tert-butyl 4-{3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-oxopropyl}piperidine-1-carboxylate | 721455-06-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl 4-{3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-oxopropyl}piperidine-1-carboxylate
• 英文别名: tert-butyl 4-[3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-oxopropyl]piperidine-1-carboxylate
• CAS: 721455-06-7
• 化学式: C₂₃H₃₂N₂O₅
• 分子量: 416.517
• InChiKey: PNZMTUPQVQFFOR-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-{3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-oxopropyl}piperidine-1-carboxylate 在 六甲基磷酰三胺 、 lithium hydroxide 、 双氧水 、 sodium hexamethyldisilazane 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 苯 为溶剂， 生成
  参考文献：
  名称：

  Potent and selective aggrecanase inhibitors containing cyclic P1 substituents

  摘要：

  Anti-succinate hydroxamates with cyclic PI motifs were synthesized as aggrecanase inhibitors. The N-methanesulfonyl piperidine 23 and the N-trifluoroacetyl azetidine 26 were the most potent aggrecanase inhibitors both having an IC50 = 3 nM while maintaining > 100-fold selectivity over MMP-1, -2, and -9. The cyclic moieties were also capable of altering in vivo metabolism, hence delivering low clearance compounds in both rat and dog studies as shown for compound 14. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00124-0
• 作为产物：
  描述：

  (R)-4-苄基-2-噁唑烷酮 、 1-N-BOC-4-哌啶丙酸 在 三甲基乙酰氯 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl 4-{3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-oxopropyl}piperidine-1-carboxylate
  参考文献：
  名称：

  Potent and selective aggrecanase inhibitors containing cyclic P1 substituents

  摘要：

  Anti-succinate hydroxamates with cyclic PI motifs were synthesized as aggrecanase inhibitors. The N-methanesulfonyl piperidine 23 and the N-trifluoroacetyl azetidine 26 were the most potent aggrecanase inhibitors both having an IC50 = 3 nM while maintaining > 100-fold selectivity over MMP-1, -2, and -9. The cyclic moieties were also capable of altering in vivo metabolism, hence delivering low clearance compounds in both rat and dog studies as shown for compound 14. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00124-0

文献信息

• [EN] 4-[(4-(CARBOXYETHYL) PIPERIDINYL) METHYL] PYRROLIDINES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] 4-[(4-(CARBOXYETHYL)PIPERIDINYL)METHYL]PYRROLIDINES SERVANT DE MODULATEURS DE L'ACTIVITE DES RECEPTEURS DES CHIMIOKINES
  申请人：MERCK & CO INC

  公开号：WO2004058702A3

  公开（公告）日：2004-08-26
• Potent and selective aggrecanase inhibitors containing cyclic P1 substituents
  作者：Robert J Cherney、Ruowei Mo、Dayton T Meyer、Li Wang、Wenqing Yao、Zelda R Wasserman、Rui-Qin Liu、Maryanne B Covington、Micky D Tortorella、Elizabeth C Arner、Mingxin Qian、David D Christ、James M Trzaskos、Robert C Newton、Ron L Magolda、Carl P Decicco

  DOI：10.1016/s0960-894x(03)00124-0

  日期：2003.4

  Anti-succinate hydroxamates with cyclic PI motifs were synthesized as aggrecanase inhibitors. The N-methanesulfonyl piperidine 23 and the N-trifluoroacetyl azetidine 26 were the most potent aggrecanase inhibitors both having an IC50 = 3 nM while maintaining > 100-fold selectivity over MMP-1, -2, and -9. The cyclic moieties were also capable of altering in vivo metabolism, hence delivering low clearance compounds in both rat and dog studies as shown for compound 14. (C) 2003 Elsevier Science Ltd. All rights reserved.