(4S)-4-[((4-[(([2-(dimethylamino)-2-oxoethyl]amino)carbonyl)amino]-6-phenylpyridin-2-yl)carbonyl)amino]-5-oxo-5-(4-[(pentyloxy)carbonyl]piperazin-1-yl)pentanoic acid | 1214286-37-9

• 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: (4S)-4-[((4-[(([2-(dimethylamino)-2-oxoethyl]amino)carbonyl)amino]-6-phenylpyridin-2-yl)carbonyl)amino]-5-oxo-5-(4-[(pentyloxy)carbonyl]piperazin-1-yl)pentanoic acid
• CAS: 1214286-37-9
• 化学式: C₃₂H₄₃N₇O₈
• 分子量: 653.736
• InChiKey: CFRYULMHTXPCEJ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  190.58
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  pentyl 4-[(2S)-2-[[4-[[2-(dimethylamino)-2-oxoethyl]carbamoylamino]-6-phenylpyridine-2-carbonyl]amino]-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以53 mg的产率得到(4S)-4-[((4-[(([2-(dimethylamino)-2-oxoethyl]amino)carbonyl)amino]-6-phenylpyridin-2-yl)carbonyl)amino]-5-oxo-5-(4-[(pentyloxy)carbonyl]piperazin-1-yl)pentanoic acid
  参考文献：
  名称：

  Piperazinyl Glutamate Pyridines as Potent Orally Bioavailable P2Y₁₂ Antagonists for Inhibition of Platelet Aggregation

  摘要：

  Polymer-assisted solution-phase (PASP) parallel library synthesis was used to discover a piperazinyl glutamate pyridine as a P2Y(12) antagonist. Exploitation of this lead provided compounds with excellent inhibition of platelet aggregation its measured in a human platelet rich plasma (PRP) assay. Pharmacokinetic and physiochemical properties were optimized through modifications at the 4-position or the pyridine ring and the terminal nitrogen of the piperazine ring, leading to compound (4S)4-[({4-[4-(methoxymethyl)piperdin-1-yl]-6-phenylpyridin-2-yl}carbonyl)amino]-5-oxo-5-{4-[(pentyloxy)carbonyl]piperazin-1-yl}pentanoic acid 47s with good human PRP potency, selectivity, in vivo efficacy, and oral bioavallability. Compound 47s was selected for further preclinical evaluations.

  DOI：

  10.1021/jm901518t