9-benzyl-8-hydroxy-2-pentyladenine

• 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-pentyladenine
• 英文别名: 6-amino-9-benzyl-2-pentyl-7H-purin-8-one
• 化学式: C₁₇H₂₁N₅O
• 分子量: 311.387
• InChiKey: ZAWMWDWFMSIBKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  正己酸乙酯 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-pentyladenine
  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] 8-AZABICYCLO[3.2.1]OCTANE ETHER DERIVATIVES AND THEIR USE AS NEUROKININ RECEPTOR ANTAGONISTS<br/>[FR] DERIVES D'ETHER 8-AZABICYCLO[3.2.1]OCTANE ET LEUR UTILISATION EN TANT QU'ANTAGONISTES DE RECEPTEUR DE NEUROKININE
  申请人：MERCK SHARP & DOHME

  公开号：WO2004031185A1

  公开（公告）日：2004-04-15

  The present invention relates compounds of the formula (I) : wherein X represents hydrogen, C1-4alkyl optionally substituted by a hydroxy, methoxy or benzyloxy group, or CO2(C1-2alkyl); Z is -CR9R10CH2- or -CH2CR9R10-; and R1, R2, R3, R4, R5 and R6 are as defined herein. The compounds are of particular use in the treatment or prevention of depression, anxiety, pain, inflammation, migaine, emesis or postherpetic neuralgia.

  本发明涉及以下式(I)的化合物：其中X代表氢，C1-4烷基，可选择地被羟基，甲氧基或苄氧基取代，或CO2(C1-2烷基)；Z为-CR9R10CH2-或-CH2CR9R10-；而R1、R2、R3、R4、R5和R6如本文所定义。这些化合物在治疗或预防抑郁症、焦虑、疼痛、炎症、偏头痛、呕吐或带状疱疹后神经痛方面具有特殊用途。
• Type 2 helper T cell-selective immune response suppressors
  申请人：Japan Energy Corporation

  公开号：US06376501B1

  公开（公告）日：2002-04-23

  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.

  本发明涉及一种选择性抑制2型辅助T细胞免疫反应的免疫反应调节剂、调节免疫反应的药物和抗过敏剂，其中包括以下通式（I）所代表的嘌呤衍生物作为活性成分：其中R2是氢或烃基，其中—CH2—不直接连接到嘌呤骨架的烃基可以被CO、SO2、O或S替代，而不直接连接到嘌呤骨架的C—H可以被N、C-卤素或C—CN替代；R6是羟基、氨基或被一个或两个烃基取代的氨基；R8是羟基、巯基、酰氧基或被烃基取代的氧羧酸酯基；R9是烃基，其中—CH2—不直接连接到嘌呤骨架的烃基可以被CO、SO2、O或S替代，而不直接连接到嘌呤骨架的C—H可以被N、C-卤素或C—CN替代；或其互变异构体或嘌呤衍生物或互变异构体的盐。
• 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。
• US6028076
  申请人：——

  公开号：——

  公开（公告）日：——
• 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