2-chloro-4-methyl-7-methylamino-4H-imidazo[4,5-d]thiazolo[5,4-b]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-chloro-4-methyl-7-methylamino-4H-imidazo[4,5-d]thiazolo[5,4-b]pyridine
• 英文别名: N5,8-dimethyl-2-chloro-8H-imidazo[4,5-d]thiazolo[5,4-b]pyridine-5-amine；4-chloro-N,12-dimethyl-5-thia-3,7,10,12-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2(6),3,7,10-pentaen-8-amine
• 化学式: C₉H₈ClN₅S
• 分子量: 253.715
• InChiKey: KQUYNSOABMROIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,3,6-四氢吡啶 、 2-chloro-4-methyl-7-methylamino-4H-imidazo[4,5-d]thiazolo[5,4-b]pyridine 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 4-methyl-7-methylamino-2-[1,2,3,6-tetrahydropyridine]-4Himidazo[4,5-d]thiazolo[5,4-b]pyridine
  参考文献：
  名称：

  Novel Tricyclic Inhibitors of IκB Kinase

  摘要：

  The design and synthesis of a novel series of oxazole-, thiazole-, and imidazole-based inhibitors of I kappa B kinase (IKK) are reported. Biological activity was improved compared to the pyrazolopurine lead, and the expedient synthesis of the new tricyclic systems allowed for efficient exploration of structure-activity relationships. This, combined with an iterative rat cassette dosing strategy, was used to identify compounds with improved pharmacokinetic (PK) profiles to advance for in vivo evaluation.

  DOI：

  10.1021/jm8015816
• 作为产物：
  描述：

  2-hydroxy-4-methyl-7-methylamino-4H-imidazo[4,5-d]thiazolo[5,4-b]pyridine 在 吡啶 、 三氯氧磷 作用下， 反应 48.0h， 以90%的产率得到2-chloro-4-methyl-7-methylamino-4H-imidazo[4,5-d]thiazolo[5,4-b]pyridine
  参考文献：
  名称：

  Novel Tricyclic Inhibitors of IκB Kinase

  摘要：

  The design and synthesis of a novel series of oxazole-, thiazole-, and imidazole-based inhibitors of I kappa B kinase (IKK) are reported. Biological activity was improved compared to the pyrazolopurine lead, and the expedient synthesis of the new tricyclic systems allowed for efficient exploration of structure-activity relationships. This, combined with an iterative rat cassette dosing strategy, was used to identify compounds with improved pharmacokinetic (PK) profiles to advance for in vivo evaluation.

  DOI：

  10.1021/jm8015816

文献信息

• [EN] OXAZOLYL - AND THIAZOLYL - PURINE BASED TRICYCLIC COMPOUNDS.<br/>[FR] COMPOSES TRICYCLIQUES A BASE D'OXAZOLO[4,5-B]PYRIDINE CONDENSEE A UN IMIDAZO ET DE THIAZOLO[4,5-B]PYRIDINE CONDENSEE A UN IMIDAZO, ET COMPOSITIONS PHARMACEUTIQUES RENFERMANT CEUX-CI
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2004106293A3

  公开（公告）日：2005-03-24
• US7176214B2
  申请人：——

  公开号：US7176214B2

  公开（公告）日：2007-02-13
• Novel Tricyclic Inhibitors of IκB Kinase
  作者：James Kempson、Steven H. Spergel、Junqing Guo、Claude Quesnelle、Patrice Gill、Dominique Belanger、Alaric J. Dyckman、Tianle Li、Scott H. Watterson、Charles M. Langevine、Jagabandhu Das、Robert V. Moquin、Joseph A. Furch、Anne Marinier、Marco Dodier、Alain Martel、David Nirschl、Katy Van Kirk、James R. Burke、Mark A. Pattoli、Kathleen Gillooly、Kim W. McIntyre、Laishun Chen、Zheng Yang、Punit H. Marathe、David Wang-Iverson、John H. Dodd、Murray McKinnon、Joel C. Barrish、William J. Pitts

  DOI：10.1021/jm8015816

  日期：2009.4.9

  The design and synthesis of a novel series of oxazole-, thiazole-, and imidazole-based inhibitors of I kappa B kinase (IKK) are reported. Biological activity was improved compared to the pyrazolopurine lead, and the expedient synthesis of the new tricyclic systems allowed for efficient exploration of structure-activity relationships. This, combined with an iterative rat cassette dosing strategy, was used to identify compounds with improved pharmacokinetic (PK) profiles to advance for in vivo evaluation.