9-butyl-8-hydroxyadenine

• 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-butyl-8-hydroxyadenine
• 英文别名: 6-amino-9-butyl-7H-purin-8-one
• 化学式: C₉H₁₃N₅O
• 分子量: 207.235
• InChiKey: IXCGAPZSWYHFCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  8-溴-9-丁基-9h-嘌呤-6-胺 以63%的产率得到9-butyl-8-hydroxyadenine
  参考文献：
  名称：

  Type 2 helper T cell-selective immune response suppressors

  摘要：

  本发明涉及一种选择性抑制T细胞辅助型2型免疫应答的免疫应答调节剂、免疫调节剂和抗过敏剂，分别包括一种以通式(I)表示的嘌呤衍生物作为活性成分：其中R2是氢或烃基，在其中—CH2—不直接与嘌呤骨架结合的部分可能被CO、SO2、O或S取代，而未直接与嘌呤骨架结合的部分可能被N、C-卤或C—CN取代；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、酰氧基或烃基取代的氧羰氧基；以及R9是烃基，在其中—CH2—不直接与嘌呤骨架结合的部分可能被CO、SO2、O或S取代，而未直接与嘌呤骨架结合的部分可能被N、C-卤或C—CN取代；或其互变异构体或嘌呤衍生物或其互变异构体的盐。

  公开号：

  US06376501B1

文献信息

• Efficient synthesis of 2,9-disubstituted 8-hydroxyadenine derivatives
  作者：Kosaku Hirota、Kazunori Kazaoka、Itaru Niimoto、Hironao Sajiki

  DOI：10.1039/b300557g

  日期：2003.4.14

  An efficient and general method for the synthesis of 2,9-disubstituted 8-hydroxyadenines, which are expected to have various biological activities, was realized. 5-Amino-4-cyano-2-hydroxyimidazoles (1) were prepared from aminomalononitrile and isocyanates as key intermediates. The condensation of 1a with amidines, imidates, guanidine, urea and thioureas afforded 8-hydroxyadenines (2–6) possessing various substituents at the 2-position. Furthermore, selective alkylation of 2-amino- and 2-hydroxyadenines (4 and 6) successively proceeded to give the corresponding 2-alkylamino- and 2-alkoxyadenines (5 and 7), respectively. 2-Alkylthioadenines (15) were prepared by an analogous reaction of 1a with benzoyl isothiocyanate and subsequent S-alkylation. The imidazoles 1 are most useful intermediates for the synthesis of 8-hydroxyadenine derivatives.

  一种高效且通用的方法被实现，用于合成预期具有多种生物活性的2,9-二取代的8-羟基腺苷。5-氨基-4-氰基-2-羟基咪唑（1）是从氨基丙腈和异氰酸酯作为关键中间体制备的。将1a与氨基脲、咪唑、胍、尿素和硫脲缩合，得到在2位具有各种取代基的8-羟基腺苷（2–6）。此外，对2-氨基和2-羟基腺苷（4和6）进行选择性烷基化，顺利实现，分别得到相应的2-烷基氨基和2-烷氧腺苷（5和7）。2-烷基硫腺苷（15）是通过1a与苯甲酰异硫氰酸酯的类似反应以及随后S-烷基化制备的。咪唑类化合物1是合成8-羟基腺苷衍生物最有用的中间体。
• 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：——
• Novel and Efficient Synthesis of 8-Oxoadenine Derivatives
  作者：Kosaku Hirota、Kazunori Kazaoka、Itaru Niimoto、Hironao Sajiki

  DOI：10.3987/com-01-9356

  日期：——

  A novel synthetic method of 8-oxoadenine derivatives (3 and 4) is reported. This widely applicable synthetic method was realized through the use of 5-aminlo-4-cyano-2-oxoimidazole derivatives (2) as the key intermediates. A variety of substituents were successfully introduced to the 2- and 9-position of the 8-oxoadenine nucleus.
• 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