine derivatives as potential HGF-mimetic agents

  摘要：

  We synthesized boron containing 2-(4-methoxybenzyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioaborolan-2-yl)phenyl) phthalazin-1(2H)-one 3 and 7-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2H-benzo[b][1,4] oxazine 8. The reaction of compound 2 with B(2)pin(2) using potassium acetate as the base and Pd(PPh3)(2)Cl-2 as the catalyst, produced the corresponding boron-containing derivative 3 as a white solid in 65% yield. Alternatively, we have synthesized compound 8 as a yellow solid in 59% yield using the Miyaura borylation reaction. The potassium trifluoro(44-methyl-2H-benzo[b][1,4]oxazine-3-yl)phenylborate 9 was then obtained after treatment of 8 with aqueous solution of KF2H in methanol as white solid product in 60% yield. The biological activities of the synthetic compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.032
• 作为产物：
  描述：

  4-(4-溴苯基)-1(2H)-酞嗪酮 、 4-甲氧基氯苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以89%的产率得到4-(4-Bromophenyl)-2-[(4-methoxyphenyl)methyl]phthalazin-1-one
  参考文献：
  名称：

  Design and synthesis of boron containing 2,4-disubstituted-phthalazin-1(2H)-one and 3,7-disubstituted-2H-benzo[b][1,4] oxazine derivatives as potential HGF-mimetic agents

  摘要：

  We synthesized boron containing 2-(4-methoxybenzyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioaborolan-2-yl)phenyl) phthalazin-1(2H)-one 3 and 7-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2H-benzo[b][1,4] oxazine 8. The reaction of compound 2 with B(2)pin(2) using potassium acetate as the base and Pd(PPh3)(2)Cl-2 as the catalyst, produced the corresponding boron-containing derivative 3 as a white solid in 65% yield. Alternatively, we have synthesized compound 8 as a yellow solid in 59% yield using the Miyaura borylation reaction. The potassium trifluoro(44-methyl-2H-benzo[b][1,4]oxazine-3-yl)phenylborate 9 was then obtained after treatment of 8 with aqueous solution of KF2H in methanol as white solid product in 60% yield. The biological activities of the synthetic compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.032

文献信息

• PHTHALAZINONES AND ISOQUINOLINONES AS ROCK INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20150353505A1

  公开（公告）日：2015-12-10

  The present invention provides compounds of Formula (I) or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供了公式（I）的化合物或其立体异构体，互变异构体或药学上可接受的盐，其中所有变量如此定义。这些化合物是选择性ROCK抑制剂。本发明还涉及包含这些化合物的制药组合物以及使用它们治疗心血管，平滑肌，肿瘤，神经病理，自身免疫，纤维化和/或炎症性疾病的方法。
• Phthalazinones and isoquinolinones as rock inhibitors
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US10385026B2

  公开（公告）日：2019-08-20

  The present invention provides compounds of Formula (I): or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供了式 (I) 的化合物： 或其立体异构体、同系物或药学上可接受的盐，其中所有变量如本文所定义。这些化合物是选择性 ROCK 抑制剂。本发明还涉及包含这些化合物的药物组合物，以及使用这些化合物治疗心血管、平滑肌、肿瘤、神经病理、自身免疫、纤维化和/或炎症性疾病的方法。
• US9926282B2
  申请人：——

  公开号：US9926282B2

  公开（公告）日：2018-03-27
• [EN] PHTHALAZINONES AND ISOQUINOLINONES AS ROCK INHIBITORS<br/>[FR] PHTALAZINONES ET ISOQUINOLINONES EN TANT QU'INHIBITEURS DE ROCK
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2014113620A2

  公开（公告）日：2014-07-24

  The present invention provides compounds of Formula (I) or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.
• Design and synthesis of boron containing 2,4-disubstituted-phthalazin-1(2H)-one and 3,7-disubstituted-2H-benzo[b][1,4] oxazine derivatives as potential HGF-mimetic agents
  作者：Bhaskar C. Das、Xiang-Ying Tang、Swarnava Sanyal

  DOI：10.1016/j.tetlet.2011.06.032

  日期：2011.8

  We synthesized boron containing 2-(4-methoxybenzyl)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioaborolan-2-yl)phenyl) phthalazin-1(2H)-one 3 and 7-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2H-benzo[b][1,4] oxazine 8. The reaction of compound 2 with B(2)pin(2) using potassium acetate as the base and Pd(PPh3)(2)Cl-2 as the catalyst, produced the corresponding boron-containing derivative 3 as a white solid in 65% yield. Alternatively, we have synthesized compound 8 as a yellow solid in 59% yield using the Miyaura borylation reaction. The potassium trifluoro(44-methyl-2H-benzo[b][1,4]oxazine-3-yl)phenylborate 9 was then obtained after treatment of 8 with aqueous solution of KF2H in methanol as white solid product in 60% yield. The biological activities of the synthetic compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.