3,3'-propanediyl-di-phenol | 82052-15-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3,3'-propanediyl-di-phenol
• 英文别名: 3,3'-Propandiyl-di-phenol
• CAS: 82052-15-1
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: XPBRVRQFVQCYQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,3'-propanediyl-di-phenol 、 叔丁醇 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 生成 5,5'-(propane-1,3-diyl)bis(2-(tert-butyl)phenol)
  参考文献：
  名称：

  A Bisphenolic Honokiol Analog Outcompetes Oral Antimicrobial Agent Cetylpyridinium Chloride via a Membrane-Associated Mechanism

  摘要：

  Targeting Streptococcus mutans is the primary focus in reducing dental caries, one of the most common maladies in the world. Previously, our groups discovered a potent bactericidal biaryl compound that was inspired by the natural product honokiol. Herein, a structure activity relationship (SAR) study to ascertain structural motifs key to inhibition is outlined. Furthermore, mechanism studies show that bacterial membrane disruption is central to the bacterial growth inhibition. During this process, it was discovered that analog C2 demonstrated a 4-fold better therapeutic index compared to the commercially available antimicrobial cetylpyridinium chloride (CPC) making it a viable alternative for oral care.

  DOI：

  10.1021/acsinfecdis.9b00190
• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 6.0h， 生成 3,3'-propanediyl-di-phenol
  参考文献：
  名称：

  A Bisphenolic Honokiol Analog Outcompetes Oral Antimicrobial Agent Cetylpyridinium Chloride via a Membrane-Associated Mechanism

  摘要：

  Targeting Streptococcus mutans is the primary focus in reducing dental caries, one of the most common maladies in the world. Previously, our groups discovered a potent bactericidal biaryl compound that was inspired by the natural product honokiol. Herein, a structure activity relationship (SAR) study to ascertain structural motifs key to inhibition is outlined. Furthermore, mechanism studies show that bacterial membrane disruption is central to the bacterial growth inhibition. During this process, it was discovered that analog C2 demonstrated a 4-fold better therapeutic index compared to the commercially available antimicrobial cetylpyridinium chloride (CPC) making it a viable alternative for oral care.

  DOI：

  10.1021/acsinfecdis.9b00190

文献信息

• Dodds et al., Proceedings of the Royal Society of London. Series B, Biological sciences, 1953, vol. 140, p. 470,478
  作者：Dodds et al.

  DOI：——

  日期：——
• A Bisphenolic Honokiol Analog Outcompetes Oral Antimicrobial Agent Cetylpyridinium Chloride via a Membrane-Associated Mechanism
  作者：Cristian Ochoa、Amy E. Solinski、Marcus Nowlan、Madeline M. Dekarske、William M. Wuest、Marisa C. Kozlowski

  DOI：10.1021/acsinfecdis.9b00190

  日期：2020.1.10

  Targeting Streptococcus mutans is the primary focus in reducing dental caries, one of the most common maladies in the world. Previously, our groups discovered a potent bactericidal biaryl compound that was inspired by the natural product honokiol. Herein, a structure activity relationship (SAR) study to ascertain structural motifs key to inhibition is outlined. Furthermore, mechanism studies show that bacterial membrane disruption is central to the bacterial growth inhibition. During this process, it was discovered that analog C2 demonstrated a 4-fold better therapeutic index compared to the commercially available antimicrobial cetylpyridinium chloride (CPC) making it a viable alternative for oral care.