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Novel Thiazole-Hydrazide Derivatives and Their Anticancer Properties

Yıl 2024, Cilt: 14 Sayı: 3, 783 - 789, 30.09.2024
https://doi.org/10.33808/clinexphealthsci.1414252

Öz

Objective: Cancer is described as uncontrolled cell division, and it is a major problem in Türkiye, as well as around the world. Current treatment options are insufficient in some cases, particularly the treatment rate for lung cancer cases, which is very low. Meanwhile, current pharmaceuticals have several side effects, such as drug-drug interactions, and cognitive disorders. Additionally, developing drug resistance is a major problem for current and future management of the disease. Accordingly, the search for new molecules or alternative treatment options is actively achieved.
Methods: In this study, eight novel thiazole-hydrazide analogs were designed and synthesized, and their structural elucidation was performed via HRMS, 1H-NMR, and 13C-NMR. Their biological activity profile was investigated on A549 lung carcinoma and MCF7 breast adenocarcinoma cells. To determine the selective cytotoxicity on cancer cells, they were also tested against NIH/3T3 healthy cell line. Besides that, an in silico study was performed to understand the binding modes of the compounds.
Results: The results showed that in the serial 4f and 4g, the most bulky analogues, showed no inhibition against any cell type, even at the highest concentration tested. On the other hand, 4a, 4b, 4d, 4e, and 4h showed less cytotoxicity on healthy cells than A549 cells, so they exhibited significant cytotoxicity and a selective profile against A549 cancer cells. While they also inhibited MCF7 cells. The major point is that para-chlorophenyl analogs at the fourth position on thiazole (4a and 4d) displayed a better anticancer profile than ortho-chlorophenyl analogs. These two compounds were also investigated for their apoptotic effects using in silico studies. Both experimental and in silicon studies revealed that the combination of thiazole and hydrazinoacetyl has a significant impact against cancer cells, and in silico study also suggested that tri-substitute thiazole ring has anticancer potential that induced cancer cell death via apoptosis.
Conclusion: Results of this study was presented that compound 4a was the most potent compound against lung cancer cells (A549) and 4d was the most potent compound against breast cancer cells (MCF-7). Furthermore, analyzing the molecular docking study for promising compounds (4a and 4d) suggested that interactions with the loop region residues have a pivotal role in inducing caspase-3 enzyme activity.
It was concluded that hybridization of thiazole and hydrazinoacetyl moieties is responsible for the anticancer activity.

Kaynakça

  • Ozmen V, Dagoglu N, Dede I, Akcakaya A, Kerem M, Goksel F, Ozgur E, Baskan E, Yaylaci M, Ceydeli A, Baykara M, Kiziltan HS, Komurcu S, Gumus M, Turk HM, Demirhan R, Akgun A, Kadoglou N, Yatman E, Elbi CC, Gulec S, Soran A, Ozet A, Kelestimur F. Turkish Ministry of Health, 2(nd) Turkish medical general assembly clinical oncology study group report. J Breast Health. 2016;12(1):9-17. DOl:10.5152/tjbh.2015.2869.
  • Observatory GC. Turkey: Globocan 2020. 2021; Available from: https://gco.iarc.fr/today/data/factsheets/populations/792-turkey-fact-sheets.pdf.
  • Housman G, Byler S, Heerboth S, Lapinska K, Longacre M, Snyder N, Sarkar S. Drug resistance in cancer: an overview. Cancers (Basel) 2014;6(3):1769-1792. DOl:10.3390/cancers6031769.
  • Vasan N, Baselga J, Hyman DM. A view on drug resistance in cancer. Nature 2019;575(7782):299-309. DOl:10.1038/s41586-019-1730-1.
  • Altun I, Sonkaya A. The most common side effects experienced by patients were receiving first cycle of chemotherapy. Iran J Public Health 2018;47(8):1218-1219.
  • Amjad MT, Chidharla A, Kasi A. Cancer Chemotherapy. [Updated 2023 Feb 27]. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; Available from: https://www.ncbi.nlm.nih.gov/books/NBK564367/
  • Gomha SM, Abdelhady HA, Hassain DZ, Abdelmonsef AH, El-Naggar M, Elaasser MM, Mahmoud HK. Thiazole-based thiosemicarbazones: Synthesis, cytotoxicity evaluation and molecular docking study. Drug Des Devel Ther. 2021;15:659-677. DOl:10.2147/DDDT.S291579.
  • Coşkun G, Erdoğan Ö, Çevik O, Şahin Z, Demirayak Ş. Benzimidazole-thiazole hybrids; synthesis, structure elucidation and cytotoxic properties. Acta Medica Nicomedia 2023;6(1):65-70. DOI:10.53446/actamednicomedia.1229450.
  • Cankilic MY, Yurttaş L. Study on the antimicrobial effects of novel thiazole derivatives. Marmara Pharm J. 2017;21(3):654-659. DOI:10.12991/marupj.323584.
  • Hosseininezhad S, Ramazani A. Thiazole ring-the antimicrobial, anti-inflammatory, and anticancer active scaffold. Arabian J Chem. 2023;16(11):105234.
  • Ashmawy FO, Gomha SM, Abdallah MA, Zaki MEA, Al-Hussain SA, El-Desouky MA. Synthesis, in vitro evaluation and molecular docking studies of novel thiophenyl thiazolyl-pyridine hybrids as potential anticancer agents. Molecules 2023;28(11):4270. DOl:10.3390/molecules28114270.
  • Yurttas L, Temel HE, Aksoy MO, Bulbul EF, Ciftci GA. New chromanone derivatives containing thiazoles: Synthesis and antitumor activity evaluation on A549 lung cancer cell line. Drug Dev Res. 2022;83(2):470-484. DOl:10.1002/ddr.21879.
  • Gomha SM, Riyadh SM, Huwaimel B, Zayed MEM, Abdellattif MH. Synthesis, molecular docking study, and cytotoxic activity against MCF cells of new thiazole-thiophene scaffolds. Molecules 2022;27(14):4639. DOl:10.3390/molecules27144639.
  • Sabry MA, Ghaly MA, Maarouf AR, El-Subbagh HI. New thiazole-based derivatives as EGFR/HER2 and DHFR inhibitors: Synthesis, molecular modeling simulations and anticancer activity. Eur J Med Chem. 2022;241:114661. DOl:10.1016/j.ejmech.2022.114661.
  • Sharma PC, Bansal KK, Sharma A, Sharma D, Deep A. Thiazole-containing compounds as therapeutic targets for cancer therapy. Eur J Med Chem. 2020;188:112016. DOl:10.1016/j.ejmech.2019.112016.
  • Wang G, Liu W, Fan M, He M, Li Y, Peng Z. Design, synthesis and biological evaluation of novel thiazole-naphthalene derivatives as potential anticancer agents and tubulin polymerisation inhibitors. J Enzyme Inhib Med Chem. 2021;36(1):1694-1702. DOl:10.1080/14756366.2021.1958213.
  • Petrou A, Fesatidou M, Geronikaki A. Thiazole ring-a biologically active scaffold. Molecules 2021;26(11):3166. DOl:10.3390/molecules26113166.
  • Jadhav PM, Kantevari S, Tekale AB, Bhosale SV, Pawar RP, Tekale SU. A review on biological and medicinal significance of thiazoles. Phosphorus Sulfur Silicon Relat Elem. 2021;196(10):879-895. DOl:10.1080/10426507.2021.1945601.
  • Evren AE, Nuha D, Dawbaa S, Saglik BN, Yurttas L. Synthesis of novel thiazolyl hydrazone derivatives as potent dual monoamine oxidase-aromatase inhibitors. Eur J Med Chem. 2022;229:114097. DOl:10.1016/j.ejmech.2021.114097.
  • Mayhoub AS, Marler L, Kondratyuk TP, Park EJ, Pezzuto JM, Cushman M. Optimization of the aromatase inhibitory activities of pyridylthiazole analogues of resveratrol. Bioorg Med Chem. 2012;20(7):2427-2434. DOl:10.1016/j.bmc.2012.01.047.
  • George RF, Samir EM, Abdelhamed MN, Abdel-Aziz HA, Abbas SE. Synthesis and anti-proliferative activity of some new quinoline based 4,5-dihydropyrazoles and their thiazole hybrids as EGFR inhibitors. Bioorg Chem. 2019;83:186-197. DOl:10.1016/j.bioorg.2018.10.038.
  • Omar AM, Bajorath J, Ihmaid S, Mohamed HM, El-Agrody AM, Mora A, El-Araby ME, Ahmed HEA. Novel molecular discovery of promising amidine-based thiazole analogues as potent dual matrix metalloproteinase-2 and 9 inhibitors: Anticancer activity data with prominent cell cycle arrest and DNA fragmentation analysis effects. Bioorg Chem. 2020;101:103992. DOl:10.1016/j.bioorg.2020.103992.
  • Bimoussa A, Oubella A, El Mansouri Ae, Fawzi M, Laamari Y, Auhmani A, Itto MYA, Morjani H, Auhmani A. Synthesis and biological evaluation of novel thiazole analogs with both anti‐proliferative and mechanistic analyses and molecular docking studies. ChemistrySelect. 2022;7:e202104270. DOl:10.1002/slct.202104270.
  • Birukova V, Scherbakov A, Ilina A, Salnikova D, Andreeva O, Dzichenka Y, Zavarzin I, Volkova Y. Discovery of highly potent proapoptotic antiestrogens in a series of androst-5,16-dienes D-modified with imidazole-annulated pendants. J Steroid Biochem Mol Biol. 2023;231:106309. DOl:10.1016/j.jsbmb.2023.106309.
  • Sahil, Kaur K, Jaitak V. Thiazole and related heterocyclic systems as anticancer agents: A review on synthetic strategies, mechanisms of action and sar studies. Curr Med Chem. 2022;29(29):4958-5009. DOl:10.2174/0929867329666220318100019.
  • Evren AE, Karaduman AB, Saglik BN, Ozkay Y, Yurttas L. Investigation of novel quinoline-thiazole derivatives as antimicrobial agents: In vitro and in silico approaches. ACS Omega 2023;8(1):1410-1429. DOl:10.1021/acsomega.2c06871.
  • Al-Wahaibi LH, El-Sheref EM, Hassan AA, Brase S, Nieger M, Youssif BGM, Ibrahim MAA, Tawfeek HN. Synthesis and structure determination of substituted thiazole derivatives as EGFR/BRAF(V600E) dual inhibitors endowed with antiproliferative activity. Pharmaceuticals (Basel) 2023;16(7):1014. DOl:10.3390/ph16071014.
  • Ramos-Inza S, Aydillo C, Sanmartín C, Plano D. In book: Heterocycles - Synthesis and Biological Activities. Chapter: Thiazole moiety: An interesting scaffold for developing new antitumoral compounds. 2019; 2-21. DOl:10.5772/intechopen.82741.
  • Jain S, Pattnaik S, Pathak K, Kumar S, Pathak D, Jain S, Vaidya A. Anticancer potential of thiazole derivatives: A retrospective review. Mini Rev Med Chem. 2018;18(8):640-655. DOl:10.2174/1389557517666171123211321.
  • Zhu Y, Wang H, Guo Y, Cao J, Li H. Advances in the therapeutic potential of inhibitors targeting glycogen synthase kinase 3 in inflammatory diseases. Mini Rev Med Chem. 2023;23(19):1893-1904. DOl:10.2174/1389557523666230412083123.
  • Xie Y, Chen C, Lin S, Yu X, Ye S, Chen X, Ouyang N, Xiong W, Li C, Xu C, Song G, Wu H. Design, synthesis and anti-AD effects of dual inhibitor targeting glutaminyl cyclase/GSK-3beta. Eur J Med Chem. 2023;248:115089. DOl:10.1016/j.ejmech.2023.115089.
  • Fields GB. The rebirth of matrix metalloproteinase inhibitors: Moving beyond the dogma. Cells 2019;8(9):984. DOl:10.3390/cells8090984.
  • Laronha H, Carpinteiro I, Portugal J, Azul A, Polido M, Petrova KT, Salema-Oom M, Caldeira J. Challenges in matrix metalloproteinases inhibition. Biomolecules 2020;10(5):717. DOl:10.3390/biom10050717.
  • Fingleton B. MMPs as therapeutic targets--still a viable option? Semin Cell Dev Biol. 2008;19(1):61-68. DOl:10.1016/j.semcdb.2007.06.006.
  • Evren AE, Yurttas L, Ekselli B, Akalin-Ciftci G. Synthesis and biological evaluation of 5-methyl-4-phenyl thiazole derivatives as anticancer agents. Phosphorus Sulfur Silicon Relat Elem. 2019;194(8):820-828. DOl:10.1080/10426507.2018.1550642.
  • Zhang Z-H, Wu H-M, Deng S-N, Chai R-X, Mwenda MC, Peng Y-Y, Cai D, Chen Y. Synthesis and biological evaluation of 2,4-disubstituted thiazole amide derivatives as anticancer agent. Chemical Papers 2018;73(2):355-364. DOl:10.1007/s11696-018-0587-3.
  • Krishnan KG, Ashothai P, Padmavathy K, Lim W-M, Mai C-W, Thanikachalam PV, Ramalingan C. Hydrazide-integrated carbazoles: Synthesis, computational, anticancer and molecular docking studies. New J Chem. 2019;43(30):12069-12077. DOl:10.1039/c9nj01912j.
  • Han MI, Bekci H, Uba AI, Yildirim Y, Karasulu E, Cumaoglu A, Karasulu HY, Yelekci K, Yilmaz O, Kucukguzel SG. Synthesis, molecular modeling, in vivo study, and anticancer activity of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen. Arch Pharm. 2019;352(6):e1800365. DOl:10.1002/ardp.201800365.
  • Evren AE, Nuha D, Dawbaa S, Karaduman AB, Saglik BN, Yurttas L. Novel oxadiazole-thiadiazole derivatives: Synthesis, biological evaluation, and in silico studies. J Biomol Struct Dyn. 2023:1-13. DOl:10.1080/07391102.2023.2247087.
  • Daina A, Michielin O, Zoete V. Swiss ADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. (2017);7(1):42717. DOl:10.1038/srep42717.
  • Daina A, Michielin O, Zoete V. iLOGP: a simple, robust, and efficient description of n-octanol/water partition coefficient for drug design using the GB/SA approach. J Chem Inf Model. 2014;54(12):3284-3301. DOl:10.1021/ci500467k.
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  • Council NR. Prudent practices in the laboratory: handling and management of chemical hazards, updated version (2011).
  • Yurttas L, Evren AE, AlChaib H, Temel HE, Akalin Ciftci G. Synthesis, molecular docking, and molecular dynamic simulation studies of new 1,3,4-thiadiazole derivatives as potential apoptosis inducers in A549 lung cancer cell line. J Biomol Struct Dyn. 2024:1-16. DOl:10.1080/07391102.2023.2300125.
  • Elsayed RW, Bayoumi SM, El-Subbagh HI, El-Sayed SM. Hydrazinecarbonyl-thiazol-2-acetamides with pronounced apoptotic behavior: synthesis, in vitro/in vivo anti-proliferative activity and molecular modeling simulations. Bioorg Med Chem Lett. 2023;87:129285. DOl:10.1016/j.bmcl.2023.129285.
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Yıl 2024, Cilt: 14 Sayı: 3, 783 - 789, 30.09.2024
https://doi.org/10.33808/clinexphealthsci.1414252

Öz

Kaynakça

  • Ozmen V, Dagoglu N, Dede I, Akcakaya A, Kerem M, Goksel F, Ozgur E, Baskan E, Yaylaci M, Ceydeli A, Baykara M, Kiziltan HS, Komurcu S, Gumus M, Turk HM, Demirhan R, Akgun A, Kadoglou N, Yatman E, Elbi CC, Gulec S, Soran A, Ozet A, Kelestimur F. Turkish Ministry of Health, 2(nd) Turkish medical general assembly clinical oncology study group report. J Breast Health. 2016;12(1):9-17. DOl:10.5152/tjbh.2015.2869.
  • Observatory GC. Turkey: Globocan 2020. 2021; Available from: https://gco.iarc.fr/today/data/factsheets/populations/792-turkey-fact-sheets.pdf.
  • Housman G, Byler S, Heerboth S, Lapinska K, Longacre M, Snyder N, Sarkar S. Drug resistance in cancer: an overview. Cancers (Basel) 2014;6(3):1769-1792. DOl:10.3390/cancers6031769.
  • Vasan N, Baselga J, Hyman DM. A view on drug resistance in cancer. Nature 2019;575(7782):299-309. DOl:10.1038/s41586-019-1730-1.
  • Altun I, Sonkaya A. The most common side effects experienced by patients were receiving first cycle of chemotherapy. Iran J Public Health 2018;47(8):1218-1219.
  • Amjad MT, Chidharla A, Kasi A. Cancer Chemotherapy. [Updated 2023 Feb 27]. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; Available from: https://www.ncbi.nlm.nih.gov/books/NBK564367/
  • Gomha SM, Abdelhady HA, Hassain DZ, Abdelmonsef AH, El-Naggar M, Elaasser MM, Mahmoud HK. Thiazole-based thiosemicarbazones: Synthesis, cytotoxicity evaluation and molecular docking study. Drug Des Devel Ther. 2021;15:659-677. DOl:10.2147/DDDT.S291579.
  • Coşkun G, Erdoğan Ö, Çevik O, Şahin Z, Demirayak Ş. Benzimidazole-thiazole hybrids; synthesis, structure elucidation and cytotoxic properties. Acta Medica Nicomedia 2023;6(1):65-70. DOI:10.53446/actamednicomedia.1229450.
  • Cankilic MY, Yurttaş L. Study on the antimicrobial effects of novel thiazole derivatives. Marmara Pharm J. 2017;21(3):654-659. DOI:10.12991/marupj.323584.
  • Hosseininezhad S, Ramazani A. Thiazole ring-the antimicrobial, anti-inflammatory, and anticancer active scaffold. Arabian J Chem. 2023;16(11):105234.
  • Ashmawy FO, Gomha SM, Abdallah MA, Zaki MEA, Al-Hussain SA, El-Desouky MA. Synthesis, in vitro evaluation and molecular docking studies of novel thiophenyl thiazolyl-pyridine hybrids as potential anticancer agents. Molecules 2023;28(11):4270. DOl:10.3390/molecules28114270.
  • Yurttas L, Temel HE, Aksoy MO, Bulbul EF, Ciftci GA. New chromanone derivatives containing thiazoles: Synthesis and antitumor activity evaluation on A549 lung cancer cell line. Drug Dev Res. 2022;83(2):470-484. DOl:10.1002/ddr.21879.
  • Gomha SM, Riyadh SM, Huwaimel B, Zayed MEM, Abdellattif MH. Synthesis, molecular docking study, and cytotoxic activity against MCF cells of new thiazole-thiophene scaffolds. Molecules 2022;27(14):4639. DOl:10.3390/molecules27144639.
  • Sabry MA, Ghaly MA, Maarouf AR, El-Subbagh HI. New thiazole-based derivatives as EGFR/HER2 and DHFR inhibitors: Synthesis, molecular modeling simulations and anticancer activity. Eur J Med Chem. 2022;241:114661. DOl:10.1016/j.ejmech.2022.114661.
  • Sharma PC, Bansal KK, Sharma A, Sharma D, Deep A. Thiazole-containing compounds as therapeutic targets for cancer therapy. Eur J Med Chem. 2020;188:112016. DOl:10.1016/j.ejmech.2019.112016.
  • Wang G, Liu W, Fan M, He M, Li Y, Peng Z. Design, synthesis and biological evaluation of novel thiazole-naphthalene derivatives as potential anticancer agents and tubulin polymerisation inhibitors. J Enzyme Inhib Med Chem. 2021;36(1):1694-1702. DOl:10.1080/14756366.2021.1958213.
  • Petrou A, Fesatidou M, Geronikaki A. Thiazole ring-a biologically active scaffold. Molecules 2021;26(11):3166. DOl:10.3390/molecules26113166.
  • Jadhav PM, Kantevari S, Tekale AB, Bhosale SV, Pawar RP, Tekale SU. A review on biological and medicinal significance of thiazoles. Phosphorus Sulfur Silicon Relat Elem. 2021;196(10):879-895. DOl:10.1080/10426507.2021.1945601.
  • Evren AE, Nuha D, Dawbaa S, Saglik BN, Yurttas L. Synthesis of novel thiazolyl hydrazone derivatives as potent dual monoamine oxidase-aromatase inhibitors. Eur J Med Chem. 2022;229:114097. DOl:10.1016/j.ejmech.2021.114097.
  • Mayhoub AS, Marler L, Kondratyuk TP, Park EJ, Pezzuto JM, Cushman M. Optimization of the aromatase inhibitory activities of pyridylthiazole analogues of resveratrol. Bioorg Med Chem. 2012;20(7):2427-2434. DOl:10.1016/j.bmc.2012.01.047.
  • George RF, Samir EM, Abdelhamed MN, Abdel-Aziz HA, Abbas SE. Synthesis and anti-proliferative activity of some new quinoline based 4,5-dihydropyrazoles and their thiazole hybrids as EGFR inhibitors. Bioorg Chem. 2019;83:186-197. DOl:10.1016/j.bioorg.2018.10.038.
  • Omar AM, Bajorath J, Ihmaid S, Mohamed HM, El-Agrody AM, Mora A, El-Araby ME, Ahmed HEA. Novel molecular discovery of promising amidine-based thiazole analogues as potent dual matrix metalloproteinase-2 and 9 inhibitors: Anticancer activity data with prominent cell cycle arrest and DNA fragmentation analysis effects. Bioorg Chem. 2020;101:103992. DOl:10.1016/j.bioorg.2020.103992.
  • Bimoussa A, Oubella A, El Mansouri Ae, Fawzi M, Laamari Y, Auhmani A, Itto MYA, Morjani H, Auhmani A. Synthesis and biological evaluation of novel thiazole analogs with both anti‐proliferative and mechanistic analyses and molecular docking studies. ChemistrySelect. 2022;7:e202104270. DOl:10.1002/slct.202104270.
  • Birukova V, Scherbakov A, Ilina A, Salnikova D, Andreeva O, Dzichenka Y, Zavarzin I, Volkova Y. Discovery of highly potent proapoptotic antiestrogens in a series of androst-5,16-dienes D-modified with imidazole-annulated pendants. J Steroid Biochem Mol Biol. 2023;231:106309. DOl:10.1016/j.jsbmb.2023.106309.
  • Sahil, Kaur K, Jaitak V. Thiazole and related heterocyclic systems as anticancer agents: A review on synthetic strategies, mechanisms of action and sar studies. Curr Med Chem. 2022;29(29):4958-5009. DOl:10.2174/0929867329666220318100019.
  • Evren AE, Karaduman AB, Saglik BN, Ozkay Y, Yurttas L. Investigation of novel quinoline-thiazole derivatives as antimicrobial agents: In vitro and in silico approaches. ACS Omega 2023;8(1):1410-1429. DOl:10.1021/acsomega.2c06871.
  • Al-Wahaibi LH, El-Sheref EM, Hassan AA, Brase S, Nieger M, Youssif BGM, Ibrahim MAA, Tawfeek HN. Synthesis and structure determination of substituted thiazole derivatives as EGFR/BRAF(V600E) dual inhibitors endowed with antiproliferative activity. Pharmaceuticals (Basel) 2023;16(7):1014. DOl:10.3390/ph16071014.
  • Ramos-Inza S, Aydillo C, Sanmartín C, Plano D. In book: Heterocycles - Synthesis and Biological Activities. Chapter: Thiazole moiety: An interesting scaffold for developing new antitumoral compounds. 2019; 2-21. DOl:10.5772/intechopen.82741.
  • Jain S, Pattnaik S, Pathak K, Kumar S, Pathak D, Jain S, Vaidya A. Anticancer potential of thiazole derivatives: A retrospective review. Mini Rev Med Chem. 2018;18(8):640-655. DOl:10.2174/1389557517666171123211321.
  • Zhu Y, Wang H, Guo Y, Cao J, Li H. Advances in the therapeutic potential of inhibitors targeting glycogen synthase kinase 3 in inflammatory diseases. Mini Rev Med Chem. 2023;23(19):1893-1904. DOl:10.2174/1389557523666230412083123.
  • Xie Y, Chen C, Lin S, Yu X, Ye S, Chen X, Ouyang N, Xiong W, Li C, Xu C, Song G, Wu H. Design, synthesis and anti-AD effects of dual inhibitor targeting glutaminyl cyclase/GSK-3beta. Eur J Med Chem. 2023;248:115089. DOl:10.1016/j.ejmech.2023.115089.
  • Fields GB. The rebirth of matrix metalloproteinase inhibitors: Moving beyond the dogma. Cells 2019;8(9):984. DOl:10.3390/cells8090984.
  • Laronha H, Carpinteiro I, Portugal J, Azul A, Polido M, Petrova KT, Salema-Oom M, Caldeira J. Challenges in matrix metalloproteinases inhibition. Biomolecules 2020;10(5):717. DOl:10.3390/biom10050717.
  • Fingleton B. MMPs as therapeutic targets--still a viable option? Semin Cell Dev Biol. 2008;19(1):61-68. DOl:10.1016/j.semcdb.2007.06.006.
  • Evren AE, Yurttas L, Ekselli B, Akalin-Ciftci G. Synthesis and biological evaluation of 5-methyl-4-phenyl thiazole derivatives as anticancer agents. Phosphorus Sulfur Silicon Relat Elem. 2019;194(8):820-828. DOl:10.1080/10426507.2018.1550642.
  • Zhang Z-H, Wu H-M, Deng S-N, Chai R-X, Mwenda MC, Peng Y-Y, Cai D, Chen Y. Synthesis and biological evaluation of 2,4-disubstituted thiazole amide derivatives as anticancer agent. Chemical Papers 2018;73(2):355-364. DOl:10.1007/s11696-018-0587-3.
  • Krishnan KG, Ashothai P, Padmavathy K, Lim W-M, Mai C-W, Thanikachalam PV, Ramalingan C. Hydrazide-integrated carbazoles: Synthesis, computational, anticancer and molecular docking studies. New J Chem. 2019;43(30):12069-12077. DOl:10.1039/c9nj01912j.
  • Han MI, Bekci H, Uba AI, Yildirim Y, Karasulu E, Cumaoglu A, Karasulu HY, Yelekci K, Yilmaz O, Kucukguzel SG. Synthesis, molecular modeling, in vivo study, and anticancer activity of 1,2,4-triazole containing hydrazide-hydrazones derived from (S)-naproxen. Arch Pharm. 2019;352(6):e1800365. DOl:10.1002/ardp.201800365.
  • Evren AE, Nuha D, Dawbaa S, Karaduman AB, Saglik BN, Yurttas L. Novel oxadiazole-thiadiazole derivatives: Synthesis, biological evaluation, and in silico studies. J Biomol Struct Dyn. 2023:1-13. DOl:10.1080/07391102.2023.2247087.
  • Daina A, Michielin O, Zoete V. Swiss ADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci Rep. (2017);7(1):42717. DOl:10.1038/srep42717.
  • Daina A, Michielin O, Zoete V. iLOGP: a simple, robust, and efficient description of n-octanol/water partition coefficient for drug design using the GB/SA approach. J Chem Inf Model. 2014;54(12):3284-3301. DOl:10.1021/ci500467k.
  • Schrödinger Release 2020-3, Maestro. Schrödinger, LLC, New York, NY, USA; 2020.
  • Kaya AZ, Osmaniye D, Evren AE, Yurttaş L, Demirayak Ş. Synthesis, cytotoxic activity evaluation and molecular docking studies of some benzimidazole derivatives. Cumhuriyet Sci J. 2024;45(1):80-87. DOl:10.17776/csj.1392037.
  • Council NR. Prudent practices in the laboratory: handling and management of chemical hazards, updated version (2011).
  • Yurttas L, Evren AE, AlChaib H, Temel HE, Akalin Ciftci G. Synthesis, molecular docking, and molecular dynamic simulation studies of new 1,3,4-thiadiazole derivatives as potential apoptosis inducers in A549 lung cancer cell line. J Biomol Struct Dyn. 2024:1-16. DOl:10.1080/07391102.2023.2300125.
  • Elsayed RW, Bayoumi SM, El-Subbagh HI, El-Sayed SM. Hydrazinecarbonyl-thiazol-2-acetamides with pronounced apoptotic behavior: synthesis, in vitro/in vivo anti-proliferative activity and molecular modeling simulations. Bioorg Med Chem Lett. 2023;87:129285. DOl:10.1016/j.bmcl.2023.129285.
  • Lipinski CA. Lead- and drug-like compounds: the rule-of-five revolution. Drug Discov Today Technol. 2004;1(4):337-341. DOl:10.1016/j.ddtec.2004.11.007.
Toplam 47 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Farmasotik Kimya, Farmasotik Toksikoloji, Temel Farmakoloji
Bölüm Articles
Yazarlar

Asaf Evrim Evren 0000-0002-8651-826X

Demokrat Nuha 0000-0002-7271-6791

Sam Dawbaa 0000-0001-7001-0739

Abdullah Burak Karaduman 0000-0002-0434-1334

Leyla Yurttaş 0000-0002-0957-6044

Erken Görünüm Tarihi 27 Eylül 2024
Yayımlanma Tarihi 30 Eylül 2024
Gönderilme Tarihi 5 Ocak 2024
Kabul Tarihi 24 Temmuz 2024
Yayımlandığı Sayı Yıl 2024 Cilt: 14 Sayı: 3

Kaynak Göster

APA Evren, A. E., Nuha, D., Dawbaa, S., Karaduman, A. B., vd. (2024). Novel Thiazole-Hydrazide Derivatives and Their Anticancer Properties. Clinical and Experimental Health Sciences, 14(3), 783-789. https://doi.org/10.33808/clinexphealthsci.1414252
AMA Evren AE, Nuha D, Dawbaa S, Karaduman AB, Yurttaş L. Novel Thiazole-Hydrazide Derivatives and Their Anticancer Properties. Clinical and Experimental Health Sciences. Eylül 2024;14(3):783-789. doi:10.33808/clinexphealthsci.1414252
Chicago Evren, Asaf Evrim, Demokrat Nuha, Sam Dawbaa, Abdullah Burak Karaduman, ve Leyla Yurttaş. “Novel Thiazole-Hydrazide Derivatives and Their Anticancer Properties”. Clinical and Experimental Health Sciences 14, sy. 3 (Eylül 2024): 783-89. https://doi.org/10.33808/clinexphealthsci.1414252.
EndNote Evren AE, Nuha D, Dawbaa S, Karaduman AB, Yurttaş L (01 Eylül 2024) Novel Thiazole-Hydrazide Derivatives and Their Anticancer Properties. Clinical and Experimental Health Sciences 14 3 783–789.
IEEE A. E. Evren, D. Nuha, S. Dawbaa, A. B. Karaduman, ve L. Yurttaş, “Novel Thiazole-Hydrazide Derivatives and Their Anticancer Properties”, Clinical and Experimental Health Sciences, c. 14, sy. 3, ss. 783–789, 2024, doi: 10.33808/clinexphealthsci.1414252.
ISNAD Evren, Asaf Evrim vd. “Novel Thiazole-Hydrazide Derivatives and Their Anticancer Properties”. Clinical and Experimental Health Sciences 14/3 (Eylül 2024), 783-789. https://doi.org/10.33808/clinexphealthsci.1414252.
JAMA Evren AE, Nuha D, Dawbaa S, Karaduman AB, Yurttaş L. Novel Thiazole-Hydrazide Derivatives and Their Anticancer Properties. Clinical and Experimental Health Sciences. 2024;14:783–789.
MLA Evren, Asaf Evrim vd. “Novel Thiazole-Hydrazide Derivatives and Their Anticancer Properties”. Clinical and Experimental Health Sciences, c. 14, sy. 3, 2024, ss. 783-9, doi:10.33808/clinexphealthsci.1414252.
Vancouver Evren AE, Nuha D, Dawbaa S, Karaduman AB, Yurttaş L. Novel Thiazole-Hydrazide Derivatives and Their Anticancer Properties. Clinical and Experimental Health Sciences. 2024;14(3):783-9.

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