9-benzyl-2-butyladenine | 200292-54-2

• 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: 9-benzyl-2-butyladenine
• 英文别名: 6-amino-9-benzyl-2-n-butyl-9H-purine；9-Benzyl-2-butylpurin-6-amine
• CAS: 200292-54-2
• 化学式: C₁₆H₁₉N₅
• 分子量: 281.36
• InChiKey: LIZPPWLIHFJANQ-UHFFFAOYSA-N

物化性质

• 沸点：
  441.9±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-benzyl-2-butyladenine 在 盐酸 、 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 10.0h， 生成 9-benzyl-2-butyl-8-hydroxyadenine
  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
• 作为产物：
  描述：

  戊酸乙酯 在 乙醇 、 氨 、 sodium 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 25.0h， 生成 9-benzyl-2-butyladenine
  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

• Amide derivatives
  申请人：Otsuka Pharmaceutical Factory, Inc.

  公开号：US06166016A1

  公开（公告）日：2000-12-26

  The invention provides amide derivatives which are useful as analgesics, anti-inflammatory agents, antimicrobial drugs, hypoglycemic agents, hypolipidemic agents, antihypertensive agents, anti-cancer agents, etc., the derivatives being represented by the formula ##STR1## wherein ring A represents a benzene ring, a naphthalene ring, a pyridine ring or a furan ring; R.sup.4 represents a heterocyclic group selected from the group consisting of a lower alkyl-substituted thieno[3,2-d]pyrimidin-4-yl group, an optionally substituted pyrazolo[1,5-a]-1,3,5-triazin-4-yl group, a pyrazolo[3,4-d]pyrimidin-4-yl group substituted at the 6-position and a purin-6-yl group substituted at the 2-position; and R.sup.5 represents a hydrogen atom or a group represented by ##STR2##

  该发明提供了一种酰胺衍生物，可用作止痛药、抗炎药、抗微生物药、降糖药、降脂药、降压药、抗癌药等，所述衍生物由下式表示： 其中环A代表苯环、萘环、吡啶环或呋喃环；R.sup.4代表从以下群组中选择的杂环基团，即低烷基取代的噻吩[3,2-d]嘧啶-4-基团、可取代的吡唑并[1,5-a]-1,3,5-三嗪-4-基团、在6-位取代的吡唑并[3,4-d]嘧啶-4-基团以及在2-位取代的嘌呤-6-基团；R.sup.5代表氢原子或由以下式表示的基团：
• AMIDE DERIVATIVES
  申请人：OTSUKA PHARMACEUTICAL FACTORY, INC.

  公开号：EP0915093A1

  公开（公告）日：1999-05-12

  The invention provides amide derivatives which are useful as analgesics, anti-inflammatory agents, antimicrobial drugs, hypoglycemic agents, hypolipidemic agents, antihypertensive agents, anti-cancer agents, etc., the derivatives being represented by the formula wherein ring A represents a benzene ring, a naphthalene ring, a pyridine ring or a furan ring; R4 represents a heterocyclic group selected from the group consisting of a lower alkyl-substituted thieno[3,2-d]pyrimidin-4-yl group, an optionally substituted pyrazolo[1,5-a]-1,3,5-triazin-4-yl group, a pyrazolo[3,4-d]pyrimidin-4-yl group substituted at the 6-position and a purin-6-yl group substituted at the 2-position; and R5 represents a hydrogen atom or a group represented by

  本发明提供了可用作镇痛药、消炎药、抗菌药、降血糖药、降血脂药、降血压药、抗癌药等的酰胺衍生物，这些衍生物由式表示 其中环 A 代表苯环、萘环、吡啶环或呋喃环；R4 代表杂环基团，该杂环基团选自由低级烷基取代的噻吩并[3,2-d]嘧啶-4-基、任选取代的吡唑并[1,5-a]-1,3,5-三嗪-4-基、在 6 位取代的吡唑并[3,4-d]嘧啶-4-基和在 2 位取代的嘌呤-6-基组成的基团；以及 R5 代表氢原子或由以下各项代表的基团
• US6166016A
  申请人：——

  公开号：US6166016A

  公开（公告）日：2000-12-26
• Synthesis and structure–activity relationships of 2-substituted-8-hydroxyadenine derivatives as orally available interferon inducers without emetic side effects
  作者：Yoshiaki Isobe、Masanori Tobe、Haruhisa Ogita、Ayumu Kurimoto、Tetsuhiro Ogino、Hajime Kawakami、Haruo Takaku、Hironao Sajiki、Kosaku Hirota、Hideya Hayashi

  DOI：10.1016/s0968-0896(03)00369-9

  日期：2003.8

  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.