Determination of the Lipophilicity of Some New Derivatives of Thiosemicarbazide and 1,2,4-triazoline-5-thione with Potential Antituberculosis Activity

The chromatographic behavior of newly obtained derivatives of thiosemicarbazide and 1,2,4- triazoline-5-thione was determined. The lipophilicity was confirmed by the use of the Reversed Phase Thin-Layer Chromatography (RP-TLC) method. For both groups of solutes the lipophilicity depended on the substituents. All obtained compounds were tested for their antimycotic activity. The strongest antituberculosis activity was observed for 4-(2-iodophenyl)-1-(pyridine-4-ylacetyl)thiosemicarbazide 4 and 4- phenyl-3-(pyridine-4-ylmethyl)-1,2,4-triazoline-5-thione 27

Sinteza i antimikotsko djelovanje 4-supstituiranih 3-(tiofen-2-il-metil)- Δ2-1,2,4-triazolin-5-tiona

In the reaction of hydrazide of thiophene-2-acetic acid (1) with isothiocyanates, the respective thiosemicarbazides 2a-g were obtained. Further cyclization with 2% NaOH led to formation of 4-substituted-3-(thiophene-2-yl-methyl)-delta2-1,2,4-triazoline-5-thiones (3a-g). These compounds showed promising antimycotic activity.Rekacijom hidrazida tiofen-2-octene kiseline (1) s izotiocijanatima sintetizirani su odgovarajući tiosemikarbazidi (2a-2g), a njihovom ciklizacijom u 2% NaOH 4-supstituirani 3-(tiofen-2-il-metil)-Δ2-1,2,4-triazolin-5-tioni (3a-3g). Ti spojevi su potencijalni antimikotici

Determination of the Lipophilicity of Some New Derivatives of Thiosemicarbazide and 1,2,4-triazoline-5-thione with Potential Antituberculosis Activity

The chromatographic behavior of newly obtained derivatives of thiosemicarbazide and 1,2,4- triazoline-5-thione was determined. The lipophilicity was confirmed by the use of the Reversed Phase Thin-Layer Chromatography (RP-TLC) method. For both groups of solutes the lipophilicity depended on the substituents. All obtained compounds were tested for their antimycotic activity. The strongest antituberculosis activity was observed for 4-(2-iodophenyl)-1-(pyridine-4-ylacetyl)thiosemicarbazide 4 and 4- phenyl-3-(pyridine-4-ylmethyl)-1,2,4-triazoline-5-thione 27

2,4-Dichlorophenoxyacetic Thiosemicarbazides as a New Class of Compounds against Stomach Cancer Potentially Intercalating with DNA

Thiosemicarbazide is a useful structural moiety that has the biological potential. Optimization of this structure can result in groundbreaking discovery of a new class of therapeutic agents. In the light of this, 1-(2,4-dichlorophenoxy)acetyl-4-(1-naphthyl)thiosemicarbazide (1) and 1,4-bis[(2,4-dichlorophenoxy)acetylthiosemicarbazide]phenyl (2) were synthesized and characterized by spectroscopic method. Cytotoxicity of obtained compounds was evaluated on MKN74 gastric cancer cell line and human skin fibroblast BJ based on methylthiazolyldiphenyl-tetrazolium bromide (MTT) test. The apoptosis/necrosis and cell cycle analysis were conducted using image cytometry. Additionally, in DNA of treated cells, abasic sites (AP) and double strands breaks (DSB) presence were measured. Intercalating properties of active compounds were evaluated using the UV–spectroscopic method. Among newly synthesized derivatives, compound 2 showed toxic effects on gastric cancer cells with simultaneous lack of toxicity to normal fibroblasts. Cell cycle analysis revealed that both compounds influence cell division mainly at the stage of replication. Simultaneously with DNA synthesis disorders, DNA damages like AP-sites and DSBs were observed. Spectroscopic studies revealed possible DNA intercalating properties of tested compounds. Obtained results indicate that the newly synthesized thiosemicarbazide derivatives are a promising group of compounds with potential anticancer activity resulted from interactions with DNA and cell cycle interrupt

Terminal Phenoxy Group as a Privileged Moiety of the Drug Scaffold—A Short Review of Most Recent Studies 2013–2022

The terminal phenoxy group is a moiety of many drugs in use today. Numerous literature reports indicated its crucial importance for biological activity; thus, it is a privileged scaffold in medicinal chemistry. This review focuses on the latest achievements in the field of novel potential agents bearing a terminal phenoxy group in 2013–2022. The article provided information on neurological, anticancer, potential lymphoma agent, anti-HIV, antimicrobial, antiparasitic, analgesic, anti-diabetic as well as larvicidal, cholesterol esterase inhibitors, and antithrombotic or agonistic activities towards the adrenergic receptor. Additionally, for selected agents, the Structure–Activity–Relationship (SAR) is also discussed. Thus, this study may help the readers to better understand the nature of the phenoxy group, which will translate into rational drug design and the development of a more efficient drug. To the best of our knowledge, this is the first review devoted to an in-depth analysis of the various activities of compounds bearing terminal phenoxy moiety

New Potential Agents for Malignant Melanoma Treatment—Most Recent Studies 2020–2022

Malignant melanoma (MM) is the most lethal skin cancer. Despite a 4% reduction in mortality over the past few years, an increasing number of new diagnosed cases appear each year. Long-term therapy and the development of resistance to the drugs used drive the search for more and more new agents with anti-melanoma activity. This review focuses on the most recent synthesized anti-melanoma agents from 2020–2022. For selected agents, apart from the analysis of biological activity, the structure–activity relationship (SAR) is also discussed. To the best of our knowledge, the following literature review delivers the latest achievements in the field of new anti-melanoma agents

Synthesis, Spectral, Thermal and Biological Studies of 4-Cyclohexyl-3-(4-nitrophenyl)methyl-1,2,4-triazolin-5-thione and Its Copper(II) Coordination Compound, [CuCl2(H2O)2L2]

One of the strategies for seeking new biologically active substances is to modify compounds with potential biological activity. In this paper, 1,2,4-triazolin-5-thione derivative (3) was obtained in the cyclization reaction of appropriate thiosemicarbazide (2) as an organic ligand. The copper(II) complex, [CuCl2(H2O)2L2] (L=4-cyclohexyl-3-(nitrophenyl)methyl-1,2,4-triazolin-5-thione) (Cu-3) was prepared in a reaction of free ligand (3) with a CuCl2·2H2O solution in MeOH/EtOH mixture at room temperature. TGA data show that Cu-3 and free ligand are stable at room temperature. Both compounds were screened in vitro for antibacterial and antifungal activities using the broth microdilution method. The obtained complex (Cu-3) showed higher antibacterial effect, especially towards Gram-positive bacteria (with moderate activity and Minimal Inhibitory Concentration MIC = 250–500 µg/mL) than the free ligand (3) (with mild or no bioactivity and MIC ≥ 1000 µg/mL). In turn, yeasts, belonging to Candida albicans, exhibited similar sensitivity to both the copper(II) complex (Cu-3) and the organic ligand (3). The anticandidal activity of these compounds was moderate (MIC = 500 µg/mL), or, in the case of other Candida spp., lower (MIC ≥ 1000 µg/mL)

3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

The title compound, C11H13N3S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77 (2):0.23 (2) for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002 (3) Å for the benzyl-substituted C atom, and forms dihedral angles of 88.94 (18) and 86.56 (49)° with the benzene rings of components A and B, respectively. The angle between the plane of the ethyl chain and the mean plane of 1,2,4-triazole ring is 88.55 (15)° and this conformation is stabilized by an intramolecular C—H...S contact. In the crystal, pairs of N—H...S hydrogen bonds link molecules into inversion dimers. π–π interactions are observed between the triazole and benzene rings, with centroid–centroid separations of 3.547 (4) and 3.544 (12) Å for components A and B, and slippages of 0.49 (6) and 0.58 (15) Å, respectively