Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds
Ethyl 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetate (3) which was synthesized starting from anthranilic acid (1) via 2-thioxo-3-phenylquinazolin-4(3H)-one (2) reacted with hydrazine hydrate to afford 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetohydrazide (4). Reaction of (4)...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley
2019-01-01
|
| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2019/1492316 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1850157278787796992 |
|---|---|
| author | Cong T. Nguyen Quang T. Nguyen Phuc H. Dao Thuan L. Nguyen Phuong T. Nguyen Hung H. Nguyen |
| author_facet | Cong T. Nguyen Quang T. Nguyen Phuc H. Dao Thuan L. Nguyen Phuong T. Nguyen Hung H. Nguyen |
| author_sort | Cong T. Nguyen |
| collection | DOAJ |
| description | Ethyl 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetate (3) which was synthesized starting from anthranilic acid (1) via 2-thioxo-3-phenylquinazolin-4(3H)-one (2) reacted with hydrazine hydrate to afford 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetohydrazide (4). Reaction of (4) with thiocarbonyl-bis-thioglycolic acid gave a new compound name N-(4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide (5). Knoevenagel condensation of (5) with appropriate aldehydes gave fourteen (Z)-N-(5-arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide compounds (6a–o) with moderate yield. The chemical structure of the compounds was elucidated on the basis of IR, 1H-NMR, 13C-NMR, and HR-MS spectral data. The 5-arylidene-2-thioxothiazolidinone compounds exhibited mild-to-moderate cytotoxic activity against both K562 (chronic myelogenous leukemia) cells and MCF7 (breast cancer) cells. |
| format | Article |
| id | doaj-art-3a2e4ecbc77e4b26bd9cf07a9f7febfa |
| institution | OA Journals |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2019-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-3a2e4ecbc77e4b26bd9cf07a9f7febfa2025-08-20T02:24:14ZengWileyJournal of Chemistry2090-90632090-90712019-01-01201910.1155/2019/14923161492316Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide CompoundsCong T. Nguyen0Quang T. Nguyen1Phuc H. Dao2Thuan L. Nguyen3Phuong T. Nguyen4Hung H. Nguyen5Department of Chemistry, Ho Chi Minh City University of Education, Ho Chi Minh City 72711, VietnamDepartment of Chemistry, Ho Chi Minh City University of Education, Ho Chi Minh City 72711, VietnamDepartment of Chemistry, Ho Chi Minh City University of Education, Ho Chi Minh City 72711, VietnamDepartment of Chemistry, Ho Chi Minh City University of Education, Ho Chi Minh City 72711, VietnamNguyen Tat Thanh Institute of Hi-Technology, Nguyen Tat Thanh University, Ho Chi Minh City 72820, VietnamFaculty of Biotechnology, Nguyen Tat Thanh University, Ho Chi Minh City 72820, VietnamEthyl 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetate (3) which was synthesized starting from anthranilic acid (1) via 2-thioxo-3-phenylquinazolin-4(3H)-one (2) reacted with hydrazine hydrate to afford 2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetohydrazide (4). Reaction of (4) with thiocarbonyl-bis-thioglycolic acid gave a new compound name N-(4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide (5). Knoevenagel condensation of (5) with appropriate aldehydes gave fourteen (Z)-N-(5-arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)thio)acetamide compounds (6a–o) with moderate yield. The chemical structure of the compounds was elucidated on the basis of IR, 1H-NMR, 13C-NMR, and HR-MS spectral data. The 5-arylidene-2-thioxothiazolidinone compounds exhibited mild-to-moderate cytotoxic activity against both K562 (chronic myelogenous leukemia) cells and MCF7 (breast cancer) cells.http://dx.doi.org/10.1155/2019/1492316 |
| spellingShingle | Cong T. Nguyen Quang T. Nguyen Phuc H. Dao Thuan L. Nguyen Phuong T. Nguyen Hung H. Nguyen Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds Journal of Chemistry |
| title | Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds |
| title_full | Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds |
| title_fullStr | Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds |
| title_full_unstemmed | Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds |
| title_short | Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of Some N-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds |
| title_sort | synthesis and cytotoxic activity against k562 and mcf7 cell lines of some n 5 arylidene 4 oxo 2 thioxothiazolidin 3 yl 2 4 oxo 3 phenyl 3 4 dihydroquinazoline 2 yl thio acetamide compounds |
| url | http://dx.doi.org/10.1155/2019/1492316 |
| work_keys_str_mv | AT congtnguyen synthesisandcytotoxicactivityagainstk562andmcf7celllinesofsomen5arylidene4oxo2thioxothiazolidin3yl24oxo3phenyl34dihydroquinazoline2ylthioacetamidecompounds AT quangtnguyen synthesisandcytotoxicactivityagainstk562andmcf7celllinesofsomen5arylidene4oxo2thioxothiazolidin3yl24oxo3phenyl34dihydroquinazoline2ylthioacetamidecompounds AT phuchdao synthesisandcytotoxicactivityagainstk562andmcf7celllinesofsomen5arylidene4oxo2thioxothiazolidin3yl24oxo3phenyl34dihydroquinazoline2ylthioacetamidecompounds AT thuanlnguyen synthesisandcytotoxicactivityagainstk562andmcf7celllinesofsomen5arylidene4oxo2thioxothiazolidin3yl24oxo3phenyl34dihydroquinazoline2ylthioacetamidecompounds AT phuongtnguyen synthesisandcytotoxicactivityagainstk562andmcf7celllinesofsomen5arylidene4oxo2thioxothiazolidin3yl24oxo3phenyl34dihydroquinazoline2ylthioacetamidecompounds AT hunghnguyen synthesisandcytotoxicactivityagainstk562andmcf7celllinesofsomen5arylidene4oxo2thioxothiazolidin3yl24oxo3phenyl34dihydroquinazoline2ylthioacetamidecompounds |