Synthesis, Nematicidal and Antifungal Properties of Hybrid Heterocyclics
A new series of 5-((3aR,5S,6S,6aR)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-(4-fluorophenyl)-2,6-diphenyl-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d]thiazoles 10a–r was synthesized by the reaction of chalcone derivatives of 2-((3aR,5S,6S,6...
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| Format: | Article |
| Language: | English |
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Slovenian Chemical Society
2017-12-01
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| Series: | Acta Chimica Slovenica |
| Subjects: | |
| Online Access: | https://journals.matheo.si/index.php/ACSi/article/view/3805 |
| _version_ | 1818304640415956992 |
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| author | Avula Srinivas Malladi Sunitha Pulluri Karthik K Vasumathi Reddy |
| author_facet | Avula Srinivas Malladi Sunitha Pulluri Karthik K Vasumathi Reddy |
| author_sort | Avula Srinivas |
| collection | DOAJ |
| description | A new series of 5-((3aR,5S,6S,6aR)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-(4-fluorophenyl)-2,6-diphenyl-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d]thiazoles 10a–r was synthesized by the reaction of chalcone derivatives of 2-((3aR,5S,6S,6aR)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-phenylthiazolidin-4-one 9 with aryl/alkyl hydrazines. The chemical structures of newly synthesized compounds were elucidated by IR, NMR, MS and elemental analysis. The compounds 10a–r were evaluated for their nematicidal activity against Dietylenchus myceliophagus and Caenorhabditis elegans by aqueous in vitro screening technique. Among them, compounds containing N-benzylpyrazole moiety (10d, 10j, 10p), and N- methylpyrazole moiety (10f, 10i, 10r) showed significant nematicidal activity against both tested nematodes with LD50 160–210 ppm, almost equal to oxamyl standard. Further, these compounds 10a–r were screened for their antifungal (MZI, MIC, and MFC) activity against four fungal organisms viz, Candida albicans (ATCC 102331), Aspergillus fumigates (HIC 6094), Trichophyton rubrum (IFO 9185) and Trichophyton mentagrophytes (IFO 40996). Most of the new compounds showed appreciable activity against the tested fungi, and emerged as potential molecules for further development. |
| first_indexed | 2024-12-13T06:13:54Z |
| format | Article |
| id | doaj.art-d5f2f1b90eb4416b9e5e70e08e232a3b |
| institution | Directory Open Access Journal |
| issn | 1318-0207 1580-3155 |
| language | English |
| last_indexed | 2024-12-13T06:13:54Z |
| publishDate | 2017-12-01 |
| publisher | Slovenian Chemical Society |
| record_format | Article |
| series | Acta Chimica Slovenica |
| spelling | doaj.art-d5f2f1b90eb4416b9e5e70e08e232a3b2022-12-21T23:57:01ZengSlovenian Chemical SocietyActa Chimica Slovenica1318-02071580-31552017-12-016441030104110.17344/acsi.2017.3805529Synthesis, Nematicidal and Antifungal Properties of Hybrid HeterocyclicsAvula Srinivas0Malladi SunithaPulluri KarthikK Vasumathi ReddyLec in chemistryA new series of 5-((3aR,5S,6S,6aR)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-(4-fluorophenyl)-2,6-diphenyl-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d]thiazoles 10a–r was synthesized by the reaction of chalcone derivatives of 2-((3aR,5S,6S,6aR)-6-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-phenylthiazolidin-4-one 9 with aryl/alkyl hydrazines. The chemical structures of newly synthesized compounds were elucidated by IR, NMR, MS and elemental analysis. The compounds 10a–r were evaluated for their nematicidal activity against Dietylenchus myceliophagus and Caenorhabditis elegans by aqueous in vitro screening technique. Among them, compounds containing N-benzylpyrazole moiety (10d, 10j, 10p), and N- methylpyrazole moiety (10f, 10i, 10r) showed significant nematicidal activity against both tested nematodes with LD50 160–210 ppm, almost equal to oxamyl standard. Further, these compounds 10a–r were screened for their antifungal (MZI, MIC, and MFC) activity against four fungal organisms viz, Candida albicans (ATCC 102331), Aspergillus fumigates (HIC 6094), Trichophyton rubrum (IFO 9185) and Trichophyton mentagrophytes (IFO 40996). Most of the new compounds showed appreciable activity against the tested fungi, and emerged as potential molecules for further development.https://journals.matheo.si/index.php/ACSi/article/view/3805Hybrid heterocyclicsclick reactionKnovenagel condensationcyclisationnematicidal activityanti fungal activity |
| spellingShingle | Avula Srinivas Malladi Sunitha Pulluri Karthik K Vasumathi Reddy Synthesis, Nematicidal and Antifungal Properties of Hybrid Heterocyclics Acta Chimica Slovenica Hybrid heterocyclics click reaction Knovenagel condensation cyclisation nematicidal activity anti fungal activity |
| title | Synthesis, Nematicidal and Antifungal Properties of Hybrid Heterocyclics |
| title_full | Synthesis, Nematicidal and Antifungal Properties of Hybrid Heterocyclics |
| title_fullStr | Synthesis, Nematicidal and Antifungal Properties of Hybrid Heterocyclics |
| title_full_unstemmed | Synthesis, Nematicidal and Antifungal Properties of Hybrid Heterocyclics |
| title_short | Synthesis, Nematicidal and Antifungal Properties of Hybrid Heterocyclics |
| title_sort | synthesis nematicidal and antifungal properties of hybrid heterocyclics |
| topic | Hybrid heterocyclics click reaction Knovenagel condensation cyclisation nematicidal activity anti fungal activity |
| url | https://journals.matheo.si/index.php/ACSi/article/view/3805 |
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