Synthesis, modeling, and biological studies of new thiazole-pyrazole analogues as anticancer agents
A series of various substituted thiazole-pyrazole hybrids 5, 7, 8, and 9 were synthesized, and their chemical structures were confirmed by spectral data (infrared, 1H & 13C NMR and Mass). The frontier molecular orbital structural and energetic properties of the targeting thiazole-pyrazole hy...
Saved in:
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Springer
2023-07-01
|
| Series: | Journal of Saudi Chemical Society |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S131961032300073X |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849305949844537344 |
|---|---|
| author | Gadeer R.S. Ashour Ahmad Fawzi Qarah Abdulmajeed F. Alrefaei Adel I. Alalawy Amerah Alsoliemy Alaa M. Alqahtani Wael M. Alamoudi Nashwa M. El-Metwaly |
| author_facet | Gadeer R.S. Ashour Ahmad Fawzi Qarah Abdulmajeed F. Alrefaei Adel I. Alalawy Amerah Alsoliemy Alaa M. Alqahtani Wael M. Alamoudi Nashwa M. El-Metwaly |
| author_sort | Gadeer R.S. Ashour |
| collection | DOAJ |
| description | A series of various substituted thiazole-pyrazole hybrids 5, 7, 8, and 9 were synthesized, and their chemical structures were confirmed by spectral data (infrared, 1H & 13C NMR and Mass). The frontier molecular orbital structural and energetic properties of the targeting thiazole-pyrazole hybrids were explored using the DFT/B3LYP methodology. The data indicated that they had a low energy gap (ΔEH-L), 1.51–2.42 eV, and may be sorted as 6 < 9 < 7 < 8 < 4 < 3 < 5. The synthesized thiazole-pyrazole hybrids were explored for their activities towards HepG2, MCF-7, and HCT-116 in contrast to doxorubicin. The newly synthesized thiazole-pyrazole analogues demonstrated an acceptable efficiency towards the HepG2 cancer cell line in accordance with this order: 8 > 9 > 7 > 6. Meanwhile, most of the synthesized analogues displayed a significant reduction for the activity of the CAIX inhibitor, with IC50 = 0.071 ± 0.015 to 0.902 ± 0.043 µM. Likewise, they revealed an IC50 = 0.119 ± 0.043 to 0.906 ± 0.04 µM for CAXII inhibitor. Moreover, the newly synthesized thiazole-pyrazole analogues were exposed to the theoretical molecular docking study with PDB:1RHJ as the crystal structure of caspase-3 to examine their antiapoptotic effect as well as their certain properties on the caspase-3 enzyme. |
| format | Article |
| id | doaj-art-2f1a2c2808564e4db6e5d96dfff0be1e |
| institution | Kabale University |
| issn | 1319-6103 |
| language | English |
| publishDate | 2023-07-01 |
| publisher | Springer |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj-art-2f1a2c2808564e4db6e5d96dfff0be1e2025-08-20T03:55:16ZengSpringerJournal of Saudi Chemical Society1319-61032023-07-0127410166910.1016/j.jscs.2023.101669Synthesis, modeling, and biological studies of new thiazole-pyrazole analogues as anticancer agentsGadeer R.S. Ashour0Ahmad Fawzi Qarah1Abdulmajeed F. Alrefaei2Adel I. Alalawy3Amerah Alsoliemy4Alaa M. Alqahtani5Wael M. Alamoudi6Nashwa M. El-Metwaly7Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah 24230, Saudi ArabiaDepartment of Chemistry, College of Science, Taibah University, Madinah, P. O. Box 344, Saudi ArabiaDepartment of Biology/Genetic and Molecular Biology Central Laboratory (GMCL), Jamoum University College, Umm Al-Qura University, Makkah 2203, Saudi ArabiaDepartment of Biochemistry, Faculty of Science, University of Tabuk, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah 24230, Saudi ArabiaDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Umm Al-Qura University, Makkah 21955, Saudi ArabiaDepartment of Biology, Faculty of Applied Science, Umm Al-Qura University, Makkah 24230, Saudi Arabia; Corresponding authors at: Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah 24230, Saudi Arabia (N.M. El-Metwaly).Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah 24230, Saudi Arabia; Department of Chemistry, Faculty of Science, Mansoura University, El-Gomhoria Street, 35516, Egypt; Corresponding authors at: Department of Chemistry, Faculty of Applied Science, Umm Al-Qura University, Makkah 24230, Saudi Arabia (N.M. El-Metwaly).A series of various substituted thiazole-pyrazole hybrids 5, 7, 8, and 9 were synthesized, and their chemical structures were confirmed by spectral data (infrared, 1H & 13C NMR and Mass). The frontier molecular orbital structural and energetic properties of the targeting thiazole-pyrazole hybrids were explored using the DFT/B3LYP methodology. The data indicated that they had a low energy gap (ΔEH-L), 1.51–2.42 eV, and may be sorted as 6 < 9 < 7 < 8 < 4 < 3 < 5. The synthesized thiazole-pyrazole hybrids were explored for their activities towards HepG2, MCF-7, and HCT-116 in contrast to doxorubicin. The newly synthesized thiazole-pyrazole analogues demonstrated an acceptable efficiency towards the HepG2 cancer cell line in accordance with this order: 8 > 9 > 7 > 6. Meanwhile, most of the synthesized analogues displayed a significant reduction for the activity of the CAIX inhibitor, with IC50 = 0.071 ± 0.015 to 0.902 ± 0.043 µM. Likewise, they revealed an IC50 = 0.119 ± 0.043 to 0.906 ± 0.04 µM for CAXII inhibitor. Moreover, the newly synthesized thiazole-pyrazole analogues were exposed to the theoretical molecular docking study with PDB:1RHJ as the crystal structure of caspase-3 to examine their antiapoptotic effect as well as their certain properties on the caspase-3 enzyme.http://www.sciencedirect.com/science/article/pii/S131961032300073XThiosemicarbazone4-chlorophenacyl bromideThiazole-pyrazole hybridsDFT/B3LYPCytotoxicityCarbonic anhydrases |
| spellingShingle | Gadeer R.S. Ashour Ahmad Fawzi Qarah Abdulmajeed F. Alrefaei Adel I. Alalawy Amerah Alsoliemy Alaa M. Alqahtani Wael M. Alamoudi Nashwa M. El-Metwaly Synthesis, modeling, and biological studies of new thiazole-pyrazole analogues as anticancer agents Journal of Saudi Chemical Society Thiosemicarbazone 4-chlorophenacyl bromide Thiazole-pyrazole hybrids DFT/B3LYP Cytotoxicity Carbonic anhydrases |
| title | Synthesis, modeling, and biological studies of new thiazole-pyrazole analogues as anticancer agents |
| title_full | Synthesis, modeling, and biological studies of new thiazole-pyrazole analogues as anticancer agents |
| title_fullStr | Synthesis, modeling, and biological studies of new thiazole-pyrazole analogues as anticancer agents |
| title_full_unstemmed | Synthesis, modeling, and biological studies of new thiazole-pyrazole analogues as anticancer agents |
| title_short | Synthesis, modeling, and biological studies of new thiazole-pyrazole analogues as anticancer agents |
| title_sort | synthesis modeling and biological studies of new thiazole pyrazole analogues as anticancer agents |
| topic | Thiosemicarbazone 4-chlorophenacyl bromide Thiazole-pyrazole hybrids DFT/B3LYP Cytotoxicity Carbonic anhydrases |
| url | http://www.sciencedirect.com/science/article/pii/S131961032300073X |
| work_keys_str_mv | AT gadeerrsashour synthesismodelingandbiologicalstudiesofnewthiazolepyrazoleanaloguesasanticanceragents AT ahmadfawziqarah synthesismodelingandbiologicalstudiesofnewthiazolepyrazoleanaloguesasanticanceragents AT abdulmajeedfalrefaei synthesismodelingandbiologicalstudiesofnewthiazolepyrazoleanaloguesasanticanceragents AT adelialalawy synthesismodelingandbiologicalstudiesofnewthiazolepyrazoleanaloguesasanticanceragents AT amerahalsoliemy synthesismodelingandbiologicalstudiesofnewthiazolepyrazoleanaloguesasanticanceragents AT alaamalqahtani synthesismodelingandbiologicalstudiesofnewthiazolepyrazoleanaloguesasanticanceragents AT waelmalamoudi synthesismodelingandbiologicalstudiesofnewthiazolepyrazoleanaloguesasanticanceragents AT nashwamelmetwaly synthesismodelingandbiologicalstudiesofnewthiazolepyrazoleanaloguesasanticanceragents |