1-(2-(hexadecyloxy)-6-hydroxyphenyl)ethan-1-one | 1393845-51-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(hexadecyloxy)-6-hydroxyphenyl)ethan-1-one
• 英文别名: 1-(2-(hexadecyloxy)-6-hydroxyphenyl)ethanone；1-(2-Hexadecoxy-6-hydroxyphenyl)ethanone
• CAS: 1393845-51-6
• 化学式: C₂₄H₄₀O₃
• 分子量: 376.58
• InChiKey: OKJFLYGMZPQZJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-(hexadecyloxy)-6-hydroxyphenyl)ethan-1-one 在 盐酸 、 水 、 三氟乙酸 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 (E)-1-(2-(hexadecyloxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  A SAR study on a series of synthetic lipophilic chalcones as Inhibitor of transcription factor NF-κB

  摘要：

  To define the structural features responsible for the activity of 2,4-dihydroxy-6-isopentyloxychalcone, a newly established inhibitor of LPS induced NF-kappa B activation (IC50 = 10 mu M), a series of its analogues was prepared and studied for their in vitro activities against LPS induced NF-kappa B inhibition in RAW 264.7 cells. Among the synthesized derivatives, (E)-1-(2-(decyloxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (1050 = 2.7 mu M) and (E)-1-(2-hydroxy-6-(tetradecyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (IC50 = 4.2 mu M) showed the most potent inhibition. The SAR studies confirmed that the length (C-8-C-14) and C-6 position of linear alkyl chain of ring A is an important factor for the inhibitory activity. Hydroxyl group and its location at 4-position on ring B is also important for the inhibition. The alpha,beta-unsaturated ketone moiety appears as a crucial motif of chalcones for the activity. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.019
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 、 溴代十六烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以50%的产率得到1-(2-(hexadecyloxy)-6-hydroxyphenyl)ethan-1-one
  参考文献：
  名称：

  Evaluation of a Series of Lipidated Tucaresol Adjuvants in a Hepatitis C Virus Vaccine Model

  摘要：

  Hepatitis C virus (HCV) infections represent a global health challenge; however, developing a vaccine for treatment of HCV infection has remained difficult as heterogeneous HCV contains distinct genotypes, and each genotype contains various subtypes and different envelope glycoproteins. Currently, there is no effective preventive vaccine for achieving global control over HCV. In our efforts to improve upon current HCV vaccines we designed a synthetically accessible adjuvant platform, wherein we synthesized 11 novel lipidated tucaresol analogues to assess their immunological potential. Using a tucaresol-based adjuvant approach, truncated lipid-variants together with an engineered E1E2 antigen construct, namely E2ΔTM3, elicited antibody (Ab) responses that were significantly higher than tucaresol. In sum, antibody end-point titer values largely corroborated HCV neutralization data with a simplified lipidated tucaresol variant affording the highest end point titer and % neutralization. This study lays the groundwork for additional permutations in tucaresol adjuvant design, including the examination of other proteins in vaccine development.

  DOI：

  10.1021/acsmedchemlett.0c00413

文献信息

• A SAR study on a series of synthetic lipophilic chalcones as Inhibitor of transcription factor NF-κB
  作者：Eeda Venkateswararao、Vinay K. Sharma、Ki-Cheul Lee、Niti Sharma、Sun-Hong Park、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.ejmech.2012.05.019

  日期：2012.8

  To define the structural features responsible for the activity of 2,4-dihydroxy-6-isopentyloxychalcone, a newly established inhibitor of LPS induced NF-kappa B activation (IC50 = 10 mu M), a series of its analogues was prepared and studied for their in vitro activities against LPS induced NF-kappa B inhibition in RAW 264.7 cells. Among the synthesized derivatives, (E)-1-(2-(decyloxy)-6-hydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (1050 = 2.7 mu M) and (E)-1-(2-hydroxy-6-(tetradecyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one (IC50 = 4.2 mu M) showed the most potent inhibition. The SAR studies confirmed that the length (C-8-C-14) and C-6 position of linear alkyl chain of ring A is an important factor for the inhibitory activity. Hydroxyl group and its location at 4-position on ring B is also important for the inhibition. The alpha,beta-unsaturated ketone moiety appears as a crucial motif of chalcones for the activity. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Evaluation of a Series of Lipidated Tucaresol Adjuvants in a Hepatitis C Virus Vaccine Model
  作者：Tyson F. Belz、Margaret E. Olson、Erick Giang、Mansun Law、Kim D. Janda

  DOI：10.1021/acsmedchemlett.0c00413

  日期：2020.12.10

  Hepatitis C virus (HCV) infections represent a global health challenge; however, developing a vaccine for treatment of HCV infection has remained difficult as heterogeneous HCV contains distinct genotypes, and each genotype contains various subtypes and different envelope glycoproteins. Currently, there is no effective preventive vaccine for achieving global control over HCV. In our efforts to improve upon current HCV vaccines we designed a synthetically accessible adjuvant platform, wherein we synthesized 11 novel lipidated tucaresol analogues to assess their immunological potential. Using a tucaresol-based adjuvant approach, truncated lipid-variants together with an engineered E1E2 antigen construct, namely E2ΔTM3, elicited antibody (Ab) responses that were significantly higher than tucaresol. In sum, antibody end-point titer values largely corroborated HCV neutralization data with a simplified lipidated tucaresol variant affording the highest end point titer and % neutralization. This study lays the groundwork for additional permutations in tucaresol adjuvant design, including the examination of other proteins in vaccine development.