5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid | 54367-65-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid
• 英文别名: 5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid；5-Brom-1-phenyl-4-pyrazol-carbonsaeure；5-bromo-1-phenylpyrazole-4-carboxylic acid
• CAS: 54367-65-6
• 化学式: C₁₀H₇BrN₂O₂
• mdl: MFCD22421054
• 分子量: 267.082
• InChiKey: JDXINZHHDLGKGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基喹啉 、 5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid 在 chloro-N,N,N',N'-bis(tetramethylene)formamidinium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 以60%的产率得到5-bromo-1-phenyl-N-(quinolin-2-yl)-1H-pyrazole-4-carboxamide
  参考文献：
  名称：

  Pyrazole-4-Carboxamide (YW2065): A Therapeutic Candidate for Colorectal Cancer via Dual Activities of Wnt/β-Catenin Signaling Inhibition and AMP-Activated Protein Kinase (AMPK) Activation

  摘要：

  Dysregulation of the Wnt/beta-catenin signaling pathway has been widely recognized as a pathogenic mechanism for colorectal cancer (CRC). Although numerous Wnt inhibitors have been developed, they commonly suffer from toxicity and unintended effects. Moreover, concerns have been raised in targeting this pathway because of its critical roles in maintaining stem cells and regenerating tissues and organs. On the basis of the anthelmintic drug pyrvinium and previous lead FX1128, we have developed a compound YW2065 (1c) which demonstrated excellent anti-CRC effects in vitro and in vivo. YW2065 achieves its inhibitory activity for Wnt signaling by stabilizing Axin-1, a scaffolding protein that regulates proteasome degradation of beta-catenin. Simultaneously, YW2065 also led to the activation of the tumor suppressor AMPK, providing an additional anticancer mechanism. In addition, YW2065 showed favorable pharmacokinetic properties without obvious toxicity. The anti-CRC effect of YW2065 was highlighted by its promising efficacy in a mice xenograft model.

  DOI：

  10.1021/acs.jmedchem.9b01252
• 作为产物：
  描述：

  5-溴-1-苯基吡唑-4-甲酸乙酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以64%.的产率得到5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  Herbicidal and algicidal 1,5-disubstituted-1H-pyrazole-4-carboxamides

  摘要：

  1,5-二取代-1H-吡唑-4-羧酰胺衍生物，可用作除草剂和水生藻类杀菌剂。

  公开号：

  US04620865A1

文献信息

• Herbicidal and algicidal 1,5-disubstituted-1H-pyrazole-4-carboxamides
  申请人：Eli Lilly and Company

  公开号：US04620865A1

  公开（公告）日：1986-11-04

  1,5-Disubstituted-1H-pyrazole-4-carboxamide derivatives, useful as herbicides and aquatic algicides.

  1,5-二取代-1H-吡唑-4-羧酰胺衍生物，可用作除草剂和水生藻类杀菌剂。
• ARYL-SUBSTITUTED PYRAZOLE-AMIDE COMPOUNDS USEFUL AS KINASE INHIBITORS
  申请人：Dyckman Alaric J.

  公开号：US20100016320A1

  公开（公告）日：2010-01-21

  The present invention relates to compounds having the formula, and pharmaceutically-acceptable salts, prodrugs, solvates, isomers, and/or hydrates thereof, wherein Q is an optionally-substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, or pyrazinyl ring; R 2 is alkyl or an amino group as defined herein; and Z is optionally-substituted oxadiazolyl or —C(═O)NR 6 , wherein R 6 is lower alkyl or cyclopropyl. The compounds are surprisingly advantageous in preparing pharmaceutical compositions for treating p38 kinase related conditions and/or in methods of treating conditions associated with the activity of p38 kinase in a patient.

  本发明涉及具有以下式的化合物，以及其药学上可接受的盐、前药、溶剂化物、异构体和/或水合物，其中Q为可选择取代的苯基、吡啶基、吡嗪基、嘧啶基或吡嗪啉基环；R2为定义如下的烷基或氨基基团；Z为可选择取代的噁二唑基或—C(═O)NR6，其中R6为低烷基或环丙基。这些化合物在制备用于治疗与p38激酶相关的疾病的药物组合物和/或治疗患者与p38激酶活性相关的疾病的方法中具有惊人的优势。
• Herbicidal pyrazole-(thio)-carboxamides
  申请人：ELI LILLY AND COMPANY

  公开号：EP0151866A2

  公开（公告）日：1985-08-21

  57 1,5-Disubstituted-1H-pyrazole-4-carboxamide derivatives, useful as herbicides and aquatic algicides.

  57 1,5-二取代-1H-吡唑-4-甲酰胺衍生物，可用作除草剂和水生杀藻剂。
• Aryl-substituted pyrazole-amide compounds useful as kinase inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：EP2133348A1

  公开（公告）日：2009-12-16

  The present invention relates to compounds having the formula, and pharmaceutically-acceptable salts, prodrugs, solvates, isomers, and/or hydrates thereof, wherein Q is an optionally-substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, or pyrazinyl ring; R2 is alkyl or an amino group as defined herein; and Z is optionally-substituted oxadiazolyl. The compounds are surprisingly advantageous in preparing medicaments for treating p38 kinase related conditions and/or in preparing medicaments for use in treating inflammatory disorders or conditions in a patient.

  本发明涉及具有以下式子的化合物、 及其药学上可接受的盐、原药、溶液剂、异构体和/或水合物，其中 Q 是任选取代的苯基、吡啶基、哒嗪基、嘧啶基或吡嗪基环；R2 是烷基或本文定义的氨基；Z 是任选取代的噁二唑基。这些化合物在制备治疗 p38 激酶相关病症的药物和/或制备用于治疗患者炎症性疾病或病症的药物方面具有惊人的优势。
• BECK, J. R.;LYNCH, M. P.
  作者：BECK, J. R.、LYNCH, M. P.

  DOI：——

  日期：——