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Search results for: MEDICINAL CHEMISTRY
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Amine–alkyl derivatives of hydantoin: New tool to combat resistant bacteria
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Discovery of phenylselenoether-hydantoin hybrids as ABCB1 efflux pump modulating agents with cytotoxic and antiproliferative actions in resistant T-lymphoma
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Design, synthesis and structure–activity relationships of novel phenylalanine-based amino acids as kainate receptors ligands
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Pharmacological characterization and binding modes of novel racemic and optically active phenylalanine-based antagonists of AMPA receptors
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Imidazo-thiazine, -diazinone and -diazepinone derivatives. Synthesis, structure and benzodiazepine receptor binding
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N-Substituted piperazine derivatives as potential multitarget agents acting on histamine H3 receptor and cancer resistance proteins
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Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridine-5,6-diones: Synthesis, enzymatic reduction and cytotoxic activity
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Synthesis and biological activity of novel mycophenolic acid conjugates containing nitro-acridine/acridone derivatives
PublicationOpracowano warunki reakcji kwasu mykofenolowego z aminowymi pochodnymi akrydyn i akrydonów. Tak otrzymane koniugaty zostały scharakteryzowane, a następnie przebadane in vitro pod względem aktywności przeciwbiałaczkowej oraz immunosupresyjnej.
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Photophysical properties and photocytotoxicity of free and liposome-entrapped diazepinoporphyrazines on LNCaP cells under normoxic and hypoxic conditions
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Photosensitizers Mediated Photodynamic Inactivation Against Virus Particles
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Acid-catalysed synthesis of oxathiolone fused chalkones. Comparison of their activity toward various microrganisms and human cancer lines
PublicationOtrzymano podstawione pochodne oksationolowych sprzężonych chalkonów w wyniku kondensacji 4-acetylo-5-metoksy-2-0ksobenz[1,3]oksatiolu z aldehydem benzoesowym w środowisku kwaśnym. Badano właściwości biologiczne otrzymanych związków. Trzy z otrzymanych pochodnych wykazały umiarkowaną aktywność wobec komórek HeLa, dwa były aktywne wobec Micrococcus luteus i Staphylococcus aureus, a jeden wobec Mycobacterium tuberculosis.
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Synthesis and biological activity of novel ester derivatives of N3-(4-metoxyfumaroyl)-(S)-2,3-diaminopropanoic acid containing amide and keto function as inhibitors of glucosamine-6-phosphate synthase
PublicationA short series of novel ester derivatives of N3-4-methoxyfumaroyl-(S)-2,3-diaminopropanoic acid (FMDP) containing amido or keto functions have been designed and synthesized. Their antifungal activity and inhibitory properties toward fungal glucosamine-6-phosphate synthase has also been evaluated. The obtained compounds 11-13 and 15-17 demonstrated good antifunga activity against Candida albicans. Compounds 11-13 displayed also...
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Synthesis, anticandidal activity of N3-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives – Novel inhibitors of glucosamine-6-phosphate synthase
PublicationNovel FMDP amiders 4-6 have been synthesized and tested against Candida strains. The anticandidal activity has been confined only to Candida albicans. Anticandidal activity of the tested amides has correlated with their inhibitory activity of glucosamine-6-phosphate synthase in cell free extract from Candida albicans.
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Synthesis of functionalized new conjugates of batracylin with tuftsin/ retro-tuftsin derivatives and their biological evaluation
PublicationNew batracylin conjugates with tuftsin/retro-tuftsin derivatives were designed and synthesized using T3P as a coupling agent. The conjugates possess an amide bond formed between the carboxyl group of heterocyclic molecule and the N-termini of the tuftsin/retro-tuftsin chain. The in vitro cytotoxic activity of the new analogues and their precursors was evaluated using a series of human and murine tumor cells. BAT conjugates containing...
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Structural factors affecting affinity of cytotoxic oxathiole-fused chalcones toward tubulin
PublicationSynthesis, in vitro cytotoxic activity, and interaction with tubulin of (E)-1-(6-alkoxybenzo[d][1,3]oxathiol- 5-yl)-3-phenylprop-2-en-1-one derivatives (2) are described. Some of the compounds demonstrated cytotoxic activity at submicromolar concentrations, and the activity could be related to interaction with tubulin at the colchicine binding site. Interaction of selected derivatives with tubulinwas evaluated using molecular modeling,...
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Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N'-(2-arylmethylthio-4-chloro-5- methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII
PublicationA series of novel N-substituted N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines 9 e41 have been synthesized and investigated as inhibitors of four isoforms of zinc enzyme carbonic anhydrase (CA.EC 4.2.1.1), that is the cytosolic CA I and II, and cancer-associated isozymes CA IX and XII. Against the human CA I investigated compounds showed KI in the range of 87e6506 nM, toward hCA II ranging from 7.8 to 4500 nM,...
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New Analogues of Mycophenolic Acid
PublicationMycophenolic acid (MPA) possesses antibacterial, antifungal, antiviral, immunosuppressive and anticancer properties. It is a non-competitive and reversible inhibitor of dehydrogenase inosine-5'-monophosphate (IMPDH). This compound belongs to the immunosuppressive drugs used for the prevention of both acute and chronic transplant rejection. Until now, two derivatives of MPA have been used clinically: mycophenolate mofetil (MMF,...
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Synthesis and biological evaluation of fluorinated N-benzoyl and N-phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7-O-sulfamate as steroid sulfatase inhibitors
PublicationIn the present work, we report convenient methods for the synthesis of 3-(4-aminophenyl)-coumarin-7-O-sulfamate derivatives N-acylated with fluorinated analogues of benzoic or phenylacetic acid as steroid sulfatase (STS) inhibitors. The design of these potential STS inhibitors was supported by molecular modeling techniques. Additionally, computational docking methods were used to determine the binding modes of the synthesized inhibitors...
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Novel 2-(2-alkylthiobenzenesulfonyl)-3-(phenylprop-2-ynylideneamino)guanidine derivatives as potent anticancer agents – Synthesis, molecular structure, QSAR studies and metabolic stability
PublicationA series of new 2-(2-alkylthiobenzenesulfonyl)-3-(phenylprop-2-ynylideneamino)guanidine derivatives have been synthesized and evaluated in vitro by MTT assays for their antiproliferative activity against cell lines of colon cancer HCT-116, cervical cancer HeLa and breast cancer MCF-7. The obtained results indicated that these compounds display prominent cytotoxic effect. The best anticancer properties have been observed for derivatives...
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Synthesis and biological activity of mycophenolic acid-amino acid derivatives
PublicationIn search of new immunosuppressants, mycophenolic acid (MPA) was coupled with amino acid methyl esters followed by hydrolysis to analogs bearing free carboxylic groups. The obtained compunds were tested in vitro as growth inhibitors of lymphoid cell line (Jurkat) and human peripheral blood mononuclear cells (PBMC) from healthy donors. According to obtained results recovering of free carboxylic group increased their activity. Additionally,...
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Novel 2-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)-1-(1,3,5-triazin-2-ylamino)guanidine derivatives: Inhibition of human carbonic anhydrase cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII, anticancer activity, and molecular modeling studies
PublicationA series of novel 2-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)-1-(6-substituted-4-chloro-1,3,5-triazin-2-ylamino)guanidine derivatives 9–20 have been synthesized by substitution of chlorine atom at the 1,3,5-triazine ring in compounds 5–8 with 3- or 4-aminobenzenesulfonamide and 4-(aminomethyl)benzenesulfonamide hydrochloride. All the synthesized compounds were evaluated for their inhibitory activity toward hCA I, II,...
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Synthesis and antimicrobial activity of amino acid and peptide derivatives of mycophenolic acid
PublicationThe series of 16 novel amino acid and peptide mycophenolic acid (MPA) derivatives was obtained as potential antibacterial agents. Coupling of MPA with respective amines was optimized with condensing reagents such as EDCI/DMAP and T3P/TEA. Amino acid analogs were received both as methyl esters and also with the free carboxylic group. The biological activity of the products was tested on five references bacterial strains: Klebsiella...
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Synthesis, molecular structure, and metabolic stability of new series of N' -(2-alkylthio-4-chloro-5-methylbenzenesulfonyl)-1-(5-phenyl-1 H -pyrazol-1-yl)amidine as potential anti-cancer agents
PublicationA series of new N'-(2-alkylthio-4-chloro-5-methylbenzenesulfonyl)-1-(5-phenyl-1H-pyrazol-1-yl)amidine derivatives have been synthesized and evaluated in vitro by MTT assays for their antiproliferative activity against cell lines of colon cancer HCT-116, cervical cancer HeLa and breast cancer MCF-7. The studied compounds display selective activity mainly against HCT-116 and HeLa cells. Thus, five compounds show selective cytotoxic...
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Synthesis of bicoumarin thiophosphate derivatives as steroid sulfatase inhibitors
PublicationBased on the frameworks of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one, 3-hydroxy- 7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-8,9,10,11-tetrahydro-7H-cyclohepta[c] chromen-6-one, a series of bicoumarin thiophosphate analogs have been synthesized and biologically evaluated. Additionally, their binding modes have been modeled using docking techniques. The inhibitory properties of the synthesized compounds...
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Synthesis of the inosine 5′-monophosphate dehydrogenase (IMPDH) inhibitors
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Cytochromes P450 and Skin Cancer: Role of Local Endocrine Pathways
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Synthesis of the inosine 5'-monophosphate dehydrogenase (IMPDH) inhibitors
PublicationIn this review are summrized newly described IMPDH inhibitors. The article concerns both synthetic pathways and biological activities of the most promising compounds.
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Anticancer Properties of Amino Acid and Peptide Derivatives of Mycophenolic Acid
PublicationBackground: Although Mycophenolic Acid (MPA) is applied as prodrugs in clinic as an immunosuppressant, it also possesses anticancer activity. MPA acts as Inosine-5’-Monophosphate Dehydrogenase (IMPDH) inhibitor, where the carboxylic group at the end of the side chain interacts with Ser 276 of the enzyme via hydrogen bonds. Therefore, MPA derivatives with other polar groups indicated high inhibition too. On the other hand, potent...
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New potent steroid sulphatase inhibitors based on 6-(1-phenyl-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate derivatives
PublicationIn the present work, we report a new class of potent steroid sulphatase (STS) inhibitors based on 6-(1-phenyl-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate derivatives. Within the set of new STS inhibitors, 6-(1-(1,2,3-trifluorophenyl)-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate 3L demonstrated the highest activity in the enzymatic assay inhibiting the STS activity to 7.98% at 0.5 µM concentration. Furthermore, to verify...
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9,10-Dioxoanthracenyldithiocarbamates effectively inhibit the proliferation of non-small cell lung cancer by targeting multiple protein tyrosine kinases
PublicationAnthraquinones have attracted considerable interest in the realm of cancer treatment owing to their potent anticancer properties. This study evaluates the potential of a series of new anthraquinone derivatives as anticancer agents for non-small-cell lung cancer (NSCLC). The compounds were subjected to a range of tests to assess their cytotoxic and apoptotic properties, ability to inhibit colony formation, pro-DNA damage functions,...
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Development of potent and effective SARS-CoV-2 main protease inhibitors based on maleimide analogs for the potential treatment of COVID-19
PublicationIn the present work, we report a new series of potent SARS-CoV-2 Main Protease (Mpro) inhibitors based on maleimide derivatives. The inhibitory activities were tested in an enzymatic assay using recombinant Mpro (3CL Protease from coronavirus SARS-CoV-2). Within the set of new Mpro inhibitors, 6e demonstrated the highest activity in the enzymatic assay with an IC50 value of 8.52 ± 0.44 mM. The IC50 value for Nirmatrelvir (PF-07321332,...
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Palindromic carbazole derivatives: unveiling their antiproliferative effect via topoisomerase II catalytic inhibition and apoptosis induction
PublicationHuman DNA topoisomerases are essential for crucial cellular processes, including DNA replication, transcription, chromatin condensation, and maintenance of its structure. One of the significant strategies employed in cancer treatment involves the inhibition of a specific type of topoisomerase, known as topoisomerase II (Topo II). Carbazole derivatives, recognised for their varied biological activities, have recently become a significant...
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Novel amides of mycophenolic acid and some heterocyclic derivatives as immunosuppressive agents
PublicationThe group of new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5'-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis employed uronium-type activating system (TBTU/HOBt/DIPEA) while or phosphonic acid anhydride method (T3P/Py) facilitating amides to be obtained in moderate to excellent yields without...
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Design, synthesis and biological evaluation of novel N-phosphorylated and O-phosphorylated tacrine derivatives as potential drugs against Alzheimer’s disease
PublicationIn this work, we designed, synthesised and biologically investigated a novel series of 14N- and O-phosphorylated tacrine derivatives as potential anti-Alzheimer’s disease agents. In the reaction of 9-chlorotacrine and corresponding diamines/aminoalkylalcohol we obtained diamino and aminoalkylhydroxy tacrine derivatives. Next, the compounds were acid to give final products 6–13 and 16–21 that were characterised by 1H, 13 C, 31P...
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Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics – synthesis and properties
PublicationGlucosamine-6-phosphate synthase (GlcN-6-P synthase) is known as a promising target for antimicrobial agents and antidiabetics. Several compounds of natural or synthetic origin have been identified as inhibitors of this enzyme. This set comprises highly selective L-glutamine, amino sugar phosphate or transition state intermediate cis-enolamine analogues. Relatively low antimicrobial activity of these inhibitors, poorly penetrating...
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Recent progress in the development of steroid sulfatase inhibitors – examples of the novel and most promising compounds from the last decade
PublicationThe purpose of this review article is to provide an overview of recent achievements in the synthesis of novel steroid sulfatase (STS) inhibitors. STS is a crucial enzyme in the biosynthesis of active hormones (including estrogens and androgens) and, therefore, represents an extremely attractive molecular target for the development of hormone-dependent cancer therapies. The inhibition of STS may effectively reduce the availability...
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Flavonoids as inhibitors of human neutrophil elastase
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Flavonoids as tyrosinase inhibitors in in silico and in vitro models: basic framework of SAR using a statistical modelling approach
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Antiglycoxidative properties of amantadine – a systematic review and comprehensive in vitro study
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The synthesis and biological activity of lipophilic derivatives of bicine conjugated with n3-(4-methoxyfumaroyl)-l-2,3-diaminopropanoic acid(fmdp) - an inhibitor of glucosamine-6-phosphate synthase
PublicationOtrzymano serię pochodnych bicyny połączonych z inhibitorem syntazy glukozamino-6-fosforanu (fmdp)oraz zbadano ich właściwości lipofilowe i aktywność przeciwgrzybową. otrzymane związki charakteryzowały się wyższą llipofilowością niż fmdp. wszystkie otrzymane związki wykazywały także wyższą aktywność przeciwgrzybową niż fmdp.
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Chemical reactivity and antimicrobial activity of N-substituted maleimides
PublicationZsyntezowano kilkanaście N-podstawionych maleimidów, zawierających w swojej strukturze podstawniki o różnej wielkości i polarności.Maleimidy o charakterze obojętnym wykazywały silny efekt przeciwgrzybowy; ich aktywność przeciwbakteryjna była zróżnicowana. Niską aktywność przeciwbakteryjną, ale wysoką aktywność cytostatyczną stwierdzono dla maleimidów o charakterze zasadowym. Reaktywność chemiczna i lipofilowość miały wpływ na aktywność...
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Novel synthesis scheme and in vitro antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-1-nitroethenes
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Synthesis of Combretastatin A-4 Analogs and their Biological Activities
PublicationCombretastatin A-4 (CA-4) is a natural product, which consists of two phenyl rings, linked by an ethylene bridge. CA-4, inhibitor of polymerization of tubulin to microtubules, possesses a strong antitumor and anti-vascular properties both in vitro and in vivo. Previous studies showed that disodium phosphate salt of CA-4, a water-soluble prodrug is well tolerated at therapeutically useful doses. However, it should be noted that...
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Synthesis and biological activity of ester derivatives of mycophenolic acid and acridines/acridones as potential immunosuppressive agents
PublicationImproved derivatives of mycophenolic acid (MPA) are necessary to reduce the frequency of adverse effects, this drug exerts in treated patients. In this study, MPA was coupled with N-(x-hydroxyalkyl)-9-acridone-4-carboxamides or N-(x-hydroxyalkyl)acridine-4-carboxamides to give respective ester conjugates upon Yamaguchi protocol. This esterification required protection of phenol group in MPA. Designed conjugates revealed higher...
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Recent Developments in the Synthesis of Unsymmetrical Disulfanes (Disulfides). A Review
PublicationThe synthesis of unsymmetrical disulfanes is an important transformation in organic synthesis and medicinal chemistry. The current review is intended to summarize achievements in the synthesis of unsymmetrical disulfanes over the last decade (2004–2014).
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Problematyka dotycząca zapewnienia fotostabilności substancji leczniczych w postaciach leku
PublicationUV and visible radiation may influence on the stability of some active pharmaceutical ingredients and in a consequence destabilizes such medicinal products, causes changesin its physicochemical properties also with negative pharmacological and sometimes even toxic effects. For this reason it is important to conduct the routine testing photostability. The knowledge of chemistry and technology as well as some methods of...
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Selected Methods for the Chemical Phosphorylation and Thiophosphorylation of Phenols
PublicationThis Focus Review gathers together a selection of methods for the chemical phosphorylation of phenols that employ three‐ and four‐coordinate phosphorus compounds. Phosphorylated scaffolds can exhibit enhanced properties compared to their non‐phosphorylated analogues, such as increased biological activity and increased/decreased solubility; as such, phosphorus compounds have gained more and more interest in organic and medicinal...
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Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles in the Presence of Heterogeneous Catalyst
PublicationTetrazoles are five-membered heterocyclic compounds containing in their rings four nitrogen atoms. They have wide applications as corrosion inhibitors, analytical reagents, high-energy materials and gas generating compositions. Tetrazoles also play important role in coordination chemistry as ligands and in medicinal chemistry as metabolically stable surrogates for carboxylic acids. In recent years, investigation of new method of...
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Novel chalcone-derived pyrazoles as potential therapeutic agents for the treatment of non-small cell lung cancer
PublicationLung cancer is considered to account for approximately one-fifth of all malignant tumor-related deaths worldwide and is therefore one of the most lethal malignancies. Pyrazole scaffold possesses a wide range of biological and pharmacological activities, which play important roles in medicinal chemistry. The present study reports the synthesis and in vitro biological characterization of nine pyrazoles derived from chalcones as potential...
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Clickable polysaccharides for biomedical applications: A comprehensive review
PublicationRecent advances in materials science and engineering highlight the importance of designing sophisticated biomaterials with well-defined architectures and tunable properties for emerging biomedical applications. Click chemistry, a powerful method allowing specific and controllable bioorthogonal reactions, has revolutionized our ability to make complex molecular structures with a high level of specificity, selectivity, and yield...