1-(2-cyclopropylethyl)-3-(7-iodo-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-6-fluoro-4-hydroxy-1H-quinolin-2-one | 477933-29-2

• 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)-3-(7-iodo-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-6-fluoro-4-hydroxy-1H-quinolin-2-one
• 英文别名: 1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-3-(7-iodo-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-1H-quinolin-2-one；1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-3-(7-iodo-1,1-dioxo-4H-1lambda6,2,4-benzothiadiazin-3-yl)quinolin-2-one；1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-3-(7-iodo-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-3-yl)quinolin-2-one
• CAS: 477933-29-2
• 化学式: C₂₁H₁₇FIN₃O₄S
• 分子量: 553.353
• InChiKey: XUMNQYDLDPIOCR-UHFFFAOYSA-N

物化性质

• 沸点：
  675.0±65.0 °C(Predicted)
• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-cyclopropylethyl)-3-(7-iodo-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-6-fluoro-4-hydroxy-1H-quinolin-2-one 、 丙烯酰胺 在 sodium acetate 、 palladium diacetate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以94%的产率得到(E)-3-{3-[1-(2-cyclopropylethyl)-6-fluoro-4-hydroxy-2-oxo-1,2-dihydro-quinolin-3-yl]-1,1-dioxo-1,4-dihydro-1-benzo[1,2,4]thiadiazin-7-yl}acrylamide
  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：

  (7-iodo-1,1-dioxo-1,4-dihydro-1-benzo[1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester 、 1-(2-cyclopropylethyl)-6-fluorobenzo[d][1,3]oxazin-4-one 在 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.0h， 以54%的产率得到1-(2-cyclopropylethyl)-3-(7-iodo-1,1-dioxo-1,4-dihydrobenzo[1,2,4]thiadiazin-3-yl)-6-fluoro-4-hydroxy-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

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

  公开号：WO2004052312A2

  公开（公告）日：2004-06-24

  Compounds useful as HCV anti-infectives are disclosed. Also disclosed are methods of making and using the same.