4-(3-(cyclohexylamino)imidazo[1,2-a]pyridine-2-yl)benzene-1,3-diol | 484692-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3-(cyclohexylamino)imidazo[1,2-a]pyridine-2-yl)benzene-1,3-diol
• 英文别名: 4-[3-(Cyclohexylamino)imidazo[1,2-a]pyridin-2-yl]benzene-1,3-diol
• CAS: 484692-10-6
• 化学式: C₁₉H₂₁N₃O₂
• 分子量: 323.395
• InChiKey: WEHQYQHFNLWYRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  69.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 异氰环已烷 、 2,4-二羟基苯甲醛 在 montmorillonite clay K₁₀ 作用下， 以 1,4-二氧六环 为溶剂， 反应 30.0h， 以15%的产率得到4-(3-(cyclohexylamino)imidazo[1,2-a]pyridine-2-yl)benzene-1,3-diol
  参考文献：
  名称：

  6-Substituted imidazo[1,2-a]pyridines: Synthesis and biological activity against colon cancer cell lines HT-29 and Caco-2

  摘要：

  A range of 6-substituted imidazo[1,2-a]pyridines were synthesized using a multicomponent coupling reaction. Most of these compounds were found to exhibit excellent activity against the colon cancer cell lines HT-29 and Caco-2, whilst not showing significant toxicity against white blood cells. Our studies have shown that the proteolytic phase of apoptosis was initiated 2 h after treatment with these imidazo [1,2-a]pyridines. The data suggests that the imidazo[1,2-a]pyridine-induced cell death in HT-29 and Caco-2 cells is mediated via pathway(s) that include the release of cytochrome c from the mitochondria to the cytosol and the activation of caspase 3 and caspase 8. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.036

文献信息

• IMIDAZO [1,2-A] PYRIDINE-6-CARBOXAMIDE DERIVATIVES, THEIR USE FOR THE TREATMENT OF COLON CANCER AND THEIR METHOD OF MANUFACTURE
  申请人：University Of Witwatersrand, Johannesburg

  公开号：EP2417136B1

  公开（公告）日：2016-01-06
• IMIDAZO[1,2 A] PYRIDINE 6 CARBOXAMIDE DERIVATIVES, THEIR USE FOR THE TREATMENT OF COLON CANCER AND THEIR METHOD OF MANUFACTURE
  申请人：Farkas (Nee Dahan) Nurit Esperance

  公开号：US20120101122A1

  公开（公告）日：2012-04-26

  This invention relates to the manufacture of novel chemical compounds which have biological activity, particularly to novel chemical compounds that are cytotoxic against colon cancer cells and colon cancer cell lines. The manufacturing of said chemical compounds displaying anti-cancer properties employs the use of multi-component chemical reactions. The object of this invention is to manufacture and isolate analogues of imidazo[1,2-a]pyridine, namely compounds of Formula 1, which are cytotoxic against colon cancer cells, while concomitantly being relatively inactive against white blood cells. wherein, R is bromo, methyl, phenyl, nitro, hydrogen or an amide functional group; R 1 is benzyl, 2,6-dimethylphenyl or cyclohexyl; and R 2 is methoxy, benzyloxy or hydroxy.
• US8481740B2
  申请人：——

  公开号：US8481740B2

  公开（公告）日：2013-07-09
• [EN] CERTAIN CHEMICAL ENTITIES, COMPOSITIONS, AND METHODS FOR MODULATING TRPV1<br/>[FR] CERTAINS TYPES D'ENTITES CHIMIQUES, COMPOSITIONS ET METHODE DE MODULATION DE TRPV1
  申请人：AMPHORA DISCOVERY CORP

  公开号：WO2007067711A2

  公开（公告）日：2007-06-14

  [EN] Provided are chemical entities chosen from compounds of Formula (I) and pharmaceutically or cosmetically acceptable salts, solvates, chelates, non-covalent complexes, prodrugs, and mixtures thereof. The chemical entities modulate TRPV1 and are useful in the treatment of at least one disease or disorder modulated by TRPV1 activity.
  [FR] L'invention porte sur des entités chimiques choisies parmi des composés de formule (I) et sur des sels acceptables d'un point de vue pharmaceutique ou cosmétique, des solvates, des chélates, des complexes non covalents, des promédicaments et des mélanges de ceux-ci. Les entités chimiques modulent TRPV1 et sont utiles dans le traitement d'au moins une maladie ou trouble modulé par l'activité de TRPV1.
• [EN] MODULATION OF PHOSPHORYL TRANSFERASE ACTIVITY OF GLUTAMINE SYNTHETASE<br/>[FR] MODULATION DE L'ACTIVITE PHOSPHORYL TRANSFERASE DE LA GLUTAMINE SYNTHETASE
  申请人：CSIR

  公开号：WO2007105023A1

  公开（公告）日：2007-09-20

  [EN] Methods of screening and designing compounds as inhibitors of glutamine synthetase, including adenylylated glutamine synthetase, are provided herein. Compounds and compositions useful for the treatment, prevention, and/or amelioration of bacterial infections, including Mycobacterium tuberculosis, are also provided.
  [FR] La présente invention concerne des procédés de criblage et de conception de composés en tant qu'inhibiteurs de la glutamine synthétase, y compris de la glutamine synthétase adénylylée. L'invention concerne de plus des composés et des compositions utiles pour le traitement, la prévention et/ou l'amélioration d'infections bactériennes, y compris par Mycobacterium tuberculosis.