3-((2-chloro-9H-purin-6-yl)amino)phenol | 1089014-27-6

• 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: 3-((2-chloro-9H-purin-6-yl)amino)phenol
• 英文别名: 3-(2-chloro-9H-purin-6-ylamino)phenol；3-[(2-chloro-7H-purin-6-yl)amino]phenol
• CAS: 1089014-27-6
• 化学式: C₁₁H₈ClN₅O
• 分子量: 261.67
• InChiKey: GQQGXGBYWOXQSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-((2-chloro-9H-purin-6-yl)amino)phenol 、 histamine dichloride 在 三乙胺 作用下， 以 正丁醇 为溶剂， 130.0 ℃ 、1.79 MPa 条件下， 反应 0.17h， 以35%的产率得到3-((2-((2-(1H-imidazol-4-yl)ethyl)amino)-9H-purin-6-yl)amino)phenol
  参考文献：
  名称：

  Discovery of Multitarget Antivirals Acting on Both the Dengue Virus NS5-NS3 Interaction and the Host Src/Fyn Kinases

  摘要：

  This study describes the discovery of novel dengue virus inhibitors targeting both a crucial viral protein protein interaction and an essential host cell factor as a strategy to reduce the emergence of drug resistance. Starting from known c-Src inhibitors, a virtual screening was performed to identify molecules able to interact with a recently discovered allosteric pocket on the dengue virus NS5 polymerase. The selection of cheap-to-produce scaffolds and the exploration of the biologically relevant chemical space around them suggested promising candidates for chemical synthesis. A series of purines emerged as the most interesting candidates able to inhibit virus replication at low micromolar concentrations with no Significant toxicity to the host cell. Among the identified antivirals, compound 16i proved to be 10 times More potent than ribavirin, showed a better selectivity index and represents the first-in-class DENV-NS5 allosteric inhibitor able to target both the virus NS5-NS3 interaction and the host kinases c-Src/Fyn.

  DOI：

  10.1021/acs.jmedchem.5b00108
• 作为产物：
  描述：

  2,6-二氯嘌呤 、 3-氨基苯酚 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 0.17h， 以81%的产率得到3-((2-chloro-9H-purin-6-yl)amino)phenol
  参考文献：
  名称：

  通过功能化喹啉和2,6-二氨基嘌呤支架鉴定广谱登革热/寨卡病毒复制抑制剂

  摘要：

  在过去的50年中，世界各地的社会和人口变化导致了诸如登革热病毒（DENV）和寨卡病毒（ZIKV）之类的虫媒病毒的大量爆发。尽管增加了感染威胁，但尚无批准的药物或完全保护性疫苗可抵消DENV和ZIKV的传播。与经典的“单虫/单药”方法相比，针对多种病毒常见成分的“广谱”抗病毒药（BSA）的开发可以成为一种限制病毒病原体快速出现的更有效策略。从先前确定的多靶点DENV抑制剂开始，本文报道了能够阻止Zika病毒和所有血清型登革热病毒（DENV 1-4）在感染细胞中复制的新型2,6-二氨基嘌呤衍生物的鉴定。

  DOI：

  10.1002/cmdc.201800178

文献信息

• Identification of Breast Cancer Inhibitors Specific for G Protein-Coupled Estrogen Receptor (GPER)-Expressing Cells
  作者：Francesca Aiello、Gabriele Carullo、Francesca Giordano、Elena Spina、Alessandra Nigro、Antonio Garofalo、Sabrina Tassini、Gabriele Costantino、Paolo Vincetti、Agostino Bruno、Marco Radi

  DOI：10.1002/cmdc.201700145

  日期：2017.8.22

  Together with estrogen receptors ERα and ERβ, the G protein-coupled estrogen receptor (GPER) mediates important pathophysiological signaling pathways induced by estrogens and is currently regarded as a promising target for ER-negative (ER-) and triple-negative (TN) breast cancer. Only a few selective GPER modulators have been reported to date, and their use in cancer cell lines has often led to contradictory

  G蛋白偶联雌激素受体（GPER）与雌激素受体ERα和ERβ一起介导雌激素诱导的重要病理生理信号传导途径，目前被认为是ER阴性（ER-）和三阴性（TN）乳腺癌的有希望的靶点癌症。迄今为止，仅报道了几种选择性的GPER调节剂，它们在癌细胞系中的使用常常导致矛盾的结果。在此，我们报告了虚拟筛选和基于细胞的研究在鉴定具有针对表达GPER的乳腺癌细胞系的特异性抗增殖作用的新型化学支架中的应用。在确定的四种不同支架中，发现8-氯-4-（4-氯苯基）吡咯并[1,2-a]喹喔啉14 c是最有前途的化合物，能够诱导：1）与G15相似，在表达GPER的细胞系（MCF7和SKBR3）中具有抗增殖活性；2）对不表达GPER（HEK293）的细胞无影响；3）细胞周期蛋白D1表达降低；4）持续诱导细胞周期负调节子p53和p21。
• SUBSTITUTED 6-ANILINOPURINE DERIVATIVES AS INHIBITORS OF CYTOKININ OXIDASE/DEHYDROGENASE AND PREPARATIONS CONTAINING THESE DERIVATIVES
  申请人：Spichal Lukas

  公开号：US20100190806A1

  公开（公告）日：2010-07-29

  The invention relates to substituted 6-anilinopurine derivatives of the general formula I, wherein R denotes one to five substituents independently selected from the group consisting of hydrogen, halogen, hydroxyl, amino, alkyloxy and alkyl group, and R2 denotes amino, halogen, nitro, thio, alkylthio or alkyl group for use as inhibitors of cytokinin oxidase/dehydrogenase. The invention also relates to the compositions containing these derivatives.

  该发明涉及一般式I的取代6-苯胺嘧啶衍生物，其中R表示从氢、卤素、羟基、氨基、烷氧基和烷基组成的群体中独立选择的一个至五个取代基，R2表示氨基、卤素、硝基、硫代基、烷硫基或烷基，用作细胞分裂素氧化酶/脱氢酶的抑制剂。该发明还涉及含有这些衍生物的组合物。
• Novel potent inhibitors of A. thaliana cytokinin oxidase/dehydrogenase
  作者：Marek Zatloukal、Markéta Gemrotová、Karel Doležal、Libor Havlíček、Lukáš Spíchal、Miroslav Strnad

  DOI：10.1016/j.bmc.2008.09.008

  日期：2008.10

  The synthesis of a new group of 2-X-6-anilinopurines, including compounds with potential cytokinin-like activities, with various substitutions (X = H, halogen, amino, methylthio or nitro) on the phenyl ring is described. The prepared compounds have been characterized using standard physico-chemical methods, and the influence of individual substituents on biological activity has been compared in three different bioassays, based on the stimulation of tobacco callus growth, retention of chlorophyll in excised wheat leaves and the dark induction of betacyanin synthesis in Amaranthus cotyledons. The biological activity of the prepared compounds was also assessed in receptor assays, in which the ability of the compounds to activate the cytokinin receptors AHK3 and AHK4/CRE1 was studied. Finally, the interactions of the compounds with the Arabidopsis cytokinin oxidase/dehydrogenase AtCKX2 (heterologously expressed) were investigated. Systematic testing led to the identification of two very potent inhibitors of AtCKX2: 2-chloro-6-(3-methoxyphenyl)aminopurine and 2-fluoro-6-(3-methoxyphenyl) aminopurine. (C) 2008 Elsevier Ltd. All rights reserved.
• US8222260B2
  申请人：——

  公开号：US8222260B2

  公开（公告）日：2012-07-17
• [EN] SUBSTITUTED 6-ANILINOPURINE DERIVATIVES AS INHIBITORS OF CYTOKININ OXIDASE/DEHYDROGENASE AND PREPARATIONS CONTAINING THESE DERIVATIVES<br/>[FR] DÉRIVÉS DE 6-ANILINOPURINE SUBSTITUÉE EN TANT QU'INHIBITEURS DE LA CYTOKININE OXYDASE/DÉSHYDROGÉNASE ET PRÉPARATIONS CONTENANT CES DÉRIVÉS
  申请人：UNIVERZITA PALACKEHO V OLOMOUC

  公开号：WO2009003428A2

  公开（公告）日：2009-01-08

  The invention relates to substituted 6-anilinopurine derivatives of the general formula I, wherein R denotes one to five substituents independently selected from the group consisting of hydrogen, halogen, hydroxyl, amino, alkyloxy and alkyl group, and R2 denotes amino, halogen, nitro, thio, alkylthio or alkyl group for use as inhibitors of cytokinin oxidase/dehydrogenase. The invention also relates to the compositions containing these derivatives.