2-Butyl-4-chlorothieno[3,2-d]pyrimidine | 200292-45-1

• 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-Butyl-4-chlorothieno[3,2-d]pyrimidine
• CAS: 200292-45-1
• 化学式: C₁₀H₁₁ClN₂S
• 分子量: 226.73
• InChiKey: DORDTSNQRWSRFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Butyl-4-chlorothieno[3,2-d]pyrimidine 在 ammonium hydroxide 、 正丁基锂 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 N-(2-butylthieno[3,2-d]pyrimidin-4-yl)benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Activities of New Thieno[3,2-d]pyrimidines as Selective Type 4 Phosphodiesterase Inhibitors

  摘要：

  A common pharmacophore for compounds structurally related to nitraquazone has been derived. Using this pharmacophore, new structures have been designed, synthesized, and evaluated for their inhibitory potencies against cyclic adenosine 5'-monophosphate (cAMP) specific phosphodiesterase (PDE 4). From these compounds, 4-benzylamino-2-butylthieno[3,2-d]-pyrimidine (4) was selected for optimization. The effects of changes to the lipophilic groups and the amino linkage on the PDE 4 activity have been investigated. As a result, some potent PDE 4 inhibitors, selective with respect to PDE 3, have been identified. A selected group of compounds have been further evaluated for their ability to displace [H-3]rolipram from its binding site and also to potentiate isoprenaline-induced cAMP accumulation in isolated guinea pig eosinophils. Of these, 2-butyl-4-cyclohexylaminothieno[3,2-d]pyrimidine (33) has an interesting profile, with an important improvement in PDE 4/[H-3]rolipram ratio with respect to reference drugs, and good activity in cAMP potentiation, consistent with efficient cell penetration.

  DOI：

  10.1021/jm981012m
• 作为产物：
  描述：

  戊酸酐 在 sodium hydroxide 、 三氯氧磷 作用下， 反应 1.83h， 生成 2-Butyl-4-chlorothieno[3,2-d]pyrimidine
  参考文献：
  名称：

  Design, Synthesis, and Biological Activities of New Thieno[3,2-d]pyrimidines as Selective Type 4 Phosphodiesterase Inhibitors

  摘要：

  A common pharmacophore for compounds structurally related to nitraquazone has been derived. Using this pharmacophore, new structures have been designed, synthesized, and evaluated for their inhibitory potencies against cyclic adenosine 5'-monophosphate (cAMP) specific phosphodiesterase (PDE 4). From these compounds, 4-benzylamino-2-butylthieno[3,2-d]-pyrimidine (4) was selected for optimization. The effects of changes to the lipophilic groups and the amino linkage on the PDE 4 activity have been investigated. As a result, some potent PDE 4 inhibitors, selective with respect to PDE 3, have been identified. A selected group of compounds have been further evaluated for their ability to displace [H-3]rolipram from its binding site and also to potentiate isoprenaline-induced cAMP accumulation in isolated guinea pig eosinophils. Of these, 2-butyl-4-cyclohexylaminothieno[3,2-d]pyrimidine (33) has an interesting profile, with an important improvement in PDE 4/[H-3]rolipram ratio with respect to reference drugs, and good activity in cAMP potentiation, consistent with efficient cell penetration.

  DOI：

  10.1021/jm981012m

文献信息

• Microwave-assisted synthesis of potent PDE7 inhibitors containing a thienopyrimidin-4-amine scaffold
  作者：Ana I. Sánchez、Ricardo Meneses、José M. Mínguez、Araceli Núñez、Rafael R. Castillo、Fabiana Filace、Carolina Burgos、Juan J. Vaquero、Julio Álvarez-Builla、Alvaro Cortés-Cabrera、Federico Gago、Emma Terricabras、Víctor Segarra

  DOI：10.1039/c4ob00175c

  日期：——

  Thienopyrimidin-4-amines have been synthesized, evaluated and modelled as phosphodiesterase inhibitors.

  噻唑嘧啶-4-胺已被合成、评估并建模为磷酸二酯酶抑制剂。
• Design, Synthesis, and Biological Activities of New Thieno[3,2-<i>d</i>]pyrimidines as Selective Type 4 Phosphodiesterase Inhibitors
  作者：María I. Crespo、Lluís Pagès、Armando Vega、Victor Segarra、Manel López、Teresa Doménech、Montserrat Miralpeix、Jordi Beleta、Hamish Ryder、José M. Palacios

  DOI：10.1021/jm981012m

  日期：1998.10.1

  A common pharmacophore for compounds structurally related to nitraquazone has been derived. Using this pharmacophore, new structures have been designed, synthesized, and evaluated for their inhibitory potencies against cyclic adenosine 5'-monophosphate (cAMP) specific phosphodiesterase (PDE 4). From these compounds, 4-benzylamino-2-butylthieno[3,2-d]-pyrimidine (4) was selected for optimization. The effects of changes to the lipophilic groups and the amino linkage on the PDE 4 activity have been investigated. As a result, some potent PDE 4 inhibitors, selective with respect to PDE 3, have been identified. A selected group of compounds have been further evaluated for their ability to displace [H-3]rolipram from its binding site and also to potentiate isoprenaline-induced cAMP accumulation in isolated guinea pig eosinophils. Of these, 2-butyl-4-cyclohexylaminothieno[3,2-d]pyrimidine (33) has an interesting profile, with an important improvement in PDE 4/[H-3]rolipram ratio with respect to reference drugs, and good activity in cAMP potentiation, consistent with efficient cell penetration.