6-fluoro-5-hydroxy-4-nitrohexanoic acid dimethylamide | 791074-60-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-fluoro-5-hydroxy-4-nitrohexanoic acid dimethylamide
• 英文别名: 6-fluoro-5-hydroxy-4-nitro-hexanoic acid dimethylamide；6-fluoro-5-hydroxy-N,N-dimethyl-4-nitrohexanamide
• CAS: 791074-60-7
• 化学式: C₈H₁₅FN₂O₄
• 分子量: 222.217
• InChiKey: CWLKBESAGBHMJB-UHFFFAOYSA-N

物化性质

• 沸点：
  391.0±42.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-fluoro-5-hydroxy-4-nitrohexanoic acid dimethylamide 在 镍 4-二甲氨基吡啶 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 反应 6.17h， 生成 benzyl N-[2-[[6-(dimethylamino)-1-fluoro-2-hydroxy-6-oxohexan-3-yl]amino]-2-oxoethyl]carbamate
  参考文献：
  名称：

  Design and Synthesis of Dipeptidyl Glutaminyl Fluoromethyl Ketones as Potent Severe Acute Respiratory Syndrome Coronovirus (SARS-CoV) Inhibitors

  摘要：

  This paper describes the design and synthesis of dipeptidyl N,N-dimethyl glutaminyl fluoromethyl ketones (fmk) as severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors. The compounds were tested against SARS-CoV-induced cell death in Vero or CaCo2 cells as a measurement of the inhibiting effects of the compounds on the replication of the virus. Z-Leu-Gln(NMe2)-fmk (6a) was found to be a potent inhibitor with low toxicity in cells, protecting cells with an EC50 value of 2.5 mu M and exhibiting a selectivity index of > 40.

  DOI：

  10.1021/jm0507678
• 作为产物：
  描述：

  氟乙醛 、 N,N-二甲基-4-硝基-丁酰胺 以 二氯甲烷 为溶剂， 以1.2 g的产率得到6-fluoro-5-hydroxy-4-nitrohexanoic acid dimethylamide
  参考文献：
  名称：

  Design and Synthesis of Dipeptidyl Glutaminyl Fluoromethyl Ketones as Potent Severe Acute Respiratory Syndrome Coronovirus (SARS-CoV) Inhibitors

  摘要：

  This paper describes the design and synthesis of dipeptidyl N,N-dimethyl glutaminyl fluoromethyl ketones (fmk) as severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors. The compounds were tested against SARS-CoV-induced cell death in Vero or CaCo2 cells as a measurement of the inhibiting effects of the compounds on the replication of the virus. Z-Leu-Gln(NMe2)-fmk (6a) was found to be a potent inhibitor with low toxicity in cells, protecting cells with an EC50 value of 2.5 mu M and exhibiting a selectivity index of > 40.

  DOI：

  10.1021/jm0507678

文献信息

• PROTEASE INHIBITORS FOR CORONAVIRUSES AND SARS-COV AND THE USE THEREOF
  申请人：Cai Sui Xiong

  公开号：US20080300191A1

  公开（公告）日：2008-12-04

  Disclosed are protease inhibitors for coronaviruses and SARS-CoV, or picornaviruses, and the use of these protease inhibitors for preventing, reducing, ameliorating and treating a disease or condition caused by coronaviruses and SARS-CoV, or picornaviruses. Also disclosed are methods of reducing or preventing the spread of coronavirus, or picornaviruses, and preventing or reducing the replication of coronavirus, or picornaviruses, with the compounds of the present invention

  本申请公开了用于冠状病毒和SARS-CoV，或小RNA病毒的蛋白酶抑制剂，以及利用这些蛋白酶抑制剂预防、减少、改善和治疗由冠状病毒和SARS-CoV，或小RNA病毒引起的疾病或症状的用途。还公开了使用本发明的化合物减少或预防冠状病毒，或小RNA病毒的传播，并预防或减少冠状病毒，或小RNA病毒的复制的方法。
• Protease inhibitors for coronaviruses and SARS-CoV and the use thereof
  申请人：Cytovia, Inc.

  公开号：US07504382B2

  公开（公告）日：2009-03-17

  Disclosed are protease inhibitors for coronaviruses and SARS-CoV, or picornaviruses, and the use of these protease inhibitors for preventing, reducing, ameliorating and treating a disease or condition caused by coronaviruses and SARS-CoV, or picornaviruses. Also disclosed are methods of reducing or preventing the spread of coronavirus, or picornaviruses, and preventing or reducing the replication of coronavirus, or picornaviruses, with the compounds of the present invention.

  本发明涉及用于冠状病毒、SARS-CoV或小肠病毒的蛋白酶抑制剂，以及使用这些蛋白酶抑制剂预防、减少、改善和治疗由冠状病毒、SARS-CoV或小肠病毒引起的疾病或状况。本发明还涉及使用本发明的化合物减少或预防冠状病毒或小肠病毒的传播，并预防或减少冠状病毒或小肠病毒的复制的方法。
• US7504382B2
  申请人：——

  公开号：US7504382B2

  公开（公告）日：2009-03-17
• [EN] PROTEASE INHIBITORS FOR CORONAVIRUSES AND SARS-COV AND THE USE THEREOF<br/>[FR] INHIBITEURS DE PROTEASE POUR LES CORONAVIRUS ET LE SARS-COV ET LEUR UTILISATION
  申请人：CYTOVIA INC

  公开号：WO2004101742A2

  公开（公告）日：2004-11-25

  Disclosed are protease inhibitors for coronaviruses and SARS-CoV, or picornaviruses, and the use of these protease inhibitors for preventing, reducing, ameliorating and treating a disease or condition caused by coronaviruses and SARS-CoV, or picornaviruses. Also disclosed are methods of reducing or preventing the spread of coronavirus, or picornaviruses, and preventing or reducing the replication of coronavirus, or picornaviruses, with the compounds of the present invention.
• Design and Synthesis of Dipeptidyl Glutaminyl Fluoromethyl Ketones as Potent Severe Acute Respiratory Syndrome Coronovirus (SARS-CoV) Inhibitors
  作者：Han-Zhong Zhang、Hong Zhang、William Kemnitzer、Ben Tseng、Jindrich Cinatl,、Martin Michaelis、Hans Wilhelm Doerr、Sui Xiong Cai

  DOI：10.1021/jm0507678

  日期：2006.2.1

  This paper describes the design and synthesis of dipeptidyl N,N-dimethyl glutaminyl fluoromethyl ketones (fmk) as severe acute respiratory syndrome coronovirus (SARS-CoV) inhibitors. The compounds were tested against SARS-CoV-induced cell death in Vero or CaCo2 cells as a measurement of the inhibiting effects of the compounds on the replication of the virus. Z-Leu-Gln(NMe2)-fmk (6a) was found to be a potent inhibitor with low toxicity in cells, protecting cells with an EC50 value of 2.5 mu M and exhibiting a selectivity index of > 40.