4-(3,4-dimethoxyphenyl)-2-phenyl-2H-phthalazin-1-one | 137382-40-2

• 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-(3,4-dimethoxyphenyl)-2-phenyl-2H-phthalazin-1-one
• 英文别名: 4-(3,4-dimethoxyphenyl)phthalazin-1(2H)-one；4-(3,4-Dimethoxyphenyl]-2H-phthalazin-1-one；4-(3,4-dimethoxyphenyl)-2H-phthalazin-1-one
• CAS: 137382-40-2
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: IIVDYPOZZPVJAU-UHFFFAOYSA-N

物化性质

• 熔点：
  244-249 °C
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3,4-dimethoxyphenyl)-2-phenyl-2H-phthalazin-1-one 在 tetra(n-butyl)ammonium dichromate(VI) 、 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 24.25h， 生成
  参考文献：
  名称：

  一种酞嗪酮二胺单体及其制备方法、一种聚酰 亚胺及其制备方法以及一种聚酰亚胺薄膜

  摘要：

  本发明涉及有机化学技术领域，具体涉及一种酞嗪酮二胺单体及其制备方法、一种聚酰亚胺及其制备方法以及一种聚酰亚胺薄膜。由本发明所述酞嗪酮二胺单体制备得到的聚酰亚胺薄膜能够在保持选择性的前提下，提高气体的渗透率和溶解性等；另外，由本发明提供的酞嗪酮二胺单体制备得到的聚酰亚胺具有较好的溶解性。

  公开号：

  CN111233842B
• 作为产物：
  描述：

  2-(3,4-二甲氧基苯甲酰基)苯甲酸 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-(3,4-dimethoxyphenyl)-2-phenyl-2H-phthalazin-1-one
  参考文献：
  名称：

  合成和评估苯基吡啶哒嗪酮NPD-001作为有效的锥虫TbrPDEB1磷酸二酯酶抑制剂和体外锥虫杀虫剂的类似物

  摘要：

  锥虫磷酸二酯酶B1和B2（TbrPDEB1和TbrPDEB2）在布鲁氏锥虫的生命周期中起着重要作用，布鲁氏锥虫是人类非洲锥虫病（HAT）的致病性寄生虫，也被称为非洲昏睡病。击倒这两种酶会导致细胞周期停滞，并且对寄生虫具有致命性。最近，我们报道了phenylpyridazinone，NPD-001，具有低纳摩尔IC 50个在两个TbrPDEB1值（IC 50：4 1nM）和TbrPDEB2（IC 50：3 nM）的（。传染病杂志 2012，206（229）。在这项研究中，我们现在报告一系列作为TbrPDEB1抑制剂的苯基哒嗪酮类似物的第一个结构活性关系。还显示了选择的化合物是抗寄生虫的。重要的是，观察到TbrPDEB1 IC 50和EC 50与整个寄生虫之间具有良好的相关性。对TbrPDEB1和人PDE上所选化合物的SAR的初步分析显示出很大的差异，这显示出获得寄生虫选择性PDE抑制剂的潜力

  DOI：

  10.1016/j.bmc.2016.02.032

文献信息

• Palladium-Catalyzed Acylation Reactions: A One-Pot Diversified Synthesis of Phthalazines, Phthalazinones and Benzoxazinones
  作者：Basuli Suchand、Gedu Satyanarayana

  DOI：10.1002/ejoc.201800159

  日期：2018.5.24

  proceeds through [Pd]‐catalyzed acylation and nucleophilic cyclocondensation with dinucleophilic reagents. This process was based on direct coupling with simple bench‐top aldehydes without the assistance of directing group and without activating the carbonyl group. The process is highly advantageous because it employs simple nitrogen‐based nucleophiles, and non‐toxic and readily accessible aldehydes as the

  提出了一种用于酞嗪、酞嗪酮和苯并恶嗪酮多样化合成的连续单锅策略。该策略通过 [Pd] 催化的酰化和与双亲核试剂的亲核环缩合反应进行。该过程基于与简单的台式醛直接偶联，没有导向基团的帮助，也没有活化羰基。该方法非常有利，因为它使用简单的氮基亲核试剂和无毒且易于获得的醛作为羰基来源。最重要的是，该策略被应用于 PDE-4 抑制剂的一锅合成。
• Phthalazinones
  申请人：Byk Gulden Lomberg Chemische Fabrik GmbH

  公开号：EP0934933A1

  公开（公告）日：1999-08-11

  Phthalazinones of the formula I in which R1 is 1-4C alkoxy or 1-4C alkoxy substituted by fluorine, R2 is halogen or (cyclo)alkoxy, and R3 is -CnH2n -C(O)R4. These compounds are suitable as bronchial therapeutics and for the treatment of dermatoses.

  公式为I的邻苯二氮酮中，其中R1是1-4C烷氧基或被氟取代的1-4C烷氧基，R2是卤素或(环)烷氧基，R3是-CnH2n-C(O)R4。这些化合物适用于支气管治疗和皮肤病治疗。
• Compounds effective as beta-2 adrenoreceptor agonists as well pde4-inhibitors
  申请人：——

  公开号：US20030195215A1

  公开（公告）日：2003-10-16

  The compounds of formula I in which Ar 1 , A, R6, R7, R8 and Ar 2 have the meanings as given in the description are novel effective bronchial therapeutics. 1

  式I的化合物中，其中Ar1、A、R6、R7、R8和Ar2的含义如描述所示，是一种新型有效的支气管治疗剂。
• Novel Selective PDE4 Inhibitors. 1. Synthesis, Structure−Activity Relationships, and Molecular Modeling of 4-(3,4-Dimethoxyphenyl)-2<i>H</i>-phthalazin-1-ones and Analogues
  作者：Margaretha Van der Mey、Armin Hatzelmann、Ivonne J. Van der Laan、Geert J. Sterk、Ulrich Thibaut、Hendrik Timmerman

  DOI：10.1021/jm010837k

  日期：2001.8.1

  A number of 6-(3,4-dimethoxyphenyl)-4,5-dihydro-2H-pyridazin-3-ones and a novel series of 4-(3,4-dimethoxyphenyl)-2H-phthalazin-1-ones were prepared and tested on the eGMP-inhibited phosphodiesterase (PDE3) and cAMP-specific phosphodiesterase (PDE4) enzymes. All tested compounds were found to specifically inhibit PDE4 except for pyridazinone 3b, which showed moderate PDE4 (pIC(50) = 6.5) as well as PDE3 (pIC(50) = 6.6) inhibitory activity. In both the pyridazinone and phthlazinone series it was found that N-substitution is beneficial for PDE4 inhibition, whereas in the pyridazinone series it also accounts for PDE4 selectivity. In the phthalazinone series, the cis-4a,5,6,7,8,8a-hexahydrophthalazinones and their corresponding 4a,5,8,8a-tetrahydro analogues showed potent PDE4 inhibitory potency (10/11c,d: pIC(50) = 7.6-8.4). A molecular modeling study revealed that the cis-fused cyclohexa(e)ne rings occupy a region in space different from that occupied by the other fused (un)saturated hydrocarbon rings applied; we therefore assume that the steric interactions of these rings with the binding site play an important role in enzyme inhibition.
• Novel antiasthmatic agents with dual activities of thromboxane A2 synthetase inhibition and bronchodilation. 1. 2-[2-(1-Imidazolyl)alkyl]-1(2H)-phthalazinones
  作者：Masahisa Yamaguchi、Kenshi Kamei、Takaki Koga、Michitaka Akima、Toshio Kuroki、Nobuhiro Ohi

  DOI：10.1021/jm00077a008

  日期：1993.12

  A number of 4-substituted 2-[omega-(1-imidazolyl)allryl]-1(2H)-phthalazinones were synthesized in order to develop agents possessing both thromboxane Az synthetase inhibitory and bronchodilatory activities. The pharmacological evaluation of these compounds disclosed that they have both activities to various extents. Both activities were slightly dependent on the length of the 2-substituents and largely affected by the nature of the 4-substituents. Compounds bearing phenyl and thienyl groups exhibited relatively high and well-rounded activities. Among these compounds, 12j and 15f were found to be the most effective agents having well-rounded activities in vitro and in vivo. Introduction of a carboxyl group reduced both activities contrary to our expectation. 4-(3-Pyridyl)phthalazinone 18b was of particular interest because of unexpectedly high in vivo activities in spite of an absence of significant in vitro activities.