Design, synthesis, biological evaluation, and bio-computational modeling of imidazo, thieno, pyrimidopyrimidine, pyrimidodiazepene, and motifs as antimicrobial agents
In the drug chemistry industry, synthesizing a talented exclusive series of aza-polyheterocyclic compounds was crucial. Aminopyrimidine nucleus reacted with two equivalents of benzaldehyde in the presence of KOH as a starting material to bring about imidazopyrimidine derivative, which experienced in...
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| Vydáno v: | Heterocyclic Communications Ročník 29; číslo 1; s. 1494 - 501 |
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| Hlavní autoři: | , , , , , , , , |
| Médium: | Journal Article |
| Jazyk: | angličtina |
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Berlin
Walter de Gruyter GmbH
01.01.2023
De Gruyter |
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| ISSN: | 0793-0283, 2191-0197 |
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| Abstract | In the drug chemistry industry, synthesizing a talented exclusive series of aza-polyheterocyclic compounds was crucial. Aminopyrimidine nucleus reacted with two equivalents of benzaldehyde in the presence of KOH as a starting material to bring about imidazopyrimidine derivative, which experienced intermolecular cyclization using carbon disulfide, Br2/AcOH, and/or HNO2 to produce thiazole, thieno, and/or nitro pyrimidine derivative, respectively. Accordingly, the nucleus of Aminopyrimidine was prepared and used to develop the novel polyheterocyclic systems acylated with two moles of succinic anhydride to furnish the imidazolopyrimidine derivative. Benzylidene ethyl cyanoacetate and aminopyrimidine undergo (3 + 4) intermolecular cycloaddition 1,3 H shift followed by hydrolysis and after CO2 evolution provided diazepine derivative. The diazepine derivative was attained due to the cyclo-condensation of the starting material and acetylacetone. Moreover, the structure of the novel synthesized compound series was exploited and verified via spectroscopic approaches. The synthesized series were tested for antimicrobial activity against gram-positive and gram-negative bacterial strains and antifungal activity. The thienopyrimidine derivatives and diazepine exhibited unusual antimicrobial activity. Furthermore, the molecular docking studies confirmed the biological studies with Molecular Operating Environment and petro orisis molinspiration studies, which proved the activity of compounds 4, 5, 7, 10, 13, and 16. |
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| AbstractList | In the drug chemistry industry, synthesizing a talented exclusive series of aza-polyheterocyclic compounds was crucial. Aminopyrimidine nucleus reacted with two equivalents of benzaldehyde in the presence of KOH as a starting material to bring about imidazopyrimidine derivative, which experienced intermolecular cyclization using carbon disulfide, Br2/AcOH, and/or HNO2 to produce thiazole, thieno, and/or nitro pyrimidine derivative, respectively. Accordingly, the nucleus of Aminopyrimidine was prepared and used to develop the novel polyheterocyclic systems acylated with two moles of succinic anhydride to furnish the imidazolopyrimidine derivative. Benzylidene ethyl cyanoacetate and aminopyrimidine undergo (3 + 4) intermolecular cycloaddition 1,3 H shift followed by hydrolysis and after CO2 evolution provided diazepine derivative. The diazepine derivative was attained due to the cyclo-condensation of the starting material and acetylacetone. Moreover, the structure of the novel synthesized compound series was exploited and verified via spectroscopic approaches. The synthesized series were tested for antimicrobial activity against gram-positive and gram-negative bacterial strains and antifungal activity. The thienopyrimidine derivatives and diazepine exhibited unusual antimicrobial activity. Furthermore, the molecular docking studies confirmed the biological studies with Molecular Operating Environment and petro orisis molinspiration studies, which proved the activity of compounds 4, 5, 7, 10, 13, and 16. |
| Author | El-Ahwany Maged F. Abdellattif Magda H. Assy Mohamed G. El-Gendey Marwa S. Touzani Rachid Soliman Mohamed R. Sherif Mohamed H. Titi Abderrahim Shehab Wesam S. |
| Author_xml | – sequence: 1 fullname: El-Ahwany Maged F. organization: Department of Chemistry, Faculty of Science, Zagazig University, Zagazig44523, Egypt – sequence: 2 fullname: Assy Mohamed G. organization: Department of Chemistry, Faculty of Science, Zagazig University, Zagazig44523, Egypt – sequence: 3 fullname: Sherif Mohamed H. organization: Department of Chemistry, Faculty of Science, Zagazig University, Zagazig44523, Egypt – sequence: 4 fullname: Soliman Mohamed R. organization: Department of Chemistry, Faculty of Science, Zagazig University, Zagazig44523, Egypt – sequence: 5 fullname: Titi Abderrahim organization: Laboratory of Applied and Environmental Chemistry (LCAE), Mohamed First University, Oujda, Morocco – sequence: 6 fullname: Touzani Rachid organization: Laboratory of Applied and Environmental Chemistry (LCAE), Mohamed First University, Oujda, Morocco – sequence: 7 fullname: El-Gendey Marwa S. organization: Department of Chemistry, Turabah College, Taif University, Turabah, Saudi Arabia, P. O. Box 11099, Taif21944, Saudi Arabia – sequence: 8 fullname: Shehab Wesam S. organization: Department of Chemistry, Faculty of Science, Zagazig University, Zagazig44523, Egypt – sequence: 9 fullname: Abdellattif Magda H. organization: Department of Chemistry, College of Science, Taif University, PO Box 11099, Taif21944, Saudi Arabia |
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| SubjectTerms | Acetylacetone Antimicrobial agents Benzaldehyde Carbon disulfide Chemical synthesis Condensates Cycloaddition Fungicides imidazopyrimidine Molecular docking pom studies pyrimidodiazepene pyrimidopyrimidine thienopyrimidine |
| Title | Design, synthesis, biological evaluation, and bio-computational modeling of imidazo, thieno, pyrimidopyrimidine, pyrimidodiazepene, and motifs as antimicrobial agents |
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