C-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-methylamine | 887283-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: C-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-methylamine
• 英文别名: [6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]methanamine
• CAS: 887283-36-5
• 化学式: C₁₆H₁₇N₃
• 分子量: 251.331
• InChiKey: OMHFQABYXCKFDZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  C-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-methylamine 、 氯甲酸对甲苯 在 水 、 无水氯化钙 作用下， 以 吡啶 为溶剂， 反应 24.0h， 以to give (6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-carbamic acid p-tolyl ester的产率得到(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-ylmethyl)-carbamic acid p-tolyl ester
  参考文献：
  名称：

  Imidazo [1,2-a]Pyridine Compounds, Compositions, Uses and Methods Thereto

  摘要：

  本发明涉及一种新型咪唑[1,2-a]吡啶化合物，其一般式为(I)，以及其药学上可接受的盐；其中R1、R2、R3和R4如权利要求中所定义。该化合物具有特定的GABAA受体亲和力，因此在治疗和预防α1-和α2-GABAA受体调节的疾病方面具有用处。

  公开号：

  US20080200473A1
• 作为产物：
  描述：

  6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridine-3-carbaldehyde oxime 在 sodium acetate 、 溶剂黄146 、 锌 作用下， 反应 10.0h， 生成 C-(6-methyl-2-p-tolyl-imidazo[1,2-a]pyridin-3-yl)-methylamine
  参考文献：
  名称：

  Design, Synthesis and Biological Evaluation of Imidazo[1,2-a]pyridine Derivatives as Novel DPP-4 Inhibitors

  摘要：

  A new series of DPP‐4 inhibitors with imidazo[1,2‐a]pyridine scaffold were designed by exploiting scaffold hopping strategy and docking study. Based on docking binding model, structural modifications of 2‐benzene ring and pyridine moieties of compound 5a led to the identification of compound 5d with 2, 4‐dichlorophenyl group at the 2‐position as a potent (IC50 = 0.13 μm), selective (DPP‐8/DPP‐4 = 215 and DPP‐9/DPP‐4 = 192) and in vivo efficacious DPP‐4 inhibitor. Further, molecular docking revealed that compound 5d could retain key binding features of DPP‐4 with the pyridine moiety of imidazo[1,2‐a]pyridine ring providing an additional π−π interaction with Phe357 of DPP‐4. Compound 5d might be a promising lead for further development of novel DPP‐4 inhibitor treating T2DM.

  DOI：

  10.1111/cbdd.12560

文献信息

• WO2006/51063
  申请人：——

  公开号：——

  公开（公告）日：——
• IMIDAZO[1,2-A]PYRIDINE COMPOUNDS, COMPOSITIONS, USES AND METHODS RELATED THERETO
  申请人：FERRER INTERNACIONAL, S.A.

  公开号：EP1814880A1

  公开（公告）日：2007-08-08
• [EN] IMIDAZO[1,2-A]PYRIDINE COMPOUNDS, COMPOSITIONS, USES AND METHODS RELATED THERETO<br/>[FR] DÉRIVÉS D'IMIDAZO[1,2-A]PYRIDINE, ET PRÉPARATIONS, EMPLOIS ET MÉTHODES LIÉS À CES DÉRIVÉS
  申请人：FERRER INT

  公开号：WO2006051063A1

  公开（公告）日：2006-05-18

  [EN] The present invention relates to novel imidazo[1,2- a]pyridine compounds of general formula (I) as well as pharmaceutically acceptable salts thereof; wherein R₁, R₂, R₃ and R₄ are as defined in the claims. The compounds have specific affinity for GABAA receptor and are therefore useful in the treatment and prevention of diseases modulated by a₁- and a₂-GABA_A receptors.
  [FR] La présente invention a pour objet de nouveaux dérivés d'imidazo[1,2-a]pyridine de formule générale (I), ainsi que des sels de qualité pharmaceutique desdits dérivés, où R₁, R₂, R₃ et R₄ sont tels que définis dans les revendications. Lesdits dérivés ont une affinité spécifique pour le récepteur GABA_A, et peuvent donc être employés dans le traitement prophylactique et thérapeutique de maladies régulées par les récepteurs GABA_A a₁ et a₂.
• Design, Synthesis and Biological Evaluation of Imidazo[1,2-a]pyridine Derivatives as Novel DPP-4 Inhibitors
  作者：Qing Li、Muxing Zhou、Li Han、Qing Cao、Xinning Wang、LeiLei Zhao、Jinpei Zhou、Huibin Zhang

  DOI：10.1111/cbdd.12560

  日期：2015.10

  A new series of DPP‐4 inhibitors with imidazo[1,2‐a]pyridine scaffold were designed by exploiting scaffold hopping strategy and docking study. Based on docking binding model, structural modifications of 2‐benzene ring and pyridine moieties of compound 5a led to the identification of compound 5d with 2, 4‐dichlorophenyl group at the 2‐position as a potent (IC50 = 0.13 μm), selective (DPP‐8/DPP‐4 = 215 and DPP‐9/DPP‐4 = 192) and in vivo efficacious DPP‐4 inhibitor. Further, molecular docking revealed that compound 5d could retain key binding features of DPP‐4 with the pyridine moiety of imidazo[1,2‐a]pyridine ring providing an additional π−π interaction with Phe357 of DPP‐4. Compound 5d might be a promising lead for further development of novel DPP‐4 inhibitor treating T2DM.
• Imidazo [1,2-a]Pyridine Compounds, Compositions, Uses and Methods Thereto
  申请人：Falco Jose Luis

  公开号：US20080200473A1

  公开（公告）日：2008-08-21

  The present invention relates to novel imidazo[1,2-a]pyridine compounds of general formula (I): as well as pharmaceutically acceptable salts thereof; wherein R 1 , R 2 , R 3 and R 4 are as defined in the claims. The compounds have specific affinity for GABA A receptor and are therefore useful in the treatment and prevention of diseases modulated by α 1 - and α 2 -GABA A receptors.

  本发明涉及一种新型咪唑[1,2-a]吡啶化合物，其一般式为(I)，以及其药学上可接受的盐；其中R1、R2、R3和R4如权利要求中所定义。该化合物具有特定的GABAA受体亲和力，因此在治疗和预防α1-和α2-GABAA受体调节的疾病方面具有用处。