2-bromo-1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethan-1-one hydrobromide | 107720-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-bromo-1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethan-1-one hydrobromide
• 英文别名: 2-bromo-1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethanone hydrobromide；2-Bromo-1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethanone;hydrobromide
• CAS: 107720-10-5
• 化学式: BrH*C₁₀H₉BrN₂O
• 分子量: 334.01
• InChiKey: MPBHGVWCXHXRMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  硫代草氨酸乙酯 、 2-bromo-1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethan-1-one hydrobromide 以 乙醇 为溶剂， 反应 2.0h， 以46%的产率得到4-(2-Methyl-imidazo[1,2-a]pyridin-3-yl)-thiazole-2-carboxylic acid ethyl ester; hydrobromide
  参考文献：
  名称：

  Kosary; Kasztreiner; Andrasi, Pharmazie, 1989, vol. 44, # 3, p. 191 - 193

  摘要：

  DOI：
• 作为产物：
  描述：

  3-乙酰基-2-甲基咪唑[1,2-a]吡啶 在 氢溴酸 、 溴 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以1.94 g的产率得到2-bromo-1-(2-methylimidazo[1,2-a]pyridin-3-yl)ethan-1-one hydrobromide
  参考文献：
  名称：

  [EN] PHARMACEUTICAL COMPOUNDS AND THERAPEUTIC METHODS
  [FR] COMPOSÉS PHARMACEUTIQUES ET MÉTHODES THÉRAPEUTIQUES

  摘要：

  该发明提供了式（16）和（17）的化合物；以及其盐，以及包含这些化合物和盐的组合物，包含这些化合物和盐的复合物，以及使用这些化合物、盐和复合物治疗癌症、抑制BMI1表达或治疗亨廷顿病的方法。这些化合物、盐和复合物具有使它们特别有用的潜力、渗透性和口服生物利用度，例如，用于治疗胶质母细胞瘤。

  公开号：

  WO2020112845A1

文献信息

• SAR studies of 4-pyridyl heterocyclic anilines that selectively induce autophagic cell death in von Hippel-Lindau-deficient renal cell carcinoma cells
  作者：Muriel Bonnet、Jack U. Flanagan、Denise A. Chan、Edwin W. Lai、Phuong Nguyen、Amato J. Giaccia、Michael P. Hay

  DOI：10.1016/j.bmc.2011.04.042

  日期：2011.6

  We recently identified a class of pyridyl aniline thiazoles (PAT) that displayed selective cytotoxicity for von Hippel-Lindau (VHL) deficient renal cell carcinoma (RCC) cells in vitro and in vivo. Structure-activity relationship (SAR) studies were used to develop a comparative molecular field analysis (CoMFA) model that related VHL-selective potency to the three-dimensional arrangement of chemical features of the chemotype. We now report the further molecular alignment-guided exploration of the chemotype to discover potent and selective PAT analogues. The contribution of the central thiazole ring was explored using a series of five-and six-membered ring heterocyclic replacements to vary the electronic and steric interactions in the central unit. We also explored a positive steric CoMFA contour adjacent to the pyridyl ring using Pd-catalysed cross-coupling Suzuki-Miyaura, Sonogashira and nucleophilic displacement reactions to prepare of a series of aryl-, alkynyl-, alkoxy- and alkylamino-substituted pyridines, respectively. In vitro potency and selectivity were determined using paired RCC cell lines: the VHL-null cell line RCC4 and the VHL-positive cell line RCC4-VHL. Active analogues selectively induced autophagy in RCC4 cells. We have used the new SAR data to further develop the CoMFA model, and compared this to a 2D-QSAR method. Our progress towards realising the therapeutic potential of this chemotype as a targeted cytotoxic therapy for the treatment of RCC by exploiting the absence of the VHL tumour suppressor gene is reported. (C) 2011 Elsevier Ltd. All rights reserved.
• KOSARY, JUDIT;KASZTREINER, E.;ANDRASI, F., PHARMAZIE, 44,(1989) N, C. 191-193
  作者：KOSARY, JUDIT、KASZTREINER, E.、ANDRASI, F.

  DOI：——

  日期：——
• PHARMACEUTICAL COMPOUNDS AND THERAPEUTIC METHODS
  申请人：Rutgers, The State University of New Jersey

  公开号：EP3886848A1

  公开（公告）日：2021-10-06