(R)-4-(2-fluoro-4-(5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)phenyl)piperazin-1-ium 2,2,2-trifluoroacetate | 1170353-90-8

• 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)-4-(2-fluoro-4-(5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)phenyl)piperazin-1-ium 2,2,2-trifluoroacetate
• 英文别名: (5R)-3-(3-fluoro-4-piperazin-1-ylphenyl)-5-[(4-methyltriazol-1-yl)methyl]-1,3-oxazolidin-2-one;2,2,2-trifluoroacetic acid
• CAS: 1170353-90-8
• 化学式: C₂HF₃O₂*C₁₇H₂₁FN₆O₂
• 分子量: 474.415
• InChiKey: IEWQBERWLFJZGP-UQKRIMTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (R)-4-(2-fluoro-4-(5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)phenyl)piperazin-1-ium 2,2,2-trifluoroacetate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 N-(2-(4-(2-fluoro-4-((R)-5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)-2-oxo-oxazolidin-3-yl)phenyl)piperazin-1-yl)-2-oxoethyl)tetrahydrofuran-2-carboxamide
  参考文献：
  名称：

  Synthesis and antibacterial activities of N-substituted-glycinyl 1H-1,2,3-triazolyl oxazolidinones

  摘要：

  A series of 1H-1,2,3-triazolyl piperazino oxazolidinone analogs with optionally varied glycinyl substitutions were synthesized and their antibacterial activity assessed against a panel of susceptible and resistant Gram-positive and selected Gram-negative bacteria including clinical isolates. The N-aroyl- and N-heteroaroyl-glycinyl (MIC: 0.06-4 mu g/ml) derivatives were more potent than the N-acylglycinyl (2 -8 mu g/ml) derivatives against all Gram-positive bacteria tested. Nitro substitution on aryl and heteroaryl rings significantly enhanced activity against Gram-positive bacteria, as noted with the 3,5-dinitrobenzoyl (6m and 6n) and 5-nitro-2-furoyl (6u and 6v) derivatives with MIC ranges of and 0.25-0.5 and 0.06 -0.5 mu g/ml, respectively. These nitro analogs also showed more potent extended activity against Moraxella catarrhalis, with MICs ranges of 0.25-1 mu g/ml, compared to linezolid (MIC: 8 mu g/ml). Hence, the presence of the N-aroyl and/or N-heteroaroyl glycinyl structural motifs as spacer group could significantly enhance the antibacterial activities of 1H-1,2,3-triazolyl oxazolidinone class of compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.041
• 作为产物：
  描述：

  (R)-tert-butyl 4-(4-(5-(azidomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-4-(2-fluoro-4-(5-((4-methyl-1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)phenyl)piperazin-1-ium 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Synthesis and antibacterial activities of N-substituted-glycinyl 1H-1,2,3-triazolyl oxazolidinones

  摘要：

  A series of 1H-1,2,3-triazolyl piperazino oxazolidinone analogs with optionally varied glycinyl substitutions were synthesized and their antibacterial activity assessed against a panel of susceptible and resistant Gram-positive and selected Gram-negative bacteria including clinical isolates. The N-aroyl- and N-heteroaroyl-glycinyl (MIC: 0.06-4 mu g/ml) derivatives were more potent than the N-acylglycinyl (2 -8 mu g/ml) derivatives against all Gram-positive bacteria tested. Nitro substitution on aryl and heteroaryl rings significantly enhanced activity against Gram-positive bacteria, as noted with the 3,5-dinitrobenzoyl (6m and 6n) and 5-nitro-2-furoyl (6u and 6v) derivatives with MIC ranges of and 0.25-0.5 and 0.06 -0.5 mu g/ml, respectively. These nitro analogs also showed more potent extended activity against Moraxella catarrhalis, with MICs ranges of 0.25-1 mu g/ml, compared to linezolid (MIC: 8 mu g/ml). Hence, the presence of the N-aroyl and/or N-heteroaroyl glycinyl structural motifs as spacer group could significantly enhance the antibacterial activities of 1H-1,2,3-triazolyl oxazolidinone class of compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.041

文献信息

• Effects of Varied Substituents on the Antibacterial Activity of Triazolylmethyl Oxazolidinones
  作者：Oludotun A. Phillips、Edet E. Udo、Mohammed E. Abdel-Hamid、Reny Varghese

  DOI：10.1002/ardp.201100332

  日期：2012.10

  A number of 1,2,3‐triazolylmethyl piperazino oxazolidinone derivatives with optionally varied substituents at the 4N‐piperazine position were synthesized and their antibacterial activity evaluated against a panel of susceptible and resistant Gram‐positive and selected Gram‐negative bacteria. Substitution with 5‐membered heteroaroyl and dinitrobenzoyl moieties potentiated activity against staphylococci

  合成了许多在 4N-哌嗪位置具有不同取代基的 1,2,3-三唑基甲基哌嗪基恶唑烷酮衍生物，并评估了它们对一组敏感和耐药的革兰氏阳性菌和选定的革兰氏阴性菌的抗菌活性。用 5 元杂芳酰基和二硝基苯甲酰基部分取代可增强对葡萄球菌和肠球菌菌株的活性。此外，具有二硝基苯甲酰基 7n、7o 和 5-硝基呋喃酰基 7t 取代的化合物对卡他莫拉氏菌的效力是利奈唑胺的四到八倍。然而，在 4N-哌嗪位置取代胍基和其他水溶性官能团导致化合物缺乏抗菌活性。
• Synthesis and antibacterial activity of novel 5-(4-methyl-1H-1,2,3-triazole) methyl oxazolidinones
  作者：Oludotun A. Phillips、Edet E. Udo、Mohammed E. Abdel-Hamid、Reny Varghese

  DOI：10.1016/j.ejmech.2009.03.024

  日期：2009.8

  A series of 5-(4-methyl-1,2,3-triazole)methyl oxazolidinones were synthesized and tested for their antibacterial activity against a panel of Gram-positive and Gram-negative clinical isolates in comparison with linezolid and vancomycin. Most of the compounds demonstrated strong to moderate in vitro antibacterial activity against susceptible and resistant Gram-positive pathogenic bacteria. Antibacterial activity varied with substitutions at the phenyl C4 position with bulky alkylcarbonyl and alkoxycarbonyl substitutions on the piperazine N4 being detrimental to antibacterial activity. Whereas the presence of the 4-methyl-1,2,3-triazole moiety in the acyl-piperazine containing analogs resulted in increased protein binding, and decreased antibacterial activity particularly against Streptococcus pneumoniae strains. (C) 2009 Elsevier Masson SAS. All rights reserved.