6-chloro-2,9-dimethyl-9H-purine | 40423-36-7

• 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: 6-chloro-2,9-dimethyl-9H-purine
• 英文别名: 6-chloro-2,9-dimethylpurine
• CAS: 40423-36-7
• 化学式: C₇H₇ClN₄
• 分子量: 182.612
• InChiKey: SKTPMBONYIWPAC-UHFFFAOYSA-N

物化性质

• 熔点：
  168-171 °C
• 沸点：
  237.5±50.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-2,9-dimethyl-9H-purine 、 N-甲基-P-氨基苯甲醚 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 0.17h， 以75%的产率得到N-(4-methoxyphenyl)-N,2,9-trimethyl-9H-purin-6-amine
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 6-phenylaminopurines

  摘要：

  A series of novel 6-phenylaminopurines have been efficiently synthesized in 3 steps exploring different groups at positions 2, 8 and 9 of the purine ring and at the exocyclic nitrogen atom at position 6. Among the newly described purines, five compounds showed antiproliferative activity with IC50 values below 10 mu M, the tetrahydroquinoline derivative at position 6 of phenylaminopurine being the most active of the series in the six cell lines tested. Moreover, the compounds induced G(2)/M phase arrest in human cervical carcinoma HeLa cells as reported for tubulin depolymerizing agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.093
• 作为产物：
  描述：

  2-甲基-4,6-二氯-5-氨基嘧啶 在 乙基磺酸 作用下， 以 1,4-二氧六环 、 水 、 乙酸酐 为溶剂， 反应 0.25h， 生成 6-chloro-2,9-dimethyl-9H-purine
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 6-phenylaminopurines

  摘要：

  A series of novel 6-phenylaminopurines have been efficiently synthesized in 3 steps exploring different groups at positions 2, 8 and 9 of the purine ring and at the exocyclic nitrogen atom at position 6. Among the newly described purines, five compounds showed antiproliferative activity with IC50 values below 10 mu M, the tetrahydroquinoline derivative at position 6 of phenylaminopurine being the most active of the series in the six cell lines tested. Moreover, the compounds induced G(2)/M phase arrest in human cervical carcinoma HeLa cells as reported for tubulin depolymerizing agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.093

文献信息

• [EN] SUBSTITUTED PYRAZOLO/IMIDAZOLO BICYCLIC COMPOUNDS AS PDE2 INHIBITORS<br/>[FR] COMPOSÉS BICYCLIQUES PYRAZOLO/IMIDAZOLO SUBSTITUÉS EN TANT QU'INHIBITEURS DE PDE2
  申请人：MERCK SHARP & DOHME

  公开号：WO2016209749A1

  公开（公告）日：2016-12-29

  The present invention is directed to pyrimidine carboxamide compounds of formula I which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

  本发明涉及式I的嘧啶羧酰胺化合物，其可用作治疗与磷酸二酯酶2（PDE2）相关的中枢神经系统疾病的治疗剂。本发明还涉及利用这些化合物治疗神经系统和精神疾病，如精神分裂症、精神病、帕金森病、帕金森病痴呆（PDD）或亨廷顿病，以及与纹状体功能不足或基底节功能障碍相关的疾病。
• Synthetic Studies Directed towards Agelasine Analogs - Synthesis, Tautomerism, and Alkylation of 2-Substituted<i>N</i>-Methoxy-9-methyl-9<i>H</i>-purin-6-amines
  作者：Heidi Roggen、Lise-Lotte Gundersen

  DOI：10.1002/ejoc.200800627

  日期：2008.10

  followed by a displacement of the chlorine. Great variations in the amino/imino tautomer ratio among the compounds studied were observed. The tautomers were identified by NMR methods. Treatment of N-methoxy-9-methyl-9H-purin-6-amines carrying alkyl, alkoxy, or amino substituents in the 2 position with benzyl bromide resulted in a mixture of N-7- and N6-benzylated compounds with the former as the major

  N-Methoxy-9-methyl-9H-purin-6-amines 在 2 个位置带有各种取代基，通过已知 6-氯嘌呤的 N-甲基化合成，然后置换氯。观察到所研究化合物中氨基/亚氨基互变异构体比例的巨大变化。通过NMR方法鉴定互变异构体。用苄基溴处理在 2 位带有烷基、烷氧基或氨基取代基的 N-甲氧基-9-甲基-9H-嘌呤-6-胺产生 N-7- 和 N6- 苄基化化合物的混合物，前者为主要产品。N-Methoxy-9-methyl-9H-purin-6-amines 在 C-2 上具有强电负性取代基在相同的反应条件下几乎不发生反应。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim，德国，2008）
• Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic
  申请人：Merck & Co., Inc.

  公开号：US05057517A1

  公开（公告）日：1991-10-15

  There are disclosed certain 6-piperazinopurines and heteroaromatic derivatives thereof which have oral hypoglycemic acitivity and with such ability to lower blood sugar are useful in the treatment of type II diabetes and/or obesity with associated insulin resistance. Processes for the preparation of such compounds and compositions containing such compounds as the active ingredient thereof are also disclosed.

  本文披露了某些6-哌嗪嘌呤和其杂环衍生物，具有口服降糖活性，并具有降低血糖的能力，可用于治疗II型糖尿病和/或伴随胰岛素抵抗的肥胖症。本文还披露了制备这些化合物的方法以及含有这些化合物作为其活性成分的组合物。
• Piperazinyl derivates of purines and isosteres thereof as hypoglycemic agents
  申请人：Merck & Co., Inc.

  公开号：EP0300726A1

  公开（公告）日：1989-01-25

  There are disclosed certain 6-piperazino-­purine and heteroaromatic derivatives thereof which have oral hypoglycemic activity and with such ability to lower blood sugar are useful in the treatment of type II diabetes and/or obesity with associated insulin resistance. Processes for the preparation of such compounds and compositions containing such compounds as the active ingredient thereof are also disclosed.

  已公开的某些 6-哌嗪基嘌呤及其杂芳香族衍生物具有口服降血糖活性，这种降血糖能力可用于治疗 II 型糖尿病和/或伴有胰岛素抵抗的肥胖症。 此外，还公开了制备此类化合物的工艺和含有此类化合物作为其活性成分的组合物。
• Substituted pyrazolo/imidazolo bicyclic compounds as PDE2 inhibitors
  申请人：Merck Sharp & Dohme Corp.

  公开号：US10647727B2

  公开（公告）日：2020-05-12

  The present invention is directed to pyrimidine carboxamide compounds of formula I which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

  本发明涉及式 I 的嘧啶羧酰胺化合物，该化合物可作为治疗剂用于治疗与磷酸二酯酶 2 (PDE2)相关的中枢神经系统疾病。本发明还涉及使用此类化合物治疗神经和精神疾病，如精神分裂症、精神病、帕金森病、帕金森病痴呆（PDD）或亨廷顿病，以及与纹状体功能低下或基底节功能障碍相关的疾病。