1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-3-(7-hydroxymethyl-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-1H-quinolin-2-one | 709041-99-6

• 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: 1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-3-(7-hydroxymethyl-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-1H-quinolin-2-one
• 英文别名: 1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-3-[7-(hydroxymethyl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-3-yl]quinolin-2-one；1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-3-[7-(hydroxymethyl)-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-yl]quinolin-2-one
• CAS: 709041-99-6
• 化学式: C₂₂H₂₀FN₃O₅S
• 分子量: 457.482
• InChiKey: PVXTZUGDCVQHSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-3-(7-hydroxymethyl-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-1H-quinolin-2-one 、 三氯乙酰异氰酸酯 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  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
• 作为产物：
  描述：

  3-[1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl]-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-7-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 Rochelle's salt 作用下， 以 四氢呋喃 、 水 为溶剂， 以68%的产率得到1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-3-(7-hydroxymethyl-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-1H-quinolin-2-one
  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

• 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.