3,3'-bis-(hydroxymethyl)-5,5'-dimethyl-biphenyl-4,4'-diol | 167019-58-1

• 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: 3,3'-bis-(hydroxymethyl)-5,5'-dimethyl-biphenyl-4,4'-diol
• 英文别名: 3,3'-Bis(hydroxymethyl)-5,5'-dimethylbiphenyl-4,4'-diol；4-[4-hydroxy-3-(hydroxymethyl)-5-methylphenyl]-2-(hydroxymethyl)-6-methylphenol
• CAS: 167019-58-1
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: ZRSLPMOJHRIWJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3'-bis-(hydroxymethyl)-5,5'-dimethyl-biphenyl-4,4'-diol 在 三氯化磷 、 吡啶 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.17h， 生成 2-chloro-6-(2-chloro-8-methyl-4H-1,3,2-benzodioxaphosphinin-6-yl)-8-methyl-4H-1,3,2-benzodioxaphosphinine
  参考文献：
  名称：

  Doubly Loaded cycloSaligenyl-Pronucleotides – 5,5′-Bis-(cycloSaligenyl-2′,3′-dideoxy-2′,3′-didehydrothymidine Monophosphates)

  摘要：

  Recently, we reported on 3,3'-bis-(cycloSaligenyl-2',3'-dideoxy-2',3'-didehydrothymidine monophosphates) (3,3'-bis-(cycloSal-d4TMPs) 4) as the first pronucleotides with a mask-to-drug ratio of 1:2 that is still a novelty in the field of pronucleotides. Here, we report on a new set of compounds of these unique type of cycloSaligenyl prodrugs 5 that bear a biaryl axis at the 5-position of the cycloSal residue. All compounds 5 showed pronounced in vitro activity against HIV-1 and HIV-2 in wild-type CEM cell cultures and better retained their antiviral activities in thymidine kinase-deficient CEM cells than the compound 4 series. Moreover, compound 5b is the first bis-(cycloSal-d4TMP) that even showed complete retention of antiviral activity in TK-deficient CEM cells. The complex hydrolysis behavior of 5 was investigated, and the proposed hydrolysis mechanism was proven by means of P-31 NMR spectroscopy and HPLC analysis.

  DOI：

  10.1021/jm900164g
• 作为产物：
  描述：

  bis-(isopropylidene)-3,3'-bis-(hydroxymethyl)-5,5'-dimethyl-biphenyl-4,4'-diol 在 盐酸 、 水 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.01h， 以92%的产率得到3,3'-bis-(hydroxymethyl)-5,5'-dimethyl-biphenyl-4,4'-diol
  参考文献：
  名称：

  Doubly Loaded cycloSaligenyl-Pronucleotides – 5,5′-Bis-(cycloSaligenyl-2′,3′-dideoxy-2′,3′-didehydrothymidine Monophosphates)

  摘要：

  Recently, we reported on 3,3'-bis-(cycloSaligenyl-2',3'-dideoxy-2',3'-didehydrothymidine monophosphates) (3,3'-bis-(cycloSal-d4TMPs) 4) as the first pronucleotides with a mask-to-drug ratio of 1:2 that is still a novelty in the field of pronucleotides. Here, we report on a new set of compounds of these unique type of cycloSaligenyl prodrugs 5 that bear a biaryl axis at the 5-position of the cycloSal residue. All compounds 5 showed pronounced in vitro activity against HIV-1 and HIV-2 in wild-type CEM cell cultures and better retained their antiviral activities in thymidine kinase-deficient CEM cells than the compound 4 series. Moreover, compound 5b is the first bis-(cycloSal-d4TMP) that even showed complete retention of antiviral activity in TK-deficient CEM cells. The complex hydrolysis behavior of 5 was investigated, and the proposed hydrolysis mechanism was proven by means of P-31 NMR spectroscopy and HPLC analysis.

  DOI：

  10.1021/jm900164g