5-amino-1-(3,4-dichlorobenzyl)-1H-indazole-3-ol | 197584-46-6

• 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-amino-1-(3,4-dichlorobenzyl)-1H-indazole-3-ol
• 英文别名: 5-Amino-1-(3,4-dichlorobenzyl)-1H-indazol-3-ol；5-amino-1-[(3,4-dichlorophenyl)methyl]-2H-indazol-3-one
• CAS: 197584-46-6
• 化学式: C₁₄H₁₁Cl₂N₃O
• 分子量: 308.167
• InChiKey: XPHFPCWFIHVPPA-UHFFFAOYSA-N

物化性质

• 密度：
  1.491±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5-amino-1-(3,4-dichlorobenzyl)-1H-indazole-3-ol 在 sodium hydroxide 、 sodium nitrite 作用下， 以 正丁醇 为溶剂， 生成 1-(3,4-dichlorobenzyl)-1H-indazole-3,5-diol
  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
• 作为产物：
  描述：

  3,4-二氯氯苄 在 Ra-Ni sodium hydroxide 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.5h， 生成 5-amino-1-(3,4-dichlorobenzyl)-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

• 1,3,5-tribsubstituted indazole derivatives, processes for preparing, and
  申请人：Arzneimittelwerk Dresden G.m.b.H.

  公开号：US05776932A1

  公开（公告）日：1998-07-07

  1,3,5-trisubstituted indazole derivatives of the formula ##STR1## wherein R1 is H, (b) a C.sub.1-6 straight or branched, substituted or unsubstituted alkyl residue, (c) a C.sub.3-7 cycloalkyl residue, (d) an unsustituted or substituted phenyl, naphthyl, anthranyl, or fluorenyl residue, (e) a quinolin-2-ylmethoxy, or pyridin-2-ylmethoxy residue; X is O, or a --NH, --NH--(C.dbd.O)--NH--, --NH--(C.dbd.O)--O--, --NH--(C.dbd.O)--, or --NH--CH.sub.2 --(C.dbd.O)-- residue; Y is O, or S; R.sub.2 is H; Z is a SO, SO.sub.2, --(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --O--, --O--(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --(C.dbd.O)--, --(C.dbd.O)--(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --(C.dbd.O)--NH--, --NH--(C.dbd.O)--(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --CHOH--, --CHOH--(CH.sub.2).sub.p --, --(CH.sub.2).sub.p --CH.dbd.CH--, or --CH.dbd.CH--(CH.sub.2).sub.p -- residue, wherein p is between 1 and 6; A is a phenyl, naphthyl, anthranyl, fluorenyl, thiophenyl, pyridinyl, isoxazolyl, benzimidazolyl, benz\x9b1,3!dioxolyl, pyrimidyl, pyrimidine-2,4-dionyl, quinolinyl, quinoxazolinyl, morpholinyl, or pyrrolidinyl residue; and, R.sub.3, R.sub.4, and R.sub.5, the same or different, are defined in the specification; and pharmaceutically acceptable salts, stereoisomers, racemates, racemic modifications, and enantiomers thereof. The invention also relates to specific compounds, processes for preparing and for treating an allergic, asthmatic, inflamed condition of a host, or for modulating the immune system of a host.

  该专利涉及一种化合物，其为1,3,5-三取代吲唑衍生物，化学式为##STR1##其中R1为H，(b)为C.sub.1-6直链或支链，取代或未取代的烷基残基，(c)为C.sub.3-7环烷基残基，(d)为未取代或取代的苯基，萘基，蒽基或芴基残基，(e)为喹啉-2-基甲氧基或吡啶-2-基甲氧基残基；X为O，或--NH，--NH--(C.dbd.O)--NH--，--NH--(C.dbd.O)--O--，--NH--(C.dbd.O)--，或--NH--CH.sub.2--(C.dbd.O)--残基；Y为O，或S；R.sub.2为H；Z为SO，SO.sub.2，--(CH.sub.2).sub.p--，--(CH.sub.2).sub.p--O--，--O--(CH.sub.2).sub.p--，--(CH.sub.2).sub.p--(C.dbd.O)--，--(C.dbd.O)--(CH.sub.2).sub.p--，--(CH.sub.2).sub.p--(C.dbd.O)--NH--，--NH--(C.dbd.O)--(CH.sub.2).sub.p--，--(CH.sub.2).sub.p--CHOH--，--CHOH--(CH.sub.2).sub.p--，--(CH.sub.2).sub.p--CH.dbd.CH--，或--CH.dbd.CH--(CH.sub.2).sub.p--残基，其中p为1到6之间；A为苯基，萘基，蒽基，芴基，噻吩基，吡啶基，异噁唑基，苯并咪唑基，苯并[1,3]二氧杂环基，嘧啶基，嘧啶-2,4-二酮基，喹啉基，喹啉氧杂唑基，吗啉基或吡咯烷基残基；以及其药物可接受的盐，立体异构体，外消旋体，外消旋体修饰物和对映体。该发明还涉及特定化合物，制备和治疗宿主的过敏，哮喘，炎症状况或调节宿主免疫系统的过程。
• [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%).