- Biological evaluation of arylsemicarbazone derivatives as potential anticancer agents
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Fourteen arylsemicarbazone derivatives were synthesized and evaluated in order to find agents with potential anticancer activity. Cytotoxic screening was performed against K562, HL-60, MOLT-4, HEp-2, NCI-H292, HT-29 and MCF-7 tumor cell lines. Compounds 3c and 4a were active against the tested cancer cell lines, being more cytotoxic for the HL-60 cell line with IC50 values of 13.08 μμM and 11.38 μμM, respectively. Regarding the protein kinase inhibition assay, 3c inhibited seven different kinases and 4a strongly inhibited the CK1δ/ε kinase. The studied kinases are involved in several cellular functions such as proliferation, migration, cell death and cell cycle progression. Additional analysis by flow cytometry revealed that 3c and 4a caused depolarization of the mitochondrial membrane, suggesting apoptosis mediated by the intrinsic pathway. Compound 3c induced arrest in G1 phase of the cell cycle on HL-60 cells, and in the annexin V assay approximately 50% of cells were in apoptosis at the highest concentration tested (26 μμM). Compound 4a inhibited cell cycle by accumulation of abnormal postmitotic cells at G1 phase and induced DNA fragmentation at the highest concentration (22 μμM).
- da Cruz, Anne Cecília Nascimento,Brondani, Dalci José,de Santana, Temístocles I′Talo,da Silva, Lucas Oliveira,Borba, Elizabeth Fernanda da Oliveira,de Faria, Ant?nio Rodolfo,de Albuquerque, Julianna Ferreira Cavalcanti,Piessard, Sylvie,Ximenes, Rafael Matos,Baratte, Blandine,Bach, Stéphane,Ruchaud, Sandrine,Mendon?a Junior, Francisco Jaime Bezerra,Bazin, Marc-Antoine,Rabello, Marcelo Montenegro,Hernandes, Marcelo Zaldini,Marchand, Pascal,da Silva, Teresinha Gon?alves
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- Semicarbazone derivatives as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation
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A series of hydrazinecarboxamide derivatives were synthesized and examined against urease for their inhibitory activity. Among the series, the 1-(3-fluorobenzylidene)semicarbazide (4a) (IC50 = 0.52 ± 0.45 μM), 4u (IC50 = 1.23 ± 0.32 μM) and 4h (IC50 = 2.22 ± 0.32 μM) were found most potent. Furthermore, the molecular docking study was also performed to demonstrate the binding mode of the active hydrazinecarboxamide with the enzyme, urease. In order to estimate drug likeness of compounds, in silico ADME evaluation was carried out. All compounds exhibited favorable ADME profiles with good predicted oral bioavailability.
- Qazi, Syeda Uroos,Rahman, Shafiq Ur,Awan, Asia Naz,al-Rashida, Mariya,Alharthy, Rima D.,Asari, Asnuzilawati,Hameed, Abdul,Iqbal, Jamshed
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- Synthesis of nitrogenated lignin-derived compounds and reactivity with laccases. Study of their application in mild chemoenzymatic oxidative processes
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The chemical synthesis of a series of lignin-derived nitrogenated compounds was performed in high yields (73-99%) through simple conventional chemical transformations starting from natural monomers such as vanillin, syringaldehyde or 3,4-dihydroxybenzaldehyde. The study of the vanillin-derived compounds as substrates for commercially available laccases from Trametes versicolor and Myceliophthora thermophila in oxidative transformations, generally led to the isolation of several dimeric species in high to excellent conversions (>70%), while for hydrazone derivatives a more rapidly oxidative coupling was evidenced by the formation of oligomers and/or polymers. Remarkably, vanillin was obtained due to the hydrolysis of some of the nitrogenated functional groups, such as the hydrazone or the hydrazono tetrazole. The three families of lignin-derived compounds can provide a great source of new laccase-mediator systems (LMS), the possibility of employing them for lignin modification being particularly attractive. Preliminary experiments showed promising levels of activity towards the oxidation of a monomer (veratryl alcohol, up to 70% conversion) and a dimer (adlerol, up to 22% conversion) lignin models, higher than those achieved with the natural vanillin and syringaldehyde (up to 7% conversion with veratryl alcohol and almost negligible conversion with adlerol), these processes being also highly influenced by the pH of the reaction medium.
- Albarrán-Velo, Jesús,López-Iglesias, María,Gotor, Vicente,Gotor-Fernández, Vicente,Lavandera, Iván
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p. 50459 - 50471
(2017/11/10)
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- Synthesis, properties, and application of 4-nitrosemicarbazones
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The studies of the condensation of 4-nitrosemicarbazide (4-NSC) with various aldehydes and ketones resulted in the development of an approach to the synthesis of N-nitrosemicarbazones, promising high-energy and biologically active compounds. Subsequent treatment with amines and alkalis led to the synthesis of water-soluble salts of nitrosemicarbazones, as well as the corresponding semicarbazones. The reaction of N,N′-diisopropyl- or N,N′-di-tert-butyl-1,2-ethanediimine with 4-nitrosemicarbazide led to the synthesis of glyoxal bis(nitrosemicarbazone) derivatives. A computer-aided screening using the PASS software showed a probability of high biological activity for the compounds obtained, whereas antiarrhythmic properties of camphor nitrosemicarbazone potassium salt were confirmed in experiments in rats.
- Glukhacheva,Il’yasov,Sakovich,Tolstikova,Bryzgalov,Pleshkova
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p. 550 - 560
(2017/03/08)
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- Synthetic, structural, and antimicrobial studies of organotin(IV) complexes of semicarbazone, thiosemicarbazone derived from 4-hydroxy-3- methoxybenzaldehyde
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Reaction of dibutyltin dichloride, dimethyltin dichloride, and tributyltin chloride with ligands derived from thiosemicarbazone and semicarbazone leads to the formation of a new series of organotin(IV) complexes of general formula R2SnCl2
- Singh,Singh,Sharma
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experimental part
p. 53 - 65
(2012/05/20)
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- Synthesis, antimicrobial and insecticidal activity of some 4H-1, 2, 4 triazole derivatives
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1-(Substituted benzylidene) semicarbazide has been used as a precursor to synthesize some important biologically active 3- substituted phenyl, 4H-1, 2, 4 triazole derivatives. Reaction of ethanolic solution of schiff s base of substituted aromatic aldehyde 1 with ethanolic solution of FeCl 3.6H2O (1 mole FeCl3.6H2O in 10 mL ethanol) yields the 4N-1, 2, 4 triazole-3-derivative 2. Several derivatives have been synthesized and screened for their antibacterial efficacy against Bacillus subtilis, Escherichia coli, Staphyllococcus aureus and Klebsiella pneumoniae, Antifungal activity against Aspergillus flavus, Fusarium oxysporum, Aspergillus niger and Trichoderma viridae and insecticidal activity against Periplaneta americana.
- Gautam, Nidhi,Chourasia
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experimental part
p. 956 - 959
(2010/10/18)
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- Spectroscopic and biochemical studies of chromium(III) and manganese(II) complexes with p-vanillin containing thiosemicarbazone and semicarbazone ligands
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A new series of chromium(III) and manganese(II) complexes with p-vanillin thiosemicarbazone (L1) and p-vanillin semicarbazone (L2) have been synthesized and characterized. The nature of bonding and stereochemistry of the complexes ha
- Chandra, Sulekh,Tyagi, Monika
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experimental part
p. 42 - 47
(2009/04/06)
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- Evaluation of semicarbazones for anticonvulsant and sedative-hypnotic properties
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A series of semicarbazones and thiosemicarbazones were synthesized and evaluated for anti-convulsant activity. Some compounds provided significant protection against Maximal Electroshock (MES) and subcutaneous strychnine induced seizures. Compound 1 was the most active in the series with activity in a dose of 30 mg/kg in the strychnine seizure pattern test and an ED50 of 10 mg/kg in the MES test. Hence it could serve as a prototype molecule for future development. Also compounds with a p-nitrophenyl substitution in place of the amino hydrogen of semicarbazone moiety showed activity in a dose of 30 mg/kg and an ED50 of 83 mg/kg in the MES test.
- Pandeya,Aggarwal,Jain
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p. 300 - 302
(2007/10/03)
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- Structural modifications of the primary amino group of anticonvulsant aryl semicarbazones
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A number of aryl semicarbazones had been shown previously to possess significant anticonvulsant properties. The principal objective of the present investigation was to determine the importance of the primary amino group in this series of compounds by replacing it with other substituents. The results indicate that the amino group was not essential for anticonvulsant activity. However its replacement by an aryl ring generally abolished activity while a terminal phenylamino function was better tolerated. Thus both the size of the group and its hydrogen bonding capabilities appear to influence bioactivity. Alteration of the oxygen atom of the semicarbazones by isosteres did not enhance anticonvulsant properties.
- Dimmock,Puthucode,Lo,Quail,Yang,Stables
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