(S)-5-(4-(ethoxycarbonyl)piperazin-1-yl)-5-oxo-4-(6-phenyl-4-(piperidin-4-ylmethylamino)picolinamido)pentanoic acid | 1188276-19-8

• 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: (S)-5-(4-(ethoxycarbonyl)piperazin-1-yl)-5-oxo-4-(6-phenyl-4-(piperidin-4-ylmethylamino)picolinamido)pentanoic acid
• 英文别名: (4S)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[6-phenyl-4-(piperidin-4-ylmethylamino)pyridine-2-carbonyl]amino]pentanoic acid
• CAS: 1188276-19-8
• 化学式: C₃₀H₄₀N₆O₆
• 分子量: 580.684
• InChiKey: RHDWACJNMCMZPZ-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  153
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-{(S)-4-carboxy-2-[(4-chloro-6-phenyl-pyridine-2-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester 、 4-氨甲基哌啶 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 (S)-5-(4-(ethoxycarbonyl)piperazin-1-yl)-5-oxo-4-(6-phenyl-4-(piperidin-4-ylmethylamino)picolinamido)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 as measured in a human platelet rich plasma (PRP) assay. Pharmacokinetic and physiochemical properties were optimized leading to compound (4S)-4-[({4-[4-(methoxymethyl)piperidin-1-yl]-6-phenylpyridin-2-yl} carbonyl)amino]-5-oxo-5-{4-[(pentyloxy) carbonyl]piperazin-1-yl}pentanoic acid 22J with good human PRP potency, selectivity, in vivo efficacy and oral bioavailability. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.075

文献信息

• Piperazinyl-glutamate-pyridines as potent orally bioavailable P2Y12 antagonists for inhibition of platelet aggregation
  作者：John J. Parlow、Mary W. Burney、Brenda L. Case、Thomas J. Girard、Kerri A. Hall、Ronald R. Hiebsch、Rita M. Huff、Rhonda M. Lachance、Deborah A. Mischke、Stephen R. Rapp、Rhonda S. Woerndle、Michael D. Ennis

  DOI：10.1016/j.bmcl.2009.06.075

  日期：2009.8

  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 as measured in a human platelet rich plasma (PRP) assay. Pharmacokinetic and physiochemical properties were optimized leading to compound (4S)-4-[(4-[4-(methoxymethyl)piperidin-1-yl]-6-phenylpyridin-2-yl} carbonyl)amino]-5-oxo-5-4-[(pentyloxy) carbonyl]piperazin-1-yl}pentanoic acid 22J with good human PRP potency, selectivity, in vivo efficacy and oral bioavailability. (C) 2009 Elsevier Ltd. All rights reserved.