Synthesis of 1<i>H</i>-Indole-2,3-Dione-3-Thiosemicarbazone Ribonucleosides as Antibacterial Agents

Kassab, Shaymaa E.; Hegazy, Gehan H.; Eid, Nahed M.; Amin, Kamelia M.

doi:10.1080/15257770903459267

Cited by 24 publications

(10 citation statements)

References 20 publications

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“…Isatin is a core constituent of many alkaloids (Trost et al, 2009) and drugs (Aboul-Fadl et al, 2010) as well as dyes (Domé nech et al, 2009), pesticides and analytical reagents. Isatin derivatives possess diverse activities such as antibacterial (Kassab et al, 2010), antiviral (Jarrahpour et al, 2007), anti-HIV (Sriram et al, 2006), anticancer (Gü rsoy et al, 2003) and anti-inflammatory (Sridhar et al, 2001) activities. As a continuation of our research work devoted to the development of isatin derivatives (Ben-Yahia et al, 2018;Rayni et al, 2019), we report in this work the synthesis and the Hirshfeld surface analysis of a new indoline-2,3-dione derivative obtained by the action of nonyl bromide on isatin under phase-transfer catalysis conditions.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, DFT study and Hirshfeld surface analysis of 1-nonyl-2,3-dihydro-1H-indole-2,3-dione

Rayni¹,

Bakri

Lai

et al. 2019

Acta Cryst E

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In the title molecule, C17H23NO2, the dihydroindole portion is planar (r.m.s. deviation = 0.0157 Å) and the nonyl substituent is in an `extended' conformation. In the crystal, the nonyl chains intercalate and the dihydroindoledione units are associated through C—H...O hydrogen bonds to form micellar blocks. Based on the Hirshfeld surface analysis, the most important intermolecular interaction is the H...H interaction.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure, DFT study and Hirshfeld surface analysis of 1-nonyl-2,3-dihydro-1H-indole-2,3-dione

Rayni¹,

Bakri

Lai

et al. 2019

Acta Cryst E

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“…1) were shown to possess biological and pharmacological properties. [1][2][3][4] In addition, the anti-poxviral drug isatin β-thiosemicarbazone and its derivatives (5) exhibited anti-HIV activity and induced the viral postreplicative transcription apparatus to synthesize longer than normal mRNAs in the treatment of wild-type vaccinia virus infected cells. 5,6 Moreover, 5-chloro-7-methylisatin β-thiosemicarbazone behaved as a potential ketone inhibitor of parasitic cysteine proteases identified in trypanosomes (cruzain and rhodesain) and malaria parasites.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial screening of novel 1,3-dioxolanes linked to N-5 of 5H-[1,2,4]triazino[5,6-b]indole-3-thiol

2019

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Synthesis of 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-1H-indole-2,3-dione (10) was achieved by coupling 1H-indole-2,3-dione (16) with (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (15) in the presence of sodium hydride in dry N,N-dimethylformamide at room temperature in a closed Erlenmeyer flask. Condensation of 10 with hydrazinecarbothioamide in water afforded the thiosemicarbazone derivative 17; its subsequent cyclization with potassium carbonate in water gave the corresponding thione 18 in good yield. The 3-allylthio and 3-benzylthio derivatives 20 and 21 were also prepared by alkylating thiol 19 with alkyl halides in aqueous sodium hydroxide or coupling of 3-(allylthio/benzylthio)-5H-1,2,4-triazino[5,6-b]indoles (23 and 24) with compound 15 in NaH/DMF. Compound 20 was isomerized to a mixture of geometrical isomers (E/Z)-5-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-3-(prop-1-en-1-ylthio)-5H-1,2,4-triazino[5,6-b]indoles (25 and 26), evidenced by their 1 Hand 13 C-NMR spectra taken in deuterodimethyl sulfoxide. Structural elucidation of the synthesized compounds was realized using FT-IR, 1 H-NMR, 13 C-NMR, mass spectrometry and elemental analysis. The newly synthesized compounds were found to possess moderate inhibitory activity against the fungus Candida albicans compared to clotrimazole as reference control. Compounds 10, 17, 19, 20, 21, 23 and 24 had mean growth inhibition zones (IZ) and minimal inhibitory concentrations (MIC) in the range of 12-15 mm and 31.25-200 μg mL-1 , respectively, with inhibition levels in the range 70.58-88.23 %. Compound 19 exhibited moderate activity against Gram-positive bacteria Staphylococcus aureus relative to imipenem as the standard drug. All compounds were inactive against Escherichia coli and Pseudomonas aeruginosa.

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“…The isatin (1 H ‐indole‐2,3‐dione) is a molecule with immense and diverse biological profile, offering wide array of applications in the field of medicinal chemistry with ease of its synthesis. Some of the reported activities of isatin in the literature are antibacterial , antifungal , antiviral , anti‐HIV , anti‐mycobacterial , anticancer , anti‐inflammatory , anticonvulsant , anti‐TB , antimalarial, and anti‐plasmodial activities.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Characterization, and In Vitro Evaluation of Isatin‐Pomalidomide Hybrids for Cytotoxicity against Multiple Myeloma Cell Lines

Panga

Podila²,

Veeresham

2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).Inspired by the concept of molecular hybridization, a series of new isatin-pomalidomide hybrids (9a-9g) were designed, synthesized, characterized, and evaluated for in vitro cytotoxic activity against U266B1 and RPMI 8226 multiple myeloma cell lines. Sandmeyer methodology and N-halomethylketo alkylation reaction are the two important reactions involved in the synthesis of isatin-pomalidomide hybrids (9a-9g). All the synthesized compounds (3a-3d, 4, 5, 6, and 9a-9g) were characterized by using IR, mass, 1 H-NMR, and 13 C-NMR spectral techniques. The efficacy of all the synthesized compounds was tested against the aforementioned cell lines by employing MTT assay (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) standard protocols while using pomalidomide as a standard. The test concentrations used in the MTT assay were 1, 10, 20, 30, and 40 μM, and the period of incubation was 24 h. All the synthesized compounds were found to have moderate to greater cytotoxic activity against the aforementioned cell lines. Among them, synthesized hybrids 9f (IC 50 , U266B1 = 5.15 ± 0.72 μM, RPMI8226 = 11.66 ± 0.79 μM) and 9g (IC 50 , U266B1 = 2.50 ± 0.37 μM, RPMI8226 = 6.70 ± 0.55 μM) displayed better cytotoxic activity against both the cell lines used in the present study.

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Synthesis of 1H-Indole-2,3-Dione-3-Thiosemicarbazone Ribonucleosides as Antibacterial Agents

Cited by 24 publications

References 20 publications

Crystal structure, DFT study and Hirshfeld surface analysis of 1-nonyl-2,3-dihydro-1H-indole-2,3-dione

Crystal structure, DFT study and Hirshfeld surface analysis of 1-nonyl-2,3-dihydro-1H-indole-2,3-dione

Synthesis and antimicrobial screening of novel 1,3-dioxolanes linked to N-5 of 5H-[1,2,4]triazino[5,6-b]indole-3-thiol

Design, Synthesis, Characterization, and In Vitro Evaluation of Isatin‐Pomalidomide Hybrids for Cytotoxicity against Multiple Myeloma Cell Lines

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