(R)-2-(4-(4-(5-((1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl) piperazin-1-yl)-2-oxoethanaminium 2,2,2-trifluoroacetate | 1448996-60-8

• 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)-2-(4-(4-(5-((1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl) piperazin-1-yl)-2-oxoethanaminium 2,2,2-trifluoroacetate
• 英文别名: (5R)-3-[4-[4-(2-aminoacetyl)piperazin-1-yl]-3-fluorophenyl]-5-(triazol-1-ylmethyl)-1,3-oxazolidin-2-one;2,2,2-trifluoroacetic acid
• CAS: 1448996-60-8
• 化学式: C₂HF₃O₂*C₁₈H₂₂FN₇O₃
• 分子量: 517.44
• InChiKey: FPBUECOSRWVRSN-UQKRIMTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  丙二酸单乙酯 、 (R)-2-(4-(4-(5-((1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl) piperazin-1-yl)-2-oxoethanaminium 2,2,2-trifluoroacetate 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以30%的产率得到(R)-ethyl 3-((2-(4-(4-(5-((1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazin-1-yl)-2-oxoethyl)amino)-3-oxopropanoate
  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：

  tert-butyl 4-{2-fluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}piperazine-1-carboxylate 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-2-(4-(4-(5-((1H-1,2,3-triazol-1-yl)methyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl) piperazin-1-yl)-2-oxoethanaminium 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

• Synthesis and antibacterial activities of N-substituted-glycinyl 1H-1,2,3-triazolyl oxazolidinones
  作者：Oludotun A. Phillips、Edet E. Udo、Mohammed E. Abdel-Hamid、Reny Varghese

  DOI：10.1016/j.ejmech.2013.05.041

  日期：2013.8

  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.