3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-1,2,3,7-tetrahydro-6H-purin-6-one | 488705-95-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-1,2,3,7-tetrahydro-6H-purin-6-one
• 英文别名: 3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-2,7-dihydropurin-6-one
• CAS: 488705-95-9
• 化学式: C₁₄H₁₄Cl₂N₄O
• 分子量: 325.197
• InChiKey: VYBBRSAHJFIVBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  200-201 °C
• 沸点：
  600.3±55.0 °C(Predicted)
• 密度：
  1.430±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-戊醇 、 3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-1,2,3,7-tetrahydro-6H-purin-6-one 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-7-(2-pentyl)-1,2,3,7-tetrahydro-6H-purin-6-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of 1,2,3,7-Tetrahydro-6H-purin-6-one and 3,7-Dihydro-1H-purine-2,6-dione Derivatives as Corticotropin-Releasing Factor₁ Receptor Antagonists

  摘要：

  A growing body of evidence suggests that CRF1, receptor antagonism offers considerable therapeutic potential in the treatment of diseases resulting from elevated levels of CRF, such as anxiety and depression. A series of novel 1,2,3,7-tetrahydro-6H-purin-6-one and 3,7-dihydro-1H-purine-2,6-dione derivatives was synthesized and evaluated as corticotropin releasing factor-1 (CRF1) receptor antagonists. Compounds within this series, represented by compound 12d (IC50 = 5.4 nM), were found to be highly potent CRF, receptor antagonists. In addition, compounds 12d and 12j were determined to be selective CRF, antagonists. The synthesis, structure-activity relationships and pharmacokinetic properties of compounds within this series is presented.

  DOI：

  10.1021/jm049787k
• 作为产物：
  描述：

  2,4-二氯苯基异氰酸酯 在 ammonium hydroxide 、 sodium hydroxide 、 sodium dithionite 、 乙酸酐 、 四丁基碘化铵 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 三氟乙酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.66h， 生成 3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-1,2,3,7-tetrahydro-6H-purin-6-one
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of 1,2,3,7-Tetrahydro-6H-purin-6-one and 3,7-Dihydro-1H-purine-2,6-dione Derivatives as Corticotropin-Releasing Factor₁ Receptor Antagonists

  摘要：

  A growing body of evidence suggests that CRF1, receptor antagonism offers considerable therapeutic potential in the treatment of diseases resulting from elevated levels of CRF, such as anxiety and depression. A series of novel 1,2,3,7-tetrahydro-6H-purin-6-one and 3,7-dihydro-1H-purine-2,6-dione derivatives was synthesized and evaluated as corticotropin releasing factor-1 (CRF1) receptor antagonists. Compounds within this series, represented by compound 12d (IC50 = 5.4 nM), were found to be highly potent CRF, receptor antagonists. In addition, compounds 12d and 12j were determined to be selective CRF, antagonists. The synthesis, structure-activity relationships and pharmacokinetic properties of compounds within this series is presented.

  DOI：

  10.1021/jm049787k

文献信息

• Tetrahydropurinones and derivatives thereof as corticotropin releasing factor receptor ligands
  申请人：——

  公开号：US20030149059A1

  公开（公告）日：2003-08-07

  Compounds provided herein are novel substituted tetrahydropurinones of Formula (I): 1 Such compounds are particularly useful as CRF receptor ligands, and hence, in the treatment of various neurologically-related disorders such as affective disorder, anxiety and depression.

  本文提供的化合物是具有式(I)的新型取代四氢嘌呤酮。这些化合物特别适用作为CRF受体配体，因此在治疗各种神经相关疾病，如情感障碍、焦虑和抑郁症方面具有重要作用。
• US6894045B2
  申请人：——

  公开号：US6894045B2

  公开（公告）日：2005-05-17
• Design, Synthesis, and Biological Evaluation of 1,2,3,7-Tetrahydro-6<i>H</i>-purin-6-one and 3,7-Dihydro-1<i>H</i>-purine-2,6-dione Derivatives as Corticotropin-Releasing Factor₁ Receptor Antagonists
  作者：Richard A. Hartz、Kausik K. Nanda、Charles L. Ingalls、Vijay T. Ahuja、Thaddeus F. Molski、Ge Zhang、Harvey Wong、Yong Peng、Michelle Kelley、Nicholas J. Lodge、Robert Zaczek、Paul J. Gilligan、George L. Trainor

  DOI：10.1021/jm049787k

  日期：2004.9.1

  A growing body of evidence suggests that CRF1, receptor antagonism offers considerable therapeutic potential in the treatment of diseases resulting from elevated levels of CRF, such as anxiety and depression. A series of novel 1,2,3,7-tetrahydro-6H-purin-6-one and 3,7-dihydro-1H-purine-2,6-dione derivatives was synthesized and evaluated as corticotropin releasing factor-1 (CRF1) receptor antagonists. Compounds within this series, represented by compound 12d (IC50 = 5.4 nM), were found to be highly potent CRF, receptor antagonists. In addition, compounds 12d and 12j were determined to be selective CRF, antagonists. The synthesis, structure-activity relationships and pharmacokinetic properties of compounds within this series is presented.