2-mercapto-3-methylthieno[3,2-d]pyrimidin-4-(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 2-mercapto-3-methylthieno[3,2-d]pyrimidin-4-(3H)-one
• 英文别名: 2-mercapto-3-methylthieno[3,2-d]pyrimidin-4(3H)-one；3-methyl-2-sulfanylidene-1H-thieno[3,2-d]pyrimidin-4-one
• 化学式: C₇H₆N₂OS₂
• mdl: MFCD08444211
• 分子量: 198.269
• InChiKey: NUWPXBHTEMDQJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-mercapto-3-methylthieno[3,2-d]pyrimidin-4-(3H)-one 、 4-(4-chlorobenzoyl)benzyl bromide 在 sodium hydroxide 作用下， 以 ethanol (12 ml)-DMF 、 水 为溶剂， 生成 2-[4-(4-Chlorobenzoyl)benzyl]thio-3-methylthieno-[3,2-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Heterocyclic compounds, their production and use

  摘要：

  一种新的化合物，其化学式为：A--Z--Ar.sup.1 1'CO--Ar.sup.2，其中A是一个紧凑的嘧啶酮或紧凑的吡啶并酮环；Ar.sup.1和Ar.sup.2分别是一个环；Z是一个二价基团，或其盐，具有出色的抗肿瘤活性。

  公开号：

  US05753664A1
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 、 异硫氰酸甲酯 以 甲苯 为溶剂， 反应 120.0h， 以21%的产率得到2-mercapto-3-methylthieno[3,2-d]pyrimidin-4-(3H)-one
  参考文献：
  名称：

  CODES, a novel procedure for ligand-based virtual screening: PDE7 inhibitors as an application example

  摘要：

  Phosphodiesterase (PDE) 7 is a high affinity cAMP-specific PDE whose functional role in T-cells has been the subject of some controversy. Recent findings on tissue distribution, however, support the hypothesis that PDE7 could be a good target for the treatment of airway diseases, T-cell related diseases or central nervous system (CNS) disorders. Therefore, the identification of selective inhibitors targeted against PDE7 enzyme has become an attractive area of research. We report here the first use of the descriptors generated by the CODES program for ligand-based virtual screening. This program codifies molecules from a topological point of view and the generated descriptors are related to the chemical nature of the atoms, the atomic bonds and the connectivity with the rest of the molecule. They are also able to distinguish among stereoisomers. By using this approach, 173 compounds were codified, and their similarity with the reference compound was analysed. Based on the analysis, new potential PDE7 inhibitors have been identified, synthesized and biologically evaluated confirming that CODES descriptors are valid for ligand-based virtual screening and provided new lead compounds for further optimization as potent and selective PDE7 inhibitors. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.027

文献信息

• FUNGICIDAL PYRIMIDINONES
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0836602B1

  公开（公告）日：2002-01-30
• US5753664A
  申请人：——

  公开号：US5753664A

  公开（公告）日：1998-05-19
• US6872727B1
  申请人：——

  公开号：US6872727B1

  公开（公告）日：2005-03-29
• Heterocyclic compounds, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05753664A1

  公开（公告）日：1998-05-19

  A novel compound of the formula: A--Z--Ar.sup.1 1'CO--Ar.sup.2 wherein A is a condensed pyrimidinone or condensed pyridazinone ring; Ar.sup.1 and Ar.sup.2 are independently a ring; Z is a divalent group, or a salt thereof which have an excellent antitumor activity.

  一种新的化合物，其化学式为：A--Z--Ar.sup.1 1'CO--Ar.sup.2，其中A是一个紧凑的嘧啶酮或紧凑的吡啶并酮环；Ar.sup.1和Ar.sup.2分别是一个环；Z是一个二价基团，或其盐，具有出色的抗肿瘤活性。
• CODES, a novel procedure for ligand-based virtual screening: PDE7 inhibitors as an application example
  作者：Ana Castro、María José Jerez、Carmen Gil、Félix Calderón、Teresa Doménech、Arsenio Nueda、Ana Martínez

  DOI：10.1016/j.ejmech.2007.10.027

  日期：2008.7

  Phosphodiesterase (PDE) 7 is a high affinity cAMP-specific PDE whose functional role in T-cells has been the subject of some controversy. Recent findings on tissue distribution, however, support the hypothesis that PDE7 could be a good target for the treatment of airway diseases, T-cell related diseases or central nervous system (CNS) disorders. Therefore, the identification of selective inhibitors targeted against PDE7 enzyme has become an attractive area of research. We report here the first use of the descriptors generated by the CODES program for ligand-based virtual screening. This program codifies molecules from a topological point of view and the generated descriptors are related to the chemical nature of the atoms, the atomic bonds and the connectivity with the rest of the molecule. They are also able to distinguish among stereoisomers. By using this approach, 173 compounds were codified, and their similarity with the reference compound was analysed. Based on the analysis, new potential PDE7 inhibitors have been identified, synthesized and biologically evaluated confirming that CODES descriptors are valid for ligand-based virtual screening and provided new lead compounds for further optimization as potent and selective PDE7 inhibitors. (c) 2007 Elsevier Masson SAS. All rights reserved.