tert-butyl (E)-4-amino-4-((4-(3-ethoxy-3-oxoprop-1-enyl)phenyl)carbamoyl)piperidine-1-carboxylate | 877273-07-9

• 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: tert-butyl (E)-4-amino-4-((4-(3-ethoxy-3-oxoprop-1-enyl)phenyl)carbamoyl)piperidine-1-carboxylate
• 英文别名: (E)-tert-butyl 4-amino-4-((4-(3-ethoxy-3-oxoprop-1-enyl)phenyl)carbamoyl)piperidine-1-carboxylate；tert-butyl 4-amino-4-[[4-[(E)-3-ethoxy-3-oxoprop-1-enyl]phenyl]carbamoyl]piperidine-1-carboxylate
• CAS: 877273-07-9
• 化学式: C₂₂H₃₁N₃O₅
• 分子量: 417.505
• InChiKey: ZBWLSMWMKNSXRY-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (E)-4-amino-4-((4-(3-ethoxy-3-oxoprop-1-enyl)phenyl)carbamoyl)piperidine-1-carboxylate 、 1-环己基-2-(3-呋喃)-1H-苯并咪唑-5-羧酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 反应 20.0h， 生成 tert-butyl (E)-4-(1-cyclohexyl-2-(furan-3-yl)-1H-benzo[d]imidazole-5-carboxamido)-4-((4-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl)carbamoyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Importance of Ligand Bioactive Conformation in the Discovery of Potent Indole-Diamide Inhibitors of the Hepatitis C Virus NS5B

  摘要：

  Significant advances have led to receptor induced-fit and conformational selection models for describing bimolecular recognition, but a more comprehensive view must evolve to also include ligand shape and conformational changes. Here, we describe an example where a ligand's "structural hinge" influences potency by inducing an "L-shape" bioactive conformation, and due to its solvent exposure in the complex, reasonable conformation-activity-relationships can be qualitatively attributed. From a ligand design perspective, this feature was exploited by successful linker hopping to an alternate "structural hinge" that led to a new and promising chemical series which matched the ligand bioactive conformation and the pocket bioactive space. Using a combination of X-ray crystallography, NMR and modeling with support from binding-site resistance mutant studies and photoaffinity labeling experiments, we were able to derive inhibitor-polymerase complexes for various chemical series.

  DOI：

  10.1021/ja101358s
• 作为产物：
  描述：

  tert-butyl (E)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-((4-(3-ethoxy-3-oxoprop-1-en-1-yl)phenyl)carbamoyl)piperidine-1-carboxylate 在 二甲胺 作用下， 以 DMF (N,N-dimethyl-formamide) 、 乙醇 、 水 为溶剂， 反应 1.0h， 以55%的产率得到tert-butyl (E)-4-amino-4-((4-(3-ethoxy-3-oxoprop-1-enyl)phenyl)carbamoyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Inhibitors of HCV replication

  摘要：

  化合物I的吲哚类化合物已被描述。这些化合物对丙型肝炎病毒（HCV）具有活性，并可用于治疗感染HCV的人。还描述了包含这些化合物的不同形式和组成，以及制备这些化合物的方法。

  公开号：

  US20060046983A1

文献信息

• WO2007/92000
  申请人：——

  公开号：——

  公开（公告）日：——
• INHIBITORS OF HCV REPLICATION
  申请人：Bristol-Myers Squibb Company

  公开号：EP1776368A1

  公开（公告）日：2007-04-25
• US7153848B2
  申请人：——

  公开号：US7153848B2

  公开（公告）日：2006-12-26
• US7348425B2
  申请人：——

  公开号：US7348425B2

  公开（公告）日：2008-03-25
• [EN] INHIBITORS OF HCV REPLICATION<br/>[FR] INHIBITEURS DE REPLICATION DU HCV
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2006020082A1

  公开（公告）日：2006-02-23

  Indole compounds of Formula (I) are described. The compounds have activity against hepatitis C virus (HCV) and are useful in treating those infected with HCV. Different forms and compositions comprising the compounds are also described as well as methods of preparing the compounds.