3-[[2-Bromo-6-methoxy-5-(trifluoromethyl)naphthalene-1-carbonyl]-methoxycarbonyl-amino]propanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[[2-Bromo-6-methoxy-5-(trifluoromethyl)naphthalene-1-carbonyl]-methoxycarbonyl-amino]propanoic acid
• 英文别名: 3-[[2-bromo-6-methoxy-5-(trifluoromethyl)naphthalene-1-carbonyl]-methoxycarbonylamino]propanoic acid
• 化学式: C₁₈H₁₅BrF₃NO₆
• 分子量: 478.219
• InChiKey: FSXUSCXQRAZQOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  6-amino-2-methoxy-5-methyl-1-(trifluoromethyl)naphthalene 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 jones reagent 、 copper(I) bromide 、 sodium nitrite 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 丙酮 为溶剂， 反应 71.0h， 生成 3-[[2-Bromo-6-methoxy-5-(trifluoromethyl)naphthalene-1-carbonyl]-methoxycarbonyl-amino]propanoic acid
  参考文献：
  名称：

  Identification of [(naphthalene-1-carbonyl)-amino]-acetic acid derivatives as nonnucleoside inhibitors of HCV NS5B RNA dependent RNA polymerase

  摘要：

  A novel series of HCV NS5B RNA dependent RNA polymerase inhibitors containing a naphthalene carboxamide scaffold were identified by high throughput screening. Optimization of substituents by parallel synthesis and the iterative design towards understanding structure-activity relationship to improve potency are described. Tetra substituted naphthalene 31 displayed potent activity with IC50 of 120 nM against HCV NS5B enzyme and was selective over a panel of polymerases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.013

文献信息

• Identification of [(naphthalene-1-carbonyl)-amino]-acetic acid derivatives as nonnucleoside inhibitors of HCV NS5B RNA dependent RNA polymerase
  作者：Ariamala Gopalsamy、Kitae Lim、John W Ellingboe、Girija Krishnamurthy、Mark Orlowski、Boris Feld、Marja van Zeijl、Anita Y.M Howe

  DOI：10.1016/j.bmcl.2004.06.013

  日期：2004.8

  A novel series of HCV NS5B RNA dependent RNA polymerase inhibitors containing a naphthalene carboxamide scaffold were identified by high throughput screening. Optimization of substituents by parallel synthesis and the iterative design towards understanding structure-activity relationship to improve potency are described. Tetra substituted naphthalene 31 displayed potent activity with IC50 of 120 nM against HCV NS5B enzyme and was selective over a panel of polymerases. (C) 2004 Elsevier Ltd. All rights reserved.