tert-butyl N-[(1S,2R,4S)-1-benzyl-2-hydroxy-4-[(E)-(5-nitro-2-furyl)methyleneamino]-5-phenyl-pentyl]carbamate | 1353055-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl N-[(1S,2R,4S)-1-benzyl-2-hydroxy-4-[(E)-(5-nitro-2-furyl)methyleneamino]-5-phenyl-pentyl]carbamate
• 英文别名: tert-butyl N-[(2S,3R,5S)-3-hydroxy-5-[(5-nitrofuran-2-yl)methylideneamino]-1,6-diphenylhexan-2-yl]carbamate
• CAS: 1353055-02-3
• 化学式: C₂₈H₃₃N₃O₆
• 分子量: 507.587
• InChiKey: RSOJLBIBKHJXJO-ZKMPZPQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1S,2R,4S)-1-benzyl-2-hydroxy-4-[(E)-(5-nitro-2-furyl)methyleneamino]-5-phenyl-pentyl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S,3R,5S)-2-amino-5-[(E)-(5-nitro-2-furyl)methyleneamino]-1,6-diphenyl-hexan-3-ol
  参考文献：
  名称：

  Synthesis and Antimycobacterial Activity of Novel Amino Alcohols Containing Central Core of the Anti-HIV Drugs Lopinavir and Ritonavir

  摘要：

  Eleven new amino alcohol derivatives have been synthesized from reactions of lopinavir intermediate and heteroaromatic aldehyde in good yields. These compounds, the antiretrovirals (lopinavir and ritonavir) and lopinavir key intermediate were evaluated as antibacterial agents against Mycobacterium tuberculosis H37Rv using the Alamar Blue susceptibility test and their activity expressed as the minimum inhibitory concentration (MIC) in μm. Ten amino alcohols evaluated displayed significant activity (MIC between 6.15 and 108.4 μm) when compared to first‐line drug ethambutol (MIC = 15.9 μm). Three of them showed more activity than ethambutol (MIC = 6.15; 6.21 and 13.4 μm). The appreciable activity of these compounds can be considered an important finding for the rational design of new leads for anti‐TB compounds.

  DOI：

  10.1111/j.1747-0285.2011.01244.x
• 作为产物：
  描述：

  5-硝基糠醛 、 tert-butyl (1S,2R,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentylcarbamate 以 乙醇 为溶剂， 反应 6.0h， 以74%的产率得到tert-butyl N-[(1S,2R,4S)-1-benzyl-2-hydroxy-4-[(E)-(5-nitro-2-furyl)methyleneamino]-5-phenyl-pentyl]carbamate
  参考文献：
  名称：

  Synthesis and Antimycobacterial Activity of Novel Amino Alcohols Containing Central Core of the Anti-HIV Drugs Lopinavir and Ritonavir

  摘要：

  Eleven new amino alcohol derivatives have been synthesized from reactions of lopinavir intermediate and heteroaromatic aldehyde in good yields. These compounds, the antiretrovirals (lopinavir and ritonavir) and lopinavir key intermediate were evaluated as antibacterial agents against Mycobacterium tuberculosis H37Rv using the Alamar Blue susceptibility test and their activity expressed as the minimum inhibitory concentration (MIC) in μm. Ten amino alcohols evaluated displayed significant activity (MIC between 6.15 and 108.4 μm) when compared to first‐line drug ethambutol (MIC = 15.9 μm). Three of them showed more activity than ethambutol (MIC = 6.15; 6.21 and 13.4 μm). The appreciable activity of these compounds can be considered an important finding for the rational design of new leads for anti‐TB compounds.

  DOI：

  10.1111/j.1747-0285.2011.01244.x

文献信息

• Synthesis and Antimycobacterial Activity of Novel Amino Alcohols Containing Central Core of the Anti-HIV Drugs Lopinavir and Ritonavir
  作者：Claudia R. B. Gomes、Marcele Moreth、Danielle Cardinot、Valquiria Kopke、Wilson Cunico、Maria Cristina da Silva Lourenço、Marcus V. N. de Souza

  DOI：10.1111/j.1747-0285.2011.01244.x

  日期：2011.12

  Eleven new amino alcohol derivatives have been synthesized from reactions of lopinavir intermediate and heteroaromatic aldehyde in good yields. These compounds, the antiretrovirals (lopinavir and ritonavir) and lopinavir key intermediate were evaluated as antibacterial agents against Mycobacterium tuberculosis H37Rv using the Alamar Blue susceptibility test and their activity expressed as the minimum inhibitory concentration (MIC) in μm. Ten amino alcohols evaluated displayed significant activity (MIC between 6.15 and 108.4 μm) when compared to first‐line drug ethambutol (MIC = 15.9 μm). Three of them showed more activity than ethambutol (MIC = 6.15; 6.21 and 13.4 μm). The appreciable activity of these compounds can be considered an important finding for the rational design of new leads for anti‐TB compounds.