Synthesis and structure elucidation of 1-(2,5/3,5-difluorophenyl)-3-(2,3/2,4/2,5/3,4-dimethoxyphenyl)-2-propen-1-ones as anticancer agents
| العنوان: | Synthesis and structure elucidation of 1-(2,5/3,5-difluorophenyl)-3-(2,3/2,4/2,5/3,4-dimethoxyphenyl)-2-propen-1-ones as anticancer agents |
|---|---|
| المؤلفون: | Halise Inci Gul, Noriyuki Okudaira, Hiroshi Sakagami, Dilan Ozmen Ozgun, Cem Yamali, Cavit Kazaz |
| المساهمون: | Belirlenecek, Sakagami, Hiroshi -- 0000-0001-8001-2121, Yamali, Cem -- 0000-0002-4833-7900 |
| المصدر: | Medicinal Chemistry Research. 26:2015-2023 |
| بيانات النشر: | Springer Science and Business Media LLC, 2017. |
| سنة النشر: | 2017 |
| مصطلحات موضوعية: | Chalcone, 010405 organic chemistry, Stereochemistry, Cytotoxicity, Methoxy, Chemical structure, Organic Chemistry, Fluorine, Fluorine-19 NMR, DEPT, Carbon-13 NMR, 01 natural sciences, PARP, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, chemistry.chemical_compound, Anticancer, chemistry, Mechanism of action, Cell culture, medicine, General Pharmacology, Toxicology and Pharmaceutics, medicine.symptom |
| الوصف: | The compounds titled 1-(2,5/3,5-difluorophenyl)-3-(2,3/2,4/2,5/3,4-dimethoxyphenyl)-2-propen-1-ones (1-8) were synthesized via Claisen-Schmidt condensation under basic condition. The chemical structure of the compounds were identified using several spectroscopic techniques such as H-1 nuclear magnetic resonance (NMR), C-13 NMR, F-19 NMR, DEPT 90, DEPT 135, COSY, HMBC, and HMQC. Cytotoxic activities of the compounds were investigated towards several human tumour cell lines [gingival carcinoma (Ca9-22), oral squamous cell carcinoma derived from tongue (HSC-2)] and human normal oral cells [gingival fibroblasts (HGF), periodontal ligament fibroblasts (HPLF)]. Most of these compounds presented higher cytotoxicity than reference drug 5-fluorouracil while the compounds 7, [1-(3,5-difluorophenyl)-3-(2,5-dimethoxyphenyl)-2-propen-1-one)], and 2, [1-(2,5-difluorophenyl)-3-(2,4-dimethoxyphenyl)-2-propen-1-one], were presenting the best activity according to potency selectivity expression values. Type of cell death induced by compound 7 in both HSC-2 and Ca9-22 cells was investigated to understand mechanism of action of the compounds. The compound 7 produced cleaved products of PARP and caspase-3 were produced, suggesting the induction of apoptosis as a possible mechanism of action of the compounds characterized via activation of caspase-3 in both human oral squamous cell carcinomas. Ataturk University Research Found, Turkey [2015/078] This research work was supported by Ataturk University Research Found, Turkey (Project No: 2015/078). Gul HI thanks to Dr. Yusuf Ozkay (Faculty of Pharmacy, Anadolu University, Eskisehir, Turkey) and MSc. Serkan Levent (Faculty of Pharmacy, Anadolu University, Eskisehir, Turkey) for HRMS analyses. |
| تدمد: | 1554-8120 1054-2523 |
| DOI: | 10.1007/s00044-017-1911-0 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6be70a9d9ddcaf8fceec3f735a0abe92 https://doi.org/10.1007/s00044-017-1911-0 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi.dedup.....6be70a9d9ddcaf8fceec3f735a0abe92 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15548120 10542523 |
|---|---|
| DOI: | 10.1007/s00044-017-1911-0 |