N-[3-(trifluoromethyl)phenyl]-1-Piperazinecarboxamide | 1225578-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[3-(trifluoromethyl)phenyl]-1-Piperazinecarboxamide
• 英文别名: N-[3-(trifluoromethyl)phenyl]piperazine-1-carboxamide
• CAS: 1225578-90-4
• 化学式: C₁₂H₁₄F₃N₃O
• mdl: MFCD13427041
• 分子量: 273.258
• InChiKey: NXZKKDNKJPWQIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[3-(trifluoromethyl)phenyl]-1-Piperazinecarboxamide 在 三乙酰氧基硼氢化钠 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 4-{[(3S)-1-cyclopropylpiperidin-3-yl]methyl}-N-[3-(trifluoromethyl)phenyl]piperazine-1-carboxamide
  参考文献：
  名称：

  The design and synthesis of novel, potent and orally bioavailable N-aryl piperazine-1-carboxamide CCR2 antagonists with very high hERG selectivity

  摘要：

  A novel N-aryl piperazine-1-carboxamide series of human CCR2 chemokine receptor antagonists was discovered. Early analogues were potent at CCR2 but also inhibited the hERG cardiac ion channel. Structural modifications which decreased lipophilicity and basicity resulted in the identification of a sub-series with an improved margin over hERG. The pharmacological and pharmacokinetic properties of the lead compound from this series, N-(3,4-dichlorophenyl)-4-[(2R)-4-isopropylpiperazine-2-carbonyl]piperazine-1-carboxamide, are described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.118
• 作为产物：
  描述：

  tert-butyl 4-(3-(trifluoromethyl)phenylcarbamoyl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-[3-(trifluoromethyl)phenyl]-1-Piperazinecarboxamide
  参考文献：
  名称：

  Novel 5-anilinoquinazoline-8-nitro derivatives as inhibitors of VEGFR-2 tyrosine kinase: synthesis, biological evaluation and molecular docking

  摘要：

  血管内皮生长因子受体-2（VEGFR-2）激酶抑制是一种公认的策略，旨在通过抑制血管生成来迅速应对肿瘤生长。本文报告了一系列以1,3-双取代脲为取代基的5-氨基喹唑啉衍生物。所有新合成的化合物均经过评估，以测试其对VEGFR-2激酶的抑制作用和对多种癌细胞的抗增殖活性。新型的1-芳基、3-芳基-双取代脲喹唑啉是有效的VEGFR-2激酶抑制剂，其体外IC50值在亚微摩尔范围内（化合物6f，IC50为12.0 nM），但在癌细胞上表现出较弱到中等的抑制活性。采用分子对接研究了这些化合物的分子相互作用。

  DOI：

  10.1039/c3ob40368h

文献信息

• Tie-2 Modulators and Methods of Use
  申请人：Bannen Canne Lynne

  公开号：US20070275952A1

  公开（公告）日：2007-11-29

  The present invention provides compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. Compounds of the invention inhibit, regulate and/or modulate kinases, particularly Tie-2. Methods of using the compounds and pharmaceutical compositions thereof to treat kinase-dependent diseases and conditions are also an aspect of the invention.

  本发明提供了用于调节蛋白激酶酶活性以调节细胞活动，如增殖、分化、程序性细胞死亡、迁移和化学侵袭的化合物。本发明的化合物抑制、调节和/或调节激酶，特别是Tie-2。使用这些化合物及其制药组合物治疗激酶依赖性疾病和病况的方法也是本发明的一个方面。
• POLY (ADP-RIBOSE) POLYMERASE INHIBITOR
  申请人：Chengdu Di'ao Pharmaceutical Group Co., Ltd.

  公开号：EP2799435B1

  公开（公告）日：2018-03-28
• US8013156B2
  申请人：——

  公开号：US8013156B2

  公开（公告）日：2011-09-06
• US9187430B2
  申请人：——

  公开号：US9187430B2

  公开（公告）日：2015-11-17
• Novel 5-anilinoquinazoline-8-nitro derivatives as inhibitors of VEGFR-2 tyrosine kinase: synthesis, biological evaluation and molecular docking
  作者：Liang Xi、Jian-Qiang Zhang、Zhi-Cheng Liu、Ji-Hong Zhang、Ju-Fang Yan、Yi Jin、Jun Lin

  DOI：10.1039/c3ob40368h

  日期：——

  Vascular endothelial growth factor receptor-2 (VEGFR-2) kinase inhibition is a well-established strategy to promptly tackle tumor growth by suppression of angiogenesis. We report herein a series of 5-anilinoquinazoline derivatives substituted by 1,3-disubstituted urea. All the newly synthesized compounds described were evaluated for VEGFR-2 kinase inhibition and antiproliferative activity against various cancer cells. The novel 1-aryl, 3-aryl-disubstituted urea quinazolines were effective VEGFR-2 kinase inhibitors with in vitro IC50 values in the submicromolar range (compound 6f, IC50 12.0 nM), but showed a weak to moderate inhibitory activity on cancer cells. Molecular interactions of the compounds were studied using molecular docking studies.

  血管内皮生长因子受体-2（VEGFR-2）激酶抑制是一种公认的策略，旨在通过抑制血管生成来迅速应对肿瘤生长。本文报告了一系列以1,3-双取代脲为取代基的5-氨基喹唑啉衍生物。所有新合成的化合物均经过评估，以测试其对VEGFR-2激酶的抑制作用和对多种癌细胞的抗增殖活性。新型的1-芳基、3-芳基-双取代脲喹唑啉是有效的VEGFR-2激酶抑制剂，其体外IC50值在亚微摩尔范围内（化合物6f，IC50为12.0 nM），但在癌细胞上表现出较弱到中等的抑制活性。采用分子对接研究了这些化合物的分子相互作用。