2-(3-chloro-4-hydroxyphenyl)-N-(2-(diethylamino)ethyl)acetamide

• 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: 2-(3-chloro-4-hydroxyphenyl)-N-(2-(diethylamino)ethyl)acetamide
• 英文别名: 2-(3-chloro-4-hydroxy-phenyl)-N-(2-diethylaminoethyl)acetamide；2-(3-chloro-4-hydroxyphenyl)-N-[2-(diethylamino)ethyl]acetamide
• 化学式: C₁₄H₂₁ClN₂O₂
• 分子量: 284.786
• InChiKey: APHHWDWGZCQSKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氯-4羟基苯乙酸 在 对甲苯磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 64.0h， 生成 2-(3-chloro-4-hydroxyphenyl)-N-(2-(diethylamino)ethyl)acetamide
  参考文献：
  名称：

  Design and Synthesis of a Screening Library Using the Natural Product Scaffold 3-Chloro-4-hydroxyphenylacetic Acid

  摘要：

  The fungal metabolite 3-chloro-4-hydroxyphenylacetic acid (1) was utilized in the generation of a unique drug-like screening library using parallel solution-phase synthesis. A 20-membered amide library (3-22) was generated by first converting 1 to methyl (3-chloro-4-hydroxyphenyl)acetate (2), then reacting this scaffold with a diverse series of primary amines via a solvent-free aminolysis procedure. The structures of the synthetic analogues (3-22) were elucidated by spectroscopic data analysis. The structures of compounds 8, 12, and 22 were confirmed by single X-ray crystallographic analysis. All compounds were evaluated for cytotoxicity against a human prostate cancer cell line (LNCaP) and for antiparasitic activity toward Trypanosoma brucei brucei and Plasmodium falciparum and showed no significant activity at 10 mu M. The library was also tested for effects on the lipid content of LNCaP and PC-3 prostate cancer cells, and it was demonstrated that the fluorobenzyl analogues (12-14) significantly reduced cellular phospholipid and neutral lipid levels.

  DOI：

  10.1021/np500856u

文献信息

• Design and Synthesis of a Screening Library Using the Natural Product Scaffold 3-Chloro-4-hydroxyphenylacetic Acid
  作者：Rohitesh Kumar、Martin C. Sadowski、Claire Levrier、Colleen C. Nelson、Amy J. Jones、John P. Holleran、Vicky M. Avery、Peter C. Healy、Rohan A. Davis

  DOI：10.1021/np500856u

  日期：2015.4.24

  The fungal metabolite 3-chloro-4-hydroxyphenylacetic acid (1) was utilized in the generation of a unique drug-like screening library using parallel solution-phase synthesis. A 20-membered amide library (3-22) was generated by first converting 1 to methyl (3-chloro-4-hydroxyphenyl)acetate (2), then reacting this scaffold with a diverse series of primary amines via a solvent-free aminolysis procedure. The structures of the synthetic analogues (3-22) were elucidated by spectroscopic data analysis. The structures of compounds 8, 12, and 22 were confirmed by single X-ray crystallographic analysis. All compounds were evaluated for cytotoxicity against a human prostate cancer cell line (LNCaP) and for antiparasitic activity toward Trypanosoma brucei brucei and Plasmodium falciparum and showed no significant activity at 10 mu M. The library was also tested for effects on the lipid content of LNCaP and PC-3 prostate cancer cells, and it was demonstrated that the fluorobenzyl analogues (12-14) significantly reduced cellular phospholipid and neutral lipid levels.