1-cyclopentyl-4-(4-nitrophenyl)piperazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-cyclopentyl-4-(4-nitrophenyl)piperazine
• 化学式: C₁₅H₂₁N₃O₂
• 分子量: 275.351
• InChiKey: BPQLMOSHJDBMDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-cyclopentyl-4-(4-nitrophenyl)piperazine 在 5%-palladium/activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 水 、 正丁醇 为溶剂， 反应 15.0h， 生成 5-cyclopentyl-7-((4-(4-cyclopentylpiperazin-1-yl)phenyl)amino)-[1,2,4]triazolo[4,3-f]pteridin-4(5H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 7-amino-[1,2,4]triazolo[4,3-f]pteridinone, and 7-aminotetrazolo[1,5-f]pteridinone derivative as potent antitumor agents

  摘要：

  To develop novel therapeutic agents with anticancer activities, two series of novel 7-amino-[1,2,4]triazolo[4,3-f]pteridinone, and 7-aminotetrazolo[1,5-f]pteridinone derivatives were designed and synthesized. All compounds were tested for anti-proliferative activities against five cancer cell lines. The structure-activity relationships (SARs) studies were conducted through the variation in two regions, the moiety of A ring and the terminal aniline B on pteridinone core. 1-Methyl-1,2,4-triazole derivative L-7 with 2,6-dimethylpiperazine showed the most potent antiproliferative activity against A549, PC-3, HCT116, MCF-7 and MDA-MB-231 cell lines with IC50 values of 0.16 mu M, 0.30 mu M, 0.511 mu M, 0.30 mu M, and 0.70 mu M, respectively. Combined with the results of the molecular docking and enzymatic studies, the PLK1 was very likely to be one of the drug targets of compound L7. Furthermore, to clarify the anticancer mechanism of compound L7, further explorations in the bioactivity were conducted. The results showed that compound L7 obviously inhibited proliferation of A549 cell lines, induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells, suppressed the migration of tumor cells, and arrested G1 phase of A549 cells. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.12.009
• 作为产物：
  描述：

  碘代环戊烷 、 1-(4-硝基苯基)哌嗪 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 1-cyclopentyl-4-(4-nitrophenyl)piperazine
  参考文献：
  名称：

  Diaminothiazoles having antiproliferative activity

  摘要：

  揭示了一种新型的二氨基噻唑，它们是Cdk4的选择性抑制剂。这些化合物及其药学上可接受的盐和酯是抗增殖剂，在治疗或控制实体肿瘤，特别是乳腺、结肠、肺和前列腺肿瘤方面非常有用。还公开了含有这些化合物的药物组合物，以及制备这些化合物的中间体。

  公开号：

  US20020151554A1

文献信息

• Intermediates useful in the preparation of diaminothiazoles
  申请人：——

  公开号：US20040082595A1

  公开（公告）日：2004-04-29

  Disclosed are novel diaminothiazoles that are selective inhibitors of Cdk4. These compounds and their pharmaceutically acceptable salts and esters are anti-proliferative agents useful in the treatment or control of solid tumors, in particular breast, colon, lung and prostate tumors. Also disclosed are pharmaceutical compositions containing these compounds as well as intermediates useful in the preparation of the compounds.

  本发明涉及新型二氨基噻唑，它们是Cdk4的选择性抑制剂。这些化合物及其药学上可接受的盐和酯是抗增殖剂，可用于治疗或控制实体肿瘤，特别是乳腺、结肠、肺和前列腺肿瘤。还公开了包含这些化合物的药物组合物以及用于制备这些化合物的中间体。
• [EN] INHIBITORS OF BRUTON'S TYROSINE KINASE<br/>[FR] INHIBITEURS DE LA TYROSINE KINASE DE BRUTON
  申请人：PHARMACYCLICS LLC

  公开号：WO2016196776A3

  公开（公告）日：2017-01-05
• DIAMINOTHIAZOLES AND THEIR USE AS INHIBITORS OF CYCLIN-DEPENDENT KINASE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1358169A2

  公开（公告）日：2003-11-05
• INHIBITORS OF BRUTON'S TYROSINE KINASE
  申请人：Pharmacyclics LLC

  公开号：EP3310776A2

  公开（公告）日：2018-04-25
• INHIBITORS OF BRUTONS TYROSINE KINASE
  申请人：Pharmacyclics LLC

  公开号：US20180305348A1

  公开（公告）日：2018-10-25

  Disclosed herein are reversible and irreversible inhibitors of Bruton's tyrosine kinase (Btk). Also disclosed are pharmaceutical compositions that include the compounds. Methods of using the Btk inhibitors are described, alone or in combination with other therapeutic agents, for the treatment of autoimmune diseases or conditions, heteroimmune diseases or conditions, cancer, including lymphoma, and inflammatory diseases or conditions.