4-amino-2-n-butylthieno[3,2-d]pyrimidine | 200292-44-0

• 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: 4-amino-2-n-butylthieno[3,2-d]pyrimidine
• 英文别名: 2-Butylthieno[3,2-d]pyrimidin-4-amine
• CAS: 200292-44-0
• 化学式: C₁₀H₁₃N₃S
• 分子量: 207.299
• InChiKey: LVGXPQBLAXQDDW-UHFFFAOYSA-N

物化性质

• 沸点：
  297.8±22.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  80
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 4-amino-2-n-butylthieno[3,2-d]pyrimidine 在 正丁基锂 作用下， 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 ammonium hydroxide 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 5.83h， 生成 4-amino-2-n-butylthieno[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

• AMIDE DERIVATIVES
  申请人：OTSUKA PHARMACEUTICAL FACTORY, INC.

  公开号：EP0915093A1

  公开（公告）日：1999-05-12

  The invention provides amide derivatives which are useful as analgesics, anti-inflammatory agents, antimicrobial drugs, hypoglycemic agents, hypolipidemic agents, antihypertensive agents, anti-cancer agents, etc., the derivatives being represented by the formula wherein ring A represents a benzene ring, a naphthalene ring, a pyridine ring or a furan ring; R4 represents a heterocyclic group selected from the group consisting of a lower alkyl-substituted thieno[3,2-d]pyrimidin-4-yl group, an optionally substituted pyrazolo[1,5-a]-1,3,5-triazin-4-yl group, a pyrazolo[3,4-d]pyrimidin-4-yl group substituted at the 6-position and a purin-6-yl group substituted at the 2-position; and R5 represents a hydrogen atom or a group represented by

  本发明提供了可用作镇痛药、消炎药、抗菌药、降血糖药、降血脂药、降血压药、抗癌药等的酰胺衍生物，这些衍生物由式表示 其中环 A 代表苯环、萘环、吡啶环或呋喃环；R4 代表杂环基团，该杂环基团选自由低级烷基取代的噻吩并[3,2-d]嘧啶-4-基、任选取代的吡唑并[1,5-a]-1,3,5-三嗪-4-基、在 6 位取代的吡唑并[3,4-d]嘧啶-4-基和在 2 位取代的嘌呤-6-基组成的基团；以及 R5 代表氢原子或由以下各项代表的基团
• US6166016A
  申请人：——

  公开号：US6166016A

  公开（公告）日：2000-12-26
• 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.