7-Methoxy-4-(2-methoxy-ethoxymethoxy)-quinoline-2-carboxylic acid methyl ester | 300830-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-Methoxy-4-(2-methoxy-ethoxymethoxy)-quinoline-2-carboxylic acid methyl ester
• 英文别名: Methyl 7-methoxy-4-(2-methoxyethoxymethoxy)quinoline-2-carboxylate
• CAS: 300830-86-8
• 化学式: C₁₆H₁₉NO₆
• 分子量: 321.33
• InChiKey: WXFLIMTYLIMXGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-Methoxy-4-(2-methoxy-ethoxymethoxy)-quinoline-2-carboxylic acid methyl ester 在 乙醇 、 肼 作用下， 生成 7-Methoxy-5-(2-methoxy-ethoxymethoxy)-quinoline-2-carboxylic acid N'-acetyl-hydrazide
  参考文献：
  名称：

  Structure−Activity Study on a Novel Series of Macrocyclic Inhibitors of the Hepatitis C Virus NS3 Protease Leading to the Discovery of BILN 2061

  摘要：

  From the discovery of competitive hexapeptide inhibitors, potent and selective HCV NS3 protease macrocyclic inhibitors have been identified. Structure-activity relationship studies were per-formed focusing on optimizing the N-terminal carbamate and the aromatic substituent on the (4R)-hydroxyproline moiety. Inhibitors meeting the potency criteria in the cell-based assay and with improved oral bioavailability in rats were identified. BILN 2061 was selected as the best compound, the first NS3 protease inhibitor reported with antiviral activity in man.

  DOI：

  10.1021/jm0342414
• 作为产物：
  描述：

  2-甲氧基乙氧基甲基氯 、 7-甲氧基-4-氧代-1,4-二氢-喹啉-2-羧酸甲酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-Methoxy-4-(2-methoxy-ethoxymethoxy)-quinoline-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure−Activity Study on a Novel Series of Macrocyclic Inhibitors of the Hepatitis C Virus NS3 Protease Leading to the Discovery of BILN 2061

  摘要：

  From the discovery of competitive hexapeptide inhibitors, potent and selective HCV NS3 protease macrocyclic inhibitors have been identified. Structure-activity relationship studies were per-formed focusing on optimizing the N-terminal carbamate and the aromatic substituent on the (4R)-hydroxyproline moiety. Inhibitors meeting the potency criteria in the cell-based assay and with improved oral bioavailability in rats were identified. BILN 2061 was selected as the best compound, the first NS3 protease inhibitor reported with antiviral activity in man.

  DOI：

  10.1021/jm0342414

文献信息

• Structure−Activity Study on a Novel Series of Macrocyclic Inhibitors of the Hepatitis C Virus NS3 Protease Leading to the Discovery of BILN 2061
  作者：Montse Llinàs-Brunet、Murray D. Bailey、Gordon Bolger、Christian Brochu、Anne-Marie Faucher、Jean Marie Ferland、Michel Garneau、Elise Ghiro、Vida Gorys、Chantal Grand-Maître、Ted Halmos、Nicole Lapeyre-Paquette、Francine Liard、Martin Poirier、Manon Rhéaume、Youla S. Tsantrizos、Daniel Lamarre

  DOI：10.1021/jm0342414

  日期：2004.3.1

  From the discovery of competitive hexapeptide inhibitors, potent and selective HCV NS3 protease macrocyclic inhibitors have been identified. Structure-activity relationship studies were per-formed focusing on optimizing the N-terminal carbamate and the aromatic substituent on the (4R)-hydroxyproline moiety. Inhibitors meeting the potency criteria in the cell-based assay and with improved oral bioavailability in rats were identified. BILN 2061 was selected as the best compound, the first NS3 protease inhibitor reported with antiviral activity in man.