Showing papers in "Journal of The Iranian Chemical Society in 2022"

Competent synthesis of biaryl analogs via asymmetric Suzuki–Miyaura cross-coupling for the development of anti-inflammatory and analgesic agents

Abstract: Based on the core structure of diflunisal drug, herein, we report a resembling series of biaryl analogs (3a–j) containing halogens, nitro, and methoxy substituents. They were designed and synthesized via a Suzuki–Miyaura cross-coupling reaction using Pd (OH)2 as a catalyst at a temperature of 65 °C with an intent to obtain improved and safer anti-inflammatory and analgesic agents. Suzuki–Miyaura transformation is the most significant among the cross-coupling reactions since its practical advantages include the commercially available low toxic reagents, mild reaction conditions, and functional group compatibility. On the other hand, a few conditions can be used to cross-couple aryl boronic acids or esters with aryl halides, especially 2-benzyl halides. Because of this, a novel Suzuki–Miyaura protocol is investigated that facilitates the selective conversion of halo aromatics, with an emphasis on the reaction to convert substituted bromobenzene to conjugated biphenyls. Finally, the obtained biaryl analogs (3a–j) were tested for in vitro and in vivo anti-inflammatory and analgesic applications. The results showed that compound 3b performed better than the standard drug with IC50 values comparable to that of the standard drug for COX-1 and COX-2 inhibition. Finally, molecular docking tests for the effective compound were carried out.

Synthesis, characterization, and in vitro antibacterial activity of some new pyridinone and pyrazole derivatives with some in silico ADME and molecular modeling study

Abstract: Abstract A new series of pyridine-2-one and pyrazole derivatives were designed and synthesized based on cyanoacrylamide derivatives containing 2,4-dichlro aniline and 6-methyl 2-amino pyridine as an aryl group. Condensation of cyanoacrylamide derivatives 3a–d with different active methylene (malononitrile, ethyl cyanoacetate cyanoacetamide, and ethyl acetoacetate) in the presence of piperidine as basic catalyst afforded the corresponding pyridinone derivatives 4a–c , 5 , 9 , and 13 . Furthermore, the reaction of cyanoacrylamide derivatives 3a–d with bi-nucleophile as hydrazine hydrate and thiosemicarbazide afforded the corresponding pyrazole derivatives 14a,b and 16 . The newly designed derivatives were confirmed and established based on the elemental analysis and spectra data (IR, 1 H NMR, 13 C NMR, and mass). The in vitro antibacterial activity was evaluated against four bacterial strains with weak to good antibacterial activity. Moreover, the results indicated that the most active derivatives 3a , 4a , 4b , 9 , and 16 might lead to antibacterial agents, especially against B. subtilis and P. vulgaris . The DFT calculations were performed to estimate its geometric structure and electronic properties. In addition, the most active pyridinone and pyrazole derivatives were further evaluated for in silico physicochemical, drug-likeness, and toxicity prediction. These derivatives obeyed all Lipinski’s and Veber’s rules without any violation and displayed non-immunotoxin, non-mutagenic, and non-cytotoxic. Molecular docking simulation was performed inside the active site of Topoisomerase IV (PDB:3FV5). It displayed binding energy ranging from -14.97 kcal/mol to -18.86 kcal/mol with hydrogen bonding and arene–cation interaction. Therefore, these derivatives were suggested to be good antibacterial agents via topoisomerase IV inhibitor. Graphical abstract

Electrospun composites nanofibers from cellulose acetate/carbon black as efficient adsorbents for heavy and light machine oil from aquatic environment

Abstract: Abstract The feasibility of preparing cellulose acetate/carbon black (CA/CB) composite nanofiber in one step through electrospinning process and investigating its potential oil absorbability and application for machine oil removal from aquatic environment was reported. Different CA/CB composite nanofibers were fabricated by electrospinning of cellulose acetate (CA) solution containing different loads of 0.7, 1.5, and 2.2% CB relative to the weight of CA and labeled as CA/CB0.7, CA/CB1.5, and CA/CB2.2. The scanning electron microscope (SEM) images showed continuous and smooth fiber with submicron diameter ranging from 400–900 nm with good adhering of CB into CA nanofiber. Furthermore, the CA/CB composite nanofibers exhibited high surface area compared with CA nanofiber, which reached 3.057, 2.8718 and 8.244 m 2 /g for CA/CB0.7, CA/CB1.5 and CA/CB2.2, respectively. Oil adsorption tests were performed with heavy and light machine oils. The CA/CB composite nanofibers showed higher affinity for oil removal from an aqueous solution than pure CA nanofiber. The CA/CB1.5 composite nanofiber has an exceptional performance for the adsorption of both oils, and the maximum oil adsorbed reached 10.6 and 18.3 g/g for light and heavy machine oils, respectively. The kinetic of machine oils adsorption was fitted well by the pseudo-second-order model. Besides, CA/CB composite nanofiber exposed good adsorption properties and respectable reusability after regeneration for four consecutive cycles. The results advocate the excellent potential of as-fabricated CA/CB composite nanofiber as a promising reusable oil adsorbent for oil spill cleanup applications.

Probing the biomolecular (DNA/BSA) interaction by new Pd(II) complex via in-depth experimental and computational perspectives: synthesis, characterization, cytotoxicity, and DFT approach

Abstract: Scientists should not forget that the rate of death as a result of cancer is far more than that of other diseases like influenza or coronavirus (COVID-19), so the research in this field is of cardinal significance. Therefore, a new and hydrophilic palladium(II) complex of the general formula [Pd(bpy)(proli-dtc)]NO3, in which bpy and proli-dtc are 2,2'-bipyridine and pyrroline dithiocarbamate ligands, respectively, was synthesized and characterized utilizing spectral and analytical procedures. Density functional theory (DFT) calculation was also performed with B3LYP method in the gas phase. The DFT and spectral analysis specified that the Pd(II) atom is found in a square-planar geometry. HOMO/LUMO analysis, quantum chemical parameters and MEP surface of the complex were investigated to acquire an intuition about the nature of the compound. Partition coefficient and water solubility determination showed that both lipophilicity and hydrophilicity of the compound are more than cisplatin. The 50% inhibition concentration (IC50) value was evaluated against K562 cancer cells, the obtained result has revealed a promising cytotoxic effect. DNA and BSA binding of the complex were explored through multi-spectroscopic (UV–Vis, fluorescence, FRET, and CD) and non-spectroscopic (gel electrophoresis, viscosity and docking simulation) techniques. The obtained findings demonstrated that the complex strongly interacts with CT-DNA by hydrophobic interactions and possesses medium interaction with BSA via hydrogen bond and van der Waals forces, thus BSA could efficiently carry out complex transportation. Furthermore, the results of docking simulation agree well with the experimental findings. In conclusion, the new Pd(II) complex has cytotoxic activity and could interact with DNA and BSA effectively.

Boosting the antimicrobial performance based on new fused spirothiazolidine framework analogs

Abstract: Abstract New spiro[cyclohexane-1,2'-thiazolo[4,5- b ]pyridine derivatives ( 3 – 23 ) were investigated. Then there is in vitro antimicrobial potency against possible organisms Staphylococcus aurous ATCC-47,077, Bacillus cereus ATCC-12228, Escherichia coli ATCC-25922, Salmonella typhi ATCC-15566, and Candida albicans ATCC-10231 were tested utilizing commercially available antibiotics ampicillin as a reference drug. A preliminary antimicrobial test represented that derivatives: (Aldoses) 3'-(4-fluorophenyl)-5'-(methyleneamino)-7'-( p -tolyl)- 3'H -spiro[cyclohexane-1,2'-thiazolo[4,5-b]pyridine]-6'-carbonitrile ( 16–19 ) and (Acetyl aldoses) 3'-(4-fluorophenyl)-5'-(methyleneamino)-7'-( p -tolyl)- 3'H -spiro [cyclohexane-1,2'-thiazolo[4,5-b]pyridine]-6'-carbonitrile ( 20–23 ) exhibited higher antifungal, and antibacterial performance with minimum inhibitory concentrations values of (39–67 µg/ml) toward all pathogenic strains compared to common reference drug ampicillin.

Removal of anti-inflammatory drugs using activated carbon from agro-industrial origin: current advances in kinetics, isotherms, and thermodynamic studies

Abstract: Nonsteroidal anti-inflammatory drugs (NSAIDs) are highly consumed around the world and consequently found as emerging pollutants in water; they are found in concentrations up to µg L−1 making their removal a priority. In this matter, adsorption is an efficient alternative for drug removal, so using activated carbon (AC) as an adsorbent is a highly explored subject. The current interest is to obtain AC from waste, for example, those of agro-industrial origin, reducing this way the overall costs of the process. Although information regarding the use of AC from agro-industrial origin in the removal of NSAIDs is limited, an exclusive compilation is required to understand the state of the art to date. This work aims to update information related to the adsorption of ibuprofen, diclofenac, and naproxen on agro-industrial AC, and it is focused on the period 2016–2021. It highlights the characteristics of agro-industrial AC responsible for efficient adsorption. Recent adsorption studies, including kinetics, isotherms, and thermodynamics, are analyzed and compared. Progress on removing NSAIDs from real wastewater is also presented and finally proposed adsorption mechanisms and costs related to these removal processes.