9-benzyl-8-hydroxy-2-isobutyladenine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-benzyl-8-hydroxy-2-isobutyladenine
• 英文别名: 6-amino-9-benzyl-2-(2-methylpropyl)-7H-purin-8-one
• 化学式: C₁₆H₁₉N₅O
• 分子量: 297.36
• InChiKey: YPPPULAIGIANQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异戊酸乙酯 在 盐酸 、 乙醇 、 氨 、 溴 、 sodium acetate 、 sodium 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 35.0h， 生成 9-benzyl-8-hydroxy-2-isobutyladenine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 2-substituted-8-hydroxyadenine derivatives as orally available interferon inducers without emetic side effects

  摘要：

  Recently we reported the adenine derivatives (2-4) as new interferon (IFN) inducers. In the present study, we conducted a detailed structure and activity relationship study of 4 and its related derivatives on IFN inducing activity. From this study, we found that compound 4 exhibited the most potent IFN inducing activity in vitro with a minimum effective concentration of 0.01 muM, and 4 also showed strong IFN-inducing activity at doses of more than 0.3 mg/kg by oral administration in mice. This potency was 10-fold stronger than that of Imiquimod. Moreover, 4 did not cause emesis in ferrets even at doses as high as 10 mg/kg, whereas. 80% of animals, were emetic when orally administered with the same dose of Imiquimod. These results indicate that compound 4 is superior to Imiquimod with respect to efficacy and safety. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00369-9

文献信息

• [EN] NITRIC OXIDE RELEASING PRODRUGS OF DIARYL-2-(5H)-FURANONES AS CYCLOOXYGENASE-2 INHIBITORS<br/>[FR] PROMEDICAMENTS DE DIARYL-2-(5H)-FURANONES EN TANT QU'INHIBITEURS DE LA CYCLO-OXYGENASE-2 LIBERANT DE L'OXYDE NITRIQUE
  申请人：MERCK FROSST CANADA INC

  公开号：WO2004011421A1

  公开（公告）日：2004-02-05

  The invention encompasses novel compounds of Formula I, which are nitric oxide-releasing prodrugs of diaryl-2-(5H) furanones useful in the treatment of cyclooxygenase-2 mediated diseases. The invention also encompasses certain pharmaceutical compositions and methods for treatment of cyclooxygenase-2 mediated diseases comprising the use of compounds of Formula I. The above compounds may be used as a combination therapy with low-dose aspirin to treat chronic cyclooxygenase-2 mediated diseases or conditions while simultaneously reducing the risk of thrombotic cardiovascular events.

  该发明涵盖了一种新颖的Formula I化合物，这些化合物是一种二苯基-2-(5H)呋喃酮的一氧化氮释放前药，用于治疗环氧合酶-2介导的疾病。该发明还涵盖了某些用于治疗环氧合酶-2介导疾病的药物组合和方法，包括使用Formula I化合物。上述化合物可作为低剂量阿司匹林的联合治疗，用于治疗慢性环氧合酶-2介导的疾病或症状，同时减少血栓性心血管事件的风险。
• TYPE 2 HELPER T CELL-SELECTIVE IMMUNE RESPONSE SUPPRESSORS
  申请人：Japan Energy Corporation

  公开号：EP1043021A1

  公开（公告）日：2000-10-11

  The present invention relates to a type 2 helper T cell-selective immune response inhibitor, an immune response regulator and an anti-allergic agent, individually comprising, as an active ingredient, a purine derivative represented by General Formula (I):    wherein R2 is hydrogen or a hydrocarbon group in which -CH2- not directly bound to the purine skeleton may be substituted by CO, SO2, O or S, and C-H not directly bound to the purine skeleton may be substituted by N, C-halogen or C-CN; R6 is hydroxyl, amino or amino which is mono- or di-substituted by a hydrocarbon group(s); R8 is hydroxyl, mercapto, acyloxy or hydrocarbon group-substituting oxycarbonyloxy; and R9 is a hydrocarbon group in which -CH2- not directly bound to the purine skeleton may be substituted by CO, SO2, O or S, and C-H not directly bound to the purine skeleton may be substituted by N, C-halogen or C-CN; or its tautomer or a salt of the purine derivative or the tautomer.

  本发明涉及一种 2 型辅助性 T 细胞选择性免疫应答抑制剂、免疫应答调节剂和抗过敏剂，其活性成分分别包括通式 (I) 所代表的嘌呤衍生物： 其中 R2 是氢或烃基，其中与嘌呤骨架不直接结合的-CH2-可被 CO、SO2、O 或 S 取代，与嘌呤骨架不直接结合的 C-H 可被 N、C-卤素或 C-CN 取代； R6 是羟基、氨基或被烃基单取代或二取代的氨基； R8 是羟基、巯基、酰氧基或被烃基取代的氧羰氧基；以及 R9 是烃基，其中与嘌呤骨架不直接结合的-CH2-可被 CO、SO2、O 或 S 取代，与嘌呤骨架不直接结合的 C-H 可被 N、C-卤素或 C-CN 取代； 或其同系物，或该嘌呤衍生物或其同系物的盐。
• PURINE DERIVATIVES FOR THE TREATMENT OF ALLERGIC DISEASES AND SYSTEMIC LUPUS ERYTHEMATOSUS
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1043021B1

  公开（公告）日：2006-05-03
• NOVEL PURINE DERIVATIVES
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：EP0882727B1

  公开（公告）日：2004-12-01
• NITRIC OXIDE RELEASING PRODRUGS OF DIARYL-2-(5H)-FURANONES AS CYCLOOXYGENASE-2 INHIBITORS
  申请人：MERCK FROSST CANADA & CO.

  公开号：EP1527045A1

  公开（公告）日：2005-05-04