1,2,4-Triazolo-quinazolinones as Effective Antifoulants: Molecular Design, Synthesis, and Biological Evaluation
A series of 1,2,4-triazolo-quinazolinones and 1,2-benzisothiazolone derivatives (S1–S12) were successfully synthesized as environmentally friendly alternatives to copper-based antifouling paints using N-alkylation, cyclocondensation, and one-pot three-component and amide coupling reactions. The mono...
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| Published in | Langmuir Vol. 40; no. 30; pp. 15650 - 15660 |
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| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
American Chemical Society
16.07.2024
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| Abstract | A series of 1,2,4-triazolo-quinazolinones and 1,2-benzisothiazolone derivatives (S1–S12) were successfully synthesized as environmentally friendly alternatives to copper-based antifouling paints using N-alkylation, cyclocondensation, and one-pot three-component and amide coupling reactions. The monoclinic structure of single-crystal 1,2,4-triazolo-quinazolin-acetic acid (S8) was confirmed by single-crystal X-ray diffraction analysis. All the synthesized molecules were studied for their in silico molecular docking interactions with three target proteins, namely, RbmA, ToxR, and Bap. Following that, the antialgal activity was assessed against two types of marine algae: Chlorella sp. and Chaetoceros curvisetus. The minimal inhibitory concentration and zone of inhibition have been used to evaluate the antibacterial activities of S1–S12 against both marine Gram-positive (Staphylococcus aureus) and Gram-negative (Vibrio parahemolyticus and Vibrio vulnificus) bacteria. Additionally, antifouling studies have been done on all the compounds, and among them, 1,2,4-triazolo-quinazolinyl-acetate (S7), 1,2,4-triazolo-quinazolinyl-acetic acid (S8), 1,2,4-triazolo-quinazolinyl-oxobutanoate (S9), benzo[d]isothiazolyl butanoate (S10), benzo[d]isothiazolyl-acetic acid (S11), and 1,2,4-triazolo-quinazolinyl-acetyl-benzo[d]isothiazolone (S12) exhibited good antialgal, antibacterial, and antifouling activities. |
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| AbstractList | A series of 1,2,4-triazolo-quinazolinones and 1,2-benzisothiazolone derivatives (S1–S12) were successfully synthesized as environmentally friendly alternatives to copper-based antifouling paints using N-alkylation, cyclocondensation, and one-pot three-component and amide coupling reactions. The monoclinic structure of single-crystal 1,2,4-triazolo-quinazolin-acetic acid (S8) was confirmed by single-crystal X-ray diffraction analysis. All the synthesized molecules were studied for their in silico molecular docking interactions with three target proteins, namely, RbmA, ToxR, and Bap. Following that, the antialgal activity was assessed against two types of marine algae: Chlorella sp. and Chaetoceros curvisetus. The minimal inhibitory concentration and zone of inhibition have been used to evaluate the antibacterial activities of S1–S12 against both marine Gram-positive (Staphylococcus aureus) and Gram-negative (Vibrio parahemolyticus and Vibrio vulnificus) bacteria. Additionally, antifouling studies have been done on all the compounds, and among them, 1,2,4-triazolo-quinazolinyl-acetate (S7), 1,2,4-triazolo-quinazolinyl-acetic acid (S8), 1,2,4-triazolo-quinazolinyl-oxobutanoate (S9), benzo[d]isothiazolyl butanoate (S10), benzo[d]isothiazolyl-acetic acid (S11), and 1,2,4-triazolo-quinazolinyl-acetyl-benzo[d]isothiazolone (S12) exhibited good antialgal, antibacterial, and antifouling activities. A series of 1,2,4-triazolo-quinazolinones and 1,2-benzisothiazolone derivatives (S1-S12) were successfully synthesized as environmentally friendly alternatives to copper-based antifouling paints using -alkylation, cyclocondensation, and one-pot three-component and amide coupling reactions. The monoclinic structure of single-crystal 1,2,4-triazolo-quinazolin-acetic acid (S8) was confirmed by single-crystal X-ray diffraction analysis. All the synthesized molecules were studied for their in silico molecular docking interactions with three target proteins, namely, RbmA, ToxR, and Bap. Following that, the antialgal activity was assessed against two types of marine algae: sp. and . The minimal inhibitory concentration and zone of inhibition have been used to evaluate the antibacterial activities of S1-S12 against both marine Gram-positive ( ) and Gram-negative ( and ) bacteria. Additionally, antifouling studies have been done on all the compounds, and among them, 1,2,4-triazolo-quinazolinyl-acetate (S7), 1,2,4-triazolo-quinazolinyl-acetic acid (S8), 1,2,4-triazolo-quinazolinyl-oxobutanoate (S9), benzo[ ]isothiazolyl butanoate (S10), benzo[ ]isothiazolyl-acetic acid (S11), and 1,2,4-triazolo-quinazolinyl-acetyl-benzo[ ]isothiazolone (S12) exhibited good antialgal, antibacterial, and antifouling activities. A series of 1,2,4-triazolo-quinazolinones and 1,2-benzisothiazolone derivatives (S1-S12) were successfully synthesized as environmentally friendly alternatives to copper-based antifouling paints using N-alkylation, cyclocondensation, and one-pot three-component and amide coupling reactions. The monoclinic structure of single-crystal 1,2,4-triazolo-quinazolin-acetic acid (S8) was confirmed by single-crystal X-ray diffraction analysis. All the synthesized molecules were studied for their in silico molecular docking interactions with three target proteins, namely, RbmA, ToxR, and Bap. Following that, the antialgal activity was assessed against two types of marine algae: Chlorella sp. and Chaetoceros curvisetus. The minimal inhibitory concentration and zone of inhibition have been used to evaluate the antibacterial activities of S1-S12 against both marine Gram-positive (Staphylococcus aureus) and Gram-negative (Vibrio parahemolyticus and Vibrio vulnificus) bacteria. Additionally, antifouling studies have been done on all the compounds, and among them, 1,2,4-triazolo-quinazolinyl-acetate (S7), 1,2,4-triazolo-quinazolinyl-acetic acid (S8), 1,2,4-triazolo-quinazolinyl-oxobutanoate (S9), benzo[d]isothiazolyl butanoate (S10), benzo[d]isothiazolyl-acetic acid (S11), and 1,2,4-triazolo-quinazolinyl-acetyl-benzo[d]isothiazolone (S12) exhibited good antialgal, antibacterial, and antifouling activities.A series of 1,2,4-triazolo-quinazolinones and 1,2-benzisothiazolone derivatives (S1-S12) were successfully synthesized as environmentally friendly alternatives to copper-based antifouling paints using N-alkylation, cyclocondensation, and one-pot three-component and amide coupling reactions. The monoclinic structure of single-crystal 1,2,4-triazolo-quinazolin-acetic acid (S8) was confirmed by single-crystal X-ray diffraction analysis. All the synthesized molecules were studied for their in silico molecular docking interactions with three target proteins, namely, RbmA, ToxR, and Bap. Following that, the antialgal activity was assessed against two types of marine algae: Chlorella sp. and Chaetoceros curvisetus. The minimal inhibitory concentration and zone of inhibition have been used to evaluate the antibacterial activities of S1-S12 against both marine Gram-positive (Staphylococcus aureus) and Gram-negative (Vibrio parahemolyticus and Vibrio vulnificus) bacteria. Additionally, antifouling studies have been done on all the compounds, and among them, 1,2,4-triazolo-quinazolinyl-acetate (S7), 1,2,4-triazolo-quinazolinyl-acetic acid (S8), 1,2,4-triazolo-quinazolinyl-oxobutanoate (S9), benzo[d]isothiazolyl butanoate (S10), benzo[d]isothiazolyl-acetic acid (S11), and 1,2,4-triazolo-quinazolinyl-acetyl-benzo[d]isothiazolone (S12) exhibited good antialgal, antibacterial, and antifouling activities. |
| Author | Wang, Dazhuang Lin, Xinrui Jha, Anubhuti Yang, Jianxin Liu, Ruotong Gudala, Satish Sharma, Archi Dong, Miao Vinothkanna, Annadurai Liu, Xinghua |
| AuthorAffiliation | Department of Biotechnology, St. Thomas College Key Laboratory of Green Catalysis and Reaction Engineering of Haikou, College of Chemistry and Chemical Engineering Jawaharlal Nehru Technological University Hemchand Yadav University Department of Chemistry, Vardhman College of Engineering Department of Biotechnology |
| AuthorAffiliation_xml | – name: Department of Chemistry, Vardhman College of Engineering – name: Department of Biotechnology – name: Jawaharlal Nehru Technological University – name: Department of Biotechnology, St. Thomas College – name: Key Laboratory of Green Catalysis and Reaction Engineering of Haikou, College of Chemistry and Chemical Engineering – name: Hemchand Yadav University |
| Author_xml | – sequence: 1 givenname: Satish surname: Gudala fullname: Gudala, Satish organization: Key Laboratory of Green Catalysis and Reaction Engineering of Haikou, College of Chemistry and Chemical Engineering – sequence: 2 givenname: Miao surname: Dong fullname: Dong, Miao organization: Key Laboratory of Green Catalysis and Reaction Engineering of Haikou, College of Chemistry and Chemical Engineering – sequence: 3 givenname: Xinrui surname: Lin fullname: Lin, Xinrui organization: Key Laboratory of Green Catalysis and Reaction Engineering of Haikou, College of Chemistry and Chemical Engineering – sequence: 4 givenname: Ruotong surname: Liu fullname: Liu, Ruotong organization: Key Laboratory of Green Catalysis and Reaction Engineering of Haikou, College of Chemistry and Chemical Engineering – sequence: 5 givenname: Annadurai surname: Vinothkanna fullname: Vinothkanna, Annadurai organization: Department of Biotechnology – sequence: 6 givenname: Anubhuti surname: Jha fullname: Jha, Anubhuti organization: Hemchand Yadav University – sequence: 7 givenname: Archi surname: Sharma fullname: Sharma, Archi organization: Jawaharlal Nehru Technological University – sequence: 8 givenname: Dazhuang surname: Wang fullname: Wang, Dazhuang organization: Key Laboratory of Green Catalysis and Reaction Engineering of Haikou, College of Chemistry and Chemical Engineering – sequence: 9 givenname: Xinghua surname: Liu fullname: Liu, Xinghua organization: Key Laboratory of Green Catalysis and Reaction Engineering of Haikou, College of Chemistry and Chemical Engineering – sequence: 10 givenname: Jianxin orcidid: 0000-0002-0082-227X surname: Yang fullname: Yang, Jianxin email: yangjxmail@hainanu.edu.cn organization: Key Laboratory of Green Catalysis and Reaction Engineering of Haikou, College of Chemistry and Chemical Engineering |
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| Snippet | A series of 1,2,4-triazolo-quinazolinones and 1,2-benzisothiazolone derivatives (S1–S12) were successfully synthesized as environmentally friendly alternatives... A series of 1,2,4-triazolo-quinazolinones and 1,2-benzisothiazolone derivatives (S1-S12) were successfully synthesized as environmentally friendly alternatives... |
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| SubjectTerms | alkylation antifouling agents biological assessment butyrates Chaetoceros Chlorella computer simulation copper minimum inhibitory concentration Staphylococcus aureus Vibrio parahaemolyticus Vibrio vulnificus X-ray diffraction |
| Title | 1,2,4-Triazolo-quinazolinones as Effective Antifoulants: Molecular Design, Synthesis, and Biological Evaluation |
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