2-Chloro-9-(2-phenylethyl)purin-6-amine | 1026264-24-3

• 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-Chloro-9-(2-phenylethyl)purin-6-amine
• CAS: 1026264-24-3
• 化学式: C₁₃H₁₂ClN₅
• 分子量: 273.725
• InChiKey: VMFHGINYKQXEBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  2-Chloro-9-(2-phenylethyl)purin-6-amine 在 盐酸 、 溴 作用下， 以 1,4-二氧六环 、 丙醇 、 氯仿 为溶剂， 反应 17.0h， 生成 6-amino-2-(butylamino)-9-(2-phenylethyl)-7H-purin-8-one
  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
• 作为产物：
  描述：

  邻氯乙苯 、 2-氯-6-氨基嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-Chloro-9-(2-phenylethyl)purin-6-amine
  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

• A2A adenosine receptor antagonists
  申请人：——

  公开号：US20030149060A1

  公开（公告）日：2003-08-07

  Disclosed are novel A 2A adenosine receptor antagonists, useful for treating various disease states, for example cardiovascular disorders, including tissue damage due to ischemia, CNS diseases, including Parkinson's disease, depression, and the like.

  揭示了一种新型A2A腺苷受体拮抗剂，可用于治疗各种疾病状态，例如心血管疾病，包括因缺血引起的组织损伤，中枢神经系统疾病，包括帕金森病、抑郁症等。
• A3 ADENOSINE RECEPTOR ANTAGONISTS
  申请人：Zablocki Jeff

  公开号：US20090099212A1

  公开（公告）日：2009-04-16

  Disclosed are novel methods of antagonizing the A 3 adenosine receptor in a mammal, comprising administering to a mammal in need thereof a therapeutically effective dose of a compound of the formula: wherein R is hydrogen or acyl; R 1 is hydrogen, halo, optionally substituted C 1-4 alkyl, optionally substituted alkenyl, optionally substituted aryl, or optionally substituted heteroaryl; R 2 is optionally substituted C 1-4 alkyl; Y is C 1-4 alkylene; and Z is phenyl, optionally substituted with halo, optionally substituted C 1-4 alkyl, or C 1-4 alkoxy. The A 3 adenosine receptors may be antagonized in order to treat a disease state is chosen from renal failure, nephritis, hypertension, oedemas, Alzheimers disease, stress, depression, cardiac arrhythmia, restoration of cardiac function, asthma, respiratory disorders, ischemia-induced injury of the brain, heart and kidney, and diarrhea. Preferred compounds selectively antagonize A 3 adenosine receptors over A 1 adenosine receptors, A 2A adenosine receptors and A 2B adenosine receptors.

  本发明涉及一种在哺乳动物中拮抗A3腺苷受体的新方法，包括向需要治疗的哺乳动物中给予化合物的治疗有效剂量，该化合物的结构式为：其中R为氢或酰基；R1为氢、卤素、可选取代的C1-4烷基、可选取代的烯基、可选取代的芳基或可选取代的杂环基；R2为可选取代的C1-4烷基；Y为C1-4烷基；Z为苯基，可选取代卤素、可选取代的C1-4烷基或C1-4烷氧基。可以拮抗A3腺苷受体以治疗肾功能衰竭、肾炎、高血压、水肿、阿尔茨海默病、压力、抑郁症、心律失常、恢复心脏功能、哮喘、呼吸系统疾病、缺血性脑、心脏和肾脏损伤以及腹泻等疾病状态。优选的化合物选择性地拮抗A3腺苷受体而不是A1腺苷受体、A2A腺苷受体和A2B腺苷受体。
• A2B adenosine receptor antagonists
  申请人：——

  公开号：US20030064999A1

  公开（公告）日：2003-04-03

  Disclosed are novel compounds that are A 2B adenosine receptor antagonists, useful for treating various disease states, in particular asthma and diarrhea.

  本发明涉及新型化合物，其为A2B腺苷受体拮抗剂，可用于治疗各种疾病状态，特别是哮喘和腹泻。
• PURINE DERIVATIVES AS A2B ADENOSINE RECEPTOR ANTAGONISTS
  申请人：CV THERAPEUTICS, INC.

  公开号：EP1401837B1

  公开（公告）日：2005-10-19
• A2A ADENOSINE RECEPTOR ANTAGONISTS
  申请人：CV THERAPEUTICS, INC.

  公开号：EP1456209A1

  公开（公告）日：2004-09-15