(6-氯-5-甲基吡啶-3-基)甲胺 | 1256824-90-4

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: (6-氯-5-甲基吡啶-3-基)甲胺
• 英文名称: (6-chloro-5-methylpyridin-3-yl)methanamine
• CAS: 1256824-90-4
• 化学式: C₇H₉ClN₂
• 分子量: 156.615
• InChiKey: LOVAISLEGWJHKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6-氯-5-甲基吡啶-3-基)甲胺 在 2-双环己基膦-2',6'-二甲氧基联苯 、 palladium diacetate potassium phosphate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 、 仲丁醇 为溶剂， 反应 4.0h， 生成 N-((2',3-dimethyl-2,4'-bipyridin-5-yl)methyl)-5-(pyrazin-2-yl)picolinamide
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR MODULATING THE WNT SIGNALING PATHWAY
  [FR] COMPOSITIONS ET PROCÉDÉS POUR MODULER LA VOIE DE SIGNALISATION WNT

  摘要：

  本发明涉及用具有Formula（1）和（3）的化合物调节Wnt信号通路的组合物和方法：其中A、B、Y和Z均代表环，R1、R2、R3如本文所定义。

  公开号：

  WO2012003189A1
• 作为产物：
  描述：

  6-氯-5-甲基吡啶-3-羧醛 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成 (6-氯-5-甲基吡啶-3-基)甲胺
  参考文献：
  名称：

  Design, synthesis, and evaluation of novel porcupine inhibitors featuring a fused 3-ring system based on the ‘reversed’ amide scaffold

  摘要：

  The Wnt signaling pathway is an essential signal transduction pathway which leads to the regulation of cellular processes such as proliferation, differentiation and migration. Aberrant Wnt signaling is known to have an association with multiple cancers. Porcupine is an enzyme that catalyses the addition of palmitoleate to a serine residue in Wnt proteins, a process which is required for the secretion of Wnt proteins. Here we report the synthesis and structure-activity-relationship of the novel porcupine inhibitors based on a 'reversed' amide scaffold. The leading compound 53 was as potent as the clinical compound LGK974 in a cell based STF reporter gene assay. Compound 53 potently inhibited the secretion of Wnt3A, therefore was confirmed to be a porcupine inhibitor. Furthermore, compound 53 showed excellent chemical and plasma stabilities. However, the clearance of compound 53 in liver microsomal tests was moderate to high, and the solubility of compound 53 was suboptimal. Collective efforts toward further optimization of this novel tricyclic template to develop better porcupine inhibitors will be subsequently undertaken and reported in due course. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.09.041

文献信息

• 具有Wnt信号通路抑制活性的杂环化合物及其应用
  申请人：苏州云轩医药科技有限公司

  公开号：CN105254613A

  公开（公告）日：2016-01-20

  本发明提供了一种具有Wnt信号通路抑制活性的杂环化合物。该杂环化合物及其药学上可接受的盐、同位素、异构体和晶型结构，具有通式I所示的结构：(I)。本发明还提供上述的具有Wnt信号通路抑制活性的杂环化合物的应用。本发明的具有Wnt信号通路抑制活性的杂环化合物，作为Wnt信号通路的有效拮抗剂，能够用于治疗或预防因Wnt信号通路失常引起的病症。
• COMPOSITIONS AND METHODS FOR MODULATING THE WNT SIGNALING PATHWAY
  申请人：Cheng Dai

  公开号：US20130079328A1

  公开（公告）日：2013-03-28

  The present invention relates to compositions and methods for modulating the Wnt signaling pathway, using compounds having Formula (1) and (3): wherein A, B, Y and Z all represent rings, and R 1 , R 2 , R 3 are as defined herein.

  本发明涉及使用具有式（1）和（3）的化合物来调节Wnt信号通路的组合物和方法：其中A、B、Y和Z均表示环，R1、R2、R3如本文所定义。
• EP2588453B1
  申请人：——

  公开号：EP2588453B1

  公开（公告）日：2015-04-01
• US9181235B2
  申请人：——

  公开号：US9181235B2

  公开（公告）日：2015-11-10
• Design, synthesis, and evaluation of novel porcupine inhibitors featuring a fused 3-ring system based on the ‘reversed’ amide scaffold
  作者：Zhixiang Xu、Xiangxiang Xu、Ruadhan O’Laoi、Haikuo Ma、Jiyue Zheng、Shuaishuai Chen、Lusong Luo、Zhilin Hu、Sudan He、Jiajun Li、Hongjian Zhang、Xiaohu Zhang

  DOI：10.1016/j.bmc.2016.09.041

  日期：2016.11

  The Wnt signaling pathway is an essential signal transduction pathway which leads to the regulation of cellular processes such as proliferation, differentiation and migration. Aberrant Wnt signaling is known to have an association with multiple cancers. Porcupine is an enzyme that catalyses the addition of palmitoleate to a serine residue in Wnt proteins, a process which is required for the secretion of Wnt proteins. Here we report the synthesis and structure-activity-relationship of the novel porcupine inhibitors based on a 'reversed' amide scaffold. The leading compound 53 was as potent as the clinical compound LGK974 in a cell based STF reporter gene assay. Compound 53 potently inhibited the secretion of Wnt3A, therefore was confirmed to be a porcupine inhibitor. Furthermore, compound 53 showed excellent chemical and plasma stabilities. However, the clearance of compound 53 in liver microsomal tests was moderate to high, and the solubility of compound 53 was suboptimal. Collective efforts toward further optimization of this novel tricyclic template to develop better porcupine inhibitors will be subsequently undertaken and reported in due course. (C) 2016 Elsevier Ltd. All rights reserved.