N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-2-phenyloxazole-4-carboxamide | 1186295-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-2-phenyloxazole-4-carboxamide
• 英文别名: ND-6492；gm7-70-1；N-[(1-benzyltriazol-4-yl)methyl]-2-phenyl-1,3-oxazole-4-carboxamide
• CAS: 1186295-72-6
• 化学式: C₂₀H₁₇N₅O₂
• 分子量: 359.387
• InChiKey: QSHQUQWRHYEZES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-phenyl-N-(prop-2-ynyl)oxazole-4-carboxamide 、 苄基叠氮 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 96.0h， 生成 N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-2-phenyloxazole-4-carboxamide
  参考文献：
  名称：

  N-((1-Benzyl-1H-1,2,3-triazol-4-yl)methyl)arylamide as a New Scaffold that Provides Rapid Access to Antimicrotubule Agents: Synthesis and Evaluation of Antiproliferative Activity Against Select Cancer Cell Lines

  摘要：

  A series of N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)arylamides was synthesized by copper-catalyzed azide alkyne cycloaddition (CuAAC) and afforded inhibitors of cancer cell growth. For example, compound 13e had an IC50 of 46 nM against MCF-7 human breast tumor cells. Structure activity relationship (SA R) studies demonstrated that (i) meta-phenoxy substitution of the N-1-benzyl group is important for antiproliferative activity and (ii) a variety of heterocyclic substitutions for the aryl group of the arylamide are tolerated. In silico COMPARE analysis of antiproliferative activity against the NCI-60 human tumor cell line panel revealed a correlation to clinically useful antimicrotubule agents such as paclitaxel and vincristine. This in silico correlation was supported by (i) in vitro inhibition of tubulin polymerization, (ii) G(2)/M-phase arrest in HeLa cells as assessed by flow cytometry, and (iii) perturbation of normal microtubule activity in HeLa cells as observed by confocal microscopy. The results demonstrate that N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)arylamide is a readily accessible small molecule scaffold for compounds that inhibit tubulin polymerization and tumor cell growth.

  DOI：

  10.1021/jm1000979

文献信息

• ANTI-CANCER COMPOUNDS, SYNTHESIS THEREOF, AND METHODS OF USING SAME
  申请人：Miller Marvin J.

  公开号：US20110021574A1

  公开（公告）日：2011-01-27

  Embodiments relate to the field of chemistry and biochemistry, and, more specifically, to anti-cancer compounds, synthesis thereof, and methods of using same. Disclosed herein are various heterocyclic compounds and methods of using the novel anti-cancer compounds to inhibit the growth of a cancer cell, for instance a leukemia, non-small cell lung, central nervous system (CNS), skin, ovarian, renal, prostate, breast, or colon cancer cell. Other embodiments include methods of treating cancer in a subject, such as using the disclosed heterocyclic anti-cancer agents.
• US8268874B2
  申请人：——

  公开号：US8268874B2

  公开（公告）日：2012-09-18
• US8729270B2
  申请人：——

  公开号：US8729270B2

  公开（公告）日：2014-05-20
• [EN] ANTI-CANCER COMPOUNDS, SYNTHESIS THEREOF, AND METHODS OF USING SAME<br/>[FR] COMPOSÉS ANTICANCÉREUX, SYNTHÈSE DE CEUX-CI, ET PROCÉDÉS UTILISANT CEUX-CI
  申请人：UNIV NOTRE DAME DU LAC

  公开号：WO2009111502A2

  公开（公告）日：2009-09-11

  Embodiments relate to the field of chemistry and biochemistry, and, more specifically, to anti-cancer compounds, synthesis thereof, and methods of using same. Disclosed herein are various heterocyclic compounds and methods of using the novel anti-cancer compounds to inhibit the growth of a cancer cell, for instance a leukemia, non-small cell lung, central nervous system (CNS), skin, ovarian, renal, prostate, breast, or colon cancer cell. Other embodiments include methods of treating cancer in a subject, such as using the disclosed heterocyclic anti-cancer agents.