6-hydroxy-2-(naphthalen-2-yl)pyridazin-3(2H)-one | 67945-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-hydroxy-2-(naphthalen-2-yl)pyridazin-3(2H)-one
• 英文别名: 1-[2]naphthyl-1,2-dihydro-pyridazine-3,6-dione；1-[2]Naphthyl-1,2-dihydro-pyridazin-3,6-dion
• CAS: 67945-32-8
• 化学式: C₁₄H₁₀N₂O₂
• 分子量: 238.246
• InChiKey: WCFFXWXANDTTMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.12
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  马来酸酐 、 2-萘肼 在 溶剂黄146 作用下， 生成 6-hydroxy-2-(naphthalen-2-yl)pyridazin-3(2H)-one
  参考文献：
  名称：

  Pyridazones and process for manufacture thereof

  摘要：

  公开号：

  US02798869A1

文献信息

• Synthesis and Biological Evaluation of Novel σ₁ Receptor Ligands for Treating Neuropathic Pain: 6-Hydroxypyridazinones
  作者：Xudong Cao、Yin Chen、Yifang Zhang、Yu Lan、Juecheng Zhang、Xiangqing Xu、Yinli Qiu、Song Zhao、Xin Liu、Bi-Feng Liu、Guisen Zhang

  DOI：10.1021/acs.jmedchem.5b01416

  日期：2016.4.14

  framework, a new series of potent σ1 receptor ligands associated with pharmacological antineuropathic pain activity was synthesized and is described in this article. In vitro receptor binding studies revealed high σ1 receptor affinity (Ki σ1 = 1.4 nM) and excellent selectivity over not only σ2 receptor (1366-fold) but also other CNS targets (adrenergic, μ-opioid, sertonerigic receptors, etc.) for 2-(3,4-d

  通过使用6- hydroxypyridazinone框架，一个新的系列有效的σ的1具有药理antineuropathic疼痛活性相关的受体的配体合成并在本文中被描述。在体外受体结合研究显示高σ 1个受体亲和力（ķ我σ 1 = 1.4纳米）和优良的选择性超过不仅σ 2受体（1366倍），但也其他CNS目标（肾上腺素，μ阿片，sertonerigic受体等-）表示2-（3,4-二氯苯基）-6-（3-（哌啶-1-基）丙氧基）哒嗪-3（2 H）-1 （化合物54）。化合物54在小鼠福尔马林模型和大鼠慢性压迫性神经损伤疼痛（CCI）模型中显示出剂量依赖性的抗痛觉过敏特性。此外，化合物的功能活性54使用苯妥英进行了评价，表明化合物为σ 1受体拮抗剂。此外，在抗痛觉过敏剂量的轮状试验中未发现运动障碍，在运动活动试验中未见镇静副作用。最后但并非最不重要的一点是，还指出了良好的安全性和良好的药代动力学特性。
• Design, synthesis, and antiviral activities of myricetin derivatives containing pyridazinone
  作者：Li Xing、Youshan An、Yishan Qin、Hui Xin、Tianyu Deng、Kaini Meng、Da Liu、Wei Xue

  DOI：10.1039/d3nj04902g

  日期：——

  myricetin containing pyridazinone were designed and synthesized from the natural product myricitrin, which were structurally characterized by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS), and the structure of A14 was further determined using an X-ray single crystal diffractometer. The in vivo anti-tobacco mosaic virus (TMV) activity was tested by the half-leaf

  以天然产物杨梅苷为原料，设计合成了26个含有哒嗪酮的杨梅素衍生物，通过核磁共振（NMR）波谱和高分辨率质谱（HRMS）对其进行了结构表征，并利用X-质谱进一步确定了A14的结构。射线单晶衍射仪。采用半叶法测定体内抗烟草花叶病毒(TMV)活性，结果表明A4、A23和A26具有较好的治疗活性，有效浓度50%(EC 50 )分别为131.6、138.5和118.9。 μg mL -1，分别优于宁南霉素（NNM）（235.6 μg mL -1）。A24和A26具有更好的保护活性，EC 50值为117.4和162.5 μg mL -1，优于NNM（263.2 μg mL -1）。微量热电泳（MST）和分子对接实验表明A23和A26与TMV-CP具有很强的结合能力。经A26处理后，烟叶叶绿素含量显着高于对照组，丙二醛含量增长速度减慢。这进一步证实了该药物分子具有良好的抗病毒活性。
• Synthesis and biological evaluation of new 6-hydroxypyridazinone benzisoxazoles: Potential multi-receptor-targeting atypical antipsychotics
  作者：Xudong Cao、Yin Chen、Yifang Zhang、Yinli Qiu、Minquan Yu、Xiangqing Xu、Xin Liu、Bi-Feng Liu、Guisen Zhang

  DOI：10.1016/j.ejmech.2016.09.008

  日期：2016.11

  In recent years, multi-targeting directed ligands have attracted great interest as possible new atypical antipsychotics. Combinations of dopamine and serotonin receptor ligands within single molecules might afford new therapeutic opportunities. Herein, we describe the synthesis of a novel series of 6-hydroxypyridazinone benzisoxazoles and their binding behaviors to different receptors in terms of atypical antipsychotic behaviors. The most potent compound (46) exhibited excellent affinities for certain receptors (D-2, K-i = 0.5 +/- 0.07 nM; 5-HT1A, K-i = 5.9 +/- 0.8 nM; 5-HT2A, K-i = 0.3 +/- 0.01 nM; 5-HT6, K-i = 0.5 +/- 0.04 nM) and combined with low affinities for the H-1, 5-HT2C, and adrenergic alpha(1) receptors. In contrast to risperidone, compound 46 exhibited a high cataleptic threshold; this may be useful in the development of a novel class of drugs treating schizophrenia. (C) 2016 Elsevier Masson SAS. All rights reserved.
• DE950287
  申请人：——

  公开号：——

  公开（公告）日：——
• Jolles, Gazzetta Chimica Italiana, 1936, vol. 66, p. 717,721
  作者：Jolles

  DOI：——

  日期：——