4-Hexadecanoyl-5-hydroxy-2,2,6,6-tetramethyl-cyclohex-4-ene-1,3-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Hexadecanoyl-5-hydroxy-2,2,6,6-tetramethyl-cyclohex-4-ene-1,3-dione
• 英文别名: 4-hexadecanoyl-5-hydroxy-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione
• 化学式: C₂₆H₄₄O₄
• 分子量: 420.633
• InChiKey: LUMNBARILNRUTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2,4,6-trihydroxyphenyl)-1-hexadecanone 、 碘甲烷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以86%的产率得到4-Hexadecanoyl-5-hydroxy-2,2,6,6-tetramethyl-cyclohex-4-ene-1,3-dione
  参考文献：
  名称：

  Triketones active against antibiotic-resistant bacteria: Synthesis, structure–activity relationships, and mode of action

  摘要：

  A series of acylated phloroglucinols and triketones was synthesized and tested for activity against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus faecalis (VRE) and multi-drug-resistant Mycobacterium tuberculosis (MDR-TB). A tetra-methylated triketone with a C-12 side chain was the most active compound (MIC of around 1.0 mu g/ml against MRSA) and was shown to stimulate oxygen consumption by resting cell suspensions, suggesting that the primary target was the cytoplasmic membrane. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.045

文献信息

• ANTIBACTERIAL COMPOUNDS
  申请人：NEW ZEALAND INSTITUTE FOR CROP & FOOD RESEARCH LIMITED

  公开号：EP1463704A1

  公开（公告）日：2004-10-06
• Antibacterial compounds
  申请人：Perry Brian Nigel

  公开号：US20060100291A1

  公开（公告）日：2006-05-11

  There is an ongoing need for new antibiotics which may be effective against bacteria that are otherwise difficult to control. The present invention therefore relates to new antibacterial triketone compounds of Formula (1), or salts, metal complexes or tautomeric forms of these compounds. The compounds have potential as novel antibiotics. Thus, the invention also relates to methods of treatment or prevention of bacterial infections using the compounds, and to compositions containing them.
• [EN] ANTIBACTERIAL COMPOUNDS<br/>[FR] COMPOSES ANTIBACTERIENS
  申请人：NEW ZEALAND INST FOR CROP AND

  公开号：WO2003051806A1

  公开（公告）日：2003-06-26

  There is an ongoing need for new antibiotics which may be effective against bacteria that are otherwise difficult to control. The present invention therefore relates to new antibacterial triketone compounds of Formula (1), or salts, metal complexes or tautomeric forms of these compounds. The compounds have potential as novel antibiotics. Thus, the invention also relates to methods of treatment or prevention of bacterial infections using the compounds, and to compositions containing them.
• Triketones active against antibiotic-resistant bacteria: Synthesis, structure–activity relationships, and mode of action
  作者：John W. van Klink、Lesley Larsen、Nigel B. Perry、Rex T. Weavers、Gregory M. Cook、Phil J. Bremer、Andrew D. MacKenzie、Teruo Kirikae

  DOI：10.1016/j.bmc.2005.07.045

  日期：2005.12

  A series of acylated phloroglucinols and triketones was synthesized and tested for activity against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus faecalis (VRE) and multi-drug-resistant Mycobacterium tuberculosis (MDR-TB). A tetra-methylated triketone with a C-12 side chain was the most active compound (MIC of around 1.0 mu g/ml against MRSA) and was shown to stimulate oxygen consumption by resting cell suspensions, suggesting that the primary target was the cytoplasmic membrane. (c) 2005 Elsevier Ltd. All rights reserved.