ethyl 2-(2,6-dichloro-9H-purin-9-yl)acetate | 171827-50-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(2,6-dichloro-9H-purin-9-yl)acetate
• 英文别名: Ethyl 2,6-dichloro-9H-purine-9-acetate；ethyl 2-(2,6-dichloropurin-9-yl)acetate
• CAS: 171827-50-2
• 化学式: C₉H₈Cl₂N₄O₂
• 分子量: 275.094
• InChiKey: CTFNNRKKJAICKH-UHFFFAOYSA-N

物化性质

• 熔点：
  112-114 °C
• 沸点：
  387.8±52.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2,6-dichloro-9H-purin-9-yl)acetate 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 2-甲基四氢呋喃 、 水 、 异丙醇 、 乙腈 为溶剂， 反应 2.75h， 生成 Ethyl 2-[2-[4-(4-methylpiperazin-1-yl)phenyl]-6-(2-morpholin-4-ylethylamino)purin-9-yl]acetate
  参考文献：
  名称：

  [EN] NOVEL IMMUNE SYSTEM MODULATORS
  [FR] NOUVEAUX MODULATEURS DU SYSTÈME IMMUNITAIRE

  摘要：

  本发明涉及一种化合物，其化学式如下：或其药用盐，其中符号如规范中定义；包含该化合物的药物组合物；以及使用该化合物治疗或预防自身免疫疾病的方法。

  公开号：

  WO2012167053A1
• 作为产物：
  描述：

  氯乙酸乙酯 、 2,6-二氯嘌呤 在 三乙胺 作用下， 以 水 为溶剂， 反应 0.13h， 以40%的产率得到ethyl 2-(2,6-dichloro-9H-purin-9-yl)acetate
  参考文献：
  名称：

  Anti-proliferative activity of 2,6-dichloro-9- or 7-(ethoxycarbonylmethyl)-9H- or 7H-purines against several human solid tumour cell lines

  摘要：

  As leads we took several benzo-fused seven- and six-membered scaffolds linked to the pyrimidine or purine moieties with notable anti-proliferative activity against human breast, colon and melanoma cancerous cell lines. We then decided to maintain the double-ringed nitrogenous bases and change the other components to the ethyl acetate moiety. This way six purine and two 5-fluorouracil derivatives were obtained and evaluated against the MCF-7, HCT-116, A-375 and G-361 cancer cell lines. Two QSARs are obtained between the anti-proliferative IC50 values for compounds 26-33 and the clog P against the melanoma cell lines A-375 and G-361. Our results show that two of the analogues [ethyl 2-(2,6-dichloro-9H- or 7H-purine-9- or 7-yl)acetates (30 and 33, respectively)] are potent cytotoxic agents against all the tumour cell lines assayed, showing single-digit micromolar IC50 values. This exemplifies the potential of our previously reported purine compounds to qualify as lead structures for medicinal chemistry campaigns, affording simplified analogues easy to synthesize and with a noteworthy bioactivity. The selective activity of 30 and 33 against the melanoma cell line A-375, via apoptosis, supposes a great advantage for a future therapeutic use. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.012

文献信息

• [EN] COMPOUNDS AS INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR<br/>[FR] COMPOSÉS EN TANT QU'INHIBITEURS DU FACTEUR INHIBITEUR DE LA MIGRATION DES MACROPHAGES
  申请人：IMMUNOPHAGE BIOMEDICAL CO LTD

  公开号：WO2020186220A1

  公开（公告）日：2020-09-17

  The present invention provides compounds of Formula (I) shown above and their pharmaceutically acceptable salt, solvates, isomers, or prodrugs, as well as pharmaceutical compositions containing these compounds. Also provided by the invention is a method for treating a disorder mediated by macrophage migration inhibitory factor in a subject, comprising administering to the subject in need thereof a compound or a pharmaceutical composition of this invention.

  本发明提供了上述公式(I)所示的化合物及其药用可接受的盐、溶剂化物、异构体或前药，以及含有这些化合物的药物组合物。本发明还提供了一种用于治疗由巨噬细胞迁移抑制因子介导的疾病的方法，包括向需要治疗的对象施用本发明的化合物或药物组合物。
• Purine derivatives as purinergic receptor antagonists
  申请人：——

  公开号：US20040102459A1

  公开（公告）日：2004-05-27

  Use of a compound of formula (I) wherein R 1 is selected from alkyl, aryl, alkoxy, aryloxy, 0thioalkyl, thioaryl, CN, halo, NR 5 R 6 , NR 4 COR 5 , NR 4 CONR 5 R 6 , NR 4 CO 2 R 7 and NR 4 SO 2 R 7 ; R 2 is selected from N, O or S-containing heteroaryl groups, wherein the heteroaryl group is attached via an unsaturated carbon atom which is adjacent to one or two N, O or S-heteroatom(s), other than ortho, ortho-disubstituted heteroaryl groups; R 3 is selected from H, alkyl, COR 8 , CONR 9 R 10 , CONR 8 NR 9 R 10 , CO 2 R 11 and SO 2 R 11 ; R 4 , R 5 and R 6 are independently selected from H, alkyl and aryl or where R 5 and R 6 are in an (NR 5 R 6 ) group then R 5 and R 6 may be linked to form a heterocyclic ring; R 7 is selected from alkyl and aryl; R 8 , R 9 and R 10 are independently selected from H, alkyl and aryl, or R 9 and R 10 may be linked to form a heterocyclic ring, or where R 8 , R 9 and R 10 are in a (CONR 8 NR 9 R 10 ) group, R 8 and R 9 may be linked to form a heterocyclic group; and R 11 , is selected from alkyl and aryl, or a pharmaceutically acceptable salt thereof or prodrug thereof, in the treatment or prevention of a disorder in which the blocking of purine receptors, particularly adenosine receptors and more particularly A 2A receptors, may be beneficial, particularly wherein said disorder is a movement disorder such as Parkinson's disease or said disorder is depression, cognitive or memory impairment, acute or chronic pain, ADHD or narcolepsy, or for neuroprotection in a subject; compounds of formula (I) for use in therapy; and novel compounds of formula (I) per se. 1

  使用公式（I）中的化合物，其中R1从烷基、芳基、烷氧基、芳氧基、0硫代烷基、硫代芳基、CN、卤素、NR5R6、NR4COR5、NR4CONR5R6、NR4CO2R7和NR4SO2R7中选择；R2从含N、O或S的杂环芳基组中选择，其中该杂环芳基组通过与一个或两个N、O或S杂原子相邻的不饱和碳原子连接，除了邻位、邻位二取代的杂环芳基组之外；R3从H、烷基、COR8、CONR9R10、CONR8NR9R10、CO2R11和SO2R11中选择；R4、R5和R6分别从H、烷基和芳基中选择，或者当R5和R6在(NR5R6)基团中时，R5和R6可以连接形成杂环戒；R7从烷基和芳基中选择；R8、R9和R10分别从H、烷基和芳基中选择，或者R9和R10可以连接形成杂环戒，或者当R8、R9和R10在(CONR8NR9R10)基团中时，R8和R9可以连接形成杂环基团；R11从烷基和芳基中选择，或者其药学上可接受的盐或前药，在治疗或预防阻断嘌呤受体，特别是腺苷受体，尤其是A2A受体，可能有益的紊乱中，特别是当该紊乱是运动障碍，如帕金森病，或该紊乱是抑郁症、认知或记忆障碍、急性或慢性疼痛、ADHD或嗜睡症时，或用于主体的神经保护；公式（I）的化合物用于治疗；以及公式（I）的新化合物本身。
• [EN] 2-MORPHOLINYLPURINES AS INHIBITORS OF PI3K<br/>[FR] 2 -MORPHOLINYLPURINES EN TANT QU'INHIBITEURS DE PI3K
  申请人：S BIO PTE LTD

  公开号：WO2009045174A1

  公开（公告）日：2009-04-09

  The present invention relates to purine compounds that are useful as kinase inhibitors. More particularly, the present invention relates to purine compounds, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative disorders. These compounds may be useful as medicaments for the treatment of a number of proliferative disorders including tumours and cancers as well as other disorders or conditions related to or associated with mTOR kinases.

  本发明涉及作为激酶抑制剂有用的嘌呤化合物。更具体地说，本发明涉及嘌呤化合物、其制备方法、含有这些化合物的药物组合物以及在治疗增殖性疾病中使用这些化合物的用途。这些化合物可能作为药物用于治疗多种增殖性疾病，包括肿瘤和癌症以及与mTOR激酶相关的其他疾病或症状。
• P13K ISOFORM SELECTIVE INHIBITORS
  申请人：Liang Congxin

  公开号：US20110130395A1

  公开（公告）日：2011-06-02

  2-Morpholin-4-yl-9H-purine and 5-Morpholin-4-yl-3H-[1,2,3]triazolo[4,5-d]pyrimidine derivatives, especially those substituted by 6-heteroaryl, are unexpected PI3 kinase isoform selective inhibitors with good drug properties and are useful in treating disorders related to abnormal PI3K activities such as cancer, immune disorders, cardiovascular disease, viral infection, inflammation, metabolism/endocrine disorders and neurological disorders.

  2-吗啡啉-4-基-9H-嘌呤和5-吗啡啉-4-基-3H-[1,2,3]三唑[4,5-d]嘧啶衍生物，特别是那些被6-杂环芳基取代的衍生物，是意外的PI3K酶亚型选择性抑制剂，具有良好的药物特性，并可用于治疗与异常PI3K活性相关的疾病，如癌症、免疫障碍、心血管疾病、病毒感染、炎症、代谢/内分泌障碍和神经系统疾病。
• 2-MORPHOLINYLPURINES AS INHIBITORS OF PI3K
  申请人：Nagaraj Harish Kumar Mysore

  公开号：US20110009403A1

  公开（公告）日：2011-01-13

  The present invention relates to purine compounds that are useful as kinase inhibitors. More particularly, the present invention relates to purine compounds, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative disorders. These compounds may be useful as medicaments for the treatment of a number of proliferative disorders including tumours and cancers as well as other disorders or conditions related to or associated with mTOR kinases.

  本发明涉及嘌呤化合物，可用作激酶抑制剂。更具体地说，本发明涉及嘌呤化合物、其制备方法、含有这些化合物的药物组合物以及这些化合物在治疗增殖性疾病方面的用途。这些化合物可以作为药物治疗多种增殖性疾病，包括肿瘤和癌症以及与mTOR激酶相关或相关的其他疾病或病况。