2,N-dimethyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide | 1208112-23-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,N-dimethyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
• 英文别名: Naphthalene and Benzamide Derivative, 21；N,2-dimethyl-N-[(1R)-1-naphthalen-1-ylethyl]benzamide
• CAS: 1208112-23-5
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: UENPHAHEZPFPCU-MRXNPFEDSA-N

物化性质

• 沸点：
  495.3±34.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对甲苯甲酸 、 (R)-(+)-N-甲基-1-(1-萘基)乙基胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到2,N-dimethyl-N-[(R)-1-(1-naphthyl)ethyl]benzamide
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Biological Evaluation of a Series of Novel and Reversible Inhibitors for the Severe Acute Respiratory Syndrome−Coronavirus Papain-Like Protease

  摘要：

  We describe here the design, Synthesis, molecular modeling. and biological evaluation of a series of small molecule, nonpeptide inhibitors of SARS-CoV PLpro. Our initial lead compound was identified via high-throughput screening of a diverse chemical library. We subsequently carried out structure-activity relationship studies and optimized the lead structure to potent inhibitors that have shown antiviral activity against SARS-CoV infected Vero E6 cells, Upon the basis of the X-ray crystal structure of inhibitor 24-bound to SARS-CoV PLpro, a drug design template was created. Our structure-based modification led to the design of a more potent inhibitor, 2 (enzyme IC50 = 0.46 mu M; antiviral EC50 = 6 mu M). Interestingly. its methylamine derivative, 49, displayed good enzyme inhibitory potency (IC50 = 1.3 mu M) and the most potent SARS antiviral activity (EC50 = 5.2 mu M) in the series, We have carried our computational docking studies and generated a predictive 3D-QSAR model for SARS-CoV PLpro inhibitors.

  DOI：

  10.1021/jm900611t

文献信息

• COMPOUNDS AND METHODS FOR TREATING RESPIRATORY DISEASES
  申请人：Ghosh Arun K.

  公开号：US20110269834A1

  公开（公告）日：2011-11-03

  Described herein are compounds and compositions, and methods for using the compounds and compositions, for treating respiratory diseases and illness, such as severe acute respiratory syndrome (SARS).

  本文描述了化合物和组合物，以及使用这些化合物和组合物治疗呼吸道疾病和疾病，如严重急性呼吸综合征（SARS）的方法。
• [EN] COMPOUNDS AND METHODS FOR TREATING RESPIRATORY DISEASES<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LE TRAITEMENT DES MALADIES RESPIRATOIRES
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2010022355A1

  公开（公告）日：2010-02-25

  Described herein are compounds and compositions, and methods for using the compounds and compositions, for treating respiratory diseases and illness, such as severe acute respiratory syndrome (SARS).
• Structure-Based Design, Synthesis, and Biological Evaluation of a Series of Novel and Reversible Inhibitors for the Severe Acute Respiratory Syndrome−Coronavirus Papain-Like Protease
  作者：Arun K. Ghosh、Jun Takayama、Yoann Aubin、Kiira Ratia、Rima Chaudhuri、Yahira Baez、Katrina Sleeman、Melissa Coughlin、Daniel B. Nichols、Debbie C. Mulhearn、Bellur S. Prabhakar、Susan C. Baker、Michael E. Johnson、Andrew D. Mesecar

  DOI：10.1021/jm900611t

  日期：2009.8.27

  We describe here the design, Synthesis, molecular modeling. and biological evaluation of a series of small molecule, nonpeptide inhibitors of SARS-CoV PLpro. Our initial lead compound was identified via high-throughput screening of a diverse chemical library. We subsequently carried out structure-activity relationship studies and optimized the lead structure to potent inhibitors that have shown antiviral activity against SARS-CoV infected Vero E6 cells, Upon the basis of the X-ray crystal structure of inhibitor 24-bound to SARS-CoV PLpro, a drug design template was created. Our structure-based modification led to the design of a more potent inhibitor, 2 (enzyme IC50 = 0.46 mu M; antiviral EC50 = 6 mu M). Interestingly. its methylamine derivative, 49, displayed good enzyme inhibitory potency (IC50 = 1.3 mu M) and the most potent SARS antiviral activity (EC50 = 5.2 mu M) in the series, We have carried our computational docking studies and generated a predictive 3D-QSAR model for SARS-CoV PLpro inhibitors.