3-{2,6-Diamino-5-[4-(4-methanesulfonyl-benzylamino)-phenyl]-pyrimidin-4-yl}-propionic acid ethyl ester | 885040-44-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-{2,6-Diamino-5-[4-(4-methanesulfonyl-benzylamino)-phenyl]-pyrimidin-4-yl}-propionic acid ethyl ester
• 英文别名: Ethyl 3-(5-(4-(4-(methylsulfonyl)benzylamino)phenyl)-2,6-diaminopyrimidin-4-yl)propanoate；ethyl 3-[2,6-diamino-5-[4-[(4-methylsulfonylphenyl)methylamino]phenyl]pyrimidin-4-yl]propanoate
• CAS: 885040-44-8
• 化学式: C₂₃H₂₇N₅O₄S
• 分子量: 469.564
• InChiKey: NDNAPUYFHLMQHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  159
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-{2,6-Diamino-5-[4-(4-methanesulfonyl-benzylamino)-phenyl]-pyrimidin-4-yl}-propionic acid ethyl ester 在 lithium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-[2,6-diamino-5-(4-{[4-(methylsulfonyl)benzyl]amino}phenyl)pyrimidin-4-yl]-N-(3,5-dimethylbenzyl)propanamide
  参考文献：
  名称：

  Optimization of 2,4-diaminopyrimidines as GHS-R antagonists: Side chain exploration

  摘要：

  The synthesis and structure-activity relationships of the 4- and 6-substituents of 2,4-diaminopyrimidine-based growth hormone secretagogue receptor (GHS-R) antagonists are described. Diaminopyrimidines with 6-norbornenyl (4n) and 6-tetrahydrofuranyl (4p) substitutents were found to exhibit potent GHS-R antagonism and good selectivity (similar to 1000-fold) against dihydrofolate reductase. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.012
• 作为产物：
  描述：

  对硝基苯乙腈 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 、 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 、 三乙胺 、 三甲基硅烷化重氮甲烷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 3-{2,6-Diamino-5-[4-(4-methanesulfonyl-benzylamino)-phenyl]-pyrimidin-4-yl}-propionic acid ethyl ester
  参考文献：
  名称：

  Optimization of 2,4-diaminopyrimidines as GHS-R antagonists: Side chain exploration

  摘要：

  The synthesis and structure-activity relationships of the 4- and 6-substituents of 2,4-diaminopyrimidine-based growth hormone secretagogue receptor (GHS-R) antagonists are described. Diaminopyrimidines with 6-norbornenyl (4n) and 6-tetrahydrofuranyl (4p) substitutents were found to exhibit potent GHS-R antagonism and good selectivity (similar to 1000-fold) against dihydrofolate reductase. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.012

文献信息

• Optimization of 2,4-diaminopyrimidines as GHS-R antagonists: Side chain exploration
  作者：Bo Liu、Mei Liu、Zhili Xin、Hongyu Zhao、Michael D. Serby、Christi Kosogof、Lissa T.J. Nelson、Bruce G. Szczepankiewicz、Wiweka Kaszubska、Verlyn G. Schaefer、H. Douglas Falls、Chun Wel Lin、Christine A. Collins、Hing L. Sham、Gang Liu

  DOI：10.1016/j.bmcl.2006.01.012

  日期：2006.4

  The synthesis and structure-activity relationships of the 4- and 6-substituents of 2,4-diaminopyrimidine-based growth hormone secretagogue receptor (GHS-R) antagonists are described. Diaminopyrimidines with 6-norbornenyl (4n) and 6-tetrahydrofuranyl (4p) substitutents were found to exhibit potent GHS-R antagonism and good selectivity (similar to 1000-fold) against dihydrofolate reductase. (C) 2006 Elsevier Ltd. All rights reserved.