Synthesis and characterizations of some new tetra thiosemicarbazones and their cyclization reactions; tetra 4-methyl-5-etoxycarbonyl-2,3-dihydro-1,3-thiazole and tetra 2-acetylamino-4-acetyl-4,5-dihydro-1,3,4-thiodiazole derivatives

Er, Mustafa; Ünver, Yasemin; Sancak, Kemal; Düğdü, Esra

doi:10.3998/ark.5550190.0009.f12

Cited by 12 publications

(1 citation statement)

References 43 publications

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“…In recent years, sulfur containing ligands such as dithiocarbamates and thiosemicarbazones and their transition metal complexes have received more attention in the area of medicinal chemistry, due to their pharmacological properties, such as antiviral [ 1 – 3 ], antibacterial [ 4 – 7 ], antifungal [ 8 – 10 ], antiparasitic [ 11 , 12 ], and antitumor [ 13 – 19 ] activities.…”

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confidence: 99%

Synthesis and Characterization of New Palladium(II) Thiosemicarbazone Complexes and Their Cytotoxic Activity against Various Human Tumor Cell Lines

Hernández

Paz

Carrasco

et al. 2013

Bioinorganic Chemistry and Applications

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The palladium(II) bis-chelate complexes of the type [Pd(TSC1-5)2] (6–10), with their corresponding ligands 4-phenyl-1-(acetone)-thiosemicarbazone, HTSC1 (1), 4-phenyl-1-(2′-chloro-benzaldehyde)-thiosemicarbazone, HTSC2 (2), 4-phenyl-1-(3′-hydroxy-benzaldehyde)-thiosemicarbazone, HTSC3 (3), 4-phenyl-1-(2′-naphthaldehyde)-thiosemicarbazone, HTSC4 (4), and 4-phenyl-1-(1′-nitro-2′-naphthaldehyde)-thiosemicarbazone, HTSC5 (5), were synthesized and characterized by elemental analysis and spectroscopic techniques (IR and 1H- and 13C-NMR). The molecular structure of HTSC3, HTSC4, and [Pd(TSC1)2] (6) have been determined by single crystal X-ray crystallography. Complex 6 shows a square planar geometry with two deprotonated ligands coordinated to PdII through the azomethine nitrogen and thione sulfur atoms in a cis arrangement. The in vitro cytotoxic activity measurements indicate that the palladium(II) complexes (IC50 = 0.01–9.87 μM) exhibited higher antiproliferative activity than their free ligands (IC50 = 23.48–70.86 and >250 μM) against different types of human tumor cell lines. Among all the studied palladium(II) complexes, the [Pd(TSC3)2] (8) complex exhibited high antitumor activity on the DU145 prostate carcinoma and K562 chronic myelogenous leukemia cells, with low values of the inhibitory concentration (0.01 and 0.02 μM, resp.).

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of New Palladium(II) Thiosemicarbazone Complexes and Their Cytotoxic Activity against Various Human Tumor Cell Lines

Hernández

Paz

Carrasco

et al. 2013

Bioinorganic Chemistry and Applications

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Synthesis, Structural Characterization, and Biological Evaluation of Novel Substituted 1,3‐Thiazole Derivatives Containing Schiff Bases

Tahtacı

Karakurt

et al. 2015

Journal of Heterocyclic Chem

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In this study, thiazole derivatives containing Schiff bases (7a, 7b, 7c, 7d, 7e, 7f, 8a, 8b, 8c, 8d, 8e, 8f, 9a, 9b, 9c, 9d, 9e, 9f) were synthesized in moderate to high yields (49–94%) using the Hantzsch reaction with thiosemicarbazone derivatives (5a, 5b, 5c) and 2‐bromo‐1‐phenylethanone derivatives (6a, 6b, 6c, 6d, 6e, 6f). The structures of synthesized compounds were elucidated by IR, 1H NMR, 13C NMR, elemental analyses, mass spectroscopy and X‐ray diffraction analysis techniques. Moreover, the synthesized compounds were tested for their in vitro antifungal activity and most of them exhibited moderate to good activity against Fusariumoxysporumf.sp. lycopersici.

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Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

Tahtacı

Karacık

Ece

et al. 2017

Molecular Informatics

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In this study, a novel series of phenyl substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives were synthesized, characterized and explored for antibacterial activity against Gram-negative Escherichia coli, Gram-positive Staphylococcus aureus and Bacillus subtilis and antifungal activity against Candida albicans. Most of the synthesized compounds exhibited remarkable antimicrobial activities, some of which being ten times more potent than positive controls. The most promising compound showed excellent activity with MIC value of 0.03 μg/ml against both S. aureus and B. subtilis (MIC values of positive compound Chloramphenicol are 0.4 μg/ml and 0.85 μg/ml, respectively). Furthermore, structure-activity relationship was also investigated with the help of computational tools. Some physicochemical and ADME properties of the compounds were calculated too. The combination of electronic structure calculations performed at PM6 level and molecular docking simulations using Glide extra-precision mode showed that the hydrophobic nature of keto aryl ring with no electron withdrawing substituents at para position enhances activity while electron-donating substituents at the second aryl ring is detrimental to activity.

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Synthesis and characterizations of some new tetra thiosemicarbazones and their cyclization reactions; tetra 4-methyl-5-etoxycarbonyl-2,3-dihydro-1,3-thiazole and tetra 2-acetylamino-4-acetyl-4,5-dihydro-1,3,4-thiodiazole derivatives

Cited by 12 publications

References 43 publications

Synthesis and Characterization of New Palladium(II) Thiosemicarbazone Complexes and Their Cytotoxic Activity against Various Human Tumor Cell Lines

Synthesis and Characterization of New Palladium(II) Thiosemicarbazone Complexes and Their Cytotoxic Activity against Various Human Tumor Cell Lines

Synthesis, Structural Characterization, and Biological Evaluation of Novel Substituted 1,3‐Thiazole Derivatives Containing Schiff Bases

Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

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