Design, synthesis and in silico molecular docking evaluation of novel 1,2,3-triazole derivatives as potent antimicrobial agents
Chalcone and triazole scaffolds have demonstrated a crucial role in the advancement of science and technology. Due to their significance, research has proceeded on the design and development of novel benzooxepine connected to 1,2,3-triazolyl chalcone structures. The new chalcone derivatives produced...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2024-04-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844024038040 |
| _version_ | 1797235517061857280 |
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| author | Sudhakar Reddy Baddam Mahesh Kumar Avula Raghunadh Akula Venkateswara Rao Battula Sudhakar Kalagara Ravinder Buchikonda Srinivas Ganta Srinivasadesikan Venkatesan Tejeswara Rao Allaka |
| author_facet | Sudhakar Reddy Baddam Mahesh Kumar Avula Raghunadh Akula Venkateswara Rao Battula Sudhakar Kalagara Ravinder Buchikonda Srinivas Ganta Srinivasadesikan Venkatesan Tejeswara Rao Allaka |
| author_sort | Sudhakar Reddy Baddam |
| collection | DOAJ |
| description | Chalcone and triazole scaffolds have demonstrated a crucial role in the advancement of science and technology. Due to their significance, research has proceeded on the design and development of novel benzooxepine connected to 1,2,3-triazolyl chalcone structures. The new chalcone derivatives produced by benzooxepine triazole methyl ketone 2 and different aromatic carbonyl compounds 3 are discussed in this paper. All prepared compounds have well-established structures to a variety of spectral approaches, including mass analysis, 1H NMR, 13C NMR, and IR. Among the tested compounds, hybrids 4c, 4d, 4i, and 4k exhibited exceptional antibacterial susceptibilities with MIC range of 3.59–10.30 μM against the tested S. aureus strain. Compounds 4c, 4d displayed superior antifungal activity against F. oxysporum with MIC 3.25, 4.89 μM, when compared to fluconazole (MIC = 3.83 μM) respectively. On the other hand, analogues 4d, 4f, and 4k demonstrated equivalent antitubercular action against H37Rv strain with MIC range of 2.16–4.90 μM. The capacity of ligand 4f to form a stable compound on the active site of CYP51 from M. tuberculosis (1EA1) was confirmed by docking studies using amino acids Leu321(A), Pro77(A), Phe83(A), Lys74(A), Tyr76(A), Ala73(A), Arg96(A), Thr80(A), Met79(A), His259(A), and Gln72(A). Additionally, the chalcone‒1,2,3‒triazole hybrids ADME (absorption, distribution, metabolism, and excretion), characteristics of molecules, estimations of toxicity, and bioactivity parameters were assessed. |
| first_indexed | 2024-04-24T16:49:13Z |
| format | Article |
| id | doaj.art-193392dd86dd40b6b22c971125ba5134 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-04-24T16:49:13Z |
| publishDate | 2024-04-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-193392dd86dd40b6b22c971125ba51342024-03-29T05:50:34ZengElsevierHeliyon2405-84402024-04-01107e27773Design, synthesis and in silico molecular docking evaluation of novel 1,2,3-triazole derivatives as potent antimicrobial agentsSudhakar Reddy Baddam0Mahesh Kumar Avula1Raghunadh Akula2Venkateswara Rao Battula3Sudhakar Kalagara4Ravinder Buchikonda5Srinivas Ganta6Srinivasadesikan Venkatesan7Tejeswara Rao Allaka8University of Massachusetts Chan Medical School, RNA Therapeutic Institute, Worcester, MA, 01655, United States; Corresponding author.Technology Development Center, Custom Pharmaceutical Services, Dr. Reddy's Laboratories Pvt. Ltd., Hyderabad, Telangana, 500049, India; Department of Organic Chemistry and FDW, Andhra University, Visakhapatnam, Andhra Pradesh, 530003, IndiaTechnology Development Center, Custom Pharmaceutical Services, Dr. Reddy's Laboratories Pvt. Ltd., Hyderabad, Telangana, 500049, IndiaDepartment of Chemistry, AU College of Engineering (A), Andhra University, Visakhapatnam, Andhra Pradesh, 530003, IndiaDepartment of Chemistry and Biochemistry, University of the Texas at El Paso, El Paso, TX, 79968, United StatesTechnology Development Center, Custom Pharmaceutical Services, Dr. Reddy's Laboratories Pvt. Ltd., Hyderabad, Telangana, 500049, IndiaScieGen Pharmaceutical Inc., Hauppauge, NY, 11788, United StatesDepartment of Chemistry, School of Applied Science and Humanities, VIGNAN's Foundation for Science, Technology and Research, Vadlamudi, Andhra Pradesh, 522213, IndiaCentre for Chemical Sciences and Technology, Institute of Science and Technology, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad, Telangana, 500085, India; Corresponding author.Chalcone and triazole scaffolds have demonstrated a crucial role in the advancement of science and technology. Due to their significance, research has proceeded on the design and development of novel benzooxepine connected to 1,2,3-triazolyl chalcone structures. The new chalcone derivatives produced by benzooxepine triazole methyl ketone 2 and different aromatic carbonyl compounds 3 are discussed in this paper. All prepared compounds have well-established structures to a variety of spectral approaches, including mass analysis, 1H NMR, 13C NMR, and IR. Among the tested compounds, hybrids 4c, 4d, 4i, and 4k exhibited exceptional antibacterial susceptibilities with MIC range of 3.59–10.30 μM against the tested S. aureus strain. Compounds 4c, 4d displayed superior antifungal activity against F. oxysporum with MIC 3.25, 4.89 μM, when compared to fluconazole (MIC = 3.83 μM) respectively. On the other hand, analogues 4d, 4f, and 4k demonstrated equivalent antitubercular action against H37Rv strain with MIC range of 2.16–4.90 μM. The capacity of ligand 4f to form a stable compound on the active site of CYP51 from M. tuberculosis (1EA1) was confirmed by docking studies using amino acids Leu321(A), Pro77(A), Phe83(A), Lys74(A), Tyr76(A), Ala73(A), Arg96(A), Thr80(A), Met79(A), His259(A), and Gln72(A). Additionally, the chalcone‒1,2,3‒triazole hybrids ADME (absorption, distribution, metabolism, and excretion), characteristics of molecules, estimations of toxicity, and bioactivity parameters were assessed.http://www.sciencedirect.com/science/article/pii/S2405844024038040BenzooxepinesChalcones1,2,3-TriazolesBiological evaluationsDocking interactionsADMETlab2.0 |
| spellingShingle | Sudhakar Reddy Baddam Mahesh Kumar Avula Raghunadh Akula Venkateswara Rao Battula Sudhakar Kalagara Ravinder Buchikonda Srinivas Ganta Srinivasadesikan Venkatesan Tejeswara Rao Allaka Design, synthesis and in silico molecular docking evaluation of novel 1,2,3-triazole derivatives as potent antimicrobial agents Heliyon Benzooxepines Chalcones 1,2,3-Triazoles Biological evaluations Docking interactions ADMETlab2.0 |
| title | Design, synthesis and in silico molecular docking evaluation of novel 1,2,3-triazole derivatives as potent antimicrobial agents |
| title_full | Design, synthesis and in silico molecular docking evaluation of novel 1,2,3-triazole derivatives as potent antimicrobial agents |
| title_fullStr | Design, synthesis and in silico molecular docking evaluation of novel 1,2,3-triazole derivatives as potent antimicrobial agents |
| title_full_unstemmed | Design, synthesis and in silico molecular docking evaluation of novel 1,2,3-triazole derivatives as potent antimicrobial agents |
| title_short | Design, synthesis and in silico molecular docking evaluation of novel 1,2,3-triazole derivatives as potent antimicrobial agents |
| title_sort | design synthesis and in silico molecular docking evaluation of novel 1 2 3 triazole derivatives as potent antimicrobial agents |
| topic | Benzooxepines Chalcones 1,2,3-Triazoles Biological evaluations Docking interactions ADMETlab2.0 |
| url | http://www.sciencedirect.com/science/article/pii/S2405844024038040 |
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