2-Butylamino-8-hydroxy-9-(6-methoxy-3-pyridylmethyl)adenine | 473930-14-2

• 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: 2-Butylamino-8-hydroxy-9-(6-methoxy-3-pyridylmethyl)adenine
• 英文别名: 6-amino-2-(butylamino)-9-[(6-methoxypyridin-3-yl)methyl]-7H-purin-8-one
• CAS: 473930-14-2
• 化学式: C₁₆H₂₁N₇O₂
• 分子量: 343.388
• InChiKey: CZLMIMMJWDOSAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Butylamino-8-hydroxy-9-(6-methoxy-3-pyridylmethyl)adenine 、 氯甲酸乙酯 在 4-二甲氨基吡啶 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以71%的产率得到2-Butylamino-8-ethoxycarbonyloxy-9-(6-methoxy-3-pyridylmethyl)adenine
  参考文献：
  名称：

  NOVEL ADENINE DERIVATIVES

  摘要：

  公开号：

  EP1386923B1
• 作为产物：
  描述：

  2-N-butyl-8-methoxy-9-[(6-methoxypyridin-3-yl)methyl]purine-2,6-diamine 在 盐酸 作用下， 反应 3.0h， 生成 2-Butylamino-8-hydroxy-9-(6-methoxy-3-pyridylmethyl)adenine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel 9-Substituted-8-Hydroxyadenine Derivatives as Potent Interferon Inducers

  摘要：

  Recently we reported the adenine derivatives 3a-d as novel interferon (IFN) inducers. In the present study, we conducted a detailed structure-activity relationship study of analogues of 3a-d with respect to their IFN-inducing activity, mainly focusing on the N(9)-position of the adenine. From this study, we found that introduction of the 3-pyridylmethyl moiety was effective to increase in vitro activity, and compound 9ae was identified as being the most potent IFN inducer. This compound gave a minimum effective concentration (MEC) of 3 nM, which is comparable with that of R-848, a second generation IFN inducer. Compound 9ae also demonstrated potent IFN-inducing activity at a dose of 0.1 mg/kg by oral administration in mice. Furthermore, compound 9ae induced IFN in monkeys in a dose dependent manner, with a potency superior to that of R-848. In addition, 9ae did not cause emesis in ferrets even at a dose of 30 mg/kg. In this study the maximum plasma concentration of 9ae was 1019 ng/mL (ca. 3.1 mu M), which was approximately 1000-fold higher than the MEC value. Therefore, with respect to both the efficacy and the safety margin, compound 9ae (SM-276001) is considered to be a promising compound as an orally active IFN inducer.

  DOI：

  10.1021/jm051089s

文献信息

• Novel adenne derivatives
  申请人：——

  公开号：US20040132748A1

  公开（公告）日：2004-07-08

  This invention relates to an adenine derivative, a tautomer thereof, or a pharmaceutically acceptable salt thereof represented by general formula (I): 1 wherein X represents NR 3 (wherein R 3 represents a hydrogen atom or C 1-3 alkyl) or the like; R 1 represents substituted or unsubstituted alkyl or the like; R 2 represents hydroxyl or the like; and Y represents a substituted or unsubstituted aromatic hetero ring or the like. Also, the present invention relates to pharmaceuticals such as an interferon inducer, antiviral agent, anticancer agent, type 2 helper T cell selective immune response inhibitor, antiallergic agent, and immune response modulator comprising the above derivative as an active ingredient.

  本发明涉及一种由通式（I）表示的腺嘌呤衍生物、其互变异构体或其药学上可接受的盐，其中X代表NR3（其中R3代表氢原子或C1-3烷基）或类似物；R1代表取代或未取代的烷基或类似物；R2代表羟基或类似物；Y代表取代或未取代的芳香杂环或类似物。此外，本发明还涉及将上述衍生物作为活性成分的药物，例如干扰素诱导剂、抗病毒剂、抗癌剂、2型辅助T细胞选择性免疫反应抑制剂、抗过敏剂和免疫反应调节剂。
• Adenine derivatives
  申请人：Dainippon Simitomo Pharma Co., Ltd.

  公开号：US07157465B2

  公开（公告）日：2007-01-02

  This invention relates to an adenine derivative, a tautomer thereof, or a pharmaceutically acceptable salt thereof represented by general formula (I): wherein X represents NR3 (wherein R3 represents a hydrogen atom or C1-3 alkyl) or the like; R1 represents substituted or unsubstituted alkyl or the like; R2 represents hydroxyl or the like; and Y represents a substituted or unsubstituted aromatic hetero ring or the like. Also, the present invention relates to pharmaceuticals such as an interferon inducer, antiviral agent, anticancer agent, type 2 helper T cell selective immune response inhibitor, antiallergic agent, and immune response modulator comprising the above derivative as an active ingredient.

  本发明涉及一种腺嘌呤衍生物、其互变异构体或其药学上可接受的盐，其通式表示为（I）：其中X代表NR3（其中R3代表氢原子或C1-3烷基）或类似物；R1代表取代或未取代的烷基或类似物；R2代表羟基或类似物；Y代表取代或未取代的芳香杂环或类似物。此外，本发明还涉及一种以上述衍生物为活性成分的药物，例如干扰素诱导剂、抗病毒剂、抗癌剂、第二型辅助T细胞选择性免疫反应抑制剂、抗过敏剂和免疫反应调节剂。
• Novel adenine derivatives
  申请人：Isobe Yoshiaki

  公开号：US20070037832A1

  公开（公告）日：2007-02-15

  This invention relates to an adenine derivative, a tautomer thereof, or a pharmaceutically acceptable salt thereof represented by general formula (I): wherein X represents NR 3 (wherein R 3 represents a hydrogen atom or C 1-3 alkyl) or the like; R 1 represents substituted or unsubstituted alkyl or the like; R 2 represents hydroxyl or the like; and Y represents a substituted or unsubstituted aromatic hetero ring or the like. Also, the present invention relates to pharmaceuticals such as an interferon inducer, antiviral agent, anticancer agent, type 2 helper T cell selective immune response inhibitor, antiallergic agent, and immune response modulator comprising the above derivative as an active ingredient.

  本发明涉及一种腺嘌呤衍生物，其互变异构体或药学上可接受的盐，由下式表示：其中X代表NR3（其中R3代表氢原子或C1-3烷基）或类似物；R1代表取代或未取代的烷基或类似物；R2代表羟基或类似物；Y代表取代或未取代的芳香杂环或类似物。此外，本发明涉及上述衍生物作为活性成分的制备干扰素诱导剂、抗病毒剂、抗癌剂、选择性抑制2型辅助T细胞免疫反应抑制剂、抗过敏剂和免疫反应调节剂等药物。
• US7157465B2
  申请人：——

  公开号：US7157465B2

  公开（公告）日：2007-01-02
• US7521454B2
  申请人：——

  公开号：US7521454B2

  公开（公告）日：2009-04-21