2-(2-methyl-5-nitroimidazol-1-yl)ethanethiol | 55271-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-methyl-5-nitroimidazol-1-yl)ethanethiol
• 英文别名: 1-(2'-Thioaethyl)-2-methyl-5-nitro-imidazol；1-(2'-Thioethyl)-2-methyl-5-nitroimidazol；2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethane-1-thiol
• CAS: 55271-80-2
• 化学式: C₆H₉N₃O₂S
• 分子量: 187.222
• InChiKey: BXGDHEAXWRXKPT-UHFFFAOYSA-N

物化性质

• 熔点：
  115-118 °C(Solv: ethanol (64-17-5))
• 沸点：
  381.9±22.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-5-nitroimidazol-1-yl)ethanethiol 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 丙酮 为溶剂， 反应 96.5h， 生成 1-(2-Benzhydrylsulfonylethyl)-2-methyl-5-nitro-imidazole
  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：

  2-甲基-5-硝基-1H-咪唑-1-乙基甲磺酸酯 在 sodium hydrogensulfide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以30%的产率得到2-(2-methyl-5-nitroimidazol-1-yl)ethanethiol
  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

• [DE] PYRIDYLTHIOVERBINDUNGEN ZUR BEKÄMPFUNG VON HELICOBACTER-BAKTERIEN<br/>[EN] THIOPYRIDYL COMPOUNDS FOR CONTROLLING HELICOBACTER BACTERIA<br/>[FR] COMPOSES DE THIOPYRIDYLE UTILES POUR COMBATTRE DES BACTERIES HELICOBACTER
  申请人：BYK GULDEN LOMBERG CHEMISCHE FABRIK GMBH

  公开号：WO1996002505A1

  公开（公告）日：1996-02-01

  (DE) Verbindungen der Formel (I), worin die Substituenten und Symbole die in der Beschreibung angegebenen Bedeutungen haben, eignen siche zur Bekämpfung von Helicobacter-Bakterien.(EN) Compounds having the formula (I), in which the substituents and symbols have the meanings given in the description, are useful for controlling helicobacter bacteria.(FR) Des composés ayant la formule (I), dans laquelle les substituants et les symboles ont la notation donnée dans la description, sont utiles pour combattre des bactéries hélicobacter.

  (DE) 能够用作线粒体-turning Helicobacter-Bakterien Behandlungseffektiven Stoffe, die die Formel (I) haben, in der die Substituenten und Symbole die in der Beschreibung angegebenen Bedeutungen haben.(EN) Compounds having the formula (I), in which the substituents and symbols have the meanings given in the description, are effective in controlling the effectiveness of-line turning Helicobacter bacteria.(FR)Des composés ayant la formule (I), dans laquelle les substituents et les symboles ont la notation donnée dans la description, sont efficaces pour empêcher le turnage des bactéries hélicobacterien.
• TIHANYI, E.;FEHER, OE.;KIRALY, I.;BORSY, I.;REITER, J.;GAI, M.
  作者：TIHANYI, E.、FEHER, OE.、KIRALY, I.、BORSY, I.、REITER, J.、GAI, M.

  DOI：——

  日期：——
• PYRIDYLTHIOVERBINDUNGEN ZUR BEKÄMPFUNG VON HELICOBACTER-BAKTERIEN
  申请人：ALTANA Pharma AG

  公开号：EP0772593B1

  公开（公告）日：2003-05-02
• US6162809A
  申请人：——

  公开号：US6162809A

  公开（公告）日：2000-12-19
• 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.