ethyl [2-(4-fluorobenzoyl)-2-chloro-6-fluorophenoxy]acetate | 1443037-97-5

• 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: ethyl [2-(4-fluorobenzoyl)-2-chloro-6-fluorophenoxy]acetate
• 英文别名: Ethyl 2-[2-chloro-6-fluoro-4-(4-fluorobenzoyl)phenoxy]acetate；ethyl 2-[2-chloro-6-fluoro-4-(4-fluorobenzoyl)phenoxy]acetate
• CAS: 1443037-97-5
• 化学式: C₁₇H₁₃ClF₂O₄
• 分子量: 354.738
• InChiKey: OKRIZICXKPVBMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl [2-(4-fluorobenzoyl)-2-chloro-6-fluorophenoxy]acetate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以92%的产率得到[4-(4-fluorobenzoyl)-2-chloro-6-fluorophenoxy]ethanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles as anti-cancer agents

  摘要：

  A series of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a-j were obtained via multistep synthesis from hydroxybenzophenones 4a-e. The cytotoxicity of compounds 9a-j was evaluated against human leukemia cell lilies (K562 and CEM). The compounds exhibited moderate to good anti-cancer activity with compounds 9b and 9i having a chloro group exhibiting the best activity (IC50 = 10 mu M). Compound 9i exhibited activity against both the cell lines and 9b only exhibited activity against CEM. Further, a lactate dehydrogenase (LDH) assay and DNA fragmentation studies of the compounds 9a-j were also performed. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.040
• 作为产物：
  描述：

  2-氯-6-氟苯酚 在 aluminum (III) chloride 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 ethyl [2-(4-fluorobenzoyl)-2-chloro-6-fluorophenoxy]acetate
  参考文献：
  名称：

  二苯甲酮标记的吡啶类似物的合成及其对道尔顿淋巴瘤中胱天蛋白酶激活的DNase介导的核分裂的激活作用

  摘要：

  通过多步反应序列合成了一系列具有吡啶核8a - 1的二苯甲酮，并通过体外和体内研究评估了其对DLA细胞的抗增殖活性。结果表明，在二苯甲酮骨架的苯甲酰基环上具有氟基的化合物8b和具有氯取代基的化合物8e以及具有羟基的吡啶环均显示出显着的活性。小鼠模型的进一步研究表明化合物8b和8e 具有激活caspase活化的DNase（核酸内切酶）的能力，该酶负责DNA片段化，这是细胞凋亡的主要标志，从而抑制了道尔顿淋巴瘤腹水肿瘤的生长。

  DOI：

  10.1016/j.bioorg.2016.02.001

文献信息

• Design, Synthesis, and Anticancer Properties of Novel Benzophenone-Conjugated Coumarin Analogs
  作者：V. Lakshmi Ranganatha、Farhan Zameer、S. Meghashri、N. D. Rekha、V. Girish、H. D. Gurupadaswamy、Shaukath Ara Khanum

  DOI：10.1002/ardp.201300298

  日期：2013.12

  of anticancer drugs with specific targets is of prime importance in modern chemical biology. Observing the importance of benzophenone and coumarin nucleus, it would be worthwhile to design and synthesize novel benzophenone derivatives (8a–o) bearing the coumarin nucleus. Further, they were screened for prospective anticancer activities in vitro against the Michigan Cancer Foundation‐7 (MCF‐7) and Ehrlich's

  在当前情况下，开发具有特定靶点的抗癌药物在现代化学生物学中至关重要。观察到二苯甲酮和香豆素核的重要性，设计和合成带有香豆素核的新型二苯甲酮衍生物 (8a-o) 是值得的。此外，还筛选了它们在体外针对密歇根癌症基金会-7 (MCF-7) 和埃利希腹水瘤 (EAT) 细胞系及其生物标志物的前瞻性抗癌活性，然后进行了有关磷酸肌醇 3-激酶 (PI3K) 和caspase 通过分子对接。据报道，二苯甲酮是靶向肿瘤血管生成的潜在药物。因此，在存在化合物 8a-o 的情况下，观察到血管生成依赖的 CAM 等体内模型系统中新血管的形成。
• Synthesis and evaluation of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles as anti-cancer agents
  作者：H.D. Gurupadaswamy、V. Girish、C.V. Kavitha、Sathees C. Raghavan、Shaukath Ara Khanum

  DOI：10.1016/j.ejmech.2013.02.040

  日期：2013.5

  A series of 2,5-di(4-aryloylaryloxymethyl)-1,3,4-oxadiazoles 9a-j were obtained via multistep synthesis from hydroxybenzophenones 4a-e. The cytotoxicity of compounds 9a-j was evaluated against human leukemia cell lilies (K562 and CEM). The compounds exhibited moderate to good anti-cancer activity with compounds 9b and 9i having a chloro group exhibiting the best activity (IC50 = 10 mu M). Compound 9i exhibited activity against both the cell lines and 9b only exhibited activity against CEM. Further, a lactate dehydrogenase (LDH) assay and DNA fragmentation studies of the compounds 9a-j were also performed. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis and antiproliferative activity of benzophenone tagged pyridine analogues towards activation of caspase activated DNase mediated nuclear fragmentation in Dalton’s lymphoma
  作者：Mohammed Al-Ghorbani、Prabhu Thirusangu、H.D. Gurupadaswamy、V. Girish、H.G. Shamanth Neralagundi、B.T. Prabhakar、Shaukath Ara Khanum

  DOI：10.1016/j.bioorg.2016.02.001

  日期：2016.4

  against DLA cells by in vitro and in vivo studies. The results suggested that, compounds 8b with fluoro group and 8e with chloro substituent at the benzoyl ring of benzophenone scaffold as well as pyridine ring with hydroxy group exhibited significant activity. Further investigation in mouse model suggests that compounds 8b and 8e have the potency to activate caspase activated DNase (endonuclease) which

  通过多步反应序列合成了一系列具有吡啶核8a - 1的二苯甲酮，并通过体外和体内研究评估了其对DLA细胞的抗增殖活性。结果表明，在二苯甲酮骨架的苯甲酰基环上具有氟基的化合物8b和具有氯取代基的化合物8e以及具有羟基的吡啶环均显示出显着的活性。小鼠模型的进一步研究表明化合物8b和8e 具有激活caspase活化的DNase（核酸内切酶）的能力，该酶负责DNA片段化，这是细胞凋亡的主要标志，从而抑制了道尔顿淋巴瘤腹水肿瘤的生长。