Microwave-assisted Synthesis and Anticancer Activity of Triazolyl Thiazolidine Derivatives of Pyrene
In a one pot procedure a series of (R)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-3-phenylthiazolidin-4-ones 9a–g and 2-((2R)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-4-oxo-3-phenylthiazolidin-5-yl)ac...
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| Format: | Article |
| Language: | English |
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Slovenian Chemical Society
2019-09-01
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| Series: | Acta Chimica Slovenica |
| Subjects: | |
| Online Access: | https://journals.matheo.si/index.php/ACSi/article/view/5156 |
| _version_ | 1818526102711173120 |
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| author | Sri Nivas Avula Pulluri Karthik Malladi Sunitha Pulluri Karthik Malladi Sunitha Koduri Vasumathi Reddy Koduri Vasumathi Reddy |
| author_facet | Sri Nivas Avula Pulluri Karthik Malladi Sunitha Pulluri Karthik Malladi Sunitha Koduri Vasumathi Reddy Koduri Vasumathi Reddy |
| author_sort | Sri Nivas Avula |
| collection | DOAJ |
| description | In a one pot procedure a series of (R)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-3-phenylthiazolidin-4-ones 9a–g and 2-((2R)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-4-oxo-3-phenylthiazolidin-5-yl)acetic acids 10a–g was prepared by condensation of (2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-carbaldehyde with mercapto acids and primary amines in the presence of ZnCl2 under both microwave irradiation and conventional heating conditions. Characterization of new compounds has been done by means of IR, NMR, MS and elemental analysis. The cytotoxicity was assessed against a panel of four different human tumor cell lines: A549 derived from human alveolar adenocarcinoma epithelial cells (ATCC No. CCL-185), Hela derived from human cervical cancer cells (ATCC No. CCL-2), MDA-MB-231 derived from human breast adenocarcinoma cells (ATCC No. HTB22) and HEK 293 (normal human embryonic kidney cell line) using the MTT assays. Among the tested compounds 9e and 10e showed the most potent activity against MCF-7 breast cancer cell line with IC50 values of 1.91 and 1.95 μΜ, whereas 9b, 10b, 9g and 10g showed promising activity against MDA-MB-231 and Hela cell lines with IC50 values of 5.84, 5.74, 7.89 and 7.65 μΜ, respectively. |
| first_indexed | 2024-12-11T06:18:20Z |
| format | Article |
| id | doaj.art-589c5ec6227247488b2600f9cca6c21e |
| institution | Directory Open Access Journal |
| issn | 1318-0207 1580-3155 |
| language | English |
| last_indexed | 2024-12-11T06:18:20Z |
| publishDate | 2019-09-01 |
| publisher | Slovenian Chemical Society |
| record_format | Article |
| series | Acta Chimica Slovenica |
| spelling | doaj.art-589c5ec6227247488b2600f9cca6c21e2022-12-22T01:17:54ZengSlovenian Chemical SocietyActa Chimica Slovenica1318-02071580-31552019-09-0166370171010.17344/acsi.2019.5156749Microwave-assisted Synthesis and Anticancer Activity of Triazolyl Thiazolidine Derivatives of PyreneSri Nivas Avula0Pulluri KarthikMalladi SunithaPulluri KarthikMalladi SunithaKoduri Vasumathi ReddyKoduri Vasumathi ReddyLec in chemistryIn a one pot procedure a series of (R)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-3-phenylthiazolidin-4-ones 9a–g and 2-((2R)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-4-oxo-3-phenylthiazolidin-5-yl)acetic acids 10a–g was prepared by condensation of (2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-carbaldehyde with mercapto acids and primary amines in the presence of ZnCl2 under both microwave irradiation and conventional heating conditions. Characterization of new compounds has been done by means of IR, NMR, MS and elemental analysis. The cytotoxicity was assessed against a panel of four different human tumor cell lines: A549 derived from human alveolar adenocarcinoma epithelial cells (ATCC No. CCL-185), Hela derived from human cervical cancer cells (ATCC No. CCL-2), MDA-MB-231 derived from human breast adenocarcinoma cells (ATCC No. HTB22) and HEK 293 (normal human embryonic kidney cell line) using the MTT assays. Among the tested compounds 9e and 10e showed the most potent activity against MCF-7 breast cancer cell line with IC50 values of 1.91 and 1.95 μΜ, whereas 9b, 10b, 9g and 10g showed promising activity against MDA-MB-231 and Hela cell lines with IC50 values of 5.84, 5.74, 7.89 and 7.65 μΜ, respectively.https://journals.matheo.si/index.php/ACSi/article/view/5156Glycosidesclick reactioncyclisationThiazolidinonesAnticancer activity |
| spellingShingle | Sri Nivas Avula Pulluri Karthik Malladi Sunitha Pulluri Karthik Malladi Sunitha Koduri Vasumathi Reddy Koduri Vasumathi Reddy Microwave-assisted Synthesis and Anticancer Activity of Triazolyl Thiazolidine Derivatives of Pyrene Acta Chimica Slovenica Glycosides click reaction cyclisation Thiazolidinones Anticancer activity |
| title | Microwave-assisted Synthesis and Anticancer Activity of Triazolyl Thiazolidine Derivatives of Pyrene |
| title_full | Microwave-assisted Synthesis and Anticancer Activity of Triazolyl Thiazolidine Derivatives of Pyrene |
| title_fullStr | Microwave-assisted Synthesis and Anticancer Activity of Triazolyl Thiazolidine Derivatives of Pyrene |
| title_full_unstemmed | Microwave-assisted Synthesis and Anticancer Activity of Triazolyl Thiazolidine Derivatives of Pyrene |
| title_short | Microwave-assisted Synthesis and Anticancer Activity of Triazolyl Thiazolidine Derivatives of Pyrene |
| title_sort | microwave assisted synthesis and anticancer activity of triazolyl thiazolidine derivatives of pyrene |
| topic | Glycosides click reaction cyclisation Thiazolidinones Anticancer activity |
| url | https://journals.matheo.si/index.php/ACSi/article/view/5156 |
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