177 results match your criteria: "Ufa Institute of Chemistry[Affiliation]"

This review comprehensively describes the recent advances in the synthesis and pharmacological evaluation of steroid polyamines squalamine, trodusquemine, ceragenins, claramine, and their diverse analogs and derivatives, with a special focus on their complete synthesis from cholic acids, as well as an antibacterial and antiviral, neuroprotective, antiangiogenic, antitumor, antiobesity and weight-loss activity, antiatherogenic, regenerative, and anxiolytic properties. Trodusquemine is the most-studied small-molecule allosteric PTP1B inhibitor. The discovery of squalamine as the first representative of a previously unknown class of natural antibiotics of animal origin stimulated extensive research of terpenoids (especially triterpenoids) comprising polyamine fragments.

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Comparative Immunogenicity of the Recombinant Receptor-Binding Domain of Protein S SARS-CoV-2 Obtained in Prokaryotic and Mammalian Expression Systems.

Vaccines (Basel)

January 2022

State Research Center of Virology and Biotechnology "Vector", Rospotrebnadzor, World-Class Genomic Research Center for Biological Safety and Technological Independence, Federal Scientific and Technical Program on the Development of Genetic Technologies, 630559 Novosibirsk, Russia.

The receptor-binding domain (RBD) of the protein S SARS-CoV-2 is considered to be one of the appealing targets for developing a vaccine against COVID-19. The choice of an expression system is essential when developing subunit vaccines, as it ensures the effective synthesis of the correctly folded target protein, and maintains its antigenic and immunogenic properties. Here, we describe the production of a recombinant RBD protein using prokaryotic (pRBD) and mammalian (mRBD) expression systems, and compare the immunogenicity of prokaryotic and mammalian-expressed RBD using a BALB/c mice model.

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Article Synopsis
  • Researchers tested the antiviral effectiveness of Arbidol (Umifenovir) against SARS-CoV-2 using a simulated viral system with the virus's spike protein.
  • The study identified multiple binding sites for Arbidol on the spike protein and noted that Arbidol's binding affects the protein's structural flexibility and interaction with enzymes.
  • The findings suggest that Arbidol can bind to various parts of the spike protein, contributing to its antiviral properties, which could aid in developing effective treatments targeting the virus's entry into cells.
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A series of oleanolic acid derivatives holding oxo- or 3--polyamino-3-deoxy-substituents at C3 as well as carboxamide function at C17 with different long chain polyamines have been synthesized and evaluated for antimicrobial activities. Almost all series presented good to moderate activity against Gram-positive , and bacteria with minimum inhibitory concentration (MIC) values from 3.125 to 200 µg/mL.

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The optoelectronic properties of a new poly(2-ethyl-3-methylindole) (MPIn) are discussed in this paper. The absorption and photoluminescence spectra were studied. The electronic spectrum of MPIn showed a single absorption maximum at 269 nm that is characteristic of the entire series of polyindoles.

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The peculiarities of spin effects in photoinduced electron transfer (ET) in diastereomers of donor-acceptor dyads are considered in order to study the influence of chirality on reactivity. Thus, the spin selectivity-the difference between the enhancement coefficients of chemically induced dynamic nuclear polarization (CIDNP)-of the dyad's diastereomers reflects the difference in the spin density distribution in its paramagnetic precursors that appears upon UV irradiation. In addition, the CIDNP coefficient itself has demonstrated a high sensitivity to the change of chiral centers: when one center is changed, the hyperpolarization of all polarized nuclei of the molecule is affected.

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Hollongdione arylidene derivatives induce antiproliferative activity against melanoma and breast cancer through pro-apoptotic and antiangiogenic mechanisms.

Bioorg Chem

February 2022

Faculty of Pharmacy, "Victor Babes" University of Medicine and Pharmacy, 2nd Eftimie Murgu Sq., Timisoara 300041, Romania; Res. Ctr. Pharmacotoxicol Evaluat, Facculty of Pharmacy, "Victor Babes" University of Medicine and Pharmacy Timisoara, 2nd Eftimie Murgu Sq., Timisoara 300041, Romania.

The use of natural compounds as starting point for semisynthetic derivatives has already been proven as a valuable source of active anticancer agents. Hollongdione (4,4,8,14-tetramethyl-18-norpregnan-3,20-dion), obtained by few steps from dammarane type triterpenoid dipterocarpol, was chemically modified at C2 and C21 carbon atoms by the Claisen-Schmidt aldol condensation to give a series of arylidene derivatives. The anticancer activity of the obtained compounds was assessed on NCI-60 cancer cell panel, revealing strong antiproliferative effects against a large variety of cancer cells.

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Discovery of New Ginsenol-Like Compounds with High Antiviral Activity.

Molecules

November 2021

Department of Medicinal Chemistry, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentiev Ave. 9, 630090 Novosibirsk, Russia.

A number of framework amides with a ginsenol backbone have been synthesized using the Ritter reaction. We named the acetamide as Ginsamide. A method was developed for the synthesis of the corresponding amine and thioacetamide.

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Twenty lupane type A-ring azepano-triterpenoids were synthesized from betulin and its related derivatives and their antitubercular activity against , mono-resistant MTB strains, and nontuberculous strains and Mycobacterium were investigated in the framework of AToMIc (Anti-mycobacterial Target or Mechanism Identification Contract) realized by the Division of Microbiology and Infectious Diseases, NIAID, National Institute of Health. Of all the tested triterpenoids, 17 compounds showed antitubercular activity and 6 compounds were highly active on the H37Rv wild strain (with MIC 0.5 µM for compound ), out of which 4 derivatives also emerged as highly active compounds on the three mono-resistant MTB strains.

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Article Synopsis
  • The article focuses on the creation and evaluation of new 1,2,4-oxadiazoles with antiviral properties, particularly against influenza viruses H1N1 and H7N9.
  • The compounds were synthesized using a derivative from (+)-camphor and showed promising results in inhibiting the H1N1 virus specifically, with some activity against H7N9 as well.
  • The antiviral mechanism involves blocking the fusion activity of the viral protein hemagglutinin, with structural differences in the compounds influencing their selective effectiveness against different influenza virus subtypes.
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A series of new 5-aryl-2,2'-bipyridines and their (polyfluoro)salicylate complexes of Cu(II), Co(II) and Mn(II) were synthesized. Their antimicrobial activity was evaluated in vitro against six strains of Trichophytons, E. floccosum, M.

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Synthesis and antiviral evaluation of cytisine derivatives against dengue virus types 1 and 2.

Bioorg Med Chem Lett

December 2021

Department of Medical Laboratory Science and Biotechnology, China Medical University, 91, Hsueh-Shih Rd., Taichung 40402, Taiwan, ROC; Department of Biotechnology, Asia University, 500, Lioufeng Rd., Wufeng, Taichung 41354, Taiwan, ROC. Electronic address:

Dengue virus (DENV) causes about 50-100 million cases per year worldwide. However, there is still a big challenge in developing antiviral drugs against DENV infection. Some derivatives of alkaloid (-)-cytisine, like other alkaloid analogs, have been proposed for their antiviral potential.

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We performed an in silico, in vitro, and in vivo assessment of a potassium 2-[2-(2-oxo-4-phenylpyrrolidin-1-yl) acetamido]ethanesulfonate (compound ) as a potential prodrug for cognitive function improvement in ischemic brain injury. Using in silico methods, we predicted the pharmacological efficacy and possible safety in rat models. In addition, in silico data showed neuroprotective features of compound , which were further supported by in vitro experiments in a glutamate excitotoxicity-induced model in newborn rat cortical neuron cultures.

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A series of novel hybrid chalcone N-ethyl-piperazinyl amide derivatives of oleanonic and ursonic acids were synthesized, and their cytotoxic potential was evaluated in vitro against the NCI-60 cancer cell line panel. Compounds and exhibited the highest overall anticancer activity, with GI values in some cases reaching nanomolar values. Thus, the two compounds were further assessed in detail in order to identify a possible apoptosis- and antiangiogenic-based mechanism of action induced by the assessed compounds.

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Cancer persists as a global challenge due to the extent to which conventional anticancer therapies pose high risks counterbalanced with their therapeutic benefit. Naturally occurring substances stand as an important safer alternative source for anticancer drug development. In the current study, a series of modified lupane and ursane derivatives was subjected to in vitro screening on the NCI-60 cancer cell line panel.

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A series of A-ring modified oleanolic and ursolic acid derivatives including C28 amides (3-oxo-C2-nicotinoylidene/furfurylidene, 3β-hydroxy-C2-nicotinoylidene, 3β-nicotinoyloxy-, 2-cyano-3,4-seco-4(23)-ene, indolo-, lactame and azepane) were synthesized and screened for their cytotoxic activity against the NCI-60 cancer cell line panel. The results of the first assay of thirty-two tested compounds showed that eleven derivatives exhibited cytotoxicity against cancer cells, and six of them were selected for complete dose-response studies. A systematic study of local SARs has been carried out by comparative analysis of potency distributions and similarity relationships among the synthesized compounds using network-like similarity graphs.

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To develop new potential agents against Chlamydia trachomatis among oleanane type triterpenoids the synthesis, spectral and X-ray analysis as well as antimicrobial screening of C-12 oxygen and nitrogen derivatives of erythrodiol is presented. The reduction of methyl 3β-acetoxy-12-oxo-oleanoate with LiAlH led to isomeric erythrodiol 12β- and 12α-hydroxy-derivatives, their stereochemistry with respect to the position of hydroxyl-group at C-12 was determined based on the multiplets splitting patterns, the magnitude of the spin-spin interaction, and NOESY interactions. Methyl 3β-acetoxy-12-oxo-oleanoate was transformed to 12E-hydroxyimino- and 12E-methoxyimino-derivatives by the interaction with NHOH∙HCl or CHONH∙HCl, respectively.

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Among abietane type semisynthetic diterpenoids, a series of quinopimaric and maleopimaric acid derivatives modified at the carboxyl and carbonyl groups, and in ring were synthesised to obtain new compounds with antimicrobial potency against HRv and key ESKAPE pathogens. It was found that compound exhibited low toxicity to human embryonic kidney cell line HEK-293 (> 32 μg/mL) and showed significant bacteriostatic activity against methicillin-resistant (MRSA) (MIC ≤ 0.25 µg/mL) and excellent antifungal activity against (MICs ≤0.

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(1) Background: To compare the effect of selected triterpenoids with their structurally resembling derivatives, designing of the molecular ribbons was targeted to develop compounds with selectivity in their pharmacological effects. (2) Methods: In the synthetic procedures, Huisgen 1,3-dipolar cycloaddition was applied as a key synthetic step for introducing a 1,2,3-triazole ring as a part of a junction unit in the molecular ribbons. (3) Results: The antimicrobial activity, antiviral activity, and cytotoxicity of the prepared compounds were studied.

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Using the concept of a complete set of homodesmotic reactions for the analysis of molecular energetics of polysubstituted methyl- and fluorocyclopropanes allows assessing the strain energy SE of cyclopropanes, free from interfering effects, in full accordance with the IUPAC definition ("relative to a reference ...

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The mechanisms of enolization and reactions of nucleophilic addition to carbonyl compounds were analyzed by density functional theory (DFT) (PBE1PBE) and (DLPNO-CCSD(T)) level of theory using the interaction of water and hydrogen peroxide with acetone and 1,1,1-trifluoroacetone (TFA) as the reference reactions. The transition states of the studied reactions were localized within the integrated approach that includes both the dielectric continuum theory (polarizable continuum model (PCM)) and the cyclic or two-cluster explicit solvation models. The considered models provide proton transfer in the enolization, hydration, and peroxidation reactions by the Grotthuss mechanism.

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Synthesis of 2-Aminoethanesulfonamides of Betulinic and Betulonic Acids.

Chem Nat Compd

July 2021

Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 71 Prosp. Oktyabrya, Ufa, 450054 Russia.

New potentially biologically active sulfonamide derivatives of pentacyclic lupane-type triterpenoids, the sulfonamide group of which was bonded to C-17 of the triterpene skeleton through an amidoethane spacer, were synthesized via conjugation of 2-aminoethanesulfonamides to betulinic and betulonic acids in the presence of Mukaiyama reagent (2-bromo-1-methylpyridinium iodide).

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A series of semisynthetic triterpenoids with A-ring azepano- and A-seco-fragments as well as hydrazido/hydrazono-substituents at C3 and C28 has been synthesized and evaluated for antimicrobial activity against key ESKAPE pathogens and DNA viruses (HSV-1, HCMV, HPV-11). It was found that azepanouvaol 8, 3-amino-3,4-seco-4(23)-en derivatives of uvaol 21 and glycyrrhetol-dien 22 as well as azepano-glycyrrhetol-tosylate 32 showed strong antimicrobial activities against MRSA with MIC ≤ 0.15 μM that exceeds the effect of antibiotic vancomycin.

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A new method for the synthesis of glycyrrhizic acid (GA) conjugates with S-benzyl--cysteine using 1-ethyl-3-(3-dimethylaminoproopyl)carbodiimide is proposed. It is established that 3--{2--[-(β--glucopyranosyluronyl)--cysteine--benzyl]--(β--glucopyranosyluronyl)--cysteine--benzyl}-(3β,20β)-11-oxo-30-(-carbonyl--cysteine--benzyl)-30-norolean-12-ene is superior to GA in inhibiting the accumulation of HIV-I virus-specific protein p24 (viral antigen) in MT-4 cell culture (IC 3 μg/mL, SI 90) and is 50 - 55 times less toxic to cells than azidothymidine.

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Glycyrrhetinic acid derivatives as Zika virus inhibitors: Synthesis and antiviral activity in vitro.

Bioorg Med Chem

July 2021

Department of Medical Laboratory Science and Biotechnology, China Medical University, 91, Hsueh-Shih Rd., Taichung 40402, Taiwan, ROC; Graduate Institute of Biomedical Sciences, College of Medicine, China Medical University, Taichung 40402, Taiwan, ROC; Department of Biotechnology, Asia University, 500, Lioufeng Rd., Wufeng, Taichung 41354, Taiwan, ROC. Electronic address:

Zika virus (ZIKV) is an arbovirus of the Flaviviridae family (Flavivirus genus), causing serious neurological complications, such as Guillain-Barre Syndrome (GBS) in adults and fetal microcephaly. Licensed vaccines or specific antiviral agents against ZIKV do not currently exist. Therefore, the search and development of anti-ZIKV agents are particularly relevant and necessary.

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