6-(5-cyano-7-cyclobutyl-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-N-[(2S)-1,1,1-trifluoropropan-2-yl]pyridine-3-sulfonamide | 1247930-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(5-cyano-7-cyclobutyl-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-N-[(2S)-1,1,1-trifluoropropan-2-yl]pyridine-3-sulfonamide
• 英文别名: 6-(5-cyano-7-cyclobutyl-2-methoxy-pyrrolo[2,3-d]pyrimidin-6-yl)-N-[(1S)-2,2,2-trifluoro-1-methyl-ethyl]pyridine-3-sulfonamide；6-(5-cyano-7-cyclobutyl-2-methoxypyrrolo[2,3-d]pyrimidin-6-yl)-N-[(2S)-1,1,1-trifluoropropan-2-yl]pyridine-3-sulfonamide
• CAS: 1247930-86-4
• 化学式: C₂₀H₁₉F₃N₆O₃S
• 分子量: 480.47
• InChiKey: BYVLYIICXDQILZ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (5-bromo-2-chloro-pyrimidin-4-yl)cyclobutylamine 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 40.0h， 生成 6-(5-cyano-7-cyclobutyl-2-methoxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-N-[(2S)-1,1,1-trifluoropropan-2-yl]pyridine-3-sulfonamide
  参考文献：
  名称：

  6-(Azaindol-2-yl)pyridine-3-sulfonamides as potent and selective inhibitors targeting hepatitis C virus NS4B

  摘要：

  A structure-activity relationship investigation of various 6-(azaindol-2-yl)pyridine-3-sulfonamides using the HCV replicon cell culture assay led to the identification of a potent series of 7-azaindoles that target the hepatitis C virus NS4B. Compound 2ac, identified via further optimization of the series, has excellent potency against the HCV 1b replicon with an EC50 of 2 nM and a selectivity index of >5000 with respect to cellular GAPDH RNA. Compound 2ac also has excellent oral plasma exposure levels in rats, dogs and monkeys and has a favorable liver to plasma distribution profile in rats. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.093

文献信息

• COMPOUNDS AND METHODS FOR ANTIVIRAL TREATMENT
  申请人：Maccoss Malcolm

  公开号：US20120135999A1

  公开（公告）日：2012-05-31

  The present invention is directed to compounds and forms and pharmaceutical compositions thereof useful for treating a viral infection, or for affecting viral activity by modulating viral replication.

  本发明涉及化合物及其形式和制药组合物，可用于治疗病毒感染，或通过调节病毒复制来影响病毒活性。
• COMBINATIONS OF A HCV INHIBITOR SUCH AS BICYCLIC PYRROLE DERIVATIVES AND A THERAPEUTIC AGENT
  申请人：PTC Therapeutics, Inc.

  公开号：EP2416772A1

  公开（公告）日：2012-02-15
• US9198907B2
  申请人：——

  公开号：US9198907B2

  公开（公告）日：2015-12-01
• US9593108B2
  申请人：——

  公开号：US9593108B2

  公开（公告）日：2017-03-14
• 6-(Azaindol-2-yl)pyridine-3-sulfonamides as potent and selective inhibitors targeting hepatitis C virus NS4B
  作者：Guangming Chen、Hongyu Ren、Nanjing Zhang、William Lennox、Anthony Turpoff、Steven Paget、Chunshi Li、Neil Almstead、F. George Njoroge、Zhengxian Gu、Jason Graci、Stephen P. Jung、Joseph Colacino、Fred Lahser、Xin Zhao、Marla Weetall、Amin Nomeir、Gary M. Karp

  DOI：10.1016/j.bmcl.2014.12.093

  日期：2015.2

  A structure-activity relationship investigation of various 6-(azaindol-2-yl)pyridine-3-sulfonamides using the HCV replicon cell culture assay led to the identification of a potent series of 7-azaindoles that target the hepatitis C virus NS4B. Compound 2ac, identified via further optimization of the series, has excellent potency against the HCV 1b replicon with an EC50 of 2 nM and a selectivity index of >5000 with respect to cellular GAPDH RNA. Compound 2ac also has excellent oral plasma exposure levels in rats, dogs and monkeys and has a favorable liver to plasma distribution profile in rats. (C) 2015 Elsevier Ltd. All rights reserved.