2,6-dichloro-9-cyclohexyl-9H-purine | 737005-47-9

• 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: 2,6-dichloro-9-cyclohexyl-9H-purine
• 英文别名: 2,6-Dichloro-9-cyclohexylpurine
• CAS: 737005-47-9
• 化学式: C₁₁H₁₂Cl₂N₄
• 分子量: 271.149
• InChiKey: OOFWIULGXNWDQR-UHFFFAOYSA-N

物化性质

• 沸点：
  360.4±52.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  2,6-dichloro-9-cyclohexyl-9H-purine 在 N,N-二异丙基乙胺 作用下， 以 丙醇 、 正丁醇 为溶剂， 生成 4-((2-((4-aminocyclohexyl)amino)-9-cyclohexyl-9H-purin-6-yl)amino)phenol
  参考文献：
  名称：

  Trisubstituted purine inhibitors of PDGFRα and their antileukemic activity in the human eosinophilic cell line EOL-1

  摘要：

  Inhibition of protein kinases is a validated concept for pharmacological intervention in cancers. Many kinase inhibitors have been approved for clinical use, but their practical application is often limited. Here, we describe a collection of 23 novel 2,6,9-trisubstituted purine derivatives with nanomolar inhibitory activities against PDGFR alpha, a receptor tyrosine kinase often found constitutively activated in various tumours. The compounds demonstrated strong and selective cytotoxicity in the human eosinophilic leukemia cell line EOL-1, whereas several other cell lines were substantially less sensitive. The cytotoxicity in EOL-1, which is known to express the FIP1L1-PDGFR alpha fusion gene encoding an oncogenic kinase, correlated significantly with PDGFR alpha inhibition. EOL-1 cells treated with the compounds also exhibited dose-dependent inhibition of PDGFR alpha autophosphorylation and suppression of its downstream signaling pathways with concomitant G1 phase arrest, confirming the proposed mechanism of action. Our results show that substituted purines can be used as platforms for preparing tyrosine kinase inhibitors with specific activity towards eosinophilic leukemia. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.10.032
• 作为产物：
  描述：

  isopropenylcyclohexane 在 potassium phosphate 、 sodium persulfate 、 4,7-二苯基-1,10-菲罗啉 、 copper diacetate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2,6-dichloro-9-cyclohexyl-9H-purine
  参考文献：
  名称：

  亲芳香性通过光激发和氧化实现脱烯基化功能化

  摘要：

  脱烯基化的 Giese 型加成、肼化、硼化、Minisci 型烷基化、铜催化的 NH 烷基化、酰化、炔基化、氰化和叠氮化，已经以一锅法和高度模块化的方式在含烯烃的底物上实现。

  DOI：

  10.1002/chem.202203425

文献信息

• Development of highly selective casein kinase 1δ/1ε (CK1δ/ε) inhibitors with potent antiproliferative properties
  作者：Mathieu Bibian、Ronald J. Rahaim、Jun Yong Choi、Yoshihiko Noguchi、Stephan Schürer、Weimin Chen、Shima Nakanishi、Konstantin Licht、Laura H. Rosenberg、Lin Li、Yangbo Feng、Michael D. Cameron、Derek R. Duckett、John L. Cleveland、William R. Roush

  DOI：10.1016/j.bmcl.2013.05.075

  日期：2013.8

  The development of a series of potent and highly selective casein kinase 1δ/ε (CK1δ/ε) inhibitors is described. Starting from a purine scaffold inhibitor (SR-653234) identified by high throughput screening, we developed a series of potent and highly kinase selective inhibitors, including SR-2890 and SR-3029, which have IC50 ⩽ 50 nM versus CK1δ. The two lead compounds have ⩽100 nM EC50 values in MTT

  描述了一系列有效且高度选择性的酪蛋白激酶 1δ/ε (CK1δ/ε) 抑制剂的开发。从通过高通量筛选鉴定的嘌呤支架抑制剂 (SR-653234) 开始，我们开发了一系列强效且高激酶选择性的抑制剂，包括 SR-2890 和 SR-3029，与 CK1δ 相比，其 IC 50  ⩽ 50 nM。这两种先导化合物在针对人 A375 黑色素瘤细胞系的 MTT 测定中具有 ⩽100 nM EC 50值，并且具有适合用于针对人癌细胞系的原理动物异种移植研究的物理、体外和体内 PK 特性。
• Compositions and methods for inducing osteogenesis
  申请人：IRM LLC

  公开号：US20040157864A1

  公开（公告）日：2004-08-12

  The present invention provides compositions and methods for differentiating and transdifferentiating mammalian cells into cells of an osteoblast lineage.

  本发明提供了将哺乳动物细胞分化和转分化为成骨细胞系的组合物和方法。
• [EN] SUBSTITUTED 6-(2-HYDROXYBENZYLAMINO)PURINE DERIVATIVES, THEIR USE AS MEDICAMENTS AND COMPOSITIONS CONTAINING THESE DERIVATIVES<br/>[FR] DÉRIVÉS DE 6-(2-HYDROXYBENZYLAMINO)PURINE SUBSTITUÉS, LEUR UTILISATION EN TANT QUE MÉDICAMENTS ET COMPOSITIONS CONTENANT CES DÉRIVÉS
  申请人：UNIV PALACKEHO

  公开号：WO2010139289A1

  公开（公告）日：2010-12-09

  The invention relates to substituted 6-(2-hydroxybenzylamino)purines of general formula I, to their activity as cyclin-dependent kinases 2, 5, 7 and 9 inhibitors and to their use as medicaments, particularly in the treatment of disorders involving cell proliferation or inflammation. The invention further includes pharmaceutical compositions containing the substituted 6-(2-hydroxybenzylamino)purines.

  本发明涉及一般式I的取代6-(2-羟基苯基氨基)嘌呤，以及它们作为细胞周期素依赖性激酶2、5、7和9的抑制剂的活性，以及作为药物，特别是在治疗涉及细胞增殖或炎症的疾病中的用途。本发明还包括含有取代的6-(2-羟基苯基氨基)嘌呤的制药组合物。
• SUBSTITUTED 6-(2-AMINOBENZYLAMINO)PURINE DERIVATIVES, THEIR USE AS MEDICAMENTS AND PREPARATIONS CONTAINING THESE COMPOUNDS
  申请人：Havlicek Libor

  公开号：US20110287111A1

  公开（公告）日：2011-11-24

  The invention relates to new substituted 6-(2-aminobenzylamino)purines, represented by the general formula I, which can be used in CDK inhibition, in particular, in the treatment of viral infections and diseases involving cell proliferation. The invention further includes pharmaceutical preparations containing substituted 6-(2-aminobenzylamino)purines.

  本发明涉及一种新型的取代6-(2-氨基苯基氨基)嘌呤，其通式为I，可用于CDK抑制，特别是用于治疗病毒感染和涉及细胞增殖的疾病。本发明还包括含有取代的6-(2-氨基苯基氨基)嘌呤的药物制剂。
• Substituted 6-(2-hydroxybenzylamino)purine Derivatives, Their Use as Medicaments and Compositions Containing These Derivatives
  申请人：Zatloukal Marek

  公开号：US20120070512A1

  公开（公告）日：2012-03-22

  The invention relates to substituted 6-(2-hydroxybenzylamino)purines of general formula I, to their activity as cyclin-dependent kinases 2, 5, 7 and 9 inhibitors and to their use as medicaments, particularly in the treatment of disorders involving cell proliferation or inflammation. The invention further includes pharmaceutical compositions containing the substituted 6-(2-hydroxybenzylamino)purines.

  本发明涉及一般式I的取代6-(2-羟基苯基氨基)嘌呤，其作为周期素依赖性激酶2、5、7和9的抑制剂的活性以及它们在药物治疗中的使用，特别是在涉及细胞增殖或炎症的疾病治疗中。本发明还包括含有取代6-(2-羟基苯基氨基)嘌呤的药物组合物。