(3Z)-5-fluoro-1H-indole-2,3-dione 3-(N-hydroxy-thiosemicarbazone) | 1265622-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3Z)-5-fluoro-1H-indole-2,3-dione 3-(N-hydroxy-thiosemicarbazone)
• 英文别名: 1-[(5-fluoro-2-oxoindol-3-yl)amino]-3-hydroxythiourea
• CAS: 1265622-69-2
• 化学式: C₉H₇FN₄O₂S
• 分子量: 254.245
• InChiKey: KCUVYZQPHUEBRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.75
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (3Z)-5-fluoro-1H-indole-2,3-dione 3-(N-hydroxy-thiosemicarbazone) 、 环丙沙星 以90.62%的产率得到1-cyclopropyl-6-fluoro-7-[4-(5-fluoro-3-{(Z)-2-[(hydroxyamino)carbothioyl]hydrazono}-2-oxo-2,3-dihydro-1H-indol-1-ylmethyl)hexahydropyrazin-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
• 作为产物：
  描述：

  N-hydroxythiosemicarbazide hydrochloride salt 、 5-氟靛红 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以56.57%的产率得到(3Z)-5-fluoro-1H-indole-2,3-dione 3-(N-hydroxy-thiosemicarbazone)
  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

• N-Hydroxythiosemicarbazones: Synthesis and in vitro antitubercular activity
  作者：Dharmarajan Sriram、Perumal Yogeeswari、Prathiba Dhakla、Palaniappan Senthilkumar、Debjani Banerjee

  DOI：10.1016/j.bmcl.2007.01.037

  日期：2007.4

  N-Hydroxythiosemicarbazide was prepared by two methods starting from 2,4-dimethoxy benzyl amine and hydroxylamine hydrochloride, which in turn was reacted with various aldehydes and ketones to obtain the titled compounds. Eighteen compounds were tested for their in vitro activity against Mycobacterium tuberculosis H37Rv using the agar dilution method. Compound 10p was found to be the most potent compound (MIC: 0.28 mu M) and was 2.5 times more active than standard isoniazid. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.