(2,3-difluorophenyl)-(thiophen-2-yl)methanone | 860016-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3-difluorophenyl)-(thiophen-2-yl)methanone
• 英文别名: (2,3-Difluorophenyl)-thiophen-2-ylmethanone
• CAS: 860016-97-3
• 化学式: C₁₁H₆F₂OS
• 分子量: 224.231
• InChiKey: AECKSSQGBJAGGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,3-difluorophenyl)-(thiophen-2-yl)methanone 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到(2,3-difluorophenyl)-(thiophen-2-yl)methanol
  参考文献：
  名称：

  Novel 1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors. A Structure−Activity Relationship Investigation

  摘要：

  1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles (DAMNIs) is a novel family of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) active at submicromolar concentration. Replacement of one phenyl ring of 1-[2-(diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole (4) with heterocyclic rings, such as 2-thienyl or 3-pyridinyl, led to novel DAMNIs with increased activity. In HIV-1 WT cell-based assay the racemic 1-{2-{alpha-(thiophen-2-yl)phenylmethoxylethyl}-2-methyl-5-nitroimidazole (7) (EC50 = 0.03 mu M) proved 5 times more active than compound 4. Docking experiments showed that the introduction of a chiral center would not affect the binding of both (R)-7 and (S)-7. The internal scoring function of the Autodock program calculated the same inhibition constant (K-i = 7.9 nM) for the two enantiomers. Compounds 7 (ID50 = 8.25 mu M) were found more active than efavirenz (ID50 = 25 mu M) against the viral RT carrying the K103N mutation, suggesting for these compounds a potential use in efavirenz based anti-AIDS regimens.

  DOI：

  10.1021/jm050273a
• 作为产物：
  描述：

  噻吩 、 2,3-二氟苯甲酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以26%的产率得到(2,3-difluorophenyl)-(thiophen-2-yl)methanone
  参考文献：
  名称：

  Novel 1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors. A Structure−Activity Relationship Investigation

  摘要：

  1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles (DAMNIs) is a novel family of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) active at submicromolar concentration. Replacement of one phenyl ring of 1-[2-(diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole (4) with heterocyclic rings, such as 2-thienyl or 3-pyridinyl, led to novel DAMNIs with increased activity. In HIV-1 WT cell-based assay the racemic 1-{2-{alpha-(thiophen-2-yl)phenylmethoxylethyl}-2-methyl-5-nitroimidazole (7) (EC50 = 0.03 mu M) proved 5 times more active than compound 4. Docking experiments showed that the introduction of a chiral center would not affect the binding of both (R)-7 and (S)-7. The internal scoring function of the Autodock program calculated the same inhibition constant (K-i = 7.9 nM) for the two enantiomers. Compounds 7 (ID50 = 8.25 mu M) were found more active than efavirenz (ID50 = 25 mu M) against the viral RT carrying the K103N mutation, suggesting for these compounds a potential use in efavirenz based anti-AIDS regimens.

  DOI：

  10.1021/jm050273a

文献信息

• Novel 1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors. A Structure−Activity Relationship Investigation
  作者：Gabriella De Martino、Giuseppe La Regina、Alessandra Di Pasquali、Rino Ragno、Alberto Bergamini、Chiara Ciaprini、Anna Sinistro、Giovanni Maga、Emmanuele Crespan、Marino Artico、Romano Silvestri

  DOI：10.1021/jm050273a

  日期：2005.6.1

  1-[2-(Diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles (DAMNIs) is a novel family of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) active at submicromolar concentration. Replacement of one phenyl ring of 1-[2-(diphenylmethoxy)ethyl]-2-methyl-5-nitroimidazole (4) with heterocyclic rings, such as 2-thienyl or 3-pyridinyl, led to novel DAMNIs with increased activity. In HIV-1 WT cell-based assay the racemic 1-2-alpha-(thiophen-2-yl)phenylmethoxylethyl}-2-methyl-5-nitroimidazole (7) (EC50 = 0.03 mu M) proved 5 times more active than compound 4. Docking experiments showed that the introduction of a chiral center would not affect the binding of both (R)-7 and (S)-7. The internal scoring function of the Autodock program calculated the same inhibition constant (K-i = 7.9 nM) for the two enantiomers. Compounds 7 (ID50 = 8.25 mu M) were found more active than efavirenz (ID50 = 25 mu M) against the viral RT carrying the K103N mutation, suggesting for these compounds a potential use in efavirenz based anti-AIDS regimens.