N-(4-Chlorobenzyl)-7-[2-(diethylamino)ethyl]-2-(3-hydroxy-1-propynyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide | 292144-30-0

• 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: N-(4-Chlorobenzyl)-7-[2-(diethylamino)ethyl]-2-(3-hydroxy-1-propynyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide
• 英文别名: N-[(4-chlorophenyl)methyl]-7-(2-diethylaminoethyl)-2-(3-hydroxyprop-1-ynyl)-4-oxo-thieno[2,3-b]pyridine-5-carboxamide；N-[(4-chlorophenyl)methyl]-7-[2-(diethylamino)ethyl]-2-(3-hydroxyprop-1-ynyl)-4-oxothieno[2,3-b]pyridine-5-carboxamide
• CAS: 292144-30-0
• 化学式: C₂₄H₂₆ClN₃O₃S
• 分子量: 472.008
• InChiKey: OPBJVFBXYFEREU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-Chlorobenzyl)-7-[2-(diethylamino)ethyl]-2-(3-hydroxy-1-propynyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到N-(4-chlorobenzyl)-7-[2-(diethylamino)ethyl]-2-(3-hydroxypropyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide
  参考文献：
  名称：

  4-Oxo-4,7-dihydrothieno[2,3-b]pyridines as Non-Nucleoside Inhibitors of Human Cytomegalovirus and Related Herpesvirus Polymerases

  摘要：

  A novel series of 4-oxo-4,7-dihydrothieno[2,3-blpyridine-5-carboxamides have been identified as potential antivirals against human herpesvirus infections resulting from human cytomegalovirus (HCMV), herpes simplex virus type 1 (HSV-1), and varicella-zoster virus (VZV). Compounds 10c and 14 demonstrated broad-spectrum inhibition of the herpesvirus polymerases HCMV, HSV-1, and VZV. High specificity for the viral polymerases was observed compared to human alpha polyinerase. The antiviral activity of 10c and 14, as determined by plaque reduction assay, was comparable or superior to that of existing antiherpes drugs, ganciclovir (for HCMV) and acyclovir (for HSV-1 and VZV). Drug resistance to compound 14 correlated to point mutations in conserved domain III of the herpesvirus DNA polymerase, but these mutations do not confer resistance to existing nucleoside therapy. In addition, compound 14 maintained potent antiviral activity against acyclovir-resistant HSV-1 strains. Substitution to the pyridone nitrogen (N7) was found to be critical for enhanced in vitro antiviral activity.

  DOI：

  10.1021/jm050162b
• 作为产物：
  描述：

  4-羟基噻吩并[3,2-B]吡啶-5-甲酸乙酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium acetate 、 一氯化碘 、 potassium carbonate 、 二乙胺 作用下， 以 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 92.0h， 生成 N-(4-Chlorobenzyl)-7-[2-(diethylamino)ethyl]-2-(3-hydroxy-1-propynyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide
  参考文献：
  名称：

  4-Oxo-4,7-dihydrothieno[2,3-b]pyridines as Non-Nucleoside Inhibitors of Human Cytomegalovirus and Related Herpesvirus Polymerases

  摘要：

  A novel series of 4-oxo-4,7-dihydrothieno[2,3-blpyridine-5-carboxamides have been identified as potential antivirals against human herpesvirus infections resulting from human cytomegalovirus (HCMV), herpes simplex virus type 1 (HSV-1), and varicella-zoster virus (VZV). Compounds 10c and 14 demonstrated broad-spectrum inhibition of the herpesvirus polymerases HCMV, HSV-1, and VZV. High specificity for the viral polymerases was observed compared to human alpha polyinerase. The antiviral activity of 10c and 14, as determined by plaque reduction assay, was comparable or superior to that of existing antiherpes drugs, ganciclovir (for HCMV) and acyclovir (for HSV-1 and VZV). Drug resistance to compound 14 correlated to point mutations in conserved domain III of the herpesvirus DNA polymerase, but these mutations do not confer resistance to existing nucleoside therapy. In addition, compound 14 maintained potent antiviral activity against acyclovir-resistant HSV-1 strains. Substitution to the pyridone nitrogen (N7) was found to be critical for enhanced in vitro antiviral activity.

  DOI：

  10.1021/jm050162b

文献信息

• 4-OXO-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxamides as antiviral agents
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：US20020006937A1

  公开（公告）日：2002-01-17

  The invention provides a compound of formula I: 1 wherein R 1 , R 2 , R 3 , and R 4 have any of the values defined in the specification, or a pharmaceutically acceptable salt thereof, as well as processes and intermediates useful for preparing such compounds or salts, and methods of preventing or treating a herpesvirus infection using such compounds or salts.

  本发明提供了化合物I的公式：1其中R1，R2，R3和R4具有规范中定义的任何值，或其药学上可接受的盐，以及用于制备这些化合物或盐的有用中间体和方法，以及使用这些化合物或盐预防或治疗疱疹病毒感染的方法。
• Method of preventing or treating atherosclerosis or restenosis
  申请人：——

  公开号：US20040102473A1

  公开（公告）日：2004-05-27

  The present invention provides a method of treating atherosclerosis or restenosis in a mammal which comprises administering to said mammal an effective amount of a compound selected from the group consisting of structures of Formulae I, I′ and II, 1 wherein the substituents on the Formulae are as defined herein.

  本发明提供了一种治疗哺乳动物动脉粥样硬化或再狭窄的方法，该方法包括向所述哺乳动物施用有效量的选自由式I、I′和II结构组成的组的化合物、 1 其中式中的取代基如本文所定义。
• 4-OXO-4,7-DIHYDRO-THIENO[2,3-B]PYRIDINE-5-CARBOXAMIDES AS ANTIVIRAL AGENTS
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1159279B1

  公开（公告）日：2002-10-16
• JP2002539130A
  申请人：——

  公开号：JP2002539130A

  公开（公告）日：2002-11-19
• US6239142B1
  申请人：——

  公开号：US6239142B1

  公开（公告）日：2001-05-29