1-(6-bromopyridin-2-yl)-3-dimethylaminoprop-2-enone | 200059-63-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(6-bromopyridin-2-yl)-3-dimethylaminoprop-2-enone
• 英文别名: 1-(6-bromopyridin-2-yl)-3-(dimethylamino)prop-2-en-1-one
• CAS: 200059-63-8
• 化学式: C₁₀H₁₁BrN₂O
• 分子量: 255.114
• InChiKey: HYOMMVMFAJNUQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(6-bromopyridin-2-yl)-3-dimethylaminoprop-2-enone 、 N-{[(5S)-3-(3-fluoro-4-hydrazinophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以47.3%的产率得到(S)-N-((3-(3-fluoro-4-(5-(6-bromopyridin-2-yl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl) acetamide
  参考文献：
  名称：

  Discovery of a Teraryl Oxazolidinone Compound (S)-N-((3-(3-Fluoro-4-(4-(pyridin-2-yl)-1H-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide Phosphate as a Novel Antimicrobial Agent with Enhanced Safety Profile and Efficacies

  摘要：

  A series of novel teraryl oxazolidinone compounds was designed, synthesized, and evaluated for their antimicrobial activity and toxicities. The compounds with aromatic N-heterocyclic substituents at the 4-position of pyrazolyl ring showed better antibacterial activity against the tested bacteria than other compounds with different patterns of substitution. Among all potent compounds, 10f exhibited promising safety profile in MTT assays and in hERG K+ channel inhibition test. Furthermore, its phosphate was found to be highly soluble in water (47.1 mg/mL), which is beneficial for the subsequent in vivo test. In MRSA systemic infection mice models, 10f phosphate exerted significantly improved survival protection compared with linezolid. The compound also demonstrated high oral bioavailability (F = 99.1%). Moreover, from the results of in vivo toxicology experiments, 10f phosphate would be predicted to have less bone marrow suppression.

  DOI：

  10.1021/acs.jmedchem.5b00152

文献信息

• [EN] PYRIDINE-, PYRAZINE-, TRIAZINE- AND TETRAZINE-DERIVED MICROBIOCIDES<br/>[FR] NOUVEAUX MICROBIOCIDES
  申请人：SYNGENTA PARTICIPATIONS AG

  公开号：WO2013026866A3

  公开（公告）日：2013-04-11
• Discovery of a Teraryl Oxazolidinone Compound (<i>S</i>)-<i>N</i>-((3-(3-Fluoro-4-(4-(pyridin-2-yl)-1<i>H</i>-pyrazol-1-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide Phosphate as a Novel Antimicrobial Agent with Enhanced Safety Profile and Efficacies
  作者：Tao Yang、Gong Chen、Zitai Sang、Yuanyuan Liu、Xiaoyan Yang、Ying Chang、Haiyue Long、Wei Ang、Jianying Tang、Zhenling Wang、Guobo Li、Shengyong Yang、Jingren Zhang、Yuquan Wei、Youfu Luo

  DOI：10.1021/acs.jmedchem.5b00152

  日期：2015.8.27

  A series of novel teraryl oxazolidinone compounds was designed, synthesized, and evaluated for their antimicrobial activity and toxicities. The compounds with aromatic N-heterocyclic substituents at the 4-position of pyrazolyl ring showed better antibacterial activity against the tested bacteria than other compounds with different patterns of substitution. Among all potent compounds, 10f exhibited promising safety profile in MTT assays and in hERG K+ channel inhibition test. Furthermore, its phosphate was found to be highly soluble in water (47.1 mg/mL), which is beneficial for the subsequent in vivo test. In MRSA systemic infection mice models, 10f phosphate exerted significantly improved survival protection compared with linezolid. The compound also demonstrated high oral bioavailability (F = 99.1%). Moreover, from the results of in vivo toxicology experiments, 10f phosphate would be predicted to have less bone marrow suppression.