(4aR,7aS)-N-{3-[4-hydroxy-1-(3-methyl-butyl)-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide | 1033755-42-8

• 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: (4aR,7aS)-N-{3-[4-hydroxy-1-(3-methyl-butyl)-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide
• 英文别名: N-[3-[(4aR,7aS)-4-hydroxy-1-isopentyl-2-oxo-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridin-3-yl]-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide；N-[3-[(4aR,7aS)-4-hydroxy-1-(3-methylbutyl)-2-oxo-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridin-3-yl]-1,1-dioxo-4H-1λ6,2,4-benzothiadiazin-7-yl]methanesulfonamide
• CAS: 1033755-42-8
• 化学式: C₂₁H₂₈N₄O₆S₂
• 分子量: 496.609
• InChiKey: WNJBKXXSMIADKQ-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (1R,25)-2-[[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-(3-methyl-butyl)-amino]-cyclopentanecarboxylic acid ethyl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以36.3%的产率得到(4aR,7aS)-N-{3-[4-hydroxy-1-(3-methyl-butyl)-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide
  参考文献：
  名称：

  WO2008/73982

  摘要：

  公开号：
• 作为试剂：
  描述：

  (1R,25)-2-[[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-(3-methyl-butyl)-amino]-cyclopentanecarboxylic acid ethyl ester 、 sodium ethanolate 、 盐酸 在 乙酸乙酯 、 Sodium sulfate-III 、 crude product 、 hexanes 、 (4aR,7aS)-N-{3-[4-hydroxy-1-(3-methyl-butyl)-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以to afford the desired product, (4aR,7aS)-N-{3-[4-hydroxy-1-(3-methyl-butyl)-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (0.054 g, 0.109 mmol, 36.3% over two steps)的产率得到(4aR,7aS)-N-{3-[4-hydroxy-1-(3-methyl-butyl)-2-oxo-2,4a,5,6,7,7a-hexahydro-1H-[1]pyrindin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide
  参考文献：
  名称：

  5,6-dihydro-1H-pyridin-2-one compounds

  摘要：

  本发明涉及式I的5,6-二氢-1H-吡啶-2-酮化合物及含有此类化合物的药物组合物，其在治疗丙型肝炎病毒感染方面有用：其中Z为X为N或CR9；Y为—(CR4R5)n—；n为2、3、4或5；R1至R9在此定义。

  公开号：

  US07582626B2

文献信息

• 5,6-DIHYDRO-1H-PYRIDIN-2-ONE COMPOUNDS
  申请人：Tran Chinh V.

  公开号：US20090111798A1

  公开（公告）日：2009-04-30

  The invention is directed to 5,6-dihydro-1H-pyridin-2-one compounds and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.

  本发明涉及5,6-二氢-1H-吡啶-2-酮化合物和含有这些化合物的药物组合物，用于治疗丙型肝炎病毒感染。
• 5,6-Dihydro-1H-pyridin-2-ones as potent inhibitors of HCV NS5B polymerase
  作者：Frank Ruebsam、Chinh V. Tran、Lian-Sheng Li、Sun Hee Kim、Alan X. Xiang、Yuefen Zhou、Julie K. Blazel、Zhongxiang Sun、Peter S. Dragovich、Jingjing Zhao、Helen M. McGuire、Douglas E. Murphy、Martin T. Tran、Nebojsa Stankovic、David A. Ellis、Alberto Gobbi、Richard E. Showalter、Stephen E. Webber、Amit M. Shah、Mei Tsan、Rupal A. Patel、Laurie A. LeBrun、Huiying J. Hou、Ruhi Kamran、Maria V. Sergeeva、Darian M. Bartkowski、Thomas G. Nolan、Daniel A. Norris、Leo Kirkovsky

  DOI：10.1016/j.bmcl.2008.11.048

  日期：2009.1

  5,6-Dihydro-1H-pyridin-2-one analogs were discovered as a novel class of inhibitors of genotype 1 HCV NS5B polymerase. Among these, compound 4ad displayed potent inhibitory activities in biochemical and replicon assays (IC(50) (1b) < 10 nM; IC(50) (1a) < 25 nM, EC(50) (1b) = 16 nM), good in vitro DMPK properties, as well as moderate oral bioavailability in monkeys (F = 24%). (C) 2008 Elsevier Ltd. All rights reserved.
• US7582626B2
  申请人：——

  公开号：US7582626B2

  公开（公告）日：2009-09-01
• [EN] 5,6-DIHYDRO-1H-PYRIDIN-2-ONE COMPOUNDS<br/>[FR] COMPOSÉS DE 5,6-DIHYDRO-1H-PYRIDINE-2-ONE
  申请人：ANADYS PHARMACEUTICALS INC

  公开号：WO2008073982A2

  公开（公告）日：2008-06-19

  [EN] The invention is directed to 5,6-dihydro-1H-pyridin-2-one compounds and pharmaceutical compositions containing such compounds that are useful in treating infections by hepatitis C virus.
  [FR] L'invention concerne des composés de 5,6-dihydro-1H-pyridine-2-one et des compositions pharmaceutiques contenant de tels composés, qui sont utiles dans le traitements des infections par le virus de l'hépatite C.