Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity
Substituted-6-methyl-1-thioxo-1,2-dihydro-3<i>H</i>-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-ones (<b>5a</b>,<b>b</b>) were synthesized from condensation of visnagenone (<b>2a</b>) or khellinone (<b>2b</b>) with 6-amino-thiouracil (<b>3...
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| Format: | Article |
| Language: | English |
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MDPI AG
2018-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/23/11/2793 |
| _version_ | 1824033215277432832 |
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| author | Ameen Ali Abu-Hashem |
| author_facet | Ameen Ali Abu-Hashem |
| author_sort | Ameen Ali Abu-Hashem |
| collection | DOAJ |
| description | Substituted-6-methyl-1-thioxo-1,2-dihydro-3<i>H</i>-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-ones (<b>5a</b>,<b>b</b>) were synthesized from condensation of visnagenone (<b>2a</b>) or khellinone (<b>2b</b>) with 6-amino-thiouracil (<b>3</b>) in dimethylformamide or refluxing of (<b>4a</b>) or (<b>4b</b>) in dimethylformamide. Hence, compounds (<b>5a</b>,<b>b</b>) were used as the starting materials for preparing many new heterocyclic compounds such as; furo[3,2-g]pyrimido[1,6-a]quinazoline (<b>6a</b>,<b>b</b>), furo[3,2-g]thiazolo[2′,3′:2,3]pyrimido[1,6-a]quinazolinone (<b>7a</b>,<b>b</b>), substituted-benzylidene-furo[3,2-g]thiazolo[2′,3′:2,3]pyrimido[1,6-a]quinazoline-3,5-dione (<b>8a</b>⁻<b>f</b>), 3-oxo-furo[3,2-g]pyrimido[1,6-a]quinazoline-pentane-2,4-dione (<b>9a</b>,<b>b</b>), 1-(pyrazole)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (<b>10a</b>,<b>b</b>), 2-(oxo or thioxo)-pyrimidine-furo[3,2-g]pyrimido[1,6-a]quinazolinone (<b>11a</b>⁻<b>d</b>), 1-(methylthio)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (<b>12a</b>,<b>b</b>), 1-(methyl-sulfonyl)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (<b>13a</b>,<b>b</b>) and 6-methyl-1-((piperazine) or morpholino)-3<i>H</i>-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-one (<b>14a</b>⁻<b>d</b>). The structures of the prepared compounds were elucidated on the basis of spectral data (IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, MS) and elemental analysis. Antimicrobial activity was evaluated for the synthesized compounds against Gram-positive, Gram-negative bacteria and fungi. The new compounds, furothiazolo pyrimido quinazolines <b>8a</b>⁻<b>f</b> and <b>11a</b>⁻<b>d</b> displayed results excellent for growth inhibition of bacteria and fungi. |
| first_indexed | 2024-12-21T14:24:01Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T14:24:01Z |
| publishDate | 2018-10-01 |
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| series | Molecules |
| spelling | doaj.art-595a00dbc72d4f1f98fc0dba486ca2842022-12-21T19:00:41ZengMDPI AGMolecules1420-30492018-10-012311279310.3390/molecules23112793molecules23112793Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial ActivityAmeen Ali Abu-Hashem0Photochemistry Department (Heterocyclic Unit), National Research Centre, Dokki, Giza1 2622, EgyptSubstituted-6-methyl-1-thioxo-1,2-dihydro-3<i>H</i>-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-ones (<b>5a</b>,<b>b</b>) were synthesized from condensation of visnagenone (<b>2a</b>) or khellinone (<b>2b</b>) with 6-amino-thiouracil (<b>3</b>) in dimethylformamide or refluxing of (<b>4a</b>) or (<b>4b</b>) in dimethylformamide. Hence, compounds (<b>5a</b>,<b>b</b>) were used as the starting materials for preparing many new heterocyclic compounds such as; furo[3,2-g]pyrimido[1,6-a]quinazoline (<b>6a</b>,<b>b</b>), furo[3,2-g]thiazolo[2′,3′:2,3]pyrimido[1,6-a]quinazolinone (<b>7a</b>,<b>b</b>), substituted-benzylidene-furo[3,2-g]thiazolo[2′,3′:2,3]pyrimido[1,6-a]quinazoline-3,5-dione (<b>8a</b>⁻<b>f</b>), 3-oxo-furo[3,2-g]pyrimido[1,6-a]quinazoline-pentane-2,4-dione (<b>9a</b>,<b>b</b>), 1-(pyrazole)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (<b>10a</b>,<b>b</b>), 2-(oxo or thioxo)-pyrimidine-furo[3,2-g]pyrimido[1,6-a]quinazolinone (<b>11a</b>⁻<b>d</b>), 1-(methylthio)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (<b>12a</b>,<b>b</b>), 1-(methyl-sulfonyl)-furo[3,2-g]pyrimido[1,6-a]quinazolinone (<b>13a</b>,<b>b</b>) and 6-methyl-1-((piperazine) or morpholino)-3<i>H</i>-furo[3,2-g]pyrimido[1,6-a]quinazolin-3-one (<b>14a</b>⁻<b>d</b>). The structures of the prepared compounds were elucidated on the basis of spectral data (IR, <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, MS) and elemental analysis. Antimicrobial activity was evaluated for the synthesized compounds against Gram-positive, Gram-negative bacteria and fungi. The new compounds, furothiazolo pyrimido quinazolines <b>8a</b>⁻<b>f</b> and <b>11a</b>⁻<b>d</b> displayed results excellent for growth inhibition of bacteria and fungi.https://www.mdpi.com/1420-3049/23/11/2793visnagenonekhellinonequinazolinonepyrimidinethiazolepyrazolefuraneantimicrobial activity |
| spellingShingle | Ameen Ali Abu-Hashem Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity Molecules visnagenone khellinone quinazolinone pyrimidine thiazole pyrazole furane antimicrobial activity |
| title | Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity |
| title_full | Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity |
| title_fullStr | Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity |
| title_full_unstemmed | Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity |
| title_short | Synthesis of New Furothiazolo Pyrimido Quinazolinones from Visnagenone or Khellinone and Antimicrobial Activity |
| title_sort | synthesis of new furothiazolo pyrimido quinazolinones from visnagenone or khellinone and antimicrobial activity |
| topic | visnagenone khellinone quinazolinone pyrimidine thiazole pyrazole furane antimicrobial activity |
| url | https://www.mdpi.com/1420-3049/23/11/2793 |
| work_keys_str_mv | AT ameenaliabuhashem synthesisofnewfurothiazolopyrimidoquinazolinonesfromvisnagenoneorkhellinoneandantimicrobialactivity |