2-phenoxy-N-(4-(p-tolyl) thiazol-2-yl)acetamide | 72192-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-phenoxy-N-(4-(p-tolyl) thiazol-2-yl)acetamide
• 英文别名: 2-phenoxy-N-(4-p-tolyl-thiazol-2-yl)-acetamide；N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]-2-phenoxyacetamide
• CAS: 72192-45-1
• 化学式: C₁₈H₁₆N₂O₂S
• 分子量: 324.403
• InChiKey: CDMCSSFXBZEIJI-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C(Solv: ligroine (8032-32-4))
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 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：

  对甲基苯乙酮 在 2,6-二甲基吡啶 、 碘 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 2-phenoxy-N-(4-(p-tolyl) thiazol-2-yl)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

• Osman; Hassan Kh.; El-Kashef, Journal of the Indian Chemical Society, 1979, vol. 56, # 5, p. 521 - 524
  作者：Osman、Hassan Kh.、El-Kashef、et al.

  DOI：——

  日期：——
• OSMAN A. M.; HASSAN K. M.; EL-KASHEF H. S.; EL-MAGHRABY M. A.; HASSAN M. +, J. INDIAN CHEM. SOC., 1979, 56, NO 5, 521-524
  作者：OSMAN A. M.、 HASSAN K. M.、 EL-KASHEF H. S.、 EL-MAGHRABY M. A.、 HASSAN M. +

  DOI：——

  日期：——
• 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.