4-chloro-2-phenylthieno[2,3-c]pyridine | 1009104-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: 4-chloro-2-phenylthieno[2,3-c]pyridine
• CAS: 1009104-25-9
• 化学式: C₁₃H₈ClNS
• 分子量: 245.732
• InChiKey: ZNBJNMIUMQBIRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-2-phenylthieno[2,3-c]pyridine 、 2-(三丁基锡烷基)呋喃 在 tris(dibenzylideneacetone)dipalladium (0) 三乙胺 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以85%的产率得到4-furan-2-yl-2-phenylthieno[2,3-c]pyridine
  参考文献：
  名称：

  A facile and general synthesis of 2,4‐Di‐ and 2,4,7‐trisubstituted thieno[2,3‐c]pyridines

  摘要：

  Abstractmagnified imageTreatment of 3,5‐dibromo‐ or 3,5‐dichloro‐pyridine‐4‐carboxaldehyde 2 with one equivalent of methyl thioglycolate, followed by exposure to base, provided 4‐bromo‐ or 4‐chloro‐thieno[2,3‐c]pyridine‐2‐carboxylate 4 in good yields. Oxidation of the thieno[2,3‐c]pyridine scaffold such as 7 with mCPBA, followed by treatment with POBr3, introduced a bromine exclusively at the 7‐position of the heterocycle. The 4‐ or 7‐bromide of the thienopyridines readily underwent Suzuki, Stille coupling, and Buchwald amination reactions, to afford 4‐ or 7‐substituted analogs 6 or 11. The 2‐carboxylate of 4b or 12 was smoothly removed through saponification and decarboxylation to furnish 15 or 16. Deprotonation of the thienopyridine at C‐2 position, followed by trapping with trimethyltin chloride, afforded a 2‐stannyl analog, which was readily converted to other C‐2 derivatives via Stille reaction.

  DOI：

  10.1002/jhet.5570450106
• 作为产物：
  描述：

  4-chlorothieno[3,2-d]pyridine 、 溴苯 在 tris(dibenzylideneacetone)dipalladium (0) 正丁基锂 、 三甲基氯化锡 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以530 mg的产率得到4-chloro-2-phenylthieno[2,3-c]pyridine
  参考文献：
  名称：

  A facile and general synthesis of 2,4‐Di‐ and 2,4,7‐trisubstituted thieno[2,3‐c]pyridines

  摘要：

  Abstractmagnified imageTreatment of 3,5‐dibromo‐ or 3,5‐dichloro‐pyridine‐4‐carboxaldehyde 2 with one equivalent of methyl thioglycolate, followed by exposure to base, provided 4‐bromo‐ or 4‐chloro‐thieno[2,3‐c]pyridine‐2‐carboxylate 4 in good yields. Oxidation of the thieno[2,3‐c]pyridine scaffold such as 7 with mCPBA, followed by treatment with POBr3, introduced a bromine exclusively at the 7‐position of the heterocycle. The 4‐ or 7‐bromide of the thienopyridines readily underwent Suzuki, Stille coupling, and Buchwald amination reactions, to afford 4‐ or 7‐substituted analogs 6 or 11. The 2‐carboxylate of 4b or 12 was smoothly removed through saponification and decarboxylation to furnish 15 or 16. Deprotonation of the thienopyridine at C‐2 position, followed by trapping with trimethyltin chloride, afforded a 2‐stannyl analog, which was readily converted to other C‐2 derivatives via Stille reaction.

  DOI：

  10.1002/jhet.5570450106

文献信息

• [EN] N-ARYL-THIENOPYRIMIDIN-4-AMINES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF<br/>[FR] N-ARYL-THIENOPYRIMIDIN-4-AMINES ET ANALOGUES EN TANT QU'ACTIVATEURS DE CASPASES ET INDUCTEURS D'APOPTOSE ET UTILISATION ASSOCIEE
  申请人：CYTOVIA INC

  公开号：WO2007056215A2

  公开（公告）日：2007-05-18

  (EN) Disclosed are N-aryl-thienopyrimidin-4-amines and analogs thereof, represented by the Formulae I-II: wherein Ar and R1-R4 are defined herein. The present invention relates to the discovery that compounds having Formulae I-II are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.(FR) L'invention concerne des N-aryl-thiénopyrimidin-4-amines et des analogues de celles-ci, représentés par les formules I et II, dans lesquelles Ar et R1-R4 sont tels que définis dans la description. La présente invention concerne également la découverte que les composés représentés par les formule I et II sont des activateurs de caspases et des inducteurs d'apoptose. Par conséquent, les activateurs de caspases et inducteurs d'apoptose de l'invention peuvent être utilisés afin d'induire la mort cellulaire dans divers états cliniques dans lesquels apparaissent une croissance et une propagation incontrôlées de cellules anormales.
• [EN] N-ALKYL-N-ARYL-THIENOPYRIMIDIN-4-AMINES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF<br/>[FR] N-ALKYL-N-ARYL-THIENOPYRIMIDIN-4-AMINES ET ANALOGUES EN TANT QU'ACTIVATEURS DE CASPASES ET INDUCTEURS D'APOPTOSE ET UTILISATION ASSOCIEE
  申请人：CYTOVIA INC

  公开号：WO2007056214A2

  公开（公告）日：2007-05-18

  (EN) Disclosed are N-alkyl-N-aryl-thienopyrimidin-4-amines and analogs thereof, represented by the Formulae I-II: wherein Ar, R1 -R4 and R10 are defined herein. The present invention relates to the discovery that compounds having Formulae I- II are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.(FR) L'invention concerne des N-alkyl-N-aryl-thiénopyrimidin-4-amines et des analogues de celles-ci, représentés par les formules I et II, dans lesquelles Ar, R1 -R4 et R10 sont tels que définis dans la description. La présente invention concerne la découverte que les composés représentés par les formules I et II sont des activateurs de caspases et des inducteurs d'apoptose. Par conséquent, les activateurs de caspases et inducteurs d'apoptose de l'invention peuvent être utilisés afin d'induire la mort cellulaire dans divers états cliniques dans lesquels apparaissent une croissance et une propagation incontrôlées de cellules anormales.
• A facile and general synthesis of 2,4‐Di‐ and 2,4,7‐trisubstituted thieno[2,3‐<i>c</i>]pyridines
  作者：Gui‐Dong Zhu、Indrani W. Gunawardana、Steven A. Boyd、Laura M. Melcher

  DOI：10.1002/jhet.5570450106

  日期：2008.1

  Abstractmagnified imageTreatment of 3,5‐dibromo‐ or 3,5‐dichloro‐pyridine‐4‐carboxaldehyde 2 with one equivalent of methyl thioglycolate, followed by exposure to base, provided 4‐bromo‐ or 4‐chloro‐thieno[2,3‐c]pyridine‐2‐carboxylate 4 in good yields. Oxidation of the thieno[2,3‐c]pyridine scaffold such as 7 with mCPBA, followed by treatment with POBr3, introduced a bromine exclusively at the 7‐position of the heterocycle. The 4‐ or 7‐bromide of the thienopyridines readily underwent Suzuki, Stille coupling, and Buchwald amination reactions, to afford 4‐ or 7‐substituted analogs 6 or 11. The 2‐carboxylate of 4b or 12 was smoothly removed through saponification and decarboxylation to furnish 15 or 16. Deprotonation of the thienopyridine at C‐2 position, followed by trapping with trimethyltin chloride, afforded a 2‐stannyl analog, which was readily converted to other C‐2 derivatives via Stille reaction.