3-Nitro-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-2-amine | 1527694-86-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-Nitro-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-2-amine
• 英文别名: 3-nitro-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-2-amine
• CAS: 1527694-86-5
• 化学式: C₈H₈F₃N₃O₃
• mdl: MFCD23590120
• 分子量: 251.165
• InChiKey: OHKBVYZERBSRKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  94
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-Nitro-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-2-amine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 6-(1,1,1-Trifluoropropan-2-yloxy)pyridine-2,3-diamine
  参考文献：
  名称：

  Aminoazabenzimidazoles, a Novel Class of Orally Active Antimalarial Agents

  摘要：

  Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chemistry effort. Structure-activity relationship studies followed by pharmacokinetics optimization resulted in the identification of 23 as an attractive lead with good oral bioavailability. Compound 23 was found to be efficacious (ED90 of 28.6 mg.kg(-1)) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chemical class.

  DOI：

  10.1021/jm500535j
• 作为产物：
  描述：

  1,1,1-三氟异丙醇 、 2-氨基-3-硝基-6-氯吡啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-Nitro-6-(1,1,1-trifluoropropan-2-yloxy)pyridin-2-amine
  参考文献：
  名称：

  Aminoazabenzimidazoles, a Novel Class of Orally Active Antimalarial Agents

  摘要：

  Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chemistry effort. Structure-activity relationship studies followed by pharmacokinetics optimization resulted in the identification of 23 as an attractive lead with good oral bioavailability. Compound 23 was found to be efficacious (ED90 of 28.6 mg.kg(-1)) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chemical class.

  DOI：

  10.1021/jm500535j

文献信息

• Aminoazabenzimidazoles, a Novel Class of Orally Active Antimalarial Agents
  作者：Shahul Hameed P、Murugan Chinnapattu、Gajanan Shanbag、Praveena Manjrekar、Krishna Koushik、Anandkumar Raichurkar、Vikas Patil、Sandesh Jatheendranath、Suresh S. Rudrapatna、Shubhada P. Barde、Nikhil Rautela、Disha Awasthy、Sapna Morayya、Chandan Narayan、Stefan Kavanagh、Ramanatha Saralaya、Sowmya Bharath、Pavithra Viswanath、Kakoli Mukherjee、Balachandra Bandodkar、Abhishek Srivastava、Vijender Panduga、Jitender Reddy、K. R. Prabhakar、Achyut Sinha、María Belén Jiménez-Díaz、María Santos Martínez、Iñigo Angulo-Barturen、Santiago Ferrer、Laura María Sanz、Francisco Javier Gamo、Sandra Duffy、Vicky M. Avery、Pamela A. Magistrado、Amanda K. Lukens、Dyann F. Wirth、David Waterson、V. Balasubramanian、Pravin S. Iyer、Shridhar Narayanan、Vinayak Hosagrahara、Vasan K. Sambandamurthy、Sreekanth Ramachandran

  DOI：10.1021/jm500535j

  日期：2014.7.10

  Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chemistry effort. Structure-activity relationship studies followed by pharmacokinetics optimization resulted in the identification of 23 as an attractive lead with good oral bioavailability. Compound 23 was found to be efficacious (ED90 of 28.6 mg.kg(-1)) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chemical class.