(R)-3-(3-Fluoro-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl)-5-([1,2,3]triazol-1-yl)methyloxazolidin-2-one | 1202704-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (R)-3-(3-Fluoro-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl)-5-([1,2,3]triazol-1-yl)methyloxazolidin-2-one
• 英文别名: (5R)-3-[3-fluoro-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl]-5-(triazol-1-ylmethyl)-1,3-oxazolidin-2-one
• CAS: 1202704-50-4
• 化学式: C₁₈H₁₄FN₇O₂
• 分子量: 379.353
• InChiKey: QHFTXVUFWFILTG-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-溴-[1,2,4]三唑并[1,5-a]吡啶 、 (R)-3-(3-fluoro-4-(3,3,4,4-tetramethylborolan-1-yl)phenyl)-5-([1,2,3]triazol-1-yl)methyloxazolidin-2-one 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 以59%的产率得到(R)-3-(3-Fluoro-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)phenyl)-5-([1,2,3]triazol-1-yl)methyloxazolidin-2-one
  参考文献：
  名称：

  Potent Oxazolidinone Antibacterials with Heteroaromatic C-Ring Substructure

  摘要：

  Novel oxazolidinone analogues bearing a condensed heteroaromatic ring as the C-ring substructure were synthesized as candidate antibacterial agents. Analogues 16 and 21 bearing imidazo[1,2-a]pyridine and 18 and 23 bearing [1,2,4]triazolo[1,5-a]pyridine as the C-ring had excellent in vitro antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus faecalis (VRE), and penicillin-resistant Streptococcus pneumoniae (PRSP). They also showed promising therapeutic effects in a mouse model of lethal infection. Preliminary safety data (inhibitory effects on cytochrome P450 isoforms and monoamine oxidases) were satisfactory. Further evaluation of 18 and 23 is ongoing.

  DOI：

  10.1021/ml400280z

文献信息

• OXAZOLIDINONE DERIVATIVE HAVING FUSED RING
  申请人：Katoh Issei

  公开号：US20110098471A1

  公开（公告）日：2011-04-28

  The present invention provides a novel antimicrobial drug comprising an oxazolidinone derivative of the formula (I): or a pharmaceutically acceptable salt or solvate thereof; wherein ring A is ring B is a benzene ring optionally substituted with lower alkyl; ring C is an optionally substituted six-membered heterocycle containing at least one nitrogen atom and one to three double bond(s) in the ling wherein the atom at the point of attachment to ring B is a carbon atom; ring D is an optionally substituted five-membered ring containing one or two double bond(s) in the ring; A 1 and A 2 are independently nitrogen or carbon; m is 0 or 1; R represents H, —NHC(═O)R A , —NHC(═S)R A , —NH-het 1 , —O-het 1 , —S-het 1 , —S(═O)-het 1 , —S(═O) 2 -het 1 , het 2 , —CONHR A , —OH, lower alkyl, lower alkoxy or lower alkenyl; and het 1 and het 2 are independently a heterocyclic group; with the proviso that the fused ring C-D is not

  本发明提供了一种新型抗菌药物，包括式(I)的噁唑烷酮衍生物： 或其药学上可接受的盐或溶剂；其中环A是 环B是一个苯环，可选择地取代为较低的烷基；环C是一个可选择地取代的含有至少一个氮原子和一个到三个双键的六元杂环，在连接到环B的点的原子是一个碳原子；环D是一个可选择地取代的含有一个或两个双键的五元环；A 1 和A 2 独立地是氮或碳；m为0或1；R代表H，—NHC(═O)R A ，—NHC(═S)R A ，—NH-het 1 ，—O-het 1 ，—S-het 1 ，—S(═O)-het 1 ，—S(═O) 2 -het 1 ，het 2 ，—CONHR A ，—OH，较低的烷基，较低的烷氧基或较低的烯基；和het 1 和het 2 独立地是一个杂环基团；但附带条件是融合的环C-D不是
• US8575337B2
  申请人：——

  公开号：US8575337B2

  公开（公告）日：2013-11-05
• Potent Oxazolidinone Antibacterials with Heteroaromatic C-Ring Substructure
  作者：Hideyuki Suzuki、Iwao Utsunomiya、Koichi Shudo、Takaji Fujimura、Masakatsu Tsuji、Issei Kato、Toshiaki Aoki、Akira Ino、Tsutomu Iwaki

  DOI：10.1021/ml400280z

  日期：2013.11.14

  Novel oxazolidinone analogues bearing a condensed heteroaromatic ring as the C-ring substructure were synthesized as candidate antibacterial agents. Analogues 16 and 21 bearing imidazo[1,2-a]pyridine and 18 and 23 bearing [1,2,4]triazolo[1,5-a]pyridine as the C-ring had excellent in vitro antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus faecalis (VRE), and penicillin-resistant Streptococcus pneumoniae (PRSP). They also showed promising therapeutic effects in a mouse model of lethal infection. Preliminary safety data (inhibitory effects on cytochrome P450 isoforms and monoamine oxidases) were satisfactory. Further evaluation of 18 and 23 is ongoing.