4-chloro-7-(4-methoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidine | 947327-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 4-chloro-7-(4-methoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 4-chloro-7-[(4-methoxyphenyl)methyl]pyrrolo[2,3-d]pyrimidine
• CAS: 947327-26-6
• 化学式: C₁₄H₁₂ClN₃O
• 分子量: 273.722
• InChiKey: AOBRTFHRAUTAGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-7-(4-methoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidine 、 2-(三丁基锡烷基)呋喃 在 双三苯基磷二氯化钯 氮 、 氟化钾，无水 、 甲醇 、 silica gel 、 ethyl acetate n-hexane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 4-(2-furyl)-7-(4-methoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Purine compounds

  摘要：

  本发明提供了一种抗分枝杆菌的6-芳基-9-(m-或p-取代苄基)嘌呤和嘌呤类似化合物。

  公开号：

  US20070203159A1
• 作为产物：
  描述：

  4-甲氧基氯苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.75h， 以60%的产率得到4-chloro-7-(4-methoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Purine compounds

  摘要：

  这项发明提供了一种抗分枝杆菌的6-芳基-9-(m-或p-取代苄基)嘌呤和嘌呤类似化合物。

  公开号：

  US20070203159A1

文献信息

• Expanding the Diversity of Allosteric Bcr-Abl Inhibitors
  作者：Xianming Deng、Barun Okram、Qiang Ding、Jianming Zhang、Yongmun Choi、Francisco J. Adrián、Amy Wojciechowski、Guobao Zhang、Jianwei Che、Badry Bursulaya、Sandra W. Cowan-Jacob、Gabriele Rummel、Taebo Sim、Nathanael S. Gray

  DOI：10.1021/jm100555f

  日期：2010.10.14

  Inhibition of Bcr-Abl kinase activity by imatinib for the treatment of chronic myeloid leukemia (CML) currently serves as the paradigm for targeting dominant oncogenes with small molecules. We recently reported the discovery of GNF-2 (1) and GNF-5 (2) as selective non-ATP competitive inhibitors of cellular Bcr-Abl kinase activity that target the myristate binding site. Here, we used cell-based structure−activity

  伊马替尼对 Bcr-Abl 激酶活性的抑制用于治疗慢性粒细胞白血病 (CML)，目前作为用小分子靶向显性癌基因的范例。我们最近报道了 GNF-2 ( 1 ) 和 GNF-5 ( 2 ) 作为靶向肉豆蔻酸结合位点的细胞 Bcr-Abl 激酶活性的选择性非 ATP 竞争性抑制剂的发现。在这里，我们使用基于细胞的结构-活性关系来指导能够与肉豆蔻酸酯结合位点结合的配体的优化和多样化，并使基于 Abl-化合物1的发现合理化共晶。我们阐明了获得针对 Bcr-Abl 转化细胞的强效抗增殖活性所需的结构-活性关系，并报告了新化合物（5g、5h、6a、14d和21j-I）的发现，这些化合物显示出改进的效力或药理特性。这项工作表明，多种结构可以有效地靶向 Bcr-Abl 肉豆蔻酸酯结合位点，并为开发可靶向该结合位点的药物提供了新的线索。
• Identification and synthesis of substituted pyrrolo[2,3-d]pyrimidines as novel firefly luciferase inhibitors
  作者：Yang Liu、Jianping Fang、Haiyan Cai、Fei Xiao、Kan Ding、Youhong Hu

  DOI：10.1016/j.bmc.2012.07.035

  日期：2012.9

  A novel firefly luciferase inhibitor (3a) with a pyrrolo[2,3-d]pyrimidine core was identified in a cell-based NF-κB luciferase reporter gene assay. It potently inhibited the firefly luciferase derived from Photinus pyralis with an IC50 value of 0.36 ± 0.05 μM. Kinetic analysis of 3a inhibition showed that it is predominantly competitive with respect to d-luciferin and uncompetitive with respect to

  在基于细胞的NF-κB萤光素酶报告基因分析中鉴定出一种新型的具有吡咯并[2,3- d ]嘧啶核的萤火虫萤光素酶抑制剂（3a）。它有效地抑制了源自Photinus pyralis的萤火虫荧光素酶，其IC 50值为0.36±0.05μM。对3a抑制的动力学分析表明，它相对于d-荧光素主要竞争，而相对于ATP不竞争。因此，制备了几种吡咯并[2，3- d ]嘧啶类似物以进一步研究荧光素酶抑制的构效关系（SAR）。该系列中最有效的抑制剂是4c，显示出IC50值为0.06±0.01μM。此外，分子对接研究表明3a和4c都可以容纳在d-荧光素结合袋中，这对于d-荧光素主要是竞争性抑制剂。
• Palladium-Catalyzed Highly Regioselective C6 Arylation of Pyrrolo[2,3-<i>d</i>]pyrimidine Derivatives with Arylboronic Acids
  作者：Min Liu、Chunwei Shen、Ting Tang、Chenhong Pan、Mingrui Liu、Xingxian Zhang

  DOI：10.1021/acs.orglett.3c00680

  日期：2023.4.21

  A mild and selective C6 arylation strategy for pyrrolo[2,3-d]pyrimidine derivatives with arylboronic acids at room temperature is described. This unified protocol has been achieved by the synergistic combination of Pd(II)/TEMPO catalysis and CF3CO2H promotion under silver-, base-, and additive-free conditions. The broad substrate scope, good functional group tolerance, excellent regioselectivity, and

  描述了在室温下吡咯并 [2,3- d ] 嘧啶衍生物与芳基硼酸的温和选择性 C6 芳基化策略。该统一协议是通过 Pd(II)/TEMPO 催化和 CF 3 CO 2 H 促进在无银、无碱和无添加剂的条件下的协同组合实现的。广泛的底物范围、良好的官能团耐受性、出色的区域选择性以及空气和水分耐受性使该过程对于靶向小分子药物的有效合成和修饰具有吸引力。
• Synthesis of non-purine analogs of 6-aryl-9-benzylpurines, and their antimycobacterial activities. Compounds modified in the imidazole ring
  作者：Abhijit Datta Khoje、Aisvareya Kulendrn、Colin Charnock、Baojie Wan、Scott Franzblau、Lise-Lotte Gundersen

  DOI：10.1016/j.bmc.2010.08.016

  日期：2010.10.15

  Purine analogs modified in the five-membered ring have been synthesized and examined for antibacterial activity against Mycobacterium tuberculosis H(37)Rv in vitro employing the microplate alamar blue assay (MABA). The 9-deaza analogs were only found to be weak inhibitors, but the 8-aza-, 7-deaza- and 8-aza-7-deazapurine analogs studied displayed excellent antimycobacterial activities, some even substantially better than the parent purine. In the 7-deazapurine series, MIC values between 0.08 and 0.35 mu M, values comparable or better than the reference drugs used in the study (MIC rifampicin 0.09 mu M, MIC isoniazid 0.28 mu M and MIC PA-824 0.44 mu M). The five most active compounds were also examined against a panel of drug-resistant Mtb strain, and they all retained their activity. The compounds examined were significantly less active against M. tuberculosis in a state of non-replicating persistence (NRP). MIC in the low-oxygen-recovery assay (LORA) >= 60 mu M. The 7-deazapurines were somewhat more toxic towards mammalian cells, but still the selectivity indexes were excellent. The non-purine analogs exhibit a selective antimycobacterial activity. They were essentially inactive against Staphylococcus aureus and Escherichia coli. (C) 2010 Elsevier Ltd. All rights reserved.