4-[2-(1-Carboxymethyl-2-oxo-piperidin-3-yl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester | 146093-58-5

• 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-[2-(1-Carboxymethyl-2-oxo-piperidin-3-yl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: 2-[3-[2-[1-[(2-Methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]ethyl]-2-oxopiperidin-1-yl]acetic acid
• CAS: 146093-58-5
• 化学式: C₁₉H₃₂N₂O₅
• 分子量: 368.473
• InChiKey: WPYZENBERPAHOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[2-(1-Carboxymethyl-2-oxo-piperidin-3-yl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester 在 氢氟酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(S)-4-Guanidino-1-(thiazole-2-carbonyl)-butyl]-2-[2-oxo-3-(2-piperidin-4-yl-ethyl)-piperidin-1-yl]-acetamide
  参考文献：
  名称：

  Design, synthesis, and structure–Activity relationships of unsubstituted piperazinone-Based transition state factor Xa inhibitors

  摘要：

  A series of novel transition state factor Xa inhibitors containing a variety, of lactam ring systems as central templates was synthesized in an expedient manner and allowed for a great deal of structural variability. Among them. the piperazinone-based inhibitors were found to be not only active against factor Xa but also selective over thrombin. Optimization of the P4 moiety yielded several potent compounds with IC50 below 1 nM against factor Xa. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01037-5
• 作为产物：
  描述：

  4-乙烯基吡啶 在 platinum(IV) oxide lithium hydroxide 、 sodium hydroxide 、 氢气 、 sodium ethanolate 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， -78.0~75.0 ℃ 、275.79 kPa 条件下， 生成 4-[2-(1-Carboxymethyl-2-oxo-piperidin-3-yl)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis, and structure–Activity relationships of unsubstituted piperazinone-Based transition state factor Xa inhibitors

  摘要：

  A series of novel transition state factor Xa inhibitors containing a variety, of lactam ring systems as central templates was synthesized in an expedient manner and allowed for a great deal of structural variability. Among them. the piperazinone-based inhibitors were found to be not only active against factor Xa but also selective over thrombin. Optimization of the P4 moiety yielded several potent compounds with IC50 below 1 nM against factor Xa. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01037-5

文献信息

• Fibrinogen receptor antagonists
  申请人：Merck & Co., Inc.

  公开号：EP0512831B1

  公开（公告）日：1999-09-22
• US5281585A
  申请人：——

  公开号：US5281585A

  公开（公告）日：1994-01-25
• US5455243A
  申请人：——

  公开号：US5455243A

  公开（公告）日：1995-10-03
• [EN] FIBRINOGEN RECEPTOR ANTAGONISTS
  申请人：——

  公开号：WO1992019595A1

  公开（公告）日：1992-11-12

  [FR] Antagonistes de récepteur de fibrinogène représentés par la formule (I) lesquels sont utilisés pour inhiber la fixation du fibrinogène sur les plaquettes du sang et pour inhiber l'agrégation de ces dernières.
  [EN] Fibrinogen receptor antagonists of formula (I) are disclosed for use in inhibiting the binding of fibrinogen to blood platelets and for inhibiting the aggregation of blood platelets.
• Design, synthesis, and structure–Activity relationships of unsubstituted piperazinone-Based transition state factor Xa inhibitors
  作者：Wenrong Huang、Mary Ann Naughton、Hua Yang、Ting Su、Suiko Dam、Paul W. Wong、Ann Arfsten、Susan Edwards、Uma Sinha、Stanley Hollenbach、Robert M. Scarborough、Bing-Yan Zhu

  DOI：10.1016/s0960-894x(02)01037-5

  日期：2003.2

  A series of novel transition state factor Xa inhibitors containing a variety, of lactam ring systems as central templates was synthesized in an expedient manner and allowed for a great deal of structural variability. Among them. the piperazinone-based inhibitors were found to be not only active against factor Xa but also selective over thrombin. Optimization of the P4 moiety yielded several potent compounds with IC50 below 1 nM against factor Xa. (C) 2003 Elsevier Science Ltd. All rights reserved.