N,4-diphenylphthalazin-1-amine | 10132-04-4

• 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: N,4-diphenylphthalazin-1-amine
• 英文别名: phenyl-(4-phenyl-phthalazin-1-yl)-amine；Phenyl-(4-phenyl-phthalazin-1-yl)-amin；1-Anilino-4-phenyl-phthalazin；1-Anilino-4-phenylphthalazine
• CAS: 10132-04-4
• 化学式: C₂₀H₁₅N₃
• 分子量: 297.359
• InChiKey: BEATZJALKXTWKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-二氯酞嗪 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 水 、 异丙醇 、 甲苯 为溶剂， 反应 1.0h， 生成 N,4-diphenylphthalazin-1-amine
  参考文献：
  名称：

  Design and synthesis of 3-aminophthalazine derivatives and structural analogues as PDE5 inhibitors: anti-allodynic effect against neuropathic pain in a mouse model

  摘要：

  Neuropathic pain is a chronic pain caused by a lesion or disease affecting the somatosensory nervous system. To date, no specific treatment has been developed to cure this pain. Antidepressants and anticonvulsant drugs are used, but they do not demonstrate universal efficacy, and they often cause detrimental adverse effects. Some studies highlighted the efficacy of sildenafil, a well-known inhibitor of phosphodiesterase 5 (PDE5, (IC50=3.3 nM)), in models of pain. Based on these results, we focused our attention on MY 5445, another known PDE5 inhibitor. Homologues, isosteres and structural analogues of MY 5445 were designed and all synthesized compounds were evaluated for their inhibitory activity toward PDE5. Selectivity profiles towards other PDE1-4 isoenzymes, water solubility and stability in acidic medium of the most potent PDE5 inhibitors were determined and the aminophthalazine 16h and its mimetic 41n (3-aminoindazole) were evaluated in comparison to MY 5445 (4b) in vivo in a model of neuropathic pain induced by sciatic nerve cuffing in mice (3 and 0.5 mg/kg, ip twice a day). Both compounds showed the same efficacy on neuropathic allodynia as MY 5445, and thus produced a significant relief of mechanical hypersensitivity after 12 days of treatment. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.05.026

文献信息

• 4-Phenylphthalazine derivatives, their preparation and pharmaceutical compositions containing them
  申请人：MITSUBISHI KASEI CORPORATION

  公开号：EP0159652A2

  公开（公告）日：1985-10-30

  Certain new 1-alkylamino-4-phenylphthalazine derivatives, 1-neopentylamino-4-phenylphthalazine and 1-(1-ethylpropylamino)-4-phenylphthalazine, having in form of pharmaceutical compositions prominent activity to ameliorate circulatory disorders can be prepared from the corresponding phthalaziones.

  某些新的 1-烷基氨基-4-苯基酞嗪衍生物、1-新戊基氨基-4-苯基酞嗪和 1-（1-乙基丙基氨基）-4-苯基酞嗪，在药物组合物中具有显著的改善循环系统疾病的活性，可以从相应的酞嗪类化合物中制备出来。
• Lieck, Chemische Berichte, 1905, vol. 38, p. 3923
  作者：Lieck

  DOI：——

  日期：——
• 4-Phenylphthalazine derivatives
  申请人：Mitsubishi Chemical Corporation

  公开号：EP0449203B1

  公开（公告）日：1994-12-07
• 3,6-Disubstituted pyridazine derivatives
  申请人：Mitsubishi Chemical Corporation

  公开号：EP0534443B1

  公开（公告）日：1998-12-30
• PYRIDAZINE AND PHTHALAZINE DERIVATIVES, PROCESS OF THEIR PREPARATION AND THEIR USE AS ANTICONVULSANTS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP0975605A1

  公开（公告）日：2000-02-02