[(2-Bromo-6-methoxy-5-trifluoromethyl-naphthalene-1-carbonyl)-prop-2-ynyloxycarbonyl-amino]-acetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(2-Bromo-6-methoxy-5-trifluoromethyl-naphthalene-1-carbonyl)-prop-2-ynyloxycarbonyl-amino]-acetic acid
• 英文别名: 2-[[2-bromo-6-methoxy-5-(trifluoromethyl)naphthalene-1-carbonyl]-prop-2-ynoxycarbonylamino]acetic acid
• 化学式: C₁₉H₁₃BrF₃NO₆
• 分子量: 488.215
• InChiKey: PNRNRHPUOKENCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  [(2-Bromo-6-methoxy-5-trifluoromethyl-naphthalene-1-carbonyl)-amino]-acetic acid tert-butyl ester 在 甲酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 生成 [(2-Bromo-6-methoxy-5-trifluoromethyl-naphthalene-1-carbonyl)-prop-2-ynyloxycarbonyl-amino]-acetic 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.