Bio-computational modeling, POM analysis and molecular dynamic simulation for novel synthetic quinolone and benzo[d][1,3]oxazine candidates as antimicrobial inhibitors

The current study offers a metal-free, direct, and successful synthesis technique for a new series of quinolinone and benzo[d][1,3]oxazine, along with an assessment of their biological activities. Heteroannulation of anthranilic acid with carbonyl-containing chemicals (aroyl pyruvate, ethyl acetoace...

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Veröffentlicht in:	Scientific reports Jg. 14; H. 1; S. 28709 - 19
Hauptverfasser:	Elsayed, Doaa A., Abdu, Mohamed E., Marzouk, Mohammed A., Mahmoud, Elsayed M., El-Shwiniy, Walaa H., Spring, Andrew M., Shehab, Wesam S.
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	London Nature Publishing Group UK 20.11.2024 Nature Publishing Group Nature Portfolio
Schlagworte:	639/638 639/638/403 Anthranilic acid Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology Antibacterial agents Antifungal activity Antifungal agents Antimicrobial Benzoxazines - chemical synthesis Benzoxazines - chemistry Benzoxazines - pharmacology Bio-computational modeling Carbonyl compounds Chemotherapy Cytotoxicity Doxorubicin Humanities and Social Sciences Humans Microbial Sensitivity Tests Molecular Docking Simulation Molecular dynamic simulation Molecular Dynamics Simulation multidisciplinary Oxazine POM analysis Pyruvic acid Quinolone Quinolones Quinolones - chemical synthesis Quinolones - chemistry Quinolones - pharmacology Science Science (multidisciplinary) Toxicity Antimicrobial Quinolone Bio-computational modeling Molecular dynamic simulation POM analysis
ISSN:	2045-2322, 2045-2322
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Abstract	The current study offers a metal-free, direct, and successful synthesis technique for a new series of quinolinone and benzo[d][1,3]oxazine, along with an assessment of their biological activities. Heteroannulation of anthranilic acid with carbonyl-containing chemicals (aroyl pyruvate, ethyl acetoacetatete, maleic anhydride, and ethyl cyanoacetate) resulted in the desired quinolones and benzo[d][1,3]oxazines. This technique introduces a number of fundamental breakthroughs in organic synthesis, including metal-free catalysts, smart reaction conditions with column purification, and a wide functional scope. Furthermore, the structure of the newly synthesized chemical series was investigated and validated using spectroscopic techniques. The synthesized series were evaluated for antibacterial (against gram-positive and gram-negative bacterial strains) and antifungal activity. The quinolone and benzo[d][1,3]oxazine candidates had remarkable antibacterial action. Furthermore, molecular docking investigations corroborated the biological studies using the Molecular Operating Environment and Petro Osiris Molinspiration (POM) experiments, which confirmed the activity of compounds 8 , 15 , and 17 . Our studies on the cytotoxic activity of various chemicals have demonstrated that these compounds exhibit minimal toxicity. Specifically, when comparing the cytotoxic effects on human lung fibroblast (WI38) cells to those of Doxorubicin , a well-known chemotherapy agent, compounds 8 , 15 , and 17 showed weak cytotoxic effects on the normal WI38 cells. This indicates that these compounds may possess some level of selectivity and reduced toxicity towards normal cells, suggesting potential for further exploration as antibacterial agents with a safer profile for normal cells.
AbstractList	The current study offers a metal-free, direct, and successful synthesis technique for a new series of quinolinone and benzo[d][1,3]oxazine, along with an assessment of their biological activities. Heteroannulation of anthranilic acid with carbonyl-containing chemicals (aroyl pyruvate, ethyl acetoacetatete, maleic anhydride, and ethyl cyanoacetate) resulted in the desired quinolones and benzo[d][1,3]oxazines. This technique introduces a number of fundamental breakthroughs in organic synthesis, including metal-free catalysts, smart reaction conditions with column purification, and a wide functional scope. Furthermore, the structure of the newly synthesized chemical series was investigated and validated using spectroscopic techniques. The synthesized series were evaluated for antibacterial (against gram-positive and gram-negative bacterial strains) and antifungal activity. The quinolone and benzo[d][1,3]oxazine candidates had remarkable antibacterial action. Furthermore, molecular docking investigations corroborated the biological studies using the Molecular Operating Environment and Petro Osiris Molinspiration (POM) experiments, which confirmed the activity of compounds 8, 15, and 17. Our studies on the cytotoxic activity of various chemicals have demonstrated that these compounds exhibit minimal toxicity. Specifically, when comparing the cytotoxic effects on human lung fibroblast (WI38) cells to those of Doxorubicin, a well-known chemotherapy agent, compounds 8, 15, and 17 showed weak cytotoxic effects on the normal WI38 cells. This indicates that these compounds may possess some level of selectivity and reduced toxicity towards normal cells, suggesting potential for further exploration as antibacterial agents with a safer profile for normal cells. Abstract The current study offers a metal-free, direct, and successful synthesis technique for a new series of quinolinone and benzo[d][1,3]oxazine, along with an assessment of their biological activities. Heteroannulation of anthranilic acid with carbonyl-containing chemicals (aroyl pyruvate, ethyl acetoacetatete, maleic anhydride, and ethyl cyanoacetate) resulted in the desired quinolones and benzo[d][1,3]oxazines. This technique introduces a number of fundamental breakthroughs in organic synthesis, including metal-free catalysts, smart reaction conditions with column purification, and a wide functional scope. Furthermore, the structure of the newly synthesized chemical series was investigated and validated using spectroscopic techniques. The synthesized series were evaluated for antibacterial (against gram-positive and gram-negative bacterial strains) and antifungal activity. The quinolone and benzo[d][1,3]oxazine candidates had remarkable antibacterial action. Furthermore, molecular docking investigations corroborated the biological studies using the Molecular Operating Environment and Petro Osiris Molinspiration (POM) experiments, which confirmed the activity of compounds 8, 15, and 17. Our studies on the cytotoxic activity of various chemicals have demonstrated that these compounds exhibit minimal toxicity. Specifically, when comparing the cytotoxic effects on human lung fibroblast (WI38) cells to those of Doxorubicin, a well-known chemotherapy agent, compounds 8, 15, and 17 showed weak cytotoxic effects on the normal WI38 cells. This indicates that these compounds may possess some level of selectivity and reduced toxicity towards normal cells, suggesting potential for further exploration as antibacterial agents with a safer profile for normal cells. The current study offers a metal-free, direct, and successful synthesis technique for a new series of quinolinone and benzo[d][1,3]oxazine, along with an assessment of their biological activities. Heteroannulation of anthranilic acid with carbonyl-containing chemicals (aroyl pyruvate, ethyl acetoacetatete, maleic anhydride, and ethyl cyanoacetate) resulted in the desired quinolones and benzo[d][1,3]oxazines. This technique introduces a number of fundamental breakthroughs in organic synthesis, including metal-free catalysts, smart reaction conditions with column purification, and a wide functional scope. Furthermore, the structure of the newly synthesized chemical series was investigated and validated using spectroscopic techniques. The synthesized series were evaluated for antibacterial (against gram-positive and gram-negative bacterial strains) and antifungal activity. The quinolone and benzo[d][1,3]oxazine candidates had remarkable antibacterial action. Furthermore, molecular docking investigations corroborated the biological studies using the Molecular Operating Environment and Petro Osiris Molinspiration (POM) experiments, which confirmed the activity of compounds 8 , 15 , and 17 . Our studies on the cytotoxic activity of various chemicals have demonstrated that these compounds exhibit minimal toxicity. Specifically, when comparing the cytotoxic effects on human lung fibroblast (WI38) cells to those of Doxorubicin , a well-known chemotherapy agent, compounds 8 , 15 , and 17 showed weak cytotoxic effects on the normal WI38 cells. This indicates that these compounds may possess some level of selectivity and reduced toxicity towards normal cells, suggesting potential for further exploration as antibacterial agents with a safer profile for normal cells.
ArticleNumber	28709
Author	Spring, Andrew M. Mahmoud, Elsayed M. Elsayed, Doaa A. Shehab, Wesam S. Marzouk, Mohammed A. El-Shwiniy, Walaa H. Abdu, Mohamed E.
Author_xml	– sequence: 1 givenname: Doaa A. surname: Elsayed fullname: Elsayed, Doaa A. email: doaaatef@zu.edu.eg, doaaatef641995@gmail.com organization: Department of Chemistry, Faculty of Science, Zagazig University – sequence: 2 givenname: Mohamed E. surname: Abdu fullname: Abdu, Mohamed E. organization: Department of Chemistry, Faculty of Science, Zagazig University, Kyushu Universty – sequence: 3 givenname: Mohammed A. surname: Marzouk fullname: Marzouk, Mohammed A. organization: Department of pharmaceutical organic Chemistry, Faculty of Pharmacy, Zagazig Universty – sequence: 4 givenname: Elsayed M. surname: Mahmoud fullname: Mahmoud, Elsayed M. organization: Department of pharmaceutical organic Chemistry, Faculty of Pharmacy, Zagazig Universty – sequence: 5 givenname: Walaa H. surname: El-Shwiniy fullname: El-Shwiniy, Walaa H. organization: Department of Chemistry, College of Science, University of Bisha – sequence: 6 givenname: Andrew M. surname: Spring fullname: Spring, Andrew M. organization: Kyushu Universty – sequence: 7 givenname: Wesam S. surname: Shehab fullname: Shehab, Wesam S. organization: Department of Chemistry, Faculty of Science, Zagazig University
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CitedBy_id	crossref_primary_10_1016_j_rechem_2025_102693 crossref_primary_10_1039_D5RA04955E crossref_primary_10_1007_s44442_025_00027_9 crossref_primary_10_1038_s41598_025_11214_4 crossref_primary_10_1016_j_ejmech_2025_117859 crossref_primary_10_1155_bri_7961294 crossref_primary_10_1039_D5RA01077B
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Keywords	Antimicrobial Quinolone Bio-computational modeling Molecular dynamic simulation POM analysis
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SubjectTerms	639/638 639/638/403 Anthranilic acid Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology Antibacterial agents Antifungal activity Antifungal agents Antimicrobial Benzoxazines - chemical synthesis Benzoxazines - chemistry Benzoxazines - pharmacology Bio-computational modeling Carbonyl compounds Chemotherapy Cytotoxicity Doxorubicin Humanities and Social Sciences Humans Microbial Sensitivity Tests Molecular Docking Simulation Molecular dynamic simulation Molecular Dynamics Simulation multidisciplinary Oxazine POM analysis Pyruvic acid Quinolone Quinolones Quinolones - chemical synthesis Quinolones - chemistry Quinolones - pharmacology Science Science (multidisciplinary) Toxicity
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Title	Bio-computational modeling, POM analysis and molecular dynamic simulation for novel synthetic quinolone and benzo[d][1,3]oxazine candidates as antimicrobial inhibitors
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