3-[4-hydroxy-1-(3-methylbutyl)-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazine-7-carboxylic acid | 477930-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 3-[4-hydroxy-1-(3-methylbutyl)-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazine-7-carboxylic acid
• 英文别名: 3-(4-hydroxy-1-isopentyl-2-oxo-3-quinolyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazine-7-carboxylic acid；3-[4-hydroxy-1-(3-methylbutyl)-2-oxoquinolin-3-yl]-1,1-dioxo-4H-1λ6,2,4-benzothiadiazine-7-carboxylic acid
• CAS: 477930-98-6
• 化学式: C₂₂H₂₁N₃O₆S
• 分子量: 455.491
• InChiKey: KEBCSTASCOWEMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-[4-hydroxy-1-(3-methylbutyl)-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazine-7-carboxylic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以93%的产率得到3-[4-hydroxy-1-(3-methylbutyl)-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazine-7-carboxylic acid
  参考文献：
  名称：

  Substituted benzothiadizine inhibitors of Hepatitis C virus polymerase

  摘要：

  The synthesis and optimisation of HCV NS5B polymerase inhibitors with improved potency versus the existing compound 1 is described. Substitution in the benzothiadiazine portion of the molecule, furnishing improvement in potency in the high protein Replicon assay, is highlighted, culminating in the discovery of 12h, a highly potent oxyacetamide derivative. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.091

文献信息

• [EN] NOVEL ANTI-INFECTIVES<br/>[FR] NOUVEAUX ANTI-INFECTIEUX
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2002098424A1

  公开（公告）日：2002-12-12

  Compounds useful as HCV anti-infectives having the formula: wherein the formula variables are as defined herein, are disclosed. Also disclosed are methods of making and using the same.

  本发明揭示了具有以下式的HCV抗感染剂有用的化合物：其中，公式变量如本文所定义。同时还揭示了制备和使用该化合物的方法。
• Novel anti-infectives
  申请人：——

  公开号：US20040147739A1

  公开（公告）日：2004-07-29

  Compounds useful as HCV anti-infectives having the formula: wherein the formula variables are as defined herein, are disclosed. Also disclosed are methods of making and using the same.

  本文披露了具有以下公式的HCV抗感染剂有用的化合物：其中公式变量如本文所定义。同时，还披露了制备和使用这些化合物的方法。
• EP1401443A4
  申请人：——

  公开号：EP1401443A4

  公开（公告）日：2005-10-26
• NOVEL ANTI-INFECTIVES
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1401443A1

  公开（公告）日：2004-03-31
• Substituted benzothiadizine inhibitors of Hepatitis C virus polymerase
  作者：Antony N. Shaw、Rosanna Tedesco、Ramesh Bambal、Deping Chai、Nestor O. Concha、Michael G. Darcy、Dashyant Dhanak、Kevin J. Duffy、Duke M. Fitch、Adam Gates、Victor K. Johnston、Richard M. Keenan、Juili Lin-Goerke、Nannan Liu、Robert T. Sarisky、Kenneth J. Wiggall、Michael N. Zimmerman

  DOI：10.1016/j.bmcl.2009.05.091

  日期：2009.8

  The synthesis and optimisation of HCV NS5B polymerase inhibitors with improved potency versus the existing compound 1 is described. Substitution in the benzothiadiazine portion of the molecule, furnishing improvement in potency in the high protein Replicon assay, is highlighted, culminating in the discovery of 12h, a highly potent oxyacetamide derivative. (C) 2009 Elsevier Ltd. All rights reserved.