6-chloro-N-(4-fluorophenyl)-3-nitropyridin-2-amine | 1097004-78-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-chloro-N-(4-fluorophenyl)-3-nitropyridin-2-amine
• CAS: 1097004-78-8
• 化学式: C₁₁H₇ClFN₃O₂
• mdl: MFCD11543868
• 分子量: 267.647
• InChiKey: ARTWMBCBLVTPEX-UHFFFAOYSA-N

物化性质

• 沸点：
  361.9±42.0 °C(Predicted)
• 密度：
  1.514±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-chloro-N-(4-fluorophenyl)-3-nitropyridin-2-amine 在 氢气 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 乙酸乙酯 为溶剂， 生成 5-chloro-3-(4-fluorophenyl)-3H-[1,2,3]triazolo[4,5-b]pyridine
  参考文献：
  名称：

  Hit to lead evaluation of 1,2,3-triazolo[4,5-b]pyridines as PIM kinase inhibitors

  摘要：

  PIM kinases have become targets of interest due to their association with biochemical mechanisms affecting survival, proliferation and cytokine production. 1,2,3-Triazolo[4,5-b]pyridines were identified as PIM inhibitors applying a scaffold hopping approach. Initial exploration around this scaffold and X-ray crystallographic data are hereby described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.130
• 作为产物：
  描述：

  2,6-二氯-3-硝基吡啶 、 4-氟苯胺 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以50%的产率得到6-chloro-N-(4-fluorophenyl)-3-nitropyridin-2-amine
  参考文献：
  名称：

  Design and synthesis of diarylamines and diarylethers as cytotoxic antitumor agents

  摘要：

  Based on a shared structural core of diarylamine in several known anticancer drugs as well as a new cytotoxic hit 6-chloro-2-(4-cyanophenyl)amino-3-nitropyridine (7), 30 diarylamines and diarylethers were designed, synthesized, and evaluated for cytotoxic activity against A549, KB, KB-vin, and DU145 human tumor cell lines (HTCL). Four new leads 11e, 12, 13a, and 13b were discovered with GI(50) values ranging from 0.33 to 3.45 mu M. Preliminary SAR results revealed that a diarylamine or diarylether could serve as an active structural core, meta-chloro and ortho-nitro groups on the A-ring (either pyridine or phenyl ring) were necessary and crucial for cytotoxic activity, and the para-substituents on the other phenyl ring (B-ring) were related to inhibitory selectivity for different tumor cells. In an investigation of potential biological targets of the new leads, high thoughput kinase screening discovered that new leads 11e, 12 and 13b especially inhibit Mer tyrosine kinase, a proto-oncogene associated with munerous tumor types, with IC50 values of 2.2-3.0 mu M. Therefore, these findings provide a good starting point to optimize a new class of compounds as potential anticancer agents, particularly targeting Mer tyrosine kinase. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.014

文献信息

• CYTOKINE INHIBITORS
  申请人：Boman Erik

  公开号：US20100093734A1

  公开（公告）日：2010-04-15

  The present invention provides low molecular weight compounds useful as cytokine inhibitors, and compositions thereof. In particular, compounds of the invention are useful as anti-inflammatory agents. There are further provided methods for the preparation of such agents and their use in preventing or treating conditions mediated by cytokines such as arthritis.

  本发明提供了低分子量化合物，可用作细胞因子抑制剂及其组合物。特别是，本发明的化合物可用作抗炎剂。还提供了制备这种药剂的方法，以及其在预防或治疗由细胞因子介导的疾病，如关节炎方面的用途。
• US7919617B2
  申请人：——

  公开号：US7919617B2

  公开（公告）日：2011-04-05
• Design and synthesis of diarylamines and diarylethers as cytotoxic antitumor agents
  作者：Xiao-Feng Wang、Xing-Tao Tian、Emika Ohkoshi、Bingjie Qin、Yi-Nan Liu、Pei-Chi Wu、Mann-Jen Hour、Hsin-Yi Hung、Keduo Qian、Rong Huang、Kenneth F. Bastow、William P. Janzen、Jian Jin、Susan L. Morris-Natschke、Kuo-Hsiung Lee、Lan Xie

  DOI：10.1016/j.bmcl.2012.08.014

  日期：2012.10

  Based on a shared structural core of diarylamine in several known anticancer drugs as well as a new cytotoxic hit 6-chloro-2-(4-cyanophenyl)amino-3-nitropyridine (7), 30 diarylamines and diarylethers were designed, synthesized, and evaluated for cytotoxic activity against A549, KB, KB-vin, and DU145 human tumor cell lines (HTCL). Four new leads 11e, 12, 13a, and 13b were discovered with GI(50) values ranging from 0.33 to 3.45 mu M. Preliminary SAR results revealed that a diarylamine or diarylether could serve as an active structural core, meta-chloro and ortho-nitro groups on the A-ring (either pyridine or phenyl ring) were necessary and crucial for cytotoxic activity, and the para-substituents on the other phenyl ring (B-ring) were related to inhibitory selectivity for different tumor cells. In an investigation of potential biological targets of the new leads, high thoughput kinase screening discovered that new leads 11e, 12 and 13b especially inhibit Mer tyrosine kinase, a proto-oncogene associated with munerous tumor types, with IC50 values of 2.2-3.0 mu M. Therefore, these findings provide a good starting point to optimize a new class of compounds as potential anticancer agents, particularly targeting Mer tyrosine kinase. (C) 2012 Elsevier Ltd. All rights reserved.
• Hit to lead evaluation of 1,2,3-triazolo[4,5-b]pyridines as PIM kinase inhibitors
  作者：Joaquín Pastor、Julen Oyarzabal、Gustavo Saluste、Rosa María Alvarez、Virginia Rivero、Francisco Ramos、Elena Cendón、Carmen Blanco-Aparicio、Nuria Ajenjo、Antonio Cebriá、M.I. Albarrán、David Cebrián、Ana Corrionero、Jesús Fominaya、Guillermo Montoya、Marco Mazzorana

  DOI：10.1016/j.bmcl.2011.12.130

  日期：2012.2

  PIM kinases have become targets of interest due to their association with biochemical mechanisms affecting survival, proliferation and cytokine production. 1,2,3-Triazolo[4,5-b]pyridines were identified as PIM inhibitors applying a scaffold hopping approach. Initial exploration around this scaffold and X-ray crystallographic data are hereby described. (C) 2012 Elsevier Ltd. All rights reserved.