4-(N-benzyl-N-methylcarbamoylmethylamino)-2-phenylpyrimidine-5-carboxylic acid | 226954-93-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(N-benzyl-N-methylcarbamoylmethylamino)-2-phenylpyrimidine-5-carboxylic acid
• 英文别名: 4-[[2-[Benzyl(methyl)amino]-2-oxoethyl]amino]-2-phenylpyrimidine-5-carboxylic acid
• CAS: 226954-93-4
• 化学式: C₂₁H₂₀N₄O₃
• 分子量: 376.415
• InChiKey: NZBKHXPFNQVYPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(N-benzyl-N-methylcarbamoylmethylamino)-2-phenylpyrimidine-5-carboxylic acid 、 叠氮磷酸二苯酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以42%的产率得到N-benzyl-N-methyl-2-(8-oxo-2-phenyl-7,8-dihydro-9H-purin-9-yl)acetamide
  参考文献：
  名称：

  [18F]FEAC and [18F]FEDAC: Two novel positron emission tomography ligands for peripheral-type benzodiazepine receptor in the brain

  摘要：

  [F-18]FEAC ([F-18]4a) and [F-18]FEDAC ([F-18]4b) were developed as two novel positron emission tomography (PET) ligands for peripheral-type benzodiazepine receptor (PBR). [F-18]4a and [F-18]4b were synthesized by fluoroethylation of precursors 8a and 8b with [ 18F] FCH2CH2Br ([ 18F] 9), respectively. Small-animal PET scan for a neuroinflammatory rat model showed that the two radioligands had high uptakes of radioactivity in the kainic acid-infused striatum, a brain region where PBR density was increased. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.093
• 作为产物：
  描述：

  Ethyl 4-[[2-[benzyl(methyl)amino]-2-oxoethyl]amino]-2-phenylpyrimidine-5-carboxylate 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以83%的产率得到4-(N-benzyl-N-methylcarbamoylmethylamino)-2-phenylpyrimidine-5-carboxylic acid
  参考文献：
  名称：

  [18F]FEAC and [18F]FEDAC: Two novel positron emission tomography ligands for peripheral-type benzodiazepine receptor in the brain

  摘要：

  [F-18]FEAC ([F-18]4a) and [F-18]FEDAC ([F-18]4b) were developed as two novel positron emission tomography (PET) ligands for peripheral-type benzodiazepine receptor (PBR). [F-18]4a and [F-18]4b were synthesized by fluoroethylation of precursors 8a and 8b with [ 18F] FCH2CH2Br ([ 18F] 9), respectively. Small-animal PET scan for a neuroinflammatory rat model showed that the two radioligands had high uptakes of radioactivity in the kainic acid-infused striatum, a brain region where PBR density was increased. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.093

文献信息

• 2-ARYL-8-OXODIHYDROPURINE DERIVATIVES, PROCESS FOR PRODUCING THE SAME, MEDICINAL COMPOSITIONS CONTAINING THE SAME, AND INTERMEDIATES THEREOF
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP1036794A1

  公开（公告）日：2000-09-20

  2-Aryl-8-oxodihydropurine derivative of the following formula (I): wherein W is H, lower alkyl, halogen, lower alkoxy, amino, mono- or di-lower alkylamino, or substituted or unsubstituted phenyl; X is H, lower alkyl, cycloalkyl-lower alkyl, substituted or unsubstituted phenyl-lower alkyl, lower alkenyl, carbamoyl, di-lower alkylcarbamoyl, or a group of the formula (Q): -CH(R3)CON(R1)(R2); Y is H, lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, lower alkenyl, substituted or unsubstituted phenyl-lower alkyl, or a group of the formula (Q): -CH(R3)CON(R1)(R2); A is substituted or unsubstituted phenyl, or substituted or unsubstituted heteroaryl; provided that when one of X and Y of the above formula (I) is the group of the formula (Q), then the other is the same groups for X or Y as described above except for the group of the formula (Q), or a pharmaceutically acceptable acid addition salt thereof. These compounds are useful for the prophylaxis or treatment of central nervous disorders such as anxiety-related diseases (neurosis, somatoform disorders, anxiety disorders, and others), depression, epilepsy, etc., or circulatory organs disorders such as angina pectoris, hypertension.

  下式(I)的 2-芳基-8-氧二氢嘌呤衍生物： 其中 W 是 H、低级烷基、卤素、低级烷氧基、氨基、单或双低级烷基氨基或取代或未取代的苯基；X 是 H、低级烷基、环烷基-低级烷基、取代或未取代的苯基-低级烷基、低级烯基、氨基甲酰基、双低级烷基氨基甲酰基或式 (Q) 的基团：-CH(R3)CON(R1)(R2)； Y 是 H、低级烷基、环烷基、环烷基-低级烷基、低级烯基、取代或未取代的苯基-低级烷基或式 (Q) 的基团：-CH(R3)CON(R1)(R2)；A 是取代或未取代的苯基，或取代或未取代的杂芳基；条件是当上式（I）中的 X 和 Y 之一为式（Q）基团时，则另一个为除式（Q）基团以外的与上述 X 或 Y 相同的基团，或其药学上可接受的酸加成盐。这些化合物可用于预防或治疗中枢神经疾病，如焦虑相关疾病（神经官能症、躯体形式障碍、焦虑症等）、抑郁症、癫痫等，或循环器官疾病，如心绞痛、高血压等。
• US6372740B1
  申请人：——

  公开号：US6372740B1

  公开（公告）日：2002-04-16
• [18F]FEAC and [18F]FEDAC: Two novel positron emission tomography ligands for peripheral-type benzodiazepine receptor in the brain
  作者：Kazuhiko Yanamoto、Katsushi Kumata、Tomoteru Yamasaki、Chika Odawara、Kazunori Kawamura、Joji Yui、Akiko Hatori、Kazutoshi Suzuki、Ming-Rong Zhang

  DOI：10.1016/j.bmcl.2009.01.093

  日期：2009.3

  [F-18]FEAC ([F-18]4a) and [F-18]FEDAC ([F-18]4b) were developed as two novel positron emission tomography (PET) ligands for peripheral-type benzodiazepine receptor (PBR). [F-18]4a and [F-18]4b were synthesized by fluoroethylation of precursors 8a and 8b with [ 18F] FCH2CH2Br ([ 18F] 9), respectively. Small-animal PET scan for a neuroinflammatory rat model showed that the two radioligands had high uptakes of radioactivity in the kainic acid-infused striatum, a brain region where PBR density was increased. (C) 2009 Elsevier Ltd. All rights reserved.