2-(4-chlorophenoxy)-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]acetamide | 72192-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-chlorophenoxy)-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]acetamide
• 英文别名: 2-(4-chlorophenoxy)-N-(4-(p-tolyl) thiazol-2-yl)acetamide；2-(4-chloro-phenoxy)-N-(4-p-tolyl-thiazol-2-yl)-acetamide
• CAS: 72192-42-8
• 化学式: C₁₈H₁₅ClN₂O₂S
• 分子量: 358.848
• InChiKey: ORCHEUFGSUNLOB-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：

  4-氯苯氧乙酸乙酯 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 2-(4-chlorophenoxy)-N-[4-(4-methylphenyl)-1,3-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

• Experimental and computational studies on the synthesis and structural characterization of 2-(4-chlorophenoxy)-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]acetamide
  作者：Hamdi Hamid Sallam、Yasser Hussien Issa Mohammed、Fares Hezam Al-Ostoot、P. Akhileshwari、M.A. Sridhar、Shaukath Ara Khanum

  DOI：10.1016/j.molstruc.2021.131588

  日期：2022.2

  techniques (NMR and LC-MS) and finally, the structure was confirmed by X-ray diffraction method. The title compound has crystallized in the orthorhombic crystal system with the space group Pca21. Density functional theory calculations were carried out to compare the computational values of (1) and (2) with (3). The frontier molecular orbitals (HOMO-LUMO) and molecular electrostatic potential (MEP) of (3)

  标题化合物2-(4-氯苯氧基) -N- [4-(4-甲基苯基)-1,3-噻唑-2-基]乙酰胺(3)已通过一系列多步合成过程以良好的收率开始通过 2-(4-氯苯氧基)乙酸(1)与 4-(4-甲基苯基)噻唑-2-胺(2)在无水二氯甲烷中，然后加入二甲基吡啶和O- (苯并三唑-1-基)- N,N,N',N'-四甲基脲四氟硼酸盐作为偶联剂在冷态完成(3). 合成的化合物通过不同的光谱技术（NMR 和 LC-MS）阐明，最后通过 X 射线衍射法确认其结构。标题化合物已在具有空间群Pca2 1的斜方晶系中结晶。进行密度泛函理论计算以将（1）和（2）的计算值与（3）进行比较。分析了(3)的前沿分子轨道(HOMO-LUMO)和分子静电势(MEP) 。在晶体结构中，观察到分子间和分子内相互作用。原子N12代表(3)的手性中心它连接到四个不同的组。该分子在 N12 处的立体化学为 S 构型。Hirshfeld
• 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：——