2-benzyl-1,9-dihydropurin-6-one | 18503-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-benzyl-1,9-dihydropurin-6-one
• 英文别名: 1,9-Dihydro-2-(phenylmethyl)-6H-purin-6-one；2-benzyl-1,7-dihydropurin-6-one
• CAS: 18503-17-8
• 化学式: C₁₂H₁₀N₄O
• 分子量: 226.238
• InChiKey: KNOYESMHZQNCOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyl-1,9-dihydropurin-6-one 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 为溶剂， 反应 1.3h， 以80%的产率得到2-benzyl-6-chloro-9H-purine
  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：

  4-氨基-5-咪唑甲酰胺盐酸盐 、 苯乙酸 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 生成 2-benzyl-1,9-dihydropurin-6-one
  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

• Method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK)
  申请人：CHEN Han-Min

  公开号：US20140303112A1

  公开（公告）日：2014-10-09

  The present invention relates to a method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK) and the use of the compounds in the prevention or treatment of disease, including pre-diabetes, type 2 diabetes, syndrome X, metabolic syndrome and obesity.

  本发明涉及一种治疗疾病或病情的方法，该疾病或病情容易通过AMPK激活剂和公式化合物得到改善，这些化合物有助于激活AMP激活蛋白激酶（AMPK），并将这些化合物用于预防或治疗疾病，包括糖尿病前期、2型糖尿病、X综合症、代谢综合征和肥胖症。
• US9938279B2
  申请人：——

  公开号：US9938279B2

  公开（公告）日：2018-04-10
• [EN] MGMT INHIBITOR COMBINATIONS FOR THE TREATMENT OF NEOPLASTIC DISORDERS<br/>[FR] COMBINAISONS D'INHIBITEURS DE MGMT POUR LE TRAITEMENT DE DÉSORDRES NÉOPLASIQUES
  申请人：UNIV CASE WESTERN RESERVE

  公开号：WO2008109417A1

  公开（公告）日：2008-09-12

  [EN] A method of treating a neoplastic disease in a subject includes administering to neoplastic cells of the subject an MGMT inhibitor and at least one of an antimitotic agent or a DNA damaging agent.
  [FR] La présente invention concerne un procédé de traitement d'une maladie néoplasique chez un sujet comprenant l'administration aux cellules néoplasiques du sujet d'un inhibiteur de MGMT et d'au moins un agent antimitotique ou d'un agent endommagent l'ADN.
• 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.