Synthesis and molecular docking of new indeno[1,2-d]imidazole, indeno[1,2-e]triazine, indeno[1,2-c]pyrazole, and indeno[1,2-b]pyrrole polycyclic compounds as antibacterial and antioxidant agents

Saeed, Ali; Soliman, Ahbarah M.; Al-Taisan, Khulud M.; Abdel‐Latif, Ehab; Ahmed, Abdullah Ahmed Ali; Alaizeri, ZabnAllah M.; Alhadlaq, Hisham A.

doi:10.1016/j.molstruc.2023.135763

Cited by 6 publications

(3 citation statements)

References 39 publications

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“…The compounds containing pyrazole, thiophene, and 1,2,3-triazole rings in their molecular structures (Figure 2) have been found to possess higher binding energies on the protein of E. coli bacteria with excellent molecular docking and ADME profiles. [39][40][41][42][43][44][45] The synthesis of pyrazole-containing compounds can be achieved by using several harsh conditions, like high temperatures, organic solvents, and a long reaction time, that consume more energy and raise the overall cost of the synthesis. As a result, the current medicinal chemistry scenario needs to develop greener and more cost-effective methods, such as ultrasonic irradiation, microwave irradiation, and mortar and pestle, by using environmentally benign catalysts and solvents for the synthesis of novel molecules.…”

Section: Introductionmentioning

confidence: 99%

“…These methods aim to achieve an ideal conformation of the interaction between the ligand and receptor. The compounds containing pyrazole, thiophene, and 1,2,3‐triazole rings in their molecular structures (Figure 2) have been found to possess higher binding energies on the protein of E. coli bacteria with excellent molecular docking and ADME profiles [39–45] …”

Section: Introductionmentioning

confidence: 99%

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Greener and Highly Efficient Synthesis, In Silico ADMET and Molecular Docking Studies of Potent Antimicrobial Thiophene Clubbed Pyrazole‐1,2,3‐Triazole Hybrids

Sherashiya,

Kanjariya,

Naliapara

et al. 2024

ChemistrySelect

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To achieve environmentally benign synthesis and develop pharmacologically active compounds, a library of novel thiophene‐clubbed pyrazole‐1,2,3‐triazole hybrids was designed and successfully synthesized using L‐ascorbic acid as a green acid catalyst and ethanol as a green solvent. The reaction was carried out using microwave and ultrasonic irradiation methods to achieve a highly efficient reaction route. All title compounds were characterized and evaluated for their potential in vitro antimicrobial activity using Ciprofloxacin and Nystatin as standard drugs, in which compounds with chloro and naphthyl substitutions exhibited excellent antibacterial activity at concentrations of 25 μg/mL and compounds with methyl and methoxy substitutions exhibited excellent antifungal activity at concentrations of 100 μg/mL. Additionally, the molecular docking study showed that all compounds examined had excellent binding energies ranging from −9.3 to −10.3 kcal/mol, and naphthyl substitution displayed the highest binding energy (−10.3 kcal/mol) on the target protein of E. coli DNA gyrase subunit B. Furthermore, the final moieties were evaluated for in silico ADMET prediction to examine their drug‐likeness profile and toxic effects. The present study revealed that this structural information will be helpful in future antimicrobial drug design and development.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Greener and Highly Efficient Synthesis, In Silico ADMET and Molecular Docking Studies of Potent Antimicrobial Thiophene Clubbed Pyrazole‐1,2,3‐Triazole Hybrids

Sherashiya,

Kanjariya,

Naliapara

et al. 2024

ChemistrySelect

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“…Monocyclic pyrazoles can serve as synthetic scaffolds for fused heterocyclic systems, including pyrazolo-fused pyrimidines, quinolones, pyridines, thiazoles, isoquinolines, imidazoles, diazepines, and triazines. 7 They have potent biological activities, including immunostimulatory, anticancer, antioxidant, antibacterial, and antiviral effects. 8 …”

Section: Introductionmentioning

confidence: 99%

Vitex Negundo–Fe₃O₄–CuO green nanocatalyst (VN–Fe₃O₄–CuO): synthesis of pyrazolo[3,4-c]pyrazole derivatives via the cyclization of isoniazid with pyrazole and their antimicrobial activity, cytotoxicity, and molecular docking studies

Akbar,

Mullaivendhan,

Ahamed

et al. 2024

RSC Adv.

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Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

Almatari,

Saeed,

Abdel‐Ghani

et al. 2024

Journal of Heterocyclic Chem

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The objective of this study is to synthesize novel heterocyclic scaffolds containing a thiophene moiety using easily accessible acetoacetamide as a key synthon. The reaction of acetoacetamide with diazonium salts resulted in the formation of the corresponding thiophene derivatives 4a–c. Additionally, the reaction of acetoacetamide derivative 3 with malononitrile, ethyl cyanoacetate, or 2‐cyanoacetamide, along with elemental sulfur, under refluxing in dioxane containing triethylamine afforded thiophene‐containing derivatives 5a–c. Furthermore, compound 3 reacted with phenyl isothiocyanate in dry dimethylformamide and K2CO3 to yield compound 7. In situ alkylation of the non‐isolable salt 6 was achieved by the addition of methyl iodide, resulting in the formation of methylthio‐thiophene‐2‐carboxamide 8. Compound 7 was employed with numerous alpha‐halogenated reagents in ethanol, affording thiazole derivative 9 and thiophene derivatives 10a and 10b, respectively. Moreover, compound 8 was reacted with hydrazine to produce the 1H‐pyrazole‐4‐carboxamide derivative 11. Additionally, refluxing acetoacetamide derivative 3 with malononitrile and/or ethyl cyanoacetate in dioxane, in the presence of catalytic amount of triethylamine afforded 4‐imino‐3,7‐dimethyl‐4H‐pyrido[1,2‐a]thieno[3,2‐e]pyrimidin‐9(5H)‐one derivatives 12a and 12b. Furthermore, the reactivity of acetoacetamide derivative 3 with 2‐cyanoacetohydrazide was investigated through refluxing the reactants in dioxane, which subsequently yielded the corresponding cyanoacetamide derivative 13. The chemical identity of the newly synthesized compounds was determined by employing infrared spectroscopy (IR), 1H NMR, and 13C NMR techniques. Newly synthesized heterocycles incorporating thiophenes were evaluated for their antioxidant and antimicrobial potentials. Notably, thiophene scaffolds 5a, 10b, 11, and 13 displayed notable antioxidant and antimicrobial activities.

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Synthesis and molecular docking of new indeno[1,2-d]imidazole, indeno[1,2-e]triazine, indeno[1,2-c]pyrazole, and indeno[1,2-b]pyrrole polycyclic compounds as antibacterial and antioxidant agents

Cited by 6 publications

References 39 publications

Greener and Highly Efficient Synthesis, In Silico ADMET and Molecular Docking Studies of Potent Antimicrobial Thiophene Clubbed Pyrazole‐1,2,3‐Triazole Hybrids

Greener and Highly Efficient Synthesis, In Silico ADMET and Molecular Docking Studies of Potent Antimicrobial Thiophene Clubbed Pyrazole‐1,2,3‐Triazole Hybrids

Vitex Negundo–Fe₃O₄–CuO green nanocatalyst (VN–Fe₃O₄–CuO): synthesis of pyrazolo[3,4-c]pyrazole derivatives via the cyclization of isoniazid with pyrazole and their antimicrobial activity, cytotoxicity, and molecular docking studies

Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

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Synthesis and molecular docking of new indeno[1,2-d]imidazole, indeno[1,2-e]triazine, indeno[1,2-c]pyrazole, and indeno[1,2-b]pyrrole polycyclic compounds as antibacterial and antioxidant agents

Cited by 6 publications

References 39 publications

Greener and Highly Efficient Synthesis, In Silico ADMET and Molecular Docking Studies of Potent Antimicrobial Thiophene Clubbed Pyrazole‐1,2,3‐Triazole Hybrids

Greener and Highly Efficient Synthesis, In Silico ADMET and Molecular Docking Studies of Potent Antimicrobial Thiophene Clubbed Pyrazole‐1,2,3‐Triazole Hybrids

Vitex Negundo–Fe3O4–CuO green nanocatalyst (VN–Fe3O4–CuO): synthesis of pyrazolo[3,4-c]pyrazole derivatives via the cyclization of isoniazid with pyrazole and their antimicrobial activity, cytotoxicity, and molecular docking studies

Employing acetoacetamide as a key synthon for synthesizing novel thiophene derivatives and assessing their potential as antioxidants and antimicrobial agents

Contact Info

Product

Resources

About

Vitex Negundo–Fe₃O₄–CuO green nanocatalyst (VN–Fe₃O₄–CuO): synthesis of pyrazolo[3,4-c]pyrazole derivatives via the cyclization of isoniazid with pyrazole and their antimicrobial activity, cytotoxicity, and molecular docking studies