1,1-Dimethylethyl 4-[3-oxo-3-[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]propyl]-1-piperidinecarboxylate | 195877-48-6

• 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: 1,1-Dimethylethyl 4-[3-oxo-3-[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]propyl]-1-piperidinecarboxylate
• 英文别名: tert-butyl 4-[3-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-oxopropyl]piperidine-1-carboxylate
• CAS: 195877-48-6
• 化学式: C₂₃H₃₂N₂O₅
• 分子量: 416.517
• InChiKey: PNZMTUPQVQFFOR-IBGZPJMESA-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：

  1,1-Dimethylethyl 4-[3-oxo-3-[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]propyl]-1-piperidinecarboxylate 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 二碳酸二叔丁酯 、 2,4,6-三异丙基苯磺酰叠氮化物 、 苄基三乙基氯化铵 、 氢气 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-((S)-2-Benzyloxycarbonylamino-3-hydroxy-3-methoxycarbonyl-propyl)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Solution-phase and solid-phase synthesis of novel transition state inhibitors of coagulation enzymes incorporating a piperidinyl moiety

  摘要：

  2-Amino-3-piperidin-4-yl-propionic acid containing peptidomimetics are potent protease inhibitors when combined with an appropriate keto-thiazole or keto-carboxylic acid moiety. A novel P-1 residue in factor Xa and thrombin inhibitors has been found resulting in IC50 values as low as 0.048 mu M, a factor of ten more potent than Argatroban. Starting with non-chiral synthetic routes, a new stereospecific route was developed as well as a new solid-phase method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00179-1
• 作为产物：
  描述：

  4-哌啶丙酸 在 正丁基锂 、 三甲基乙酰氯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,1-Dimethylethyl 4-[3-oxo-3-[(4S)-2-oxo-4-(phenylmethyl)-3-oxazolidinyl]propyl]-1-piperidinecarboxylate
  参考文献：
  名称：

  Solution-phase and solid-phase synthesis of novel transition state inhibitors of coagulation enzymes incorporating a piperidinyl moiety

  摘要：

  2-Amino-3-piperidin-4-yl-propionic acid containing peptidomimetics are potent protease inhibitors when combined with an appropriate keto-thiazole or keto-carboxylic acid moiety. A novel P-1 residue in factor Xa and thrombin inhibitors has been found resulting in IC50 values as low as 0.048 mu M, a factor of ten more potent than Argatroban. Starting with non-chiral synthetic routes, a new stereospecific route was developed as well as a new solid-phase method. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00179-1

文献信息

• SERINE PROTEASE INHIBITORS
  申请人：Akzo Nobel N.V.

  公开号：EP1012164B1

  公开（公告）日：2004-09-22
• SUBSTITUTED ISOXAZOLINES AND THEIR USE AS ANTIBACTERIAL AGENTS
  申请人：AstraZeneca AB

  公开号：EP1242416A1

  公开（公告）日：2002-09-25
• US6218365B1
  申请人：——

  公开号：US6218365B1

  公开（公告）日：2001-04-17
• [EN] SUBSTITUTED ISOXAZOLINES AND THEIR USE AS ANTIBACTERIAL AGENTS<br/>[FR] ISOXAZOLINES SUBSTITUEES ET LEUR UTILISATION COMME AGENTS ANTIBACTERIENS
  申请人：ASTRAZENECA AB

  公开号：WO2001040222A1

  公开（公告）日：2001-06-07

  Compounds of formula (I), or a pharmaceutically-acceptable salt, or an in-vivo-hydrolysable ester thereof, wherein, for example, X is O, S or NH; HET is an optionally substituted C-linked 5-membered heteroaryl ring containing 2 to 4 heteroatoms independently selected from N, O and S; Q is selected from, for example, Q1 and Q2: R?2 and R3¿ are independently hydrogen or fluoro; T is selected from a range of groups, for example, an N-linked (fully unsaturated) 5-membered heteroaryl ring system or a group of formula (TC5): wherein Rc is, for example, R?13CO-, R13SO¿2-or R13CS-; wherein R13 is, for example, optionally substituted (1-10C)alkyl or R14C(O)O(1-6C)alkyl wherein R14 is optionally substituted (1-10C)alkyl; are useful as antibacterial agents; and processes for their manufacture and pharmaceutical compositions containing them are described.
• Solution-phase and solid-phase synthesis of novel transition state inhibitors of coagulation enzymes incorporating a piperidinyl moiety
  作者：Anton E.P. Adang、Co A.M. Peters、Siene Gerritsma、Edwin de Zwart、Gerrit Veeneman

  DOI：10.1016/s0960-894x(99)00179-1

  日期：1999.5

  2-Amino-3-piperidin-4-yl-propionic acid containing peptidomimetics are potent protease inhibitors when combined with an appropriate keto-thiazole or keto-carboxylic acid moiety. A novel P-1 residue in factor Xa and thrombin inhibitors has been found resulting in IC50 values as low as 0.048 mu M, a factor of ten more potent than Argatroban. Starting with non-chiral synthetic routes, a new stereospecific route was developed as well as a new solid-phase method. (C) 1999 Elsevier Science Ltd. All rights reserved.