2-chloro-4-phenylpyridazine

• 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: 2-chloro-4-phenylpyridazine
• 英文别名: 2-chloro-4-phenyl-1H-pyridazine
• 化学式: C₁₀H₉ClN₂
• 分子量: 192.648
• InChiKey: RRQJDQQFWIFDJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-4-phenylpyridazine 、 3-氯苯胺 在 (R)-1-[(S_P)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine 、 palladium diacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到N-(3-chlorophenyl)-6-phenylpyridazin-3-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
• 作为产物：
  描述：

  6-苯基-3-哒嗪酮 在 三氯氧磷 作用下， 反应 2.0h， 以99%的产率得到2-chloro-4-phenylpyridazine
  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

• 5,6-dihydroxyindolines as additives for hair dyeing preparations
  申请人：——

  公开号：US20020032938A1

  公开（公告）日：2002-03-21

  The invention concerns the use of indoline derivatives of formula (I): 1 in which R 1 , R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen or C 1-4 alkyl groups, or R 4 and R 5 together with the oxygen atoms to which they are attached represent a C 1-4 alkylenedioxy group, or of salts of such indoline derivatives, as additives to hair dyeing agents of the direct dyeing or primary intermediate/secondary intermediate type, thus producing hair dyeing with excellent color fastness characteristics.

  本发明涉及式（I）：1 中 R 1、R 2、R 3、R 4 和 R 5 相互独立地代表氢或 C 1-4 烷基，或 R 4 和 R 5 与它们所连接的氧原子一起代表 C 1-4 烷二氧基的吲哚啉衍生物，或此类吲哚啉衍生物的盐，用作直接染料或初级中间体/次级中间体类型染发剂的添加剂，从而生产出具有优异色牢度特性的染发剂。
• 5,6-Dihydroxyindolines as additives for hair dyeing preparations
  申请人：——

  公开号：US20030208857A1

  公开（公告）日：2003-11-13

  The invention concerns the use of indoline derivatives of formula (I): 1 in which R 1 , R 2 , R 3 , R 4 and R 5 independently of one another represent hydrogen or C 1-4 alkyl groups, or R 4 and R 5 together with the oxygen atoms to which they are attached represent a C 1-4 alkylenedioxy group, or of salts of such indoline derivatives, as additives to hair dyeing agents of the direct dyeing or primary intermediate/secondary intermediate type, thus producing hair dyeing with excellent color fastness characteristics.

  本发明涉及式 (I) 的吲哚啉衍生物的用途： 1 其中 R 1 , R 2 , R 3 , R 4 和 R 5 分别代表氢或 C 1-4 烷基，或 R 4 和 R 5 与它们所连接的氧原子一起代表一个 C 1-4 烷二氧基基团，或此类吲哚啉衍生物的盐，作为直接染料或初级中间体/二级中间体类型染发剂的添加剂，从而生产出具有优异色牢度特性的染发剂。
• US6569211B2
  申请人：——

  公开号：US6569211B2

  公开（公告）日：2003-05-27
• US6878170B2
  申请人：——

  公开号：US6878170B2

  公开（公告）日：2005-04-12