N-(4-(4-chlorophenyl) thiazol-2-yl)-2-(4-methylphenoxy)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-(4-chlorophenyl) thiazol-2-yl)-2-(4-methylphenoxy)acetamide
• 英文别名: N-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-2-(4-methylphenoxy)acetamide
• 化学式: C₁₈H₁₅ClN₂O₂S
• 分子量: 358.848
• InChiKey: SGDSIEACHYHCKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸-(4-甲基苯氧基)乙酯 在 2,6-二甲基吡啶 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 N-(4-(4-chlorophenyl) thiazol-2-yl)-2-(4-methylphenoxy)acetamide
  参考文献：
  名称：

  The Novel 4-Phenyl-2-Phenoxyacetamide Thiazoles modulates the tumor hypoxia leading to the crackdown of neoangiogenesis and evoking the cell death

  摘要：

  Tumor microenvironment is a complex multistep event which involves several hallmarks that transform the normal cell into cancerous cell. Designing the novel antagonistic molecule to reverse the tumor microenvironment with specific target is essential in modern biological studies. The novel 4-phenyl-2-phenoxyacetamide thiazole analogues 8(a-ab) were synthesized in multistep process, then screened and assessed for cytotoxic and anti-proliferative effects in vitro against multiple cancer cells of different origin such as MCF-7, A549, EAC and DIA cells which revealed that compound 8f with fluoro and methyl substitute has potential cytotoxic efficacy with an average IC50 value of (similar to)13 mu M. The mechanism of cytotoxicity assessed for anti-tumor studies both in ascites and solid tumor models in-vivo inferred the regressed tumor activity. This is due to changes in the cause of tumor microenvironment with crackdown of neovascularization and evoking apoptosis process as assessed by CAM, corneal vascularization and apoptotic hallmarks in 8f treated cells. The molecular gene studies inferred involvement of HIFI upregulation and stabilization of p53 which are interlinked in signaling as conferred by immunoblot analysis. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.082

文献信息

• Effect of o-difluoro and p-methyl substituents on the structure, optical properties and anti-inflammatory activity of phenoxy thiazole acetamide derivatives: Theoretical and experimental studies
  作者：Hussien Ahmed Khamees、Yasser Hussein Eissa Mohammed、Ananda S、Fares Hezam Al-Ostoot、Sangappa Y、Saad Alghamdi、Shaukath Ara Khanum、Mahendra Madegowda

  DOI：10.1016/j.molstruc.2019.127024

  日期：2020.1

  LC-MS spectra. The three-dimensional structures have been confirmed by single crystal X-ray diffraction method. 6a and 6b compounds have been crystallized in the Triclinic and the Orthorhombic systems with P-1 and Pbca space groups, respectively. Supramolecular structures revealed the stability of molecules with different intermolecular interactions and different crystal packing environment. Theoretical

  摘要 噻唑衍生物（6a 和 6b）已被合成并通过 1H –13C NMR 以及 LC-MS 光谱表征。三维结构已通过单晶X射线衍射法证实。6a 和 6b 化合物分别在具有 P-1 和 Pbca 空间群的三斜晶系​​和正交晶系中结晶。超分子结构揭示了具有不同分子间相互作用和不同晶体堆积环境的分子的稳定性。密度泛函理论 (DFT) 和基于最高基组 6-311++G(d,p) 的 B3LYP 泛函的理论研究被用来计算几何形状并与实验数据进行比较。通过使用自然布居和自然键轨道分析（NBO）研究了电子结构和分子内电荷转移。更多，进行 DFT 研究以评估前沿分子轨道 (FMO)、能隙、柔软度、硬度和其他化学反应性。研究了赫什菲尔德表面以区分不同的原子间接触，并通过基于拓扑各向异性的不同分子间相互作用能，借助能量框架了解分子的晶体堆积。合成分子的非线性光学性质 (NLO) 由 (DFT) 预测，并通过使用二次谐波产生
• The Novel 4-Phenyl-2-Phenoxyacetamide Thiazoles modulates the tumor hypoxia leading to the crackdown of neoangiogenesis and evoking the cell death
  作者：Yasser Hussein Eissa Mohammed、Vikas H. Malojirao、Prabhu Thirusangu、Mohammed Al-Ghorbani、B.T. Prabhakar、Shaukath Ara Khanum

  DOI：10.1016/j.ejmech.2017.10.082

  日期：2018.1

  Tumor microenvironment is a complex multistep event which involves several hallmarks that transform the normal cell into cancerous cell. Designing the novel antagonistic molecule to reverse the tumor microenvironment with specific target is essential in modern biological studies. The novel 4-phenyl-2-phenoxyacetamide thiazole analogues 8(a-ab) were synthesized in multistep process, then screened and assessed for cytotoxic and anti-proliferative effects in vitro against multiple cancer cells of different origin such as MCF-7, A549, EAC and DIA cells which revealed that compound 8f with fluoro and methyl substitute has potential cytotoxic efficacy with an average IC50 value of (similar to)13 mu M. The mechanism of cytotoxicity assessed for anti-tumor studies both in ascites and solid tumor models in-vivo inferred the regressed tumor activity. This is due to changes in the cause of tumor microenvironment with crackdown of neovascularization and evoking apoptosis process as assessed by CAM, corneal vascularization and apoptotic hallmarks in 8f treated cells. The molecular gene studies inferred involvement of HIFI upregulation and stabilization of p53 which are interlinked in signaling as conferred by immunoblot analysis. (C) 2017 Elsevier Masson SAS. All rights reserved.