2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-N-((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine | 911826-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-N-((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine
• 英文别名: 2-(6-fluorobenzimidazol-1-yl)-N-[(4R)-8-fluoro-3,4-dihydro-2H-chromen-4-yl]-5-nitropyrimidin-4-amine
• CAS: 911826-27-2
• 化学式: C₂₀H₁₄F₂N₆O₃
• 分子量: 424.366
• InChiKey: YYIMEEFPVKKABR-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-N-((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine 在 sodium dithionite 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)N4-((R)-8-fluorochroman-4-yl)pyrimidine-4,5-diamine
  参考文献：
  名称：

  2-Benzimidazolyl-9-(chroman-4-yl)-purinone derivatives as JAK3 inhibitors

  摘要：

  A novel class of Janus tyrosine kinase 3 (JAK3) inhibitors based on a 2-benzimidazoylpurinone core structure is described. Through substitution of the benzimidazoyl moiety and optimization of the N-9 substituent of the purinone, compound 24 was identified incorporating a chroman-based functional group. Compound 24 shows excellent kinase activity, good oral bioavailability and demonstrates efficacy in an acute mechanistic mouse model through inhibition of interleukin-2 (IL-2) induced interferon-gamma (INF-gamma) production. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.080
• 作为产物：
  描述：

  (R)-8-氟苯并二氢吡喃-4-胺盐酸盐 、 6-Fluoro-1-(4-isothiocyanato-5-nitropyrimidin-2-yl)benzimidazole 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-N-((R)-8-fluorochroman-4-yl)-5-nitropyrimidin-4-amine
  参考文献：
  名称：

  2-Benzimidazolyl-9-(chroman-4-yl)-purinone derivatives as JAK3 inhibitors

  摘要：

  A novel class of Janus tyrosine kinase 3 (JAK3) inhibitors based on a 2-benzimidazoylpurinone core structure is described. Through substitution of the benzimidazoyl moiety and optimization of the N-9 substituent of the purinone, compound 24 was identified incorporating a chroman-based functional group. Compound 24 shows excellent kinase activity, good oral bioavailability and demonstrates efficacy in an acute mechanistic mouse model through inhibition of interleukin-2 (IL-2) induced interferon-gamma (INF-gamma) production. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.080

文献信息

• Purine and imidazopyridine derivatives for immunosuppression
  申请人：Ohlmeyer J. Michael

  公开号：US20070021443A1

  公开（公告）日：2007-01-25

  The present invention provides novel purine and imidazopyridine derivatives useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formulas:

  本发明提供了新型嘌呤和咪唑吡啶衍生物，可用于预防和治疗自身免疫性疾病、炎症性疾病、肥大细胞介导疾病和移植排斥。这些化合物的一般式如下：
• PURINE AND IMIDAZOPYRIDINE DERIVATIVES FOR IMMUNOSUPPRESSION
  申请人：Ohlmeyer Michael J.

  公开号：US20080287468A1

  公开（公告）日：2008-11-20

  The present invention provides novel purine and imidazopyridine derivatives useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formulas:

  本发明提供了新型嘌呤和咪唑吡啶衍生物，用于预防和治疗自身免疫性疾病、炎症性疾病、肥大细胞介导的疾病和移植排斥。这些化合物的一般式如下：
• WO2006/108103
  申请人：——

  公开号：——

  公开（公告）日：——
• US7884109B2
  申请人：——

  公开号：US7884109B2

  公开（公告）日：2011-02-08
• [EN] PURINE AND IMIDAZOPYRIDINE DERIVATIVES FOR IMMUNOSUPPRESSION<br/>[FR] DERIVES DE PURINE ET D'IMIDAZOPYRIDINE EN VUE D'UNE IMMUNOSUPPRESSION
  申请人：PHARMACOPEIA DRUG DISCOVERY

  公开号：WO2006108103A1

  公开（公告）日：2006-10-12

  [EN] The present invention provides novel purine and imidazopyridine derivatives useful for the prevention and treatment of autoimmune diseases, inflammatory disease, mast cell mediated disease and transplant rejection. The compounds are of the general formulas ( I ) and ( II ).
  [FR] La présente invention concerne de nouveaux dérivés de purine et d'imidazopyridine utiles dans la prévention de maladies autoimmunes, d'une maladie inflammatoire, d'une maladie liée aux mastocytes et d'un rejet d'une transplantation. Les composés sont de formule générale (I) et (II).