Wyniki wyszukiwania dla: medicinal chemistry
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Vitamin D and its analogs as anticancer and anti-inflammatory agents
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Chlorophylls and their Derivatives Used in Food Industry and Medicine
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Discovery of Novel 3-Hydroxyandrosta-5,7-Diene-17-Carboxylic Acid Derivatives as Anti-Inflammatory Bowel Diseases (IBD) Agents
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Phycobilins and Phycobiliproteins Used in Food Industry and Medicine
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PdCl2-catalyzed synthesis of a new class of isocoumarin derivatives containing aminosulfonyl / aminocarboxamide moiety: First identification of a isocoumarin based PDE4 inhibitor
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Use of NMR and Fluorescence Spectroscopy as well as Theoretical Conformational Analysis in Conformation-activity Studies of Cyclic Enkephalin Analogues
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Separate synthesis and evaluation of glucitol bis-phosphate and mannitol bis-phosphate, as competitive inhibitors of fructose bis-phosphate aldolases
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Influence of bulky 3,3′-diphenylalanine enantiomers replacing position 2 of AVP analogues on their conformations: NMR and molecular modeling studies
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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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Imidazolidine-4-one derivatives in the search for novel chemosensitizers of Staphylococcus aureus MRSA: Synthesis, biological evaluation and molecular modeling studies
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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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Synthesis and biological evaluation of fluorinated N-benzoyl and N-phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7-O-sulfamate as steroid sulfatase inhibitors
PublikacjaIn 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
PublikacjaA 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 antimicrobial activity of amino acid and peptide derivatives of mycophenolic acid
PublikacjaThe 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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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
PublikacjaA 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, 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
PublikacjaA 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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New Analogues of Mycophenolic Acid
PublikacjaMycophenolic 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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new analogues of agmatine with higher activity to imidazoline receptors
PublikacjaOpracowano syntezę nowych pochodnych imidazoliny, będących kompilacją struktury agmatyny i imidazoliny w wyniku zaprojektowanej przez nas drogi syntezy. Kluczowymi substratami w syntezie były pochodne 1,2,4 -triaminobutanu, otrzymane z chronionego kwasu glutaminowego. Otrzymane nowe pochodne imidazoliny wykazywały zróżnicowane powinowactwo do receptorów imidazolinowych I1, I2 oraz do receptorów alfa -adrenergicznych.
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One Step Beyond: Design of Substrates Spanning Primed Positions of Zika Virus NS2B-NS3 Protease
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Immunosuppressive properties of amino acid and peptide derivatives of mycophenolic acid
PublikacjaMycophenolic acid (MPA) was coupled with amino acids and biologically active peptides including derivatives of tuftsin to modify its immunosuppressive properties. Both amino acid unit in the case of simple MPA amides and modifications within peptide moiety of MPA - tuftsin conjugates influenced the observed activity. Antiproliferative potential of the obtained conjugates was investigated in vitro and MPA amides with threonine methyl...
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Design, synthesis and high antitumor potential of new unsymmetrical bisacridine derivatives towards human solid tumors, specifically pancreatic cancers and their unique ability to stabilize DNA G-quadruplexes
PublikacjaNew promising unsymmetrical bisacridine derivatives (UAs), have been developed. Three groupsincluding 36 compounds were synthesized by the condensation of 4-nitro or 4-methylacridinone, imi-dazoacridinone and triazoloacridinone derivatives with 1-nitroacridine compounds linked with anaminoalkyl chain. Cytotoxicity screening revealed the high potency of these compounds against severaltumor cell lines. Particularly, imidazoacridinone-1-nitroacridine...
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Fatty acids as molecular carriers in cleavable antifungal conjugates
PublikacjaConjugates composed of C2-18 fatty acid (FA) residues as a molecular carrier and 5-fluorocytosine (5-FC) as an active agent, released upon the action of intracellular esterases on the ester bond between FA and “trimethyl lock” intramolecular linker, demonstrate good in vitro activity against human pathogenic yeasts of Candida spp. The minimal inhibitory concentrations (MIC) values for the most active conjugates containing caprylic...
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Acid-catalysed synthesis of oxathiolone fused chalkones. Comparison of their activity toward various microrganisms and human cancer lines
PublikacjaOtrzymano 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 antiproliferative activity of conjugates of adenosine with muramyl dipeptide and nor-muramyl dipeptide derivatives
PublikacjaWe synthesized a series of MDP(D,D) and nor-MDP(D,D) derivatives conjugated with adenosine through a spacer as potential immunosuppressants. New conjugates were evaluated on two leukemia cell lines (Jurkat and L1210) and PBMC from healthy donors.
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In vitro studies of antimicrobial activity of Gly-His-Lys conjugates as potential and promising candidates for therapeutics in skin and tissue infections
PublikacjaWe presented in vitro studies of antimicrobial activity of Gly-His-Lys conjugates that are important point in preliminary biological evaluation of their potential application in skin and tissue therapy. The novel compounds include the conjugation of fatty acids with a modification of the amino acid sequence in the primary structure of Gly-His-Lys.
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Synthesis of bicoumarin thiophosphate derivatives as steroid sulfatase inhibitors
PublikacjaBased 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 and biological activity of mycophenolic acid-amino acid derivatives
PublikacjaIn 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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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
PublikacjaA 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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Synthesis and biological activity of novel mycophenolic acid conjugates containing nitro-acridine/acridone derivatives
PublikacjaOpracowano 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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Synthesis, anticandidal activity of N3-(4-methoxyfumaroyl)-(S)-2,3-diaminopropanoic amide derivatives – Novel inhibitors of glucosamine-6-phosphate synthase
PublikacjaNovel 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
PublikacjaNew 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
PublikacjaSynthesis, 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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New potent steroid sulphatase inhibitors based on 6-(1-phenyl-1H-1,2,3-triazol-4-yl)naphthalen-2-yl sulphamate derivatives
PublikacjaIn 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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Anticancer Properties of Amino Acid and Peptide Derivatives of Mycophenolic Acid
PublikacjaBackground: 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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Inhibitors of glucosamine-6-phosphate synthase as potential antimicrobials or antidiabetics – synthesis and properties
PublikacjaGlucosamine-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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Novel amides of mycophenolic acid and some heterocyclic derivatives as immunosuppressive agents
PublikacjaThe 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
PublikacjaIn 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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Synthesis of the inosine 5′-monophosphate dehydrogenase (IMPDH) inhibitors
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Antiglycoxidative properties of amantadine – a systematic review and comprehensive in vitro study
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Cytochromes P450 and Skin Cancer: Role of Local Endocrine Pathways
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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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Recent progress in the development of steroid sulfatase inhibitors – examples of the novel and most promising compounds from the last decade
PublikacjaThe 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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9,10-Dioxoanthracenyldithiocarbamates effectively inhibit the proliferation of non-small cell lung cancer by targeting multiple protein tyrosine kinases
PublikacjaAnthraquinones 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
PublikacjaIn 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,...