2-[(2-chloro-4-nitrophenyl)thio]pyridine | 524955-87-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(2-chloro-4-nitrophenyl)thio]pyridine
• 英文别名: 2-(2-chloro-4-nitrophenyl)sulfanylpyridine
• CAS: 524955-87-1
• 化学式: C₁₁H₇ClN₂O₂S
• mdl: MFCD04211759
• 分子量: 266.708
• InChiKey: XLOWLZLIGWLAPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 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：
  84
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(2-chloro-4-nitrophenyl)thio]pyridine 在 铁粉 、 氯化铵 作用下， 以 甲醇 为溶剂， 生成 3-Chloro-4-(pyridin-2-ylsulfanyl)aniline
  参考文献：
  名称：

  Synthesis and evaluation of 4-Anilino-6,7-dialkoxy-3-quinolinecarbonitriles as inhibitors of kinases of the Ras-MAPK signaling cascade

  摘要：

  4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)]anilino-6,7-diethoxy-3- quinolinecarbonitrile (3) was identified as a MEK1 kinase inhibitor with exceptional activity against LoVo cells. The structure-activity relationships of the C-4 aniline substituents were explored, and water-solubilizing groups were added at the C-7 position to improve physical properties. Secondary cellular assays revealed that a compound possessing the appropriate aniline substituents inhibited MEK1 as well as MAPK phosphorylation, thereby acting as a dual inhibitor of the Ras-MAPK signaling cascade. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00640-1
• 作为产物：
  描述：

  2-巯基吡啶 、 3-氯-4-氟硝基苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以76%的产率得到2-[(2-chloro-4-nitrophenyl)thio]pyridine
  参考文献：
  名称：

  Modulation of cAMP-Specific PDE without Emetogenic Activity: New Sulfide-Like PDE7 Inhibitors

  摘要：

  A forward chemical genetic approach was followed to discover new targets and lead compounds for Parkinson's disease (PD) treatment. By analysis of the cell protection produced by some small molecules, a diphenyl sulfide compound was revealed to be a new phosphodiesterase 7 (PDE7) inhibitor and identified as a new hit. This result allows us to confirm the utility of PDE7 inhibitors as a potential pharmacological treatment of PD. On the basis of these data, a diverse family of diphenyl sulfides has been developed and pharmacologically evaluated in the present work. Moreover, to gain insight into the safety of PDE7 inhibitors for human chronic treatment, we evaluated the new compounds in a surrogate emesis model, showing nonemetic effects.

  DOI：

  10.1021/jm501090m

文献信息

• Quinazoline derivatives as antitumor agents
  申请人：Hennequin Francois Andre Laurent

  公开号：US20050043336A1

  公开（公告）日：2005-02-24

  The invention concerns quinazoline derivatives of Formula (I); wherein each of Q 1 , Q 2 , Z, R 1 , R 2 , R 3 , and m have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the prevention or treatment of tumours which are sensitive to inhibition of erbB receptor tyrosin kinases.

  该发明涉及公式（I）的喹唑啉衍生物；其中Q1，Q2，Z，R1，R2，R3和m的每个定义在说明中具有任何意义；它们的制备过程，包含它们的制药组合物以及它们在制造对erbB受体酪氨酸激酶抑制敏感的肿瘤的预防或治疗药物中的使用。
• QUNAZOLINE DERIVATIVES AS ANTITUMOR AGENTS
  申请人：AstraZeneca AB

  公开号：EP1444210A1

  公开（公告）日：2004-08-11
• [EN] QUINAZOLINE DERIVATIVES AS ANTITUMOR AGENTS<br/>[FR] DERIVES QUINAZOLINE UTILISES EN TANT QU'AGENTS ANTITUMORAUX
  申请人：ASTRAZENECA AB

  公开号：WO2003040108A1

  公开（公告）日：2003-05-15

  The invention concerns quinazoline derivatives of Formula (I); wherein each of Q?1, Z, R1 and Q2¿ have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the prevention or treatment of tumours which are sensitive to inhibition of erbB receptor tyrosine kinases.
• Synthesis and evaluation of 4-Anilino-6,7-dialkoxy-3-quinolinecarbonitriles as inhibitors of kinases of the Ras-MAPK signaling cascade
  作者：Dan Berger、Minu Dutia、Dennis Powell、Biqi Wu、Allan Wissner、Diane H. Boschelli、M.Brawner Floyd、Nan Zhang、Nancy Torres、Jeremy Levin、Xuemei Du、Donald Wojciechowicz、Carolyn Discafani、Constance Kohler、Steven C. Kim、Larry R. Feldberg、Karen Collins、Robert Mallon

  DOI：10.1016/s0960-894x(03)00640-1

  日期：2003.9

  4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)]anilino-6,7-diethoxy-3- quinolinecarbonitrile (3) was identified as a MEK1 kinase inhibitor with exceptional activity against LoVo cells. The structure-activity relationships of the C-4 aniline substituents were explored, and water-solubilizing groups were added at the C-7 position to improve physical properties. Secondary cellular assays revealed that a compound possessing the appropriate aniline substituents inhibited MEK1 as well as MAPK phosphorylation, thereby acting as a dual inhibitor of the Ras-MAPK signaling cascade. (C) 2003 Elsevier Ltd. All rights reserved.
• Modulation of cAMP-Specific PDE without Emetogenic Activity: New Sulfide-Like PDE7 Inhibitors
  作者：Ana M. García、José Brea、Jose A. Morales-García、Daniel I. Perez、Alejandro González、Sandra Alonso-Gil、Irene Gracia-Rubio、Clara Ros-Simó、Santiago Conde、María Isabel Cadavid、María Isabel Loza、Ana Perez-Castillo、Olga Valverde、Ana Martinez、Carmen Gil

  DOI：10.1021/jm501090m

  日期：2014.10.23

  A forward chemical genetic approach was followed to discover new targets and lead compounds for Parkinson's disease (PD) treatment. By analysis of the cell protection produced by some small molecules, a diphenyl sulfide compound was revealed to be a new phosphodiesterase 7 (PDE7) inhibitor and identified as a new hit. This result allows us to confirm the utility of PDE7 inhibitors as a potential pharmacological treatment of PD. On the basis of these data, a diverse family of diphenyl sulfides has been developed and pharmacologically evaluated in the present work. Moreover, to gain insight into the safety of PDE7 inhibitors for human chronic treatment, we evaluated the new compounds in a surrogate emesis model, showing nonemetic effects.