(R)-5-Azidomethyl-3-[3-fluoro-4-(4-pyridin-2-yl-piperazin-1-yl)-phenyl]-oxazolidin-2-one | 202133-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (R)-5-Azidomethyl-3-[3-fluoro-4-(4-pyridin-2-yl-piperazin-1-yl)-phenyl]-oxazolidin-2-one
• 英文别名: (5R)-5-(azidomethyl)-3-[3-fluoro-4-(4-pyridin-2-ylpiperazin-1-yl)phenyl]-1,3-oxazolidin-2-one
• CAS: 202133-39-9
• 化学式: C₁₉H₂₀FN₇O₂
• 分子量: 397.412
• InChiKey: GGHKMWSQILILAM-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  63.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-5-Azidomethyl-3-[3-fluoro-4-(4-pyridin-2-yl-piperazin-1-yl)-phenyl]-oxazolidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 (S)-5-Aminomethyl-3-[3-fluoro-4-(4-pyridin-2-yl-piperazin-1-yl)-phenyl]-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and antibacterial activity of arylpiperazinyl oxazolidinones with diversification of the N-substituents

  摘要：

  A series of 4-arylpiperazin-1-yl-3-phenyloxazolidin-2-one derivatives with diversification of the N-substituents such as methylene O-linked heterocycles, thioamide, dithiocarbamate, thiourea, and thiocarbamate were synthesized and evaluated as antibacterial agents. Their in vitro activities (MIC) were evaluated against MRSA and VRE resistant Gram-positive strains such as Staphylococcus and Enterococcus. Most of the compounds were more potent in vitro but less active in vivo than linezolid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.066
• 作为产物：
  描述：

  (5R)-3-(4-(4-(pyridin-2-yl)piperazin-1-yl)-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one 在 sodium azide 、 TEA 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-5-Azidomethyl-3-[3-fluoro-4-(4-pyridin-2-yl-piperazin-1-yl)-phenyl]-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and antibacterial activity of arylpiperazinyl oxazolidinones with diversification of the N-substituents

  摘要：

  A series of 4-arylpiperazin-1-yl-3-phenyloxazolidin-2-one derivatives with diversification of the N-substituents such as methylene O-linked heterocycles, thioamide, dithiocarbamate, thiourea, and thiocarbamate were synthesized and evaluated as antibacterial agents. Their in vitro activities (MIC) were evaluated against MRSA and VRE resistant Gram-positive strains such as Staphylococcus and Enterococcus. Most of the compounds were more potent in vitro but less active in vivo than linezolid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.05.066

文献信息

• SUBSTITUTED PIPERAZINYL-PHENYL-OXAZOLIDINONE DERIVATIVES AND THEIR USE AS ANTI-BACTERIAL AGENTS
  申请人：ZENECA LIMITED

  公开号：EP0918769A1

  公开（公告）日：1999-06-02
• PYRIDYL-PIPERAZINYL-PHENYL-OXAZOLIDINONE DERIVATIVES AND THEIR USE AS ANTIBACTERIALS
  申请人：Zeneca Limited

  公开号：EP0918770A1

  公开（公告）日：1999-06-02
• [EN] SUBSTITUTED PIPERAZINYL-PHENYL-OXAZOLIDINONE DERIVATIVES AND THEIR USE AS ANTI-BACTERIAL AGENTS<br/>[FR] DERIVES SUBSTITUES DE PIPERAZINYLE-PHENYLE-OXAZOLIDINONE ET LEUR UTILISATION EN TANT QU'AGENTS ANTIBACTERIENS
  申请人：——

  公开号：WO1998001446A1

  公开（公告）日：1998-01-15

  [EN] The invention concerns a compound of formula (I) wherein, for example: R<1> is of the formula -NHC(=O)R wherein R is for example (1-4C)alkyl; R<2> and R<3> are independently hydrogen or fluoro; R<4> and R<5> are independently hydrogen or methyl; R<6> is a 6-membered heteroaryl ring containing 2 or 3 ring nitrogen atoms as the only ring heteroatoms, and optionally substituted by substituents selected from (1-4C)alkyl (optionally substituted), halo, trifluoromethyl, (1-4C)alkylS(O)n- (wherein n is 0, 1 or 2), (1-4C)alkylS(O)2amino, (1-4C)alkanoylamino, carboxy, hydroxy, amino, (1-4C)alkylamino, di-(1-4C)alkylamino, (1-4C)alkoxycarbonyl, carbamoyl, N-(1-4C)alkylcarbamoyl, di-(N-(1-4C)alkyl)carbamoyl [wherein the (1-4C)alkyl group or groups in the last two-mentioned carbamoyl substituents is optionally substituted by hydroxy, (1-4C)alkoxy or (1-4C)alkoxycarbonyl], (2-4C)alkenyl (optionally substituted by carboxy or (1-4C)alkoxycarbonyl), (1-4C)alkoxy, cyano or nitro; pharmaceutically-acceptable salts, suitable N-oxides and in-vivo-hydrolysable esters thereof; processes for their preparation; pharmaceutical compositions containing them and their use as antibacterial agents.
  [FR] L'invention concerne un composé représenté par la formule (I) dans laquelle, par exemple: R<1> représente la formule -NHC(=O)R dans laquelle R représente, par exemple, alkyle C1-C4; R<2> et R<3> représentent hydrogène ou fluoro; R<4> et R<5> représentent indépendamment hydrogène ou méthyle; R<6> représente une chaîne hétéroaryle à 6 éléments contenant 2 ou 3 atomes d'azote en tant que seuls hétéroatomes de chaîne, et éventuellement substitué par des substituants sélectionnés dans alkyle C1-C4 (éventuellement substitué), halo, trifluorométhyle, alkyle C1-C4 S(O)n- (dans laquelle n est 0, 1 ou 2), alkyle C1-C4 S(O)2amino, alkanoylamino C1-C4, carboxy, hydroxy, amino, alkylamino C1-C4, dialkylamino C1-C4, alkoxycarbonyle C1-C4, carbamoyle, N-alkylcarbamoyle C1-C4, di-(N-alkyle C1-C4)carbamoyle [dans laquelle le ou les groupes alkyle C1-C4 dans les deux derniers substituants de carbamoyle sont éventuellement substitués par hydroxy, alkoxy C1-C4 ou alkoxycarbonyle C1-C4], alkényle C2-C4 (éventuellement substitué par carboxy ou alkoxycarbonyle C1-C4), alkoxy C1-C4, cyano ou nitro; ses sels acceptables sur le plan pharmaceutique, ses N-oxydes appropriés et ses esters hydrolysables in-vivo; leurs procédés de préparation; des compositions pharmaceutiques les contenant et leur utilisation en tant qu'agents antibactériens.
• [EN] PYRIDYL-PIPERAZINYL-PHENYL-OXAZOLIDINONE DERIVATIVES AND THEIR USE AS ANTIBACTERIALS<br/>[FR] DERIVES DE PYRIDYLE-PIPERAZINYLE-PHENYLE-OXAZOLIDINONE ET LEUR UTILISATION EN TANT QU'ANTIBACTERIENS
  申请人：ZENECA LIMITED

  公开号：WO1998001447A1

  公开（公告）日：1998-01-15

  (EN) The invention concerns a compound of formula (I) wherein, for example: R1 is of the formula -NHC(=O)Ra wherein Ra is for example (1-4C)alkyl; R2 and R3 hydrogen or fluoro; R4 and R5 are independently are independently hydrogen or methyl; R6 is pyridyl, optionally substituted by substituents selected from (1-4C)alkyl (optionally substituted), halo, trifluoromethyl, (1-4C)alkylS(O)n- (wherein n is 0, 1 or 2), (1-4C)alkylS(O)2amino, (1-4C)alkanoylamino, carboxy, hydroxy, amino, (1-4C)alkylamino, di-(1-4C)alkylamino, (1-4C)alkoxycarbonyl, carbamoyl, N-(1-4C)alkylcarbamoyl, di-(N-(1-4C)alkyl)carbamoyl [wherein the (1-4C)alkyl group or groups in the last two-mentioned carbamoyl substituents is optionally substituted by hydroxy, (1-4C)alkoxy or (1-4C)alkoxycarbonyl], (2-4C)alkenyl (optionally substituted by carboxy or (1-4C)alkoxycarbonyl), (1-4C)alkoxy, cyano or nitro; pharmaceutically-acceptable salts, suitable N-oxides and in vivo hydrolysable esters thereof; processes for their preparation; pharmaceutical compositions containing them and their use as antibacterial agents.(FR) L'invention concerne un composé représenté par la formule (I) dans laquelle, par exemple: R1 représente la formule -NHC(=O)Ra dans laquelle Ra représente, par exemple, alkyle C1-C4; R2 et R3 représentent indépendamment hydrogène ou fluoro; R4 et R5 représentent indépendamment hydrogène ou méthyle: R6 représente pyridyle, éventuellement substitué par des substituants sélectionnés dans alkyle C1-C4 (éventuellement substitué), halo, trifluorométhyle, alkyle C1-C4 S(O)n (dans laquelle n est 0, 1, 2), alkyle C1-C4 S(O)2amino, alkanoylamino C1-C4, carboxy, hydroxy, amino, alkylamino C1-C4, di-alkylamino C1-C4, alkoxycarbonyle C1-C4, carbamoyle, N-alkylcarbamoyle C1-C4, di-(N-alkyle C1-C4)carbamoyle [dans laquelle le ou les groupes alkyle C1-C4 dans les deux derniers substituants de carbamoyle sont éventuellement substitués par hydroxy, alkoxy C1-C4 ou alkoxycarbonyle C1-C4], alkényle C2-C4 (éventuellement substitué par carboxy ou alkoxycarbonyle C1-C4), alkoxy C1-C4, cyano ou nitro; ses sels acceptables sur le plan pharmaceutique, ses N-oxydes appropriés et ses esters hydrolysables in vivo; leurs procédés de préparation; des compositions pharmaceutiques les contenant et leur utilisation en tant qu'agents antibactériens.
• Synthesis and antibacterial activity of arylpiperazinyl oxazolidinones with diversification of the N-substituents
  作者：Sun-Young Jang、Young Hwan Ha、Seung Whan Ko、Wonku Lee、Jongkook Lee、Sunghoon Kim、Yong Woo Kim、Won Koo Lee、Hyun-Joon Ha

  DOI：10.1016/j.bmcl.2004.05.066

  日期：2004.8

  A series of 4-arylpiperazin-1-yl-3-phenyloxazolidin-2-one derivatives with diversification of the N-substituents such as methylene O-linked heterocycles, thioamide, dithiocarbamate, thiourea, and thiocarbamate were synthesized and evaluated as antibacterial agents. Their in vitro activities (MIC) were evaluated against MRSA and VRE resistant Gram-positive strains such as Staphylococcus and Enterococcus. Most of the compounds were more potent in vitro but less active in vivo than linezolid. (C) 2004 Elsevier Ltd. All rights reserved.