1-ethyl-6,8-difluoro-7-[4-(3-{(Z)-2-[(hydroxyamino)carbothioyl]hydrazono}-5-methyl-2-oxo-2,3-dihydro-1H-indol-1-ylmethyl)-3-methylhexahydropyrazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 1265623-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-ethyl-6,8-difluoro-7-[4-(3-{(Z)-2-[(hydroxyamino)carbothioyl]hydrazono}-5-methyl-2-oxo-2,3-dihydro-1H-indol-1-ylmethyl)-3-methylhexahydropyrazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-ethyl-6,8-difluoro-7-[4-[[(3Z)-3-(hydroxycarbamothioylhydrazinylidene)-5-methyl-2-oxoindol-1-yl]methyl]-3-methylpiperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 1265623-25-3
• 化学式: C₂₈H₂₉F₂N₇O₅S
• 分子量: 613.645
• InChiKey: WFTNEOCPVILAPJ-VAMRJTSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  43.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  142.74
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 (3Z)-5-methyl-1H-indole-2,3-dione 3-(N-hydroxy-thiosemicarbazone) 、 洛美沙星 以81.22%的产率得到1-ethyl-6,8-difluoro-7-[4-(3-{(Z)-2-[(hydroxyamino)carbothioyl]hydrazono}-5-methyl-2-oxo-2,3-dihydro-1H-indol-1-ylmethyl)-3-methylhexahydropyrazin-1-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Novel isatinyl thiosemicarbazones derivatives as potential molecule to combat HIV-TB co-infection

  摘要：

  A series of novel 5-substituted-1-(arylmethyl/alkylmethyl)-1H-indole-2,3-dione-3-(N-hydroxy/methoxy thiosemicarbazone) analogues were synthesized and evaluated for their anti-HIV activity and anti-tubercular activity in both log phase and starved cultures. The compound 2-(1-([4-(4-chlorophenyl)tetrahydropyrazin-1 (2H)-yl]methyl)-5-methyl-2-oxo-1,2-dihydro-3H-indol-3-yliden)-N-(methyloxy)hydrazine-1-carbothioamide (B21) displayed promising activity against the replication of HIV-1 cells (EC50 1.69 mu M). In anti-mycobacterial screening B21 proved effective in inhibiting the growth of both log phase (MIC 330 mu M) and starved (MIC 12.11 mu M) MTB cultures. Isocitrate lyase enzyme having momentous implication in persistent TB was shown to be inhibited by 1-cyclopropyl-6-fluoro-7-[4-{[5-methyl-3-((Z)-2-{[(methyloxy)amino]carbothioyl} hydrazono)-2-oxo-1H-indol-1(2H)-yl]methyl}tetrahydropyrazin-1(2H)-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (B30) with 63.44% inhibition at 10 mM. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.020

文献信息

• Novel isatinyl thiosemicarbazones derivatives as potential molecule to combat HIV-TB co-infection
  作者：Debjani Banerjee、Perumal Yogeeswari、Pritesh Bhat、Anisha Thomas、Madala Srividya、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2010.10.020

  日期：2011.1

  A series of novel 5-substituted-1-(arylmethyl/alkylmethyl)-1H-indole-2,3-dione-3-(N-hydroxy/methoxy thiosemicarbazone) analogues were synthesized and evaluated for their anti-HIV activity and anti-tubercular activity in both log phase and starved cultures. The compound 2-(1-([4-(4-chlorophenyl)tetrahydropyrazin-1 (2H)-yl]methyl)-5-methyl-2-oxo-1,2-dihydro-3H-indol-3-yliden)-N-(methyloxy)hydrazine-1-carbothioamide (B21) displayed promising activity against the replication of HIV-1 cells (EC50 1.69 mu M). In anti-mycobacterial screening B21 proved effective in inhibiting the growth of both log phase (MIC 330 mu M) and starved (MIC 12.11 mu M) MTB cultures. Isocitrate lyase enzyme having momentous implication in persistent TB was shown to be inhibited by 1-cyclopropyl-6-fluoro-7-[4-[5-methyl-3-((Z)-2-[(methyloxy)amino]carbothioyl} hydrazono)-2-oxo-1H-indol-1(2H)-yl]methyl}tetrahydropyrazin-1(2H)-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (B30) with 63.44% inhibition at 10 mM. (C) 2010 Elsevier Masson SAS. All rights reserved.