Journal of Saudi Chemical Society最新文献

In the dynamic area of drug development, researchers have been urged to uncover and test novel compounds with better effectiveness and fewer side effects in order to find more effective cancer treatments. In this comprehensive study, the synthesis and anticancer efficacy of new benzothiazole-thiazole have been displayed. Initially, a series of benzothiazole-thiazole conjugates 5a-c, 7a-b, and 8 were carefully designed and synthesized from the versatile 6-acetyl-2-phenylsulfonamidobenzothiazole (2), following the guidelines of rational design principles. The DFT/B3LYP approach showed that the synthesized hybrids had a non-planar configuration, where the benzene-sulfonamide group was oriented almost perpendicularly. The tested derivatives exhibited close HOMO-LUMO energies leading to small energy gaps (ΔE_H-L = 1.54–2.97 eV). Additionally, the inhibitory effects of the newly synthesized conjugates were tested on four cancer cell lines, including HepG2, HCT-116, MCF-7, and WI38. Conjugates 5a and 8 had strong inhibitory effects on the HCT-116 and MCF-7 cell lines. Additionally, the synthesized conjugates showed inhibitory action against CAIX and CAXII, where conjugate 8 also effectively inhibited both isoforms, as well as, conjugate 5a. Molecular docking analysis was performed to study the binding affinities and interactions of the newly synthesized benzothiazole-thiazole conjugates with the target PDB: 5fl4 protein. Moreover, the ADME outlines of the inspected conjugates were displayed, and conjugates 2 and 6 showed suitable characteristics for GI absorption and minor violations of Lipinski’s rules; thus, they are promising lead compounds.

Complex, kinetically stable emulsions with an average droplet size of 50–100 nm and a mean droplet diameter of 50–1000 nm is known as nanoemulsions. They are often referred to as tiny submicron, ultrafine, or finely dispersed emulsions; they have a tyndal effect and are transparent to the naked eye. Antimicrobial nanoemulsion is a type of o/w emulsion system that is stabilized by surfactants and alcohols that are used as co-surfactants. It is effective against a wide range of microorganisms, such as viruses (such as herpes simplex and HIV), fungi (such as Candida and dermatophytes), and bacteria (such as Escherichia coli, Salmonella, and Staphylococcus aureus). The nanoemulsion droplets were designed to fuse by electrostatic attraction and a thermodynamic mechanism with lipid-coated microorganisms. The active component and the trapped energy generated by the nanoemulsion break down the pathogen’s lipid membrane when a sufficient number of nanoparticles fuse with the pathogens, resulting in cell lysis and the eventual death of the invasion microorganisms. Because there is less surfactant in each droplet, the targeted bacteria become unstable without endangering the healthy cells, giving the nanoemulsions a safety margin. Nanoemulsion has many benefits, such as being clear, biocompatible, non-immunogenic, biodegradable, able to hold drugs, release them slowly and steadily, being nanometrically small, having a large surface area, being easy to make, and being thermodynamically stable.

The non-fullerene acceptor (NFA) chromophores have sparked scientific and economic interest, due to their rapid advancements in power conversion efficiencies. Therefore, a series of new chlorothiazole based compounds (STM1-STM6) with A1–π–A2–π–A1 configuration was designed using reference chromophore (STMR). Structural modifications were made via incorporating selenophene and extended acceptor units, to enhance photovoltaic response in the designed materials. Density functional theory/time dependent-density functional theory (DFT/TD-DFT) calculations were executed at M06/6-311G (d,p) level to investigate key electronic and photovoltaic properties of STM1-STM6. So, various analyses such as UV–Visible, frontier molecular orbitals (FMOs), transition density matrix (TDM), density of states (DOS), open circuit voltage (V_oc) and binding energy (E_b) were conducted to comprehend the photovoltaic properties. The designing in structural aspects with terminal acceptors and π-linker induced a reduction in energy gaps (ΔE = 2.078–2.237 eV) with an enhancement in the bathochromic shift (λ_max = 744.650–798.250 nm in chloroform) than reference compound. A higher exciton dissociation rate was observed in all the compounds due to lower binding energy values (E_b = 0.525–0.572 eV). Additionally, TDM and DOS findings further endorsed the effective charge delocalization from HOMO to LUMO. Among all the examined compounds, STM3 exhibited the smallest band gap (2.078 eV), highest absorption maxima (798.250 nm), and the lowest exciton binding energy (0.525 eV), indicating significant electronic properties. Moreover, V_oc analysis was conducted with respect to HOMO_PBDBT-LUMO_acceptor for all the designed chromophores; consequently, STM2 demonstrated a substantial V_oc value of 1.647 V. Similarly, electron hole analysis was also conducted and significant electron and hole density was observed in all the investigated compounds, especially in STM2. The entitled compounds with photovoltaic potential would be considered as promising materials for the development of solar energy devices.

Hepatocellular carcinoma (HCC) presents a significant global health challenge, necessitating the exploration of novel chemical entities or innovative therapeutic approaches targeting diverse signaling mechanisms. In this study, our focus was on developing a series of ureido/thioureido derivatives with a 4-phenylthiazol-2-amine scaffold to design structurally innovative candidates for HCC treatment, drawing inspiration from the structural characteristics of type II inhibitors like Sorafenib. The synthesized compounds underwent comprehensive evaluation for their antiproliferative activities against human MCF7, HepG2, QGY7703, SMMC-7721, Huh-7, and PLC cells. Additionally, investigations into the molecular targets of selected compounds were conducted. Notably, compound 31 emerged as a standout performer, displaying an IC₅₀ of 0.94 ± 0.29 μM against HepG2 cells, surpassing the efficacy of Sorafenib (1.62 ± 0.27 μM). Further investigations revealed its capability for G2/M phase arrest, apoptosis induction, and significant inhibition of cell cloning and migration in HepG2 cells. Moreover, compound 31 exhibited a notable positive effect on IGF1R, with a significant inhibitory activity of 69.22 % at a concentration of 10 μM. Molecular docking analyses revealed a stronger affinity between compound 31 and the receptor compared to the IGF1R inhibitor OZN2290. In conclusion, compound 31 emerges as a promising candidate for HCC treatment.

A new series of cis-dihydroxy-indeno[1,2-d]imidazolone compounds with distinct structures were synthesized to investigate their potential as inhibitors of the Glycogen synthase kinase 3 (GSK-3). The synthesized compounds were thoroughly characterized using IR, Mass, ¹H, and ¹³C NMR, and in silico screening, including molecular docking, DFT studies using the B3LYP/6-31++G(d,p) basis set in the gas phase drug likeness scores, and molecular dynamic simulation studies, was performed to evaluate protein–ligand interactions and determine the stability of the top-ranked conformation. Our results suggested that compound 4 g, among these compounds, has the potential to be a novel GSK-3 inhibitor as an anticancer agent.

The synthesis of tetrahydrospiro[pyrazole-4,5′-pyrazolo[3,4-b]pyridine] derivatives using Mg/Fe-LDH as a heterogeneous catalyst was reported. This methodology used for the condensation of pyrazolones with aldehydes in a basic medium and with the presence of the Mg/Fe-LDH catalyst presents many benefits, such as the fact of using a reusable and low-cost catalyst, environmentally friendly conditions, short reaction times and excellent yields. It has been verified and confirmed that the catalyst is relatively stable and allows its reuse without additional treatment. Condensation has been carried out with different aldehydes and bis-pyrazolone derivatives have been obtained with yields ranging from 71 to 91% of purified product. The stereo impedance of the adduct formed prevents subsequent condensation.

A facile, transition-metal-free, HFIP-promoted method for the synthesis of triarylmethanes through direct Friedel-Crafts reactions of imidazo[1,2-a]pyridines with chlorohydrocarbon derivatives has been described, which allows for efficient synthesis of triarylmethanes containing imidazo[1,2-a]pyridines in good to satisfactory yields at room temperature. This transformation features simple operation, excellent functional group tolerance, and a broad substrate scope.

Assembly of AgS^tBu and PhCOOH ligands with the assistance of soluble silver salt CH₃COOAg/CF₃SO₃Ag in methanol, N, N-dimethylformamide (DMF) and dichloromethane solution, yielded two Ag₂₀ cage isomers co-constructed by thiol and carboxylate/sulfonate ligands encapsulating a CO₃^2– anion template, [(CO₃^2–)@Ag₂₀(S^tBu)₁₀(PhCOO)₄(CH₃COO)₄(DMF)₄] (1) and [(CO₃^2–)@Ag₂₀(S^tBu)₁₀(PhCOO)₆(CF₃SO₃)₂(DMF)₄]·2DMF (2). The CO₃^2– anion template was generated in situ by fixing atmospheric CO₂. The precise structures of 1 and 2 were confirmed by single-crystal X-ray diffractometry (SCXRD). The thermal stability of compounds 1 and 2 was proved by thermogravimetric (TG) analysis, and their solution stability was characterized by nuclear magnetic resonance hydrogen spectroscopy (¹H NMR). The absorption spectra, photocurrent responses, and luminescence of compounds 1 and 2 were investigated. In addition, the photodegradation of methylene blue (MB) and cyclic voltammetry characteristic curves of 1 and 2 were also studied.

Near-infrared (NIR) persistent luminescence nanoparticles (PLNPs) have inherent advantages for high-sensitivity bioimaging due to the separation of excitation and emission light. However, the single-wavelength emission of NIR PLNPs for bioimaging limits their use in photodynamic therapy (PDT). Herein, a biological window excited up-conversion (UC) PLNPs, Zn₃Ga₂SnO₈:Cr³⁺,Yb³⁺,Ho³⁺ (ZGS), was reported for bioimaging and PDT. ZGS exhibits NIR persistent luminescence (PersL) after red LED excitation and visible UCL under 980 nm excitation. The NIR PersL is designed for in vivo bioimaging; the visible UCL is used to activate photosensitizer (PS) to generate reactive oxygen species (ROS) for PDT. The dual-functional ZGS with UCL and PersL provides an effective method for bioimaging and PDT, which is expected to further promote the application of PLNPs in the integration of efficient diagnosis and treatment.

In the current study, a series of A₁–π–A₂–π–A₁ type bisisoindigo-based organic compounds (BTIND1–BTIND9) were designed via the structural tailoring of the reference compound (BTINR) at terminal acceptors for the organic solar cells (OSCs). Density functional theory (DFT) and time-dependent density functional theory (TD-DFT) approaches were utilized to estimate the influence of end-capped engineering over their photovoltaic properties of BTIND1–BTIND9. After their structural optimization, various analyses like, open circuit voltage (V_oc), absorption spectra (λ_max), frontier molecular orbitals (FMOs), density of states (DOS), binding energy (E_b) and transition density matrix (TDM) were performed at the B3LYP/6-311G(d,p) level. The band gaps range of the engineered molecules was observed as 1.776–1.649 eV, lesser than the BTINR reference (1.812 eV). Their TDM and DOS details further revealed electronic charge transfer in the designed derivatives. The higher λ_max values were found in the visible and near-infrared regions i.e., 666.904–701.149 nm in the chloroform solvent and 661.778–895.581 nm in the gaseous phase. Furthermore, their open-circuit voltage (V_oc) was determined with PTB7 donor polymer and showed significant values. Among all, BTIND5, BTIND7 and BTIND8 compounds were investigated with remarkable photovoltaic properties. These chromophores possessed least energy gaps (1.649, 1.668 and 1.664 eV) and bathochromic shifts (698.070, 699.646 and 701.149 nm) with least binding energies and prominent V_oc results. The above-mentioned outcomes demonstrate that the end-capped modification of bisisoindigo-based molecule is an effective strategy to obtain highly efficient OSCs.