Various derivatives of thiazolidine-2,4-dione (C1–C5) were designed and synthesized by chemical reaction with 4-nitrobenzaldehyde using Knoevenagel reaction conditions which results in the reduction of nitro group to amine and further modification results in target compounds. The chemical structures of all the 2,4-thiazolidinedione derivatives have been elucidated by 1H and 13C NMR spectroscopy. These compounds were further characterized by in silico ADME (absorption, distribution, metabolism, and excretion) studies. The pharmacokinetic properties were assessed by SwissADME software. The in silico ADME (absorption, distribution, metabolism, and excretion) assessment reveals that all derivatives (C1 to C5) have 5 to 7 rotatable bonds. Lipophilicity and water solubility showed that C1, C2, and C4 are water soluble except for C3 and C5 which are moderately soluble. All the compounds have high GI absorption except C3. None of the derivatives are blood-brain barrier permeant. Drug metabolism of TZDs derivatives showed that C3 was identified as an inhibitor of CYP2C9 and C5 as an inhibitor of CYP1A2 and CYP2C19. Drug likeness properties indicate that C1 has only one violation of the Ghose rule while C3 has violations in the Ghose and Egan rules. The in silico pharmacokinetic studies revealed high GI absorption and the inability to pass blood-brain barrier which can be further assessed by in vitro and in vivo antihyperglycemic activity. This study will contribute to providing TZDs derivatives with an improved pharmacokinetic profile and decreased toxicity.

Bushra Ansari

Haroon Khan

Muhammad Saeed Jan

Khalaf F. Alsharif

Khalid J. Alzahrani

Umer Rashid

Abdul Saboor Pirzada

Synthesis, Characterization, and Pharmacokinetic Studies of Thiazolidine-2,4-Dione Derivatives

The essential oils, respectively, from fresh and dried Stropharia rugosoannulata fruiting bodies, an important edible mushroom, have been studied for their chemical composition, antibacterial capacity, and antioxidant activity. The essential oils were obtained by hydrodistillation and analyzed by gas chromatography-mass spectrometry (GC-MS) combined with Kovats retention index. The oils’ antibacterial test was evaluated by the microdilution method against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa, and antioxidant activity was determined through DPPH radical scavenging activity and ferric reducing power. Twenty-nine components were identified from the fresh mushroom, and the compositions were mainly dominated by hydrocarbons (54.72%), acids (32.99%), esters (5.07%), and terpenic compounds (0.96%). Thirty-five components were identified from the dried sample, and acids (31.22%), terpenic compounds (28.7%), alcohols (12.7%), and ketones (10.48%) were the major compounds. Strong antibacterial capacity and obvious antioxidant activity were observed for both essential oils from the fresh and dried mushrooms.

Lei Wei

Wei Wang

Yueying Hou

Xiaoyang Xie

Xiao Li

Fei Chen

Zhiyao Wang

Yong Zhou

Feifei Li

Bingnian Jing

Chemical Composition, Antibacterial Test, and Antioxidant Activity of Essential Oils from Fresh and Dried Stropharia rugosoannulata

Resistance of Candida species is a major problem in the management of Candida infection. This study investigated in vivo antifungal activities of several new imidazole and triazole derivatives in a C. albicans systemic infection. The efficacy of derivatives was determined against systemic infection by C. albicans in mice with cyclophosphamide-induced immunosuppression, and the antifungal activities of the synthesized compounds were evaluated in comparison with fluconazole. Compounds 3 and 8 had the highest efficacy with minimum inhibitory concentration (MIC) values of 0.5–1 μM against the C. albicans pathogen. In vivo activities in immunosuppressed mice were also greater than fluconazole. Furthermore, docking analysis was carried out to know the binding mode of imidazole and triazole derivatives to the CYP51 active site of C. albicans and dihydrofolate reductase as a valid antifungal target. The docking study found that the antifungal results are well correlated with docking results. ADMET and in silico physicochemical parameters were also performed. This study demonstrates that compounds 3 and 8 are potential antifungal candidates against the C. albicans pathogen.

Leila Emami

Akram Jamshidzadeh

Soghra Khabnadideh

Keyvan Pakshir

Maryam Jamshidi

Shirin Rahat

Sepideh Arya

Zahra Rezaei

In Vivo Antifungal Activity and Computational Studies of Some Azole Derivatives against Candida Albicans

Cordyceps militaris is rich in protein, polysaccharide, cordycepin, and other active components, with anticancer and antioxidation functions. In order to improve the economic value of C. militaris, the protein was extracted from its fruiting body by alkali-soluble acid precipitation process, and the extraction technology was optimized by orthogonal test. The polypeptide was obtained by digesting those proteins with a complex enzyme. And the antimicrobial and anticancer activities of those polypeptides were evaluated by measuring inhibitory zone and cytotoxicity. The results showed that the optimal extraction conditions of protein were as follows: pH of 8.5, material-to-water ratio of 1 : 28, extraction time of 3.5 h, extraction three times, and the highest protein yield was 45.06%. The optimum enzymatic hydrolysis process of C. militaris polypeptide solution was as follows: the ratio of alkaline protease to papain was 4 : 3, the optimum temperature was 55°C, pH was 7.2, the enzyme dosage was 7000 U/mL, the enzymolysis time was 3.5 h, and the highest yield of peptide was 16.73%. Under those conditions, the polypeptides prepared from C. militaris (<3000 Da) showed good antibacterial activity against Escherichia coli, Bacillus subtilis, and Staphylococcus aureus, with inhibitory zones of (12.08 ± 0.22), (6.67 ± 0.12), and (10.32 ± 0.23) mm, respectively. The results showed that the SAO-S (IC50 = 0.49 mg/L) and T24 (IC50 = 0.23 mg/L) were significantly inhibited by C. militaris polypeptide. Results from this study suggest that polypeptides can be utilized as a new approach for bioactive compounds production from C. militaris.

Lina Xu

Shang Guo

Yanting Li

Weiwei Guo

Xiaofei Guo

Shasha Hong

Ultrasound-Assisted Enzymatic Extraction and Bioactivity Analysis of Polypeptides from Cordyceps militaris

New antibacterial ligand H3hmbpa-5 (N-(2-hydroxy-5-methyl benzyl)phenylalanine) and its aluminium complexes Al(OPri)(Hhmbpa-5), Al(H2hmbpa-5)(Hhmbpa-5), and Al(H2hmbpa-5)3 were synthesized in excellent yield in a stoichiometric ratio of 1 : 1, 1 : 2, and 1 : 3 (Al(OPri)3 : ligand), based on an idea of biological activity of the phenylalanine and its substituted N-aryl derivatives and Al (III) derivatives. The complexes were characterized by FT-IR, 1H, 13C NMR, UV-visible, and elemental analysis. An inhibition zone test was used for the evaluation of the antibacterial test. The results show that the ligand and aluminium complexes have superior antibacterial activity against Pseudomonas aeruginosa (MTCC-424), Streptococcus aureus (MTCC-103), Klebsiella pneumoniae (MTCC-3389), and Klebsiella pneumoniae (MTCC-109).

Anil Kumar

Manju Kandpal

Synthesis, Characterization, and Antibacterial Activity of Biocompatible Aluminium Complexes with N-(2-Hydroxy-5-methyl benzyl)phenylalanine

In Vietnam, Macrosolen tricolor is used for the treatment of bloating, broken bones, cough, diarrhea, diuretic, rheumatism, and laxative effects. The study aimed to identify the in vitro antiproliferation and anti-inflammation of all fractions and purified compounds from the M. tricolor whole plants, as well as the in silico molecular docking of the potentially cytotoxic compounds. As the results, fractions (MTH.I, MTH.II, MTE.I, and MTE.II) strongly demonstrated antiproliferative properties against three tested cells, MDA-MB-231, RD, and HepG2 (IC50 values ranged from 4.00 ± 0.20 to 70.60 ± 1.44 μg/mL), as well as anti-inflammatory effects (IC50 values ranged from 4.45 ± 0.08 to 23.00 ± 1.18 μg/mL), whereas other fractions meaningfully evidenced selective cytotoxicity and/or anti-inflammation. Therefore, the phytochemical compositions of the active fractions were illuminated, leading to the characterization of eighteen compounds. Compounds (3–5) revealed the most cytotoxic effects towards all examined cells (IC50 values ranged from 6.88 ± 0.12 to 71.64 ± 1.17 μM) and the strongest anti-inflammatory properties (IC50 values of 16.30 ± 0.92, 7.31 ± 0.55, and 9.23 ± 0.60 μM, respectively). Compound 11 showed potential cytotoxicity against MDA-MB-231, RD, and HepG2 cells (IC50 values of 24.42 ± 0.28, 20.60 ± 0.25, and 3.20 ± 0.02 μM, respectively). Furthermore, compounds (4, 5, and 11) interacted with the active site of the apoptosis regulator Bcl-2 protein (PDB ID: 2O2F), were comparable to PAC, and were compatible with their anticancer activity. This project suggests that M. tricolor is a good source of natural antiproliferative and anti-inflammatory agents and contributes to understanding the biological activities of Macrosolen species in traditional Vietnamese medicine.

Van Son Dang

Kieu Hung Le

Thi Hong Tuoi Do

Le Thanh Tuyen Nguyen

Thi Phuong Lan Vu

Thi Kim Chi Huynh

Thi Kim Dung Hoang

Quan Hien Nguyen

Trong Nghia Ngo

Diep Xuan Ky Nguyen

Nhat Minh Phan

Trong Dat Bui

Dinh Tri Mai

Tan Phat Nguyen

Antiproliferative, Anti-Inflammatory Activities, and Molecular Docking Studies of Secondary Metabolites from Macrosolen tricolor

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Journal of Chemistry publishes original research articles as well as review articles on all aspects of fundamental and applied chemistry, including biological, environmental, forensic, inorganic, organic, physical and theoretical.

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Journal of Chemistry publishes original research articles as well as review articles on all aspects of fundamental and applied chemistry, including biological, environmental, forensic, inorganic, organic, physical and theoretical.

Journal of Chemistry