5-methoxy-1-(3-phenylpropyl)-1H-indazole-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 5-methoxy-1-(3-phenylpropyl)-1H-indazole-3-ol
• 英文别名: 5-methoxy-1-(3-phenylpropyl)-2H-indazol-3-one
• 化学式: C₁₇H₁₈N₂O₂
• 分子量: 282.342
• InChiKey: SKDXQOBXRCEIMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-氯-3-苯基丙烷 、 1,2-二氢-5-甲氧基-3H-吲唑-3-酮 在 sodium hydroxide 作用下， 生成 5-methoxy-1-(3-phenylpropyl)-1H-indazole-3-ol
  参考文献：
  名称：

  1,5-Disubstituted Indazol-3-ols with Anti-Inflammatory Activity

  摘要：

  A series of new indazol-3-ol derivatives was synthesized. Some of these compounds exhibit interesting anti-inflammatory activities in various models of inflammation. 5-Methoxy-1-[quinoline-2-yl-methoxy)-benzyl]-1H-indazol-3-ol (27) strongly inhibits the oxidation of arachidonic acid to 5-hydroperoxyeicosatetraenoic acid catalyzed by 5-lipoxygenase (IC50 = 44 nM). 27 also inhibits the contraction of sensitized guinea pig tracheal segments (IC50 = 2.9 mu M). In guinea pigs treated with 27 (1 mg/kg i.p.) 2 h before antigen provocation, there was a marked inhibition (47%) of the antigen-induced airway eosinophilia. After topical application of 1 mu g/ear 27 inhibits the arachidonic acid induced mouse ear edema (41%).

  DOI：

  10.1002/(sici)1521-4184(199801)331:1<13::aid-ardp13>3.0.co;2-m

文献信息

• [DE] 1,3,5-TRISUBSTITUIERTE INDAZOL-DERIVATE MIT ANTIASTHMATISCHER, ANTIALLERGISCHER, ENTZÜNDUNGSHEMMENDER UND IMMUNMODULIERENDER WIRKUNG<br/>[EN] 1,3,5-TRISUBSTITUTED INDAZOLE DERIVATIVES WITH AN ANTI-ASTHMATIC, ANTI-ALLERGIC, ANTI-INFLAMMATORY AND IMMUNOMODULATING ACTION<br/>[FR] DERIVES TRISUBSTITUES 1,3,5 DE L'INDAZOLE A ACTION ANTIASTHMATIQUE, ANTIALLERGIQUE, ANTI-INFLAMMATOIRE ET IMMUNOMODULATRICE
  申请人：ARZNEIMITTELWERK DRESDEN GMBH

  公开号：WO1997034874A1

  公开（公告）日：1997-09-25

  (DE) Die im Rahmen dieser Erfindung synthetisierten 1,3,5-trisubstituierten Indazol-Derivate der allgemeinen Formel (I) besitzen antiasthmatische, antiallergische, entzündungshemmende und immunmodulierende Wirkung und eignen sich zur Herstellung von Arzneimitteln.(EN) The 1,3,5-trisubstituted indazole derivatives of general formula (I) synthesized as proposed by the invention possess an anti-asthmatic, anti-allergic, anti-inflammatory and immunomodulating action and are suitable for use in the preparation of drugs.(FR) L'invention concerne des dérivés trisubstitués 1,3,5 de l'indazole de formule générale (I), synthétisés selon le procédé de l'invention, qui présentent une action antiasthmatique, antiallergique, anti-inflammatoire et immunomodulatrice, et sont appropriés pour la préparation de médicaments.

  该发明涉及合成的一类1,3,5-取代的苯并azole衍生物，其通式为(I)，这些衍生物具有抗哮喘、抗过敏、抑制炎症和免疫调节的作用，可用于药物的制备。[法语] L'invention concerne des dérivés trisubstitués 1,3,5 de l'indazole de formule générale (I), synthétisés selon le procédé de l'invention, qui présentent une action antiasthmatique, antiallergique, anti-inflammatoire et immunomodulatrice, et sont appropriés pour la préparation de médicaments.
• 1,3,5-TRISUBSTITUIERTE INDAZOL-DERIVATE MIT ANTIASTHMATISCHER, ANTIALLERGISCHER, ENTZÜNDUNGSHEMMENDER UND IMMUNMODULIERENDER WIRKUNG
  申请人：Arzneimittelwerk Dresden GmbH

  公开号：EP0888307A1

  公开（公告）日：1999-01-07
• US5776932A
  申请人：——

  公开号：US5776932A

  公开（公告）日：1998-07-07
• 1,5-Disubstituted Indazol-3-ols with Anti-Inflammatory Activity
  作者：Rudolf Schindler、Ilona Fleischhauer、Norbert Höfgen、Wolfgang Sauer、Ute Egerland、Hildegard Poppe、Sabine Heer、Istvan Szelenyi、Bernhard Kutscher、Jürgen Engel

  DOI：10.1002/(sici)1521-4184(199801)331:1<13::aid-ardp13>3.0.co;2-m

  日期：1998.1

  A series of new indazol-3-ol derivatives was synthesized. Some of these compounds exhibit interesting anti-inflammatory activities in various models of inflammation. 5-Methoxy-1-[quinoline-2-yl-methoxy)-benzyl]-1H-indazol-3-ol (27) strongly inhibits the oxidation of arachidonic acid to 5-hydroperoxyeicosatetraenoic acid catalyzed by 5-lipoxygenase (IC50 = 44 nM). 27 also inhibits the contraction of sensitized guinea pig tracheal segments (IC50 = 2.9 mu M). In guinea pigs treated with 27 (1 mg/kg i.p.) 2 h before antigen provocation, there was a marked inhibition (47%) of the antigen-induced airway eosinophilia. After topical application of 1 mu g/ear 27 inhibits the arachidonic acid induced mouse ear edema (41%).