4-{(S)-4-carboxy-2-[(2-phenyl-6-thiophen-3-yl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester | 913950-87-5

• 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-{(S)-4-carboxy-2-[(2-phenyl-6-thiophen-3-yl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester
• 英文别名: (4S)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[(2-phenyl-6-thiophen-3-ylpyrimidine-4-carbonyl)amino]pentanoic acid
• CAS: 913950-87-5
• 化学式: C₂₇H₂₉N₅O₆S
• 分子量: 551.623
• InChiKey: MZJBTSWSBMERIZ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  170
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-噻吩甲酰氯 在 potassium permanganate 、 copper(l) iodide 、 bis(triphenylphosphine) palladium (Il) acetate 、 水 、 sodium carbonate 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 4-{(S)-4-carboxy-2-[(2-phenyl-6-thiophen-3-yl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Optimization of 2-phenyl-pyrimidine-4-carboxamides towards potent, orally bioavailable and selective P2Y12 antagonists for inhibition of platelet aggregation

  摘要：

  2-Phenyl-pyrimidine-4-carboxamide analogs were identified as P2Y12 antagonists. Optimization of the carbon-linked or nitrogen-linked substituent at the 6-position of the pyrimidine ring provided compounds with excellent ex vivo potency in the platelet aggregation assay in human plasma. Compound 23u met the objectives for activity, selectivity and ADMET properties.

  DOI：

  10.1016/j.bmcl.2014.06.070

文献信息

• Pyrimidine Derivatives and Their Use as P2Y12 Receptor Antagonists
  申请人：Caroff Eva

  公开号：US20080194576A1

  公开（公告）日：2008-08-14

  The invention relates to 4-aminocarbonyl-pyrimidine derivatives and their use as P2Y 12 receptor antagonists in the treatment and/or prevention and/or treatment of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cerebrovascular diseases or conditions associated with platelet aggregation, including thrombosis in humans and other mammals.

  该发明涉及4-氨基甲酰基嘧啶衍生物及其作为P2Y12受体拮抗剂在治疗和/或预防外周血管、内脏-、肝脏-和肾脏血管、心血管和脑血管疾病或与血小板聚集有关的疾病或状况的用途，包括在人类和其他哺乳动物中的血栓形成。
• PYRIMIDINE DERIVATIVES AND THEIR USE AS P2Y12 RECEPTOR ANTAGONISTS
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP1893634B1

  公开（公告）日：2011-12-21
• US8048881B2
  申请人：——

  公开号：US8048881B2

  公开（公告）日：2011-11-01
• Optimization of 2-phenyl-pyrimidine-4-carboxamides towards potent, orally bioavailable and selective P2Y12 antagonists for inhibition of platelet aggregation
  作者：Eva Caroff、Emmanuel Meyer、Alexander Treiber、Kurt Hilpert、Markus A. Riederer

  DOI：10.1016/j.bmcl.2014.06.070

  日期：2014.9

  2-Phenyl-pyrimidine-4-carboxamide analogs were identified as P2Y12 antagonists. Optimization of the carbon-linked or nitrogen-linked substituent at the 6-position of the pyrimidine ring provided compounds with excellent ex vivo potency in the platelet aggregation assay in human plasma. Compound 23u met the objectives for activity, selectivity and ADMET properties.