4-chloro-6-(4-pyridinyl)pyrimidine | 954232-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-chloro-6-(4-pyridinyl)pyrimidine
• 英文别名: 4-chloro-6-(pyridin-4-yl)pyrimidine；4-Chloro-6-pyridin-4-ylpyrimidine
• CAS: 954232-36-1
• 化学式: C₉H₆ClN₃
• 分子量: 191.62
• InChiKey: WJPIABLRIGFPBF-UHFFFAOYSA-N

物化性质

• 沸点：
  341.9±27.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-6-(4-pyridinyl)pyrimidine 、 3-甲基苯胺 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以65%的产率得到N-(3-methylphenyl)-6-(4-pyridinyl)-4-pyrimidinamine
  参考文献：
  名称：

  SAR studies of 4-pyridyl heterocyclic anilines that selectively induce autophagic cell death in von Hippel-Lindau-deficient renal cell carcinoma cells

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2011.04.042
• 作为产物：
  描述：

  4,6-二氯嘧啶 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 4-chloro-6-(4-pyridinyl)pyrimidine
  参考文献：
  名称：

  [EN] AZAADAMANTANE DERIVATIVES AND THEIR USES AS NICOTINIC ACETYLCHOLINE RECEPTORS LIGANDS
  [FR] DÉRIVÉS D'AZA-ADAMANTANE ET PROCÉDÉS D'UTILISATION

  摘要：

  公开号：

  WO2008058096A3

文献信息

• AZAADAMANTANE DERIVATIVES AND METHODS OF USE
  申请人：AbbVie Inc.

  公开号：US20150158867A1

  公开（公告）日：2015-06-11

  The invention relates to compounds that are azaadamantane derivatives, particularly ether- or amine-substituted azaadamantane derivatives and salts and prodrugs thereof, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.

  本发明涉及的化合物是氮杂金刚烷衍生物，特别是醚或胺基取代的氮杂金刚烷衍生物及其盐和前药，包括这种化合物的组合物，使用这种化合物和组合物的方法，制备这种化合物的过程以及在这种过程中获得的中间体。
• AZAADAMANTANE DERIVATIVES AND THEIR USES AS NICOTINIC ACETYLCHOLINE RECEPTORS LIGANDS
  申请人：ABBOTT LABORATORIES

  公开号：EP2099795A2

  公开（公告）日：2009-09-16
• US8314119B2
  申请人：——

  公开号：US8314119B2

  公开（公告）日：2012-11-20
• US8987453B2
  申请人：——

  公开号：US8987453B2

  公开（公告）日：2015-03-24
• [EN] AZAADAMANTANE DERIVATIVES AND METHODS OF USE<br/>[FR] DÉRIVÉS D'AZA-ADAMANTANE ET PROCÉDÉS D'UTILISATION
  申请人：ABBOTT LAB

  公开号：WO2008058096A2

  公开（公告）日：2008-05-15

  (EN) The invention relates to compounds that are azaadamantane derivatives of formula (I), particularly ether- or amine -substituted azaadamantane derivatives and salts and prodrugs thereof, compositions comprising such compounds, methods of using such compounds and compositions, processes for preparing such compounds, and intermediates obtained during such processes.(FR) Cette invention concerne des composés qui sont des dérivés d'aza-adamantane, en particulier des dérivés d'aza-adamantane substitué par un éther ou une amine, ainsi que leurs sels et précurseurs, des compositions comprenant de tels composés, des procédés utilisant de tels composés et compositions, des procédés de préparation de tels composés et les intermédiaires obtenus au cours de tels procédés.