(S)-N-((3-(3-fluoro-4-hydroxyphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide | 790703-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-N-((3-(3-fluoro-4-hydroxyphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
• 英文别名: N-[{(5S)-3-(3-fluoro-4-hydroxyphenyl)}-2-oxooxazolidin-5-ylmethyl]acetamide；(5S)-N-[3-(3-fluoro-4-hydroxy-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide；N-[3-(3-fluoro-4-hydroxy-phenyl)-2-oxo-oxazolidin-5(S)-ylmethyl]-acetamide；N-[[(5S)-3-(3-fluoro-4-hydroxyphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
• CAS: 790703-59-2
• 化学式: C₁₂H₁₃FN₂O₄
• 分子量: 268.245
• InChiKey: YWHSWLMKAJUNJA-VIFPVBQESA-N

物化性质

• 沸点：
  518.5±40.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-N-((3-(3-fluoro-4-hydroxyphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide 在 potassium carbonate 、 calcium(II) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 36.0h， 生成 N-(((S)-3-(3-fluoro-4-((S)-2-hydroxy-3-(pyridin-4-ylamino)propoxy)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
  参考文献：
  名称：

  Discovery of novel bis-oxazolidinone compounds as potential potent and selective antitubercular agents

  摘要：

  A variety of new mono-oxazolidinone molecules by modifying the C-ring of Linezolid, a marketed antibiotic for MRSA, were synthesized and tested for their in vitro antibacterial activities against several Staphylococcus aureus, Mycobacterium smegmatis and two Gram-negative bacteria strains (Escherichia coli and Pseudomonas aeruginosa). Among them, compounds 4-7 displayed moderate antimicrobial activities. After development of a second oxazolidinone ring in the western part of the mono-oxazolidinone compounds 4-7 by a ring closure reaction with N, N'-carbonyldiimidazole (CDI), we found thus obtained bis-oxazolidinone compounds 22-25 possess excellently inhibitory activities against H(37)Rv but poor or no effects on other test bacteria. Among them, bis-oxazolidinone compound 22 and 24 are the most potent two compounds with a same MIC value of 0.125 mu g/mL against H(37)Rv virulent strain. Compound 22 also exhibited extremely low cytotoxicity on monkey kidney Vero cells with a selective index (IC50/MIC) over 40,000, which suggested bis-oxazolidinone compound 22 is a promising lead compound for subsequent investigation in search of new antitubercular agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.025
• 作为产物：
  描述：

  (5R)-5-azidomethyl-3-(4-benzyloxy-3-fluoro-phenyl)-oxazolidin-2-one 以83的产率得到(S)-N-((3-(3-fluoro-4-hydroxyphenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
  参考文献：
  名称：

  USE OF OXAZOLIDINONE-QUINOLINE HYBRID ANTIBIOTICS FOR THE TREATMENT OF ANTHRAX AND OTHER INFECTIONS

  摘要：

  本发明涉及使用化合物，其中喹诺酮和噁唑烷酮的药效团经过稳定在生理条件下的连接剂化学连接在一起，用于治疗炭疽和其他感染病。

  公开号：

  US20120322766A1

文献信息

• Oxazolidinone-quinolone hybrid antibiotics
  申请人：Morphochem Aktiengesellschaft Für Kombinatorische Chemie

  公开号：US09133213B2

  公开（公告）日：2015-09-15

  The present invention relates to compounds of the Formula (I) that are useful antimicrobial agents and effective against a variety of multi-drug resistant bacteria:

  本发明涉及具有以下式（I）的化合物，这些化合物是有用的抗菌剂，并且对各种多药耐药细菌有效。
• [DE] ZWISCHENPRODUKTE FÜR DIE HERSTELLUNG VON OXAZOLIDINON-CHINOLON HYBRIDEN<br/>[EN] INTERMEDIATE PRODUCTS FOR PRODUCING OXAZOLIDINONE-QUINOLONE HYBRIDS<br/>[FR] PRODUITS INTERMEDIAIRES DESTINES A LA FABRICATION D'HYBRIDES OXAZOLIDINONE-CHINOLONE
  申请人：MORPHOCHEM AG

  公开号：WO2005023801A1

  公开（公告）日：2005-03-17

  Die vorliegende Erfindung beschreibt Zwischenprodukte (ZP) für eine neue und effiziente Synthese von Verbindungen, bei denen die Pharmakophore von Chinolon und Oxazolidinon über einen chemisch stabilen Linker miteinander verknüpft sind.

  本发明描述了用于一种新型且高效合成化合物的中间体（ZP），其中喹诺酮和恶唑烷酮的药效团通过化学稳定的连接子相互连接。
• 噁唑烷酮类化合物及其制备方法和用途
  申请人：四川好医生药业集团有限公司

  公开号：CN104725330B

  公开（公告）日：2017-06-13

  本发明提供了一种噁唑烷酮类化合物或其药学上可接受的盐或水合物。本发明还提供了化合物的制备方法和用途。本发明提供的化合物，对结核分枝杆菌的选择性明显大于其他革兰氏阳性菌和阴性菌，且其选择性优于阳性药物利奈唑胺，说明本发明提供的化合物对结核杆菌具有极强的特异选择性，为临床用药提供了一种更为安全、有效的新选择。
• Novel Antibacterial Compounds
  申请人：Hubschwerlen Christian

  公开号：US20100222302A1

  公开（公告）日：2010-09-02

  The invention relates to novel chimeric antibiotics of formula I wherein R 1 is CH 2 NHCOR 5 , heteroarylmethyl, heteroaryloxymethyl or heteroarylaminomethyl; R 2 is H, OH, OSO 3 H, OPO 3 H 2 , OCH 2 OPO 3 H 2 , OCOCH 2 CH 2 COOH, OCOR 6 ; R 3 is H or halogen; R 4 is (C 1 -C 3 )alkyl, (C 1 -C 3 )haloalkyl or cycloalkyl; R 5 is alkyl or haloalkyl; and R 6 is the residue of a naturally occurring amino acid or of dimethylaminoglycine. These chimeric compounds are useful in the manufacture of medicaments for the treatment of infections (e.g. bacterial infections).

  该发明涉及一种新型嵌合抗生素，其化学式为I，其中R1为CH2NHCOR5，杂环烷基甲基，杂环氧甲基或杂环氨基甲基；R2为H，OH，OSO3H，OPO3H2，OCH2OPO3H2，OCOCH2CH2COOH，OCOR6；R3为H或卤素；R4为（C1-C3）烷基，（C1-C3）卤代烷基或环烷基；R5为烷基或卤代烷基；R6为天然氨基酸残基或二甲氨基甘氨酸残基。这些嵌合化合物在制造治疗感染（例如细菌感染）的药物中非常有用。
• USE OF OXAZOLIDINONE-QUINOLINE HYBRID ANTIBIOTICS FOR THE TREATMENT OF ANTHRAX AND OTHER INFECTIONS
  申请人：Hubschwerlen Christian

  公开号：US20120322766A1

  公开（公告）日：2012-12-20

  The present invention relates to the use of compounds, in which the pharmacophores of quinolone and oxazolidinone are chemically linked together through a linker that is stable under physiological conditions, for the treatment of anthrax and other infections.

  本发明涉及使用化合物，其中喹诺酮和噁唑烷酮的药效团经过稳定在生理条件下的连接剂化学连接在一起，用于治疗炭疽和其他感染病。