1-(p-Bromobenzyl)-3-formyl-5-methoxy-2-methylindole | 185516-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-(p-Bromobenzyl)-3-formyl-5-methoxy-2-methylindole
• 英文别名: 1-[(4-bromophenyl)methyl]-5-methoxy-2-methylindole-3-carbaldehyde
• CAS: 185516-60-3
• 化学式: C₁₈H₁₆BrNO₂
• 分子量: 358.235
• InChiKey: CXPIEKOQVPELKV-UHFFFAOYSA-N

物化性质

• 沸点：
  531.0±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(p-Bromobenzyl)-3-formyl-5-methoxy-2-methylindole 在 lithium hydroxide 、 三甲基氯硅烷 作用下， 以 甲苯 为溶剂， 生成 3-[1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl]butanoic acid
  参考文献：
  名称：

  From indomethacin to a selective COX-2 inhibitor: Development of indolalkanoic acids as potent and selective cyclooxygenase-2 inhibitors

  摘要：

  A series of potent and highly selective cyclooxygenase-2 inhibitors have been prepared by replacing the benzoyl group of indomethacin with a 4-bromobenzyl group, and by extending the acetic acid side chain. These compounds show anti-inflammatory activity in rats with no evidence of GI toxicity, even at high doses.

  DOI：

  10.1016/0960-894x(96)00100-x
• 作为产物：
  描述：

  5-甲氧基-2-甲基-1H-吲哚-3-甲醛 、 对溴溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(p-Bromobenzyl)-3-formyl-5-methoxy-2-methylindole
  参考文献：
  名称：

  From indomethacin to a selective COX-2 inhibitor: Development of indolalkanoic acids as potent and selective cyclooxygenase-2 inhibitors

  摘要：

  A series of potent and highly selective cyclooxygenase-2 inhibitors have been prepared by replacing the benzoyl group of indomethacin with a 4-bromobenzyl group, and by extending the acetic acid side chain. These compounds show anti-inflammatory activity in rats with no evidence of GI toxicity, even at high doses.

  DOI：

  10.1016/0960-894x(96)00100-x

文献信息

• N-benzylindol-3-yl propanoic acid derivatives as cyclooxygenase
  申请人：Merck Frosst Canada, Inc.

  公开号：US05604253A1

  公开（公告）日：1997-02-18

  The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.

  这项发明涵盖了式I的新化合物，以及一种治疗环氧合酶-2介导疾病的方法，包括向需要此类治疗的患者施用式I化合物的非毒性治疗有效量。 该发明还涵盖了用于治疗环氧合酶-2介导疾病的某些含有式I化合物的药物组合物。
• US5604253A
  申请人：——

  公开号：US5604253A

  公开（公告）日：1997-02-18
• [EN] N-BENZYLINDOL-3-YL PROPANIC ACID DERIVATIVES AS CYCLOOXYGENASE-2 INHIBITORS<br/>[FR] DERIVES DE L'ACIDE N-BENZYLINDOLE-3-YL PROPANIQUE INHIBITEURS DE LA CYCLOOXYGENASE-2
  申请人：MERCK FROSST CANADA INC.

  公开号：WO1996037469A1

  公开（公告）日：1996-11-28

  (EN) The invention encompasses the novel compound of Formula (I) as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula (I). The invention also encompasses certain pharmaceutcial compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula (I).(FR) L'invention concerne le nouveau composé selon la formule (I), ainsi qu'un procédé de traitement des maladies provoquées par la cyclooxygénase-2, consistant à administrer à un patient nécessitant un traitement non toxique de ce type une dose thérapeutiquement efficace d'un composé selon la formule (I). L'invention traite également de certaines compositions pharmaceutiques pour le traitement des maladies provoquées par la cyclooxygénase-2, comprenant les composés de la formule (I).
• From indomethacin to a selective COX-2 inhibitor: Development of indolalkanoic acids as potent and selective cyclooxygenase-2 inhibitors
  作者：W.C. Black、C. Bayly、M. Belley、C.-C. Chan、S. Charleson、D. Denis、J.Y. Gauthier、R. Gordon、D. Guay、S. Kargman、C.K. Lau、Y. Leblanc、J. Mancini、M. Ouellet、D. Percival、P. Roy、K. Skorey、P. Tagari、P. Vickers、E. Wong、L. Xu、P. Prasit

  DOI：10.1016/0960-894x(96)00100-x

  日期：1996.3

  A series of potent and highly selective cyclooxygenase-2 inhibitors have been prepared by replacing the benzoyl group of indomethacin with a 4-bromobenzyl group, and by extending the acetic acid side chain. These compounds show anti-inflammatory activity in rats with no evidence of GI toxicity, even at high doses.