Synthesis of thiazole linked chalcones and their pyrimidine analogues as anticancer agents

Kesari, Chekrapani; Rama, K.; Sedighi, Khwajanezrabodin; Stenvang, Jan; Björkling, Fredrik; Kankala, Shravankumar; Thota, Niranjan

doi:10.1080/00397911.2021.1884262

Cited by 14 publications

(31 citation statements)

References 27 publications

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“…Finally, the resulting solid was recrystallized from ethanol to provide a microcrystalline solid product (Scheme 3 and SI Appendix A Figure S4). (18E)-N-((4,5-dihydro-3-(4-nitrophenyl)-5-phenylpyrazol-1-yl)methylene)-4-phenylthiazol-2-amine (16)…”

Section: Synthesis Of 2-amino-4-(substituted-phenyl)-1 3-thiazole Der...mentioning

confidence: 99%

“…Scheme 3: Synthesis of thiazolyl-pyrazoline Schiff base hybrids derived from chalcone (16)(17)(18)(19)(20)(21)(22)(23)(24).…”

Section: Dpph Free Radical Scavenging Assaymentioning

confidence: 99%

“…ese five-membered heterocyclic compounds have been proven to possess antibacterial activity and the ability to delocalize free radicals and produce stable DPPH fragments [7]. In addition to antibacterial activity, thiazole derivatives exhibit antimicrobial [8], antiviral [9], antidiabetic [10], anticonvulsant [11], antioxidant [12], anti-HIV [13], antiinflammatory [14], Alzheimer's disease [15], and antitumor activities [16]. Previous studies revealed that 3,5-diaryl-4,5dihydro-1H-pyrazole derivatives, which are members of the 2-pyrazoline class, have been extensively investigated using a variety of structural manipulations and it has been discovered that the steric and electronic properties of the various substituents at the N-1, C-3, and C-5 positions, as well as the chirality aspects of these molecules, have a critical influence on activity [17].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Antibacterial, and Antioxidant Activities of Thiazolyl-Pyrazoline Schiff Base Hybrids: A Combined Experimental and Computational Study

Zelelew

Endale

Melaku

et al. 2022

Journal of Chemistry

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Thiazole-pyrazoline Schiff base hybrids have a broad range of pharmacological potential with an ability to control the activity of numerous metabolic enzymes. In this work, a greener and more efficient approach has been developed to synthesize a novel series of thiazole-pyrazoline Schiff base hybrids using ZnO nanoparticle-assisted protocol in good to excellent yields (78.3–96.9%) and examined their antibacterial activity against Gram-positive and Gram-negative bacteria, as well as their antioxidant activity. Compound 24 (IZD = 18.67 ± 0.58) displayed better activity against P. aeruginosa compared with amoxicillin (IZD = 14.33 ± 2.52) at 250 μg/mL, whereas compounds 22 and 24 (IZD = 13.33 ± 0.58 mm and 17.00 ± 1.00 mm, respectively) showed better activity against E. coli compared with amoxicillin (IZD = 14.67 ± 0.58 mm) at 500 μg/mL. The remaining compounds showed moderate to weak activity against the tested bacterial strains. Compound 21 displayed significant inhibition of DPPH (IC50 = 4.63 μg/mL) compared with ascorbic acid (IC50 = 3.21 μg/mL). Compound 21 displayed 80.01 ± 0.07% inhibition of peroxide formation, suggesting its potential in preventing the formation of lipid peroxides. The results of the ADMET study showed that all synthesized compounds obeyed Lipinski's rule of five. In silico pharmacokinetic study demonstrated that compound 24 had superior intestinal absorption compared with amoxicillin. In silico molecular docking analysis revealed a binding affinity of −9.9 Kcal/mol for compound 24 against PqsA compared with amoxicillin (−7.3 Kcal/mol), whereas compounds 22 and 24 displayed higher binding affinity (−8.5 and −7.9 Kcal/mol, respectively) with DNA gyrase B compared with amoxicillin (-7.1 Kcal/mol), in good agreement with in vitro antibacterial activity against P. aeruginosa and E. coli. In silico toxicity study showed that all synthesized compounds had LD50 (mg/kg) values ranging from 800 to 1,000 putting them in ProTox-II class 4. The in vitro antibacterial activity and molecular docking analysis showed that compound 24 is a promising antibacterial therapeutic agent against P. aeruginosa and E. coli and compound 22 is a promising antibacterial agent against E. coli, whereas compound 21 is found to be a potential natural antioxidant agent. Moreover, the green synthesis approach using ZnO nanoparticle as catalyst was found to be a very efficient method to synthesize biologically active thiazole-pyrazoline Schiff base hybrids compared with the conventional method.

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Section: Synthesis Of 2-amino-4-(substituted-phenyl)-1 3-thiazole Der...mentioning

confidence: 99%

“…Scheme 3: Synthesis of thiazolyl-pyrazoline Schiff base hybrids derived from chalcone (16)(17)(18)(19)(20)(21)(22)(23)(24).…”

Section: Dpph Free Radical Scavenging Assaymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Antibacterial, and Antioxidant Activities of Thiazolyl-Pyrazoline Schiff Base Hybrids: A Combined Experimental and Computational Study

Zelelew

Endale

Melaku

et al. 2022

Journal of Chemistry

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“…Pyrimidine is an essential part of DNA and RNA in living system ( Kumar and Narasimhan, 2018 ). Pyrimidine derivatives exhibited diverse biological properties, such as antineoplastic ( Kesari et al, 2021 ), anti-inflammatory ( Abdel-Aziz et al, 2021 ), antiviral ( Abu-Zaied et al, 2021 ), and antimicrobial ( El-mahdy and Farouk, 2021 ) activities. In addition, fused pyrimidine systems, such as pyrrolo [3,2- d ]pyrimidine and 1,2,4-triazolo[1,5- a ]pyrimidine, also possess extensive biological activities ( Cawrse et al, 2018 ; Wang et al, 2019 ; Baillache and Unciti-Broceta, 2020 ; Basyouni et al, 2021 ; Wang R.-X.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antifungal Activity of Novel 1,2,4-Triazolo[4,3-c]trifluoromethylpyrimidine Derivatives Bearing the Thioether Moiety

et al. 2022

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Crop disease caused by fungi seriously affected food security and economic development. Inspired by the utilization of fungicide containing 1,2,4-triazole and trifluoromethylpyrimidine, a novel series of 1,2,4-triazolo[4,3-c]trifluoromethylpyrimidine derivatives bearing the thioether moiety were synthesized. Meanwhile, the antifungal activities of the title compounds were evaluated and most compounds exhibited obvious antifungal activities against cucumber Botrytis cinerea, strawberry Botrytis cinerea, tobacco Botrytis cinerea, blueberry Botrytis cinerea, Phytophthora infestans, and Pyricularia oryzae Cav. Among the compounds, 4, 5h, 5o, and 5r showed significant antifungal activities against three of the four Botrytis cinerea, which indicated the potential to become the leading structures or candidates for resistance to Botrytis cinerea.

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“…Pyrimidine is an essential part of DNA and RNA in living system (Kumar and Narasimhan, 2018). Pyrimidine derivatives exhibited diverse biological properties, such as antineoplastic (Kesari et al, 2021), anti-inflammatory (Abdel-Aziz et al, 2021), antiviral (Abu-Zaied et al, 2021), and antimicrobial (Elmahdy and Farouk, 2021 activities. In addition, fused pyrimidine systems, such as pyrrolo [3,2-d] pyrimidine and 1,2,4-triazolo [1,5-a]pyrimidine, also possess extensive biological activities (Cawrse et al, 2018;Wang et al, 2019;Baillache and Unciti-Broceta, 2020;Basyouni et al, 2021;Wang R.-X.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of thiazole linked chalcones and their pyrimidine analogues as anticancer agents

Cited by 14 publications

References 27 publications

Synthesis, Antibacterial, and Antioxidant Activities of Thiazolyl-Pyrazoline Schiff Base Hybrids: A Combined Experimental and Computational Study

Synthesis, Antibacterial, and Antioxidant Activities of Thiazolyl-Pyrazoline Schiff Base Hybrids: A Combined Experimental and Computational Study

Design, Synthesis, and Antifungal Activity of Novel 1,2,4-Triazolo[4,3-c]trifluoromethylpyrimidine Derivatives Bearing the Thioether Moiety

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