吡啶并[2,3-d]哒嗪-8(7H)-酮 | 15375-79-8

• 物质功能分类: 医药中间体 - 哒嗪类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 吡啶并[2,3-d]哒嗪-8(7H)-酮
• 英文名称: pyrido[2,3-d]pyridazin-8(7H)-one
• 英文别名: 7H-pyrido[2,3-d]pyridazin-8-one；7H-Pyrido[2,3-d]pyridazin-8-on；Pyrido<2,3-d>-pyridazin-8(7H)-on；Pyrido<2,3-d>pyridazinon-8；7H-pyrido[2,3-d]pyridazin-8-one
• CAS: 15375-79-8
• 化学式: C₇H₅N₃O
• 分子量: 147.136
• InChiKey: SFNYPXFZPRSDTB-UHFFFAOYSA-N

物化性质

• 熔点：
  300 °C(Solv: water (7732-18-5))
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吡啶并[2,3-d]哒嗪-8(7H)-酮 在 platinum(IV) oxide 、 氢气 、 三氟乙酸 、 potassium carbonate 作用下， 以 水 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 反应 48.0h， 以97%的产率得到1,3,4,7-tetrahydropyrido[2,3-d]pyridazin-8(2H)-one
  参考文献：
  名称：

  Tetrahydropyrido[d]pyridazinones—promising scaffolds for drug discovery

  摘要：

  An approach to the synthesis of all possible tetrahydropyrido[d]pyridazinones has been developed. The method relies on the catalytic hydrogenation of the corresponding aromatic counterparts, which were obtained by cyclization of the relevant dibromomethyl-substituted pyridinecarboxylates with hydrazine. The synthetic schemes include 4-5 steps starting from commercially available materials. The tetrahydropyrido[d]pyridazinone scaffolds are combinations of a saturated heterocycle (piperidine) and a privileged aromatic heterocycle (pyridazinone); hence they are promising starting points for the design in medicinal chemistry. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.06.029
• 作为产物：
  描述：

  3-甲基-2-吡啶甲酸 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 一水合肼 作用下， 以 甲醇 、 四氯化碳 为溶剂， 反应 21.0h， 生成 吡啶并[2,3-d]哒嗪-8(7H)-酮
  参考文献：
  名称：

  Tetrahydropyrido[d]pyridazinones—promising scaffolds for drug discovery

  摘要：

  An approach to the synthesis of all possible tetrahydropyrido[d]pyridazinones has been developed. The method relies on the catalytic hydrogenation of the corresponding aromatic counterparts, which were obtained by cyclization of the relevant dibromomethyl-substituted pyridinecarboxylates with hydrazine. The synthetic schemes include 4-5 steps starting from commercially available materials. The tetrahydropyrido[d]pyridazinone scaffolds are combinations of a saturated heterocycle (piperidine) and a privileged aromatic heterocycle (pyridazinone); hence they are promising starting points for the design in medicinal chemistry. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.06.029

文献信息

• [EN] NEUROLOGICALLY-ACTIVE COMPOUNDS<br/>[FR] COMPOSÉS NEUROLOGIQUEMENT ACTIFS
  申请人：PRANA BIOTECHNOLOGY LTD

  公开号：WO2004031161A1

  公开（公告）日：2004-04-15

  The present invention relates to neurologically-active compounds, being heterocyclic compounds having two fused 6-membered rings with a nitrogen atom at position 1 and a hydroxy or mercapto group at position 8 with at least one ring being aromatic. Also disclosed are processes for the preparation of these compounds and their use as pharmaceutical or veterinary agents, in particular for the treatment of neurological conditions, more specifically neurodegenerative conditions such as Alzheimer's disease.

  本发明涉及具有两个融合的6元环，其中第1位置有一个氮原子，第8位置有一个羟基或巯基基团的神经活性化合物，其中至少一个环是芳香环。还公开了制备这些化合物的方法以及它们作为药物或兽药剂的用途，特别是用于治疗神经系统疾病，更具体地说是神经退行性疾病，如阿尔茨海默病。
• Synthesis and Pharmacological Evaluation of<i>N</i>-(Dimethylamino)ethyl Derivatives of Benzo- and Pyridopyridazinones
  作者：Wanda Pakulska、Zbigniew Malinowski、Aleksandra K. Szczesniak、Elzbieta Czarnecka、Jan Epsztajn

  DOI：10.1002/ardp.200800016

  日期：2009.1

  New N‐(dimethylamino)ethyl derivatives of phthalazinones and pyridopyridazinones 7, 9 were synthesized and assayed as potential analgesic agents in the hot‐plate, tail‐flick, and writhing tests. Pharmacological assay demonstrated that eight (in ten) of the newly synthesized compounds showed antinociceptive activity. Especially, 2‐[2‐(dimethylamino)ethyl]‐4‐phenyl‐2H‐phthalazin‐1‐one 7a showed remarkably

  合成了酞嗪酮和吡啶并哒嗪酮 7、9 的新型 N-（二甲氨基）乙基衍生物，并在热板、甩尾和扭体试验中作为潜在的镇痛剂进行了分析。药理学分析表明，新合成的化合物中有八种（十分之八）显示出镇痛活性。特别是，2-[2-(二甲氨基)乙基]-4-苯基-2H-酞嗪-1-one 7a在所有测试中都显示出显着更高的镇痛活性。这与对脊柱上、脊柱和外周结构的影响有关。热板对疼痛刺激的敏感性下降高于安乃近。
• Synthesis of Some Novel <i>N</i>-Substituted Phthalazinone and Pyridopyridazinone Derivatives
  作者：Zbigniew Malinowski、Dariusz Sroczyński、Aleksandra K. Szcześniak

  DOI：10.1080/00397911.2015.1025282

  日期：2015.8.3

  Abstract Phthalazinone and pyridopyridazinone derivatives 3, 5, and 9 were prepared via reaction ofappropriate lactams 2 and 8 with 2-bromoethylphthalimide, N-tosylaziridine, and N,O-ditosyl derivatives of N-methylethanolamine in a two-step process in the presence of MeONa/MeOH or NaH/dimethylformamide (DMF). Starting compounds 2 and 8 were obtained by reaction of hydrazine hydrate with isoindolinones

  摘要 通过合适的内酰胺 2 和 8 与 2-溴乙基邻苯二甲酰亚胺、N-甲苯磺酰氮丙啶和 N-甲基乙醇胺的 N,O-二甲苯磺酰衍生物在两步法存在下反应制备了酞嗪酮和吡啶并哒嗪酮衍生物 3、5、9。 MeONa/MeOH 或 NaH/二甲基甲酰胺 (DMF)。通过水合肼与异吲哚酮1或氮杂异吲哚酮6反应得到起始化合物2和8。选择的N-(2-邻苯二甲酰亚胺乙基)-酞嗪酮通过处理以令人满意的收率转化为相应的2-[2-(甲氨基)乙基]-衍生物用肼。图形概要
• HETEROCYCLIC COMPOUND AND MEDICINAL APPLICATION THEREOF
  申请人：Japan Tobacco, Inc.

  公开号：EP1953147A1

  公开（公告）日：2008-08-06

  The present invention aims at providing a novel heterocyclic compound having HCV entry inhibitory activity and the pharmaceutical use thereof. The present invention provides a therapeutic agent for hepatitis C comprising a heterocyclic compound represented by the following formula [1] or a pharmaceutically acceptable salt thereof as an active ingredient: wherein Q1 is -N=, etc., Q2 is -N-, etc., Q3 is -N=, etc., Q4 is -N-, etc., Q5 is -N-, etc., R1 is a hydrogen atom, etc., R2 is a hydrogen atom, etc., ring A is a monocyclic aryl group optionally having substituent(s), etc., and ring B is a monocyclic aryl group optionally having substituent(s), etc.

  本发明旨在提供一种具有HCV进入抑制活性的新型杂环化合物及其药物用途。本发明提供了一种治疗丙型肝炎的治疗剂，其包括以下式[1]所表示的杂环化合物或其药学上可接受的盐作为活性成分：其中Q1为-N=等，Q2为-N-等，Q3为-N=等，Q4为-N-等，Q5为-N-等，R1为氢原子等，R2为氢原子等，环A为单环芳基，可选地具有取代基等，环B为单环芳基，可选地具有取代基等。
• A concise regioselective synthesis of hydroxyazaisoindolinones and their conversion into pyridopyridazinones
  作者：Jacek Z. Brzeziński、Henryk B. Bzowski、Jan Epsztajn

  DOI：10.1016/0040-4020(95)01109-9

  日期：1996.2

  The synthesis of pyridopyridazinones 7 and 8 via the reaction of hydroxyazaisoindolinones 5 and 6 with hydrazine hydrate is described. Compounds 7 and 8 were then subjected to reactions with alkyl halides to furnish N-alkyl derivatives. Only in the reaction of pyridopyridazinone 8 with benzyl bromide was the O-benzylpyridopyridazine 14b formed in addition to the N-benzylpyridopyridazinone 14a.

  描述了通过羟基氮杂异吲哚满酮5和6与水合肼的反应合成吡啶并吡啶并酮7和8。然后使化合物7和8与卤代烷反应以提供N-烷基衍生物。仅在吡啶并吡啶并哒嗪酮8与苄基溴的反应中，除了N-苄基并吡啶并哒嗪酮14a之外，还形成了O-苄基并吡啶并哒嗪酮14b。