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1.
Curr Top Med Chem ; 2024 Jul 03.
Article in English | MEDLINE | ID: mdl-38963107

ABSTRACT

Visible-light-mediated reactions have recently emerged as a powerful strategy for the synthesis of diverse organic molecules under mild reaction conditions. Usually, the reactions are performed at room temperature and thus sensitive functional groups remain unaffected. Thus, this protocol has received intense interest from academia as well as industries. The heterocycles, in general, are of much interest because of their biological activities and application in therapeutics. The Oxygen- and Sulfur-containing heterocyclic compounds have recently attracted attention as these compounds showed promising activities as anti-cancer drugs, antibiotics, antifungal and anti-inflammatory agents among other applications. The synthesis of this class of compounds by efficient and greener routes has become an important target. This review highlights the various procedures for the synthesis of these compounds and their derivatives under visible light-induced reactions. The green aspects and mechanism of each procedure have been discussed.

2.
J Org Chem ; 89(11): 8137-8145, 2024 Jun 07.
Article in English | MEDLINE | ID: mdl-38757898

ABSTRACT

We have introduced a sulfoximidation reaction initiated by visible light between α-phenyl vinyl azides and NH-sulfoximines. The cost-effective and readily accessible hypervalent iodine reagent (PIDA) easily promoted the oxidative sulfoximidation process to afford N-α-ketoacylated sulfoximines in good to high yields, involving the formation of two new C-O bonds and one C-N bond. Additionally, the protocol offers noteworthy advantages, including its metal-free and photocatalyst-free reaction and its broad substrate compatibility.

3.
Pharmaceuticals (Basel) ; 17(5)2024 Apr 24.
Article in English | MEDLINE | ID: mdl-38794119

ABSTRACT

Facile access to some novel biologically relevant dihydrotriazolopyrimidine carboxylic acid-derived amide analogues using NMI/SO2Cl2, and aromatic and aliphatic primary and secondary amines, is reported herein. The role of N-methylimidazole (NMI) as the base and sulfuryl chloride (SO2Cl2) as the coupling reagent has been effectively realized in accessing these molecules in good to excellent yields. The feasibility of the developed protocol has also been extended to the gram-scale synthesis of N-benzylbenzamide in a 75% yield from benzoic acid and benzyl amine. The newly synthesized compounds were tested via in vitro anti-inflammatory and anti-tubercular activity studies. The compounds 6aa and 6be were found to be the most active anti-inflammatory agents, whereas 6cb and 6ch were found to exhibit promising anti-tubercular potency when compared to other synthesized molecules. The structure-activity relationship (SAR) studies revealed the importance of the presence of electron-donating functionalities in enhancing the anti-inflammatory potential of the newly synthesized molecules. However, the presence of electron-withdrawing substituents was found to be significant for improving their anti-tubercular potency.

4.
J Fluoresc ; 2024 Feb 13.
Article in English | MEDLINE | ID: mdl-38349481

ABSTRACT

We report the synthesis and characterization of a new 4-methoxyphenyl-2,2'-bipyridine-based ligand, such as 12, bearing dipicolylaminomethyl core as a receptor unit, as a probe for the fluorescence "turn-on" detection of Zn2+. Thus, in the presence of Zn2+ the probe 12 exhibited a fluorescence enhancement with a Stokes shift of ~ 180 nm and photoluminescence quantum yields value of ~ 1.0. In addition, 12 exhibited higher binding constant for Zn2+ (~ 2 × 105 M-1) with the LOD reaching the nanomolar level (~ 0.1 × 10-9 M) compare to the previously reported probe 1. The stoichiometry and structure of the [Zn(12)]2+ and [Zn(1)]2+ complexes were supported by XRD analysis, DFT calculations and 1H NMR experiments. It was postulated that, as a result of binding of Zn2+, the sample exhibited a bright "on" state via the PET-ICT processes. Molecular docking studies and confocal fluorescence microscopy experiments demonstrated that the probe 12 could be used for the fluorescence detection of Zn2+ not only in artificially enriched with zinc salts live cells, but also in fixed tissues with cations are in a bound state. The high binding constant of compound 12 to Zn2+ cation allows it to be used for the accurate localization of pancreatic beta cells (islets of Langerhans).

5.
J Org Chem ; 89(3): 1473-1482, 2024 Feb 02.
Article in English | MEDLINE | ID: mdl-38225732

ABSTRACT

A convenient and new synthetic approach has been developed for the oxidative cross-coupling of the C-N bond through the reaction between arylglyoxylic acids and tetraalkylthiuram disulfides. The reaction proceeds under ambient air at room temperature in the presence of visible light. This reaction offers a metal-, base-, photocatalyst-, and solvent-free synthesis of various α-ketoamides with moderate to excellent yields via the radical pathway. In addition, this protocol demonstrates the potential application of a gram-scale synthesis.

6.
Biomimetics (Basel) ; 9(1)2024 Jan 11.
Article in English | MEDLINE | ID: mdl-38248618

ABSTRACT

We have designed and synthesized a series of bioinspired pyrano[2,3-f]coumarin-based Calanolide A analogs with anti-HIV activity. The design of these new calanolide analogs involved incorporating nitrogen heterocycles or aromatic groups in lieu of ring C, effectively mimicking and preserving their bioactive properties. Three directions for the synthesis were explored: reaction of 5-hydroxy-2,2-dimethyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one with (i) 1,2,4-triazines, (ii) sulfonylation followed by Suzuki cross-coupling with (het)aryl boronic acids, and (iii) aminomethylation by Mannich reaction. Antiviral assay of the synthesized compounds showed that compound 4 has moderate activity against HIV-1 on enzymes and poor activity on the cell model. A molecular docking study demonstrates a good correlation between in silico and in vitro HIV-1 reverse transcriptase (RT) activity of the compounds when docked to the nonnucleoside RT inhibitor binding site, and alternative binding modes of the considered analogs of Calanolide A were established.

7.
J Fluoresc ; 34(2): 579-586, 2024 Mar.
Article in English | MEDLINE | ID: mdl-37326925

ABSTRACT

A series of α-cycloamine substituted 2,2'-bipyridines 3ae'-3ce' was obtained via the one-pot approach based on ipso-substitution of a cyano-group in 1,2,4-triazines, followed by aza-Diels-Alder reaction in good yields. Photophysical properties, including fluorosolvatochromism, were studied for 3ae'-3ce' and were compared with α-unsubstituted 2,2'-bipyridines. In addition, dipole moments differences in ground and excited states were calculated by both Lippert-Mataga equation and DFT studies and were compared to each other. The correlation between the size of cycloamine unit and the dipole moments differences value (based on Lippert-Mataga equation) was observed. In addition charge transfer indices (DCT, Λ, H and t) were calculated to demonstrate influence of molecular structure on the intramolecular charge transfer degree.

8.
Curr Issues Mol Biol ; 45(10): 8461-8475, 2023 Oct 19.
Article in English | MEDLINE | ID: mdl-37886976

ABSTRACT

Natural products are a boundless source for the development of pharmaceutical agents against a wide range of human diseases. Accordingly, naturally occurring aurones possess various biological benefits, such as anticancer, antioxidant, antimicrobial, antidiabetic, anti-inflammatory, antiviral and neuroprotective effects. In addition, various studies have revealed that aurones are potential templates for the regulation of diabetes mellitus and its associated complications. Likewise, certain aurones and their analogues have been found to be remarkable kinase inhibitors of DARK2, PPAR-γ, PTPM1, AGE, α-amylase and α-glucosidase, which represents a promising approach for the treatment of chronic metabolic disorders such as diabetes. Therefore, in our present study, we provide a detailed account of the advances in aurones as antidiabetic agents over the past decade.

9.
Polymers (Basel) ; 15(20)2023 Oct 20.
Article in English | MEDLINE | ID: mdl-37896404

ABSTRACT

Polyureas (PUs) have already found wide practical applications, and various methods of their synthesis have been reported. In this manuscript, we wished to report the very first mechanochemical approach towards aromatic PUs via reactions between isomeric 2,2'-, 3,3'-, and 4,4'-diaminobiphenyls and triphosgene under solvent-free conditions following ball-milling. By using this synthetic approach, both PUs and azomethine-capped Pus were obtained. The fluorescence response of the above-mentioned PUs towards various anions in solutions were studied and selective fluorescence responses towards the hydroxyl and fluoride anions were observed.

10.
Materials (Basel) ; 16(18)2023 Sep 21.
Article in English | MEDLINE | ID: mdl-37763611

ABSTRACT

Methods for the remote detection of warfare agents and explosives have been in high demand in recent times. Among the several detection methods, fluorescence methods appear to be more convenient due to their low cost, simple operation, fast response time, and naked-eye-visible sensory response. For fluorescence methods, a large variety of fluorescent materials, such as small-molecule-based fluorophores, aggregation-induced emission fluorophores/materials, and supramolecular systems, have been reported in the literature. Among them, fluorescent (bio)polymers/(bio)polymer-based materials have gained wide attention due to their excellent mechanical properties and sensory performance, their ability to recognize explosives via different sensing mechanisms and their combinations, and, finally, the so-called amplification of the sensory response. This review provides the most up-to-date data on the utilization of polymers and polymer-based materials for the detection of nitroaromatic compounds (NACs)/nitro-explosives (NEs) in the last decade. The literature data have been arranged depending on the polymer type and/or sensory mechanism.

11.
Pharmaceuticals (Basel) ; 16(9)2023 Sep 19.
Article in English | MEDLINE | ID: mdl-37765134

ABSTRACT

Four sets of previously synthesized 4-methyl-7-substituted coumarin derivatives were screened for their in vitro anti-inflammatory and anti-tubercular activities. The anti-inflammatory potential of 3a-t, 5a-o, 6a-n, and 7a-f synthesized compounds was evaluated by an anti-denaturation assay using diclofenac sodium as the reference standard. Evaluation of the anti-tuberculous activity of the mentioned compounds was performed by the Resazurin test method against four different TB strains using rifampicin and isoniazid as reference drugs. Based on the anti-inflammatory results, compounds 3o, 5f, 6c, and 7d proved to be the most active compounds in their respective series. Additionally, compounds 3k-n, 5b-d, 6d-f, 6k, 7a, and 7f were found to be the most potent anti-tuberculous agents. In fact, most of the screened compounds exhibited promising activity profiles compared to the respective standard drugs. The structure-activity connections revealed a few intriguing aspects, indicating that the presence of electron-donating and nitrogen-rich fragments boost the anti-inflammatory effects of the examined compounds. However, the presence of electron-withdrawing substituents was required to boost the anti-tubercular activity of the evaluated compounds.

12.
Viruses ; 15(9)2023 08 28.
Article in English | MEDLINE | ID: mdl-37766233

ABSTRACT

Antiviral properties of different oxa- and aza-heterocycles are identified and properly correlated with their structural features and discussed in this review article. The primary objective is to explore the activity of such ring systems as antiviral agents, as well as their synthetic routes and biological significance. Eventually, the structure-activity relationship (SAR) of the heterocyclic compounds, along with their salient characteristics are exhibited to build a suitable platform for medicinal chemists and biotechnologists. The synergistic conclusions are extremely important for the introduction of a newer tool for the future drug discovery program.


Subject(s)
Antiviral Agents , Drug Discovery , Antiviral Agents/pharmacology , Structure-Activity Relationship
13.
Pharmaceuticals (Basel) ; 16(8)2023 Aug 15.
Article in English | MEDLINE | ID: mdl-37631073

ABSTRACT

A sequence of novel 1,4-dihydropyridines (DHP) and their hybrids was developed using a multicomponent strategy under environmentally benign conditions. In addition, computational studies were performed, and the ligand-protein interactions calculated in different bacteria and two fungal strains. Para-hydroxy-linked DHP (5f) showed the best binding energies of 3.591, 3.916, 8.499 and 6.895 kcal/mol against various pathogens used and other substances received a good docking score. The pathogen resistance potential of the synthesized targets against four bacteria and two fungi showed that whole DHP substances exhibit different levels of resistance to each microorganism. Gram-positive bacteria, which are highly sensitive to all molecules, and the MTCC-1884-encoded fungus strongly rejected the studied compounds compared to comparator drugs. In particular, the 5f candidate showed remarkable antimicrobial activity, followed by the substances 5a, 5b, 5j, 5k and 5l. Furthermore, MIC and MBC/MFC properties showed that 5f had a minimum bacterial concentration of 12.5 µg/mL against E. coli and against two fungal pathogens, with its killing activity being effective even at low concentrations. On the other hand, whole motifs were tested for their cytotoxic activity, revealing that the methoxy and hydroxy-linked compounds (5h) showed greater cytotoxic potency, followed by the two hydroxy linked compounds (5d and 5f). Overall, this synthetic approach used represents a prototype for future nature-favored synthesis methods and these biological results serve as a guide for future therapeutic drug research. However, the computer results play an important role in the further development of biological experiments.

14.
ACS Appl Mater Interfaces ; 15(34): 40864-40876, 2023 Aug 30.
Article in English | MEDLINE | ID: mdl-37603418

ABSTRACT

Biofilm infections are associated with most human bacterial infections and are prone to bacterial multidrug resistance. There is an urgent need to develop an alternative approach to antibacterial and antibiofilm agents. Herein, two positively charged semiconductor conjugated polymer nanoparticles (SPPD and SPND) were prepared for additive antibacterial and antibiofilm activities with the aid of positive charge and photothermal therapy (PTT). The positive charge of SPPD and SPND was helpful in adhering to the surface of bacteria. With an 808 nm laser irradiation, the photothermal activity of SPPD and SPND could be effectively transferred to bacteria and biofilms. Under the additive effect of positive charge and PTT, the inhibition rate of Staphylococcus aureus (S. aureus) treated with SPPD and SPND (40 µg/mL) could reach more than 99.2%, and the antibacterial activities of SPPD and SPND against S. aureus biofilms were 93.5 and 95.8%. SPPD presented better biocompatibility than SPND and exhibited good antibiofilm properties in biofilm-infected mice. Overall, this additive treatment strategy of positive charge and PTT provided an optional approach to combat biofilms.


Subject(s)
Nanostructures , Staphylococcal Infections , Humans , Animals , Mice , Staphylococcus aureus , Semiconductors , Anti-Bacterial Agents/pharmacology , Biofilms , Polymers/pharmacology , Staphylococcal Infections/drug therapy
15.
Int J Biol Macromol ; 246: 125675, 2023 Aug 15.
Article in English | MEDLINE | ID: mdl-37414311

ABSTRACT

In the present work, a novel Fe3O4-GLP@CAB was successfully synthesized via a co-precipitation procedure and applied for the removal of methylene blue (MB) from aqueous environment. The structural and physicochemical characteristics of the as-prepared materials were explored using a variety of characterization methods, including pHPZC, XRD, VSM, FE-SEM/EDX, BJH/BET, and FTIR. The effects of several experimental factors on the uptake of MB using Fe3O4-GLP@CAB were examined through batch experiments. The highest MB dye removal efficiency of Fe3O4-GLP@CAB was obtained to be 95.2 % at pH 10.0. Adsorption equilibrium isotherm data at different temperatures showed an excellent agreement with the Langmuir model. The adsorption uptake of MB onto Fe3O4-GLP@CAB was determined as 136.7 mg/g at 298 K. The kinetic data were well-fitted by the pseudo-first-order model, indicating that physisorption mainly controlled it. Several thermodynamic variables derived from adsorption data, like as ΔGo, ΔSo, ΔHo, and Ea, accounted for a favourable, spontaneous, exothermic, and physisorption process. Without seeing a substantial decline in adsorptive performance, the Fe3O4-GLP@CAB was employed for five regeneration cycles. Because they can be readily separated from wastewater after treatment, the synthesized Fe3O4-GLP@CAB was thus regarded as a highly recyclable and effective adsorbent for MB dye.


Subject(s)
Nanoparticles , Psidium , Water Pollutants, Chemical , Adsorption , Powders , Methylene Blue/chemistry , Alginates/chemistry , Hydrogels , Magnetic Phenomena , Plant Leaves , Water Pollutants, Chemical/chemistry , Kinetics , Hydrogen-Ion Concentration
16.
Int J Mol Sci ; 24(12)2023 Jun 13.
Article in English | MEDLINE | ID: mdl-37373234

ABSTRACT

1,4-Bis(5-phenyl-2-oxazolyl)benzene (POPOP) is a common scintillation fluorescent laser dye. In this manuscript, the synthesis of 2-Ar-5-(4-(4-Ar'-1H-1,2,3-triazol-1-yl)phenyl)-1,3,4-oxadiazoles (Ar, Ar' = Ph, naphtalenyl-2, pyrenyl-1, triphenilenyl-2), as PAH-based aza-analogues of POPOP, by means of Cu-catalyzed click reaction between 2-(4-azidophenyl)-5-Ar-1,3,4-oxadiazole and terminal ethynyl-substituted PAHs is reported. An investigation of the photophysical properties of the obtained products was carried out, and their sensory response to nitroanalytes was evaluated. In the case of pyrenyl-1-substituted aza-POPOP, dramatic fluorescence quenching by nitroanalytes was observed.


Subject(s)
Hydrocarbons , Fluorescence
17.
Polymers (Basel) ; 15(8)2023 Apr 12.
Article in English | MEDLINE | ID: mdl-37112002

ABSTRACT

Mechanochemically induced methods are commonly used for the depolymerization of polymers, including plastic and agricultural wastes. So far, these methods have rarely been used for polymer synthesis. Compared to conventional polymerization in solutions, mechanochemical polymerization offers numerous advantages such as less or no solvent consumption, the accessibility of novel structures, the inclusion of co-polymers and post-modified polymers, and, most importantly, the avoidance of problems posed by low monomer/oligomer solubility and fast precipitation during polymerization. Consequently, the development of new functional polymers and materials, including those based on mechanochemically synthesized polymers, has drawn much interest, particularly from the perspective of green chemistry. In this review, we tried to highlight the most representative examples of transition-metal (TM)-free and TM-catalyzed mechanosynthesis of some functional polymers, such as semiconductive polymers, porous polymeric materials, sensory materials, materials for photovoltaics, etc.

18.
Pharmaceuticals (Basel) ; 16(3)2023 Mar 07.
Article in English | MEDLINE | ID: mdl-36986502

ABSTRACT

A total of 21 novel xanthone and acridone derivatives were synthesized using the reactions of 1,2,4-triazine derivatives with 1-hydroxy-3-methoxy-10-methylacridone, 1,3-dimethoxy-, and 1,3-dihydroxanthone, followed by optional dihydrotiazine ring aromatization. The synthesized compounds were evaluated for their anticancer activity against colorectal cancer HCT116, glioblastoma A-172, breast cancer Hs578T, and human embryonic kidney HEK-293 tumor cell lines. Five compounds (7a, 7e, 9e, 14a, and 14b) displayed good in vitro antiproliferative activities against these cancer cell lines. Compounds 7a and 7e demonstrated low toxicity for normal human embryonic kidney (HEK-293) cells, which determines the possibility of further development of these compounds as anticancer agents. Annexin V assay demonstrated that compound 7e activates apoptotic mechanisms and inhibits proliferation in glioblastoma cells.

19.
Int J Mol Sci ; 24(6)2023 Mar 08.
Article in English | MEDLINE | ID: mdl-36982244

ABSTRACT

Since their discovery in 2008 by N. Ogoshi and co-authors, pillararenes (PAs) have become popular hosts for molecular recognition and supramolecular chemistry, as well as other practical applications. The most useful property of these fascinating macrocycles is their ability to accommodate reversibly guest molecules of various kinds, including drugs or drug-like molecules, in their highly ordered rigid cavity. The last two features of pillararenes are widely used in various pillararene-based molecular devices and machines, stimuli-responsive supramolecular/host-guest systems, porous/nonporous materials, organic-inorganic hybrid systems, catalysis, and, finally, drug delivery systems. In this review, the most representative and important results on using pillararenes for drug delivery systems for the last decade are presented.


Subject(s)
Drug Carriers , Drug Delivery Systems , Drug Delivery Systems/methods , Drug Carriers/chemistry
20.
Int J Mol Sci ; 24(3)2023 Feb 02.
Article in English | MEDLINE | ID: mdl-36769163

ABSTRACT

This review summarizes and systematizes the literature on the anti-HIV activity of plant coumarins with emphasis on isolation and the mechanism of their antiviral action. This review summarizes the information on the anti-HIV properties of simple coumarins as well as annulated furano- and pyranocoumarins and shows that coumarins of plant origin can act by several mechanisms: inhibition of HIV reverse transcriptase and integrase, inhibition of cellular factors that regulate HIV-1 replication, and transmission of viral particles from infected macrophages to healthy ones. It is important to note that some pyranocoumarins are able to act through several mechanisms or bind to several sites, which ensures the resistance of these compounds to HIV mutations. Here we review the last two decades of research on the anti-HIV activity of naturally occurring coumarins.


Subject(s)
Anti-HIV Agents , HIV-1 , Pyranocoumarins , Coumarins/pharmacology , Reverse Transcriptase Inhibitors/pharmacology , Antiviral Agents/pharmacology , Anti-HIV Agents/pharmacology , HIV Reverse Transcriptase
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