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Year 2021, Volume: 25 Issue: 3, 305 - 317, 27.06.2025

Özlen Güzel Akdemir , Kübra Demir-yazıcı

https://doi.org/10.29228/jrp.21

Abstract

References

  • [1] Ferlay J, Colombet M, Soerjomataram I, Mathers C, Parkin DM, Piñeros M, Znaor A, Bray F. Estimating the Global Cancer Incidence and Mortality in 2018: GLOBOCAN Sources and Methods. Int J Cancer. 2019; 144(8): 1941–1953. [CrossRef]
  • [2] Goodarzi E, Khazaei Z, Moayed L, Adineh HA, Sohrabivafa M, Darvishi I, Dehghani SL. Epidemiology and Population Attributable Fraction of Melanoma to Ultraviolet Radiatıon in Asia: An Ecological Study. World Cancer Res J. 2018; 5(3): e1114. [3] Bray F, Ferlay J, Soerjomataram I, Siegel RL, Torre LA, Jemal A. Global Cancer Statistics 2018: GLOBOCAN Estimates of Incidence and Mortality Worldwide for 36 Cancers in 185 Countries. CA Cancer J Clin. 2018; 68(6): 394–424. [CrossRef]
  • [4] Miller KD, Siegel RL, Lin CC, Mariotto AB, Kramer JL, Rowland JH, Stein KD, Alteri R, Jemal A. Cancer Treatment and Survivorship Statistics. 2016. CA Cancer J Clin. 2016; 66(4): 271–289. [CrossRef]
  • [5] Roy PS, Saikia BJ. Cancer and Cure: A Critical Analysis. Indian J Cancer. 2016; 53(3): 441–442.
  • [6] Pejović A, Minić A, Bugarinović J, Pešić M, Damljanović I, Stevanović D, Mihailović V, Katanić J, Bogdanović GA. Synthesis, Characterization and Antimicrobial Activity of Novel 3-Ferrocenyl-2-pyrazolyl-1,3-thiazolidin-4-ones. Polyhedron. 2018; 155: 382–389. [CrossRef]
  • [7] Verma A, Saraf SK. 4-Thiazolidinone - A Biologically Active Scaffold. Eur J Med Chem. 2008; 43(5): 897–905. [CrossRef]
  • [8] Kunzler A, Neuenfeldt PD, Das Neves AM, Pereira CMP, Marques GH, Nascente PS, Fernandes MHV, Hübner SO, Cunico W. Synthesis, Antifungal and Cytotoxic Activities of 2-Aryl-3-((piperidin-1-yl)ethyl)thiazolidinones. Eur J Med Chem. 2013; 64: 74–80. [CrossRef]
  • [9] Küçükgüzel ŞG, Oruç EE, Rollas S, Şahin F, Özbek A. Synthesis, Characterisation and Biological Activity of Novel 4-Thiazolidinones, 1,3,4-Oxadiazoles and Some Related Compounds. Eur J Med Chem. 2002; 37(3): 197–206. [CrossRef]
  • [10] D’Ascenzio M, Bizzarri B, De Monte C, Carradori S, Bolasco A, Secci D, Rivanera D, Faulhaber N, Bordón C, Jones-Brando L. Design, Synthesis and Biological Characterization of Thiazolidin-4-one Derivatives as Promising Inhibitors of Toxoplasma gondii. Eur J Med Chem. 2014; 86: 17–30. [CrossRef]
  • [11] Secci D, Carradori S, Bizzarri B, Chimenti P, De Monte C, Mollica A, Rivanera D, Zicari A, Mari E, Zengin G, Aktumsek A. Novel 1,3-Thiazolidin-4-one Derivatives as Promising Anti-Candida Agents Endowed with Anti-oxidant and Chelating Properties. Eur J Med Chem. 2016; 117: 144–156. [CrossRef]
  • [12] Tripathi AC, Gupta SJ, Fatima GN, Sonar PK, Verma A, Saraf SK. 4-Thiazolidinones: The Advances Continue. Eur J Med Chem. 2014; 72: 52–77. [CrossRef]
  • [13] Jain AK, Vaidya A, Ravichandran V, Kashaw SK, Agrawal RK. Recent Developments and Biological Activities of Thiazolidinone Derivatives: A Review. Bioorganic Med Chem. 2012; 20(11): 3378–3395. [CrossRef]
  • [14] Güzel Ö, Salman A. Synthesis and Biological Evaluation of New 4-Thiazolidinone Derivatives. J Enzyme Inhib Med Chem 2009, 24(4): 1015–1023. 24:1015-1023. [CrossRef]
  • [15] Güzel Ö, Ilhan E, Salman A. Synthesis and Antimycobacterial Activity of New 2-Hydroxy-N-(3-oxo-1-thia- 4-azaspiro[4.4]non-4-yl)/(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2, 2-diphenylacetamide Derivatives. Monatsh Chem. 2006; 137(6): 795–801. [CrossRef]
  • [16] Ulusoy Güzeldemirci N, Pehlivan E, Naesens L. Synthesis and Antiviral Activity Evaluation of New 4-Thiazolidinones Bearing an Imidazo[2,1-b]thiazole Moiety. Marmara Pharm J. 2018; 22(2): 237–248. [CrossRef]
  • [17] Kaynak FB, Öztürk D, Özbey S, Çapan G. New N′-Alkylidene/cycloalkylidene Derivatives of 5-Methyl-3-phenyl-1H-indole-2-carbohydrazide: Synthesis, Crystal Structure, and Quantum Mechanical Calculations. J Mol Struct. 2005; 740(1-3): 213–221. [CrossRef]
  • [18] Taylor PJ. The Infra-red Spectroscopy of Some 2-Substituted Thiazolid-4-ones, a New Class of Enamino-ketone-II. Infra-red Assignments and Chemical Implications. Spectrochim Acta Part A Mol Spectrosc. 1970; 26(1): 165–194. [CrossRef]
  • [19] Gupta A, Singh R, Sonar PK, Saraf SK. Novel 4-Thiazolidinone Derivatives as Anti-infective Agents: synthesis, Characterization, and Antimicrobial Evaluation. Biochem Res Int. 2016; 2016: 1–8. [CrossRef]
  • [20] Karali N, Ilhan E, Gürsoy A, Kiraz M. New yclohexylidenehydrazide and 4-Aza-1-thiaspiro[4.5]decan-3-one Derivatives of 3-Phenyl-4 (3H)-quinazolinones. Farmaco. 1998; 53(5): 346–349. [CrossRef]
  • [21] Ulusoy N. Synthesis and Antituberculosis Activity of Cycloalkylidenehydrazide and 4-Aza-1-thiaspiro[4.5]decan-3-one Derivatives of Imidazo[2,1-b]thiazole. Arzneimittel-Forschung/Drug Res. 2002; 52(07): 565–571. [CrossRef]
  • [22] Peters R, Hellenbrand J, Mengerink Y, Van Der Wal S. On-line Determination of Carboxylic Acids, Aldehydes and Ketones by High-Performance Liquid Chromatography-Diode Array Detection-Atmospheric Pressure Chemical Ionisation Mass Spectrometry After Derivatization with 2-Nitrophenylhydrazine. J Chromatogr A. 2004; 1031(1-2): 35–50. [CrossRef]
  • [23] De Lima WT, De Lima JG, Góes AJS. Mass Spectrometry of Some N-Tryptophyl-4-Thiazolidinone and N-Tryptophyl-5-benzylidene-4-thiazolidinone Derivatives. Spectrosc Lett. 2002; 35(1): 137–144. [CrossRef]
  • [24] Alley MC, Scudiero DA, Monks A, Hursey M, Czerwinski MJ, Fine DL, Abbott BJ, Mayo JG, Shoemaker R, Boyd MR. Feasibility of Drug Screening with Panels of Human Tumor Cell Lines Using a Microculture Tetrazolium Assay. Cancer Res. 1988; 48(3): 584–588.
  • [25] Grever MR, Schepartz SA, Chabner BA. The National Cancer Institute: Cancer Drug Discovery and Development Program. Semin Oncol. 1992; 19(6): 622.
  • [26] Boyd MR, Paull KD. Some Practical Considerations and Applications of the National Cancer Institute in vitroAnticancer Drug Discovery Screen. Drug Dev Res. 1995; 34(2): 91–109. [CrossRef]
  • [27] Rollas S, Büyüktimkin S, Büyüktimkin N, Ulgen M, Yemni E. Evaluation of Some Arylhydrazones of N2-Arylidenebenzylic Acid Hydrazide as Antimicrobial Agents. Pharmazie. 1988; 43(7): 511.
  • [28] Abu Safieh K, Al-Titi AM, Zahra J, Ayoub M. Oxidative Cyclization of Arylidene Carboxyhydrazides : Synthesis of Substituted Hydroxydiphenylmenthyl-3,3,4-oxadiazoles. Jordan J Chem. 2007; 2(3): 211–218.
  • [29] Issa YM, Issa RM, Abdel-Latif SA, Abdel-Salam HA. Structural Studies of Cu(II) Chelates with Some Arylidene Derivatives of Benzilic Hydrazide. Monatsh Chem. 1998; 129(1): 19–29. [CrossRef]
  • [30] Issa RM, Abdel-Latif SA, Abdel-Salam HA. Synthesis and Characterization of New Cu(II) Complexes Derived from Benzilic and Mandelic Hydrazones. Synth React Inorg Met Chem. 2001; 31(1): 95–105. [CrossRef]

Benzilic acid based new 2-aryl-1,3-thiazolidin-4-one derivatives: Synthesis and anticancer activity

Year 2021, Volume: 25 Issue: 3, 305 - 317, 27.06.2025

Özlen Güzel Akdemir , Kübra Demir-yazıcı

https://doi.org/10.29228/jrp.21

Abstract

Some new derivatives of 2-aryl-1,3-thiazolidin-4-one derivatives were produced (3a-p and 4a-p) in the search of potentially active new molecules with antitumor features. Compounds were obtained by cyclocondensation of 2-hydroxy-2,2-diphenyl-N-[(substituted phenyl)methylene]acetohydrazides (2) and mercaptoacetic acid or 2- mercaptopropionic acid. Identification and characterization of 32 new 2-aryl substituted thiazolidin-4-ones were performed with spectral and elemental analyzes. Compound 3c, 3g, 3j, 4g, 4n, and 4p were chosen as prototypes and assayed for their anticancer activity against diverse several cancer cell lines with in vitro primary anticancer test in the National Cancer Institute. Compound 4g exhibited significant anticancer activity with the inhibition value 84.19% against a leukemia cell line MOLT-4 while compound 4p had a remarkable inhibition ratio (72.11%) against the growth of a CNS (central nervous system) cancer cell line SF-295 in the primary screen. These preliminary and important results indicated that the compounds carried 2-aryl-1,3-thiazolidin-4-one scaffold can be evaluated as potentially promising anticancer agents.

Keywords

1-3-Thiazolidin-4-one benzilic acid mercaptoacetic acid 2-mercaptopropionic acid anticancer agents.

References

  • [1] Ferlay J, Colombet M, Soerjomataram I, Mathers C, Parkin DM, Piñeros M, Znaor A, Bray F. Estimating the Global Cancer Incidence and Mortality in 2018: GLOBOCAN Sources and Methods. Int J Cancer. 2019; 144(8): 1941–1953. [CrossRef]
  • [2] Goodarzi E, Khazaei Z, Moayed L, Adineh HA, Sohrabivafa M, Darvishi I, Dehghani SL. Epidemiology and Population Attributable Fraction of Melanoma to Ultraviolet Radiatıon in Asia: An Ecological Study. World Cancer Res J. 2018; 5(3): e1114. [3] Bray F, Ferlay J, Soerjomataram I, Siegel RL, Torre LA, Jemal A. Global Cancer Statistics 2018: GLOBOCAN Estimates of Incidence and Mortality Worldwide for 36 Cancers in 185 Countries. CA Cancer J Clin. 2018; 68(6): 394–424. [CrossRef]
  • [4] Miller KD, Siegel RL, Lin CC, Mariotto AB, Kramer JL, Rowland JH, Stein KD, Alteri R, Jemal A. Cancer Treatment and Survivorship Statistics. 2016. CA Cancer J Clin. 2016; 66(4): 271–289. [CrossRef]
  • [5] Roy PS, Saikia BJ. Cancer and Cure: A Critical Analysis. Indian J Cancer. 2016; 53(3): 441–442.
  • [6] Pejović A, Minić A, Bugarinović J, Pešić M, Damljanović I, Stevanović D, Mihailović V, Katanić J, Bogdanović GA. Synthesis, Characterization and Antimicrobial Activity of Novel 3-Ferrocenyl-2-pyrazolyl-1,3-thiazolidin-4-ones. Polyhedron. 2018; 155: 382–389. [CrossRef]
  • [7] Verma A, Saraf SK. 4-Thiazolidinone - A Biologically Active Scaffold. Eur J Med Chem. 2008; 43(5): 897–905. [CrossRef]
  • [8] Kunzler A, Neuenfeldt PD, Das Neves AM, Pereira CMP, Marques GH, Nascente PS, Fernandes MHV, Hübner SO, Cunico W. Synthesis, Antifungal and Cytotoxic Activities of 2-Aryl-3-((piperidin-1-yl)ethyl)thiazolidinones. Eur J Med Chem. 2013; 64: 74–80. [CrossRef]
  • [9] Küçükgüzel ŞG, Oruç EE, Rollas S, Şahin F, Özbek A. Synthesis, Characterisation and Biological Activity of Novel 4-Thiazolidinones, 1,3,4-Oxadiazoles and Some Related Compounds. Eur J Med Chem. 2002; 37(3): 197–206. [CrossRef]
  • [10] D’Ascenzio M, Bizzarri B, De Monte C, Carradori S, Bolasco A, Secci D, Rivanera D, Faulhaber N, Bordón C, Jones-Brando L. Design, Synthesis and Biological Characterization of Thiazolidin-4-one Derivatives as Promising Inhibitors of Toxoplasma gondii. Eur J Med Chem. 2014; 86: 17–30. [CrossRef]
  • [11] Secci D, Carradori S, Bizzarri B, Chimenti P, De Monte C, Mollica A, Rivanera D, Zicari A, Mari E, Zengin G, Aktumsek A. Novel 1,3-Thiazolidin-4-one Derivatives as Promising Anti-Candida Agents Endowed with Anti-oxidant and Chelating Properties. Eur J Med Chem. 2016; 117: 144–156. [CrossRef]
  • [12] Tripathi AC, Gupta SJ, Fatima GN, Sonar PK, Verma A, Saraf SK. 4-Thiazolidinones: The Advances Continue. Eur J Med Chem. 2014; 72: 52–77. [CrossRef]
  • [13] Jain AK, Vaidya A, Ravichandran V, Kashaw SK, Agrawal RK. Recent Developments and Biological Activities of Thiazolidinone Derivatives: A Review. Bioorganic Med Chem. 2012; 20(11): 3378–3395. [CrossRef]
  • [14] Güzel Ö, Salman A. Synthesis and Biological Evaluation of New 4-Thiazolidinone Derivatives. J Enzyme Inhib Med Chem 2009, 24(4): 1015–1023. 24:1015-1023. [CrossRef]
  • [15] Güzel Ö, Ilhan E, Salman A. Synthesis and Antimycobacterial Activity of New 2-Hydroxy-N-(3-oxo-1-thia- 4-azaspiro[4.4]non-4-yl)/(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2, 2-diphenylacetamide Derivatives. Monatsh Chem. 2006; 137(6): 795–801. [CrossRef]
  • [16] Ulusoy Güzeldemirci N, Pehlivan E, Naesens L. Synthesis and Antiviral Activity Evaluation of New 4-Thiazolidinones Bearing an Imidazo[2,1-b]thiazole Moiety. Marmara Pharm J. 2018; 22(2): 237–248. [CrossRef]
  • [17] Kaynak FB, Öztürk D, Özbey S, Çapan G. New N′-Alkylidene/cycloalkylidene Derivatives of 5-Methyl-3-phenyl-1H-indole-2-carbohydrazide: Synthesis, Crystal Structure, and Quantum Mechanical Calculations. J Mol Struct. 2005; 740(1-3): 213–221. [CrossRef]
  • [18] Taylor PJ. The Infra-red Spectroscopy of Some 2-Substituted Thiazolid-4-ones, a New Class of Enamino-ketone-II. Infra-red Assignments and Chemical Implications. Spectrochim Acta Part A Mol Spectrosc. 1970; 26(1): 165–194. [CrossRef]
  • [19] Gupta A, Singh R, Sonar PK, Saraf SK. Novel 4-Thiazolidinone Derivatives as Anti-infective Agents: synthesis, Characterization, and Antimicrobial Evaluation. Biochem Res Int. 2016; 2016: 1–8. [CrossRef]
  • [20] Karali N, Ilhan E, Gürsoy A, Kiraz M. New yclohexylidenehydrazide and 4-Aza-1-thiaspiro[4.5]decan-3-one Derivatives of 3-Phenyl-4 (3H)-quinazolinones. Farmaco. 1998; 53(5): 346–349. [CrossRef]
  • [21] Ulusoy N. Synthesis and Antituberculosis Activity of Cycloalkylidenehydrazide and 4-Aza-1-thiaspiro[4.5]decan-3-one Derivatives of Imidazo[2,1-b]thiazole. Arzneimittel-Forschung/Drug Res. 2002; 52(07): 565–571. [CrossRef]
  • [22] Peters R, Hellenbrand J, Mengerink Y, Van Der Wal S. On-line Determination of Carboxylic Acids, Aldehydes and Ketones by High-Performance Liquid Chromatography-Diode Array Detection-Atmospheric Pressure Chemical Ionisation Mass Spectrometry After Derivatization with 2-Nitrophenylhydrazine. J Chromatogr A. 2004; 1031(1-2): 35–50. [CrossRef]
  • [23] De Lima WT, De Lima JG, Góes AJS. Mass Spectrometry of Some N-Tryptophyl-4-Thiazolidinone and N-Tryptophyl-5-benzylidene-4-thiazolidinone Derivatives. Spectrosc Lett. 2002; 35(1): 137–144. [CrossRef]
  • [24] Alley MC, Scudiero DA, Monks A, Hursey M, Czerwinski MJ, Fine DL, Abbott BJ, Mayo JG, Shoemaker R, Boyd MR. Feasibility of Drug Screening with Panels of Human Tumor Cell Lines Using a Microculture Tetrazolium Assay. Cancer Res. 1988; 48(3): 584–588.
  • [25] Grever MR, Schepartz SA, Chabner BA. The National Cancer Institute: Cancer Drug Discovery and Development Program. Semin Oncol. 1992; 19(6): 622.
  • [26] Boyd MR, Paull KD. Some Practical Considerations and Applications of the National Cancer Institute in vitroAnticancer Drug Discovery Screen. Drug Dev Res. 1995; 34(2): 91–109. [CrossRef]
  • [27] Rollas S, Büyüktimkin S, Büyüktimkin N, Ulgen M, Yemni E. Evaluation of Some Arylhydrazones of N2-Arylidenebenzylic Acid Hydrazide as Antimicrobial Agents. Pharmazie. 1988; 43(7): 511.
  • [28] Abu Safieh K, Al-Titi AM, Zahra J, Ayoub M. Oxidative Cyclization of Arylidene Carboxyhydrazides : Synthesis of Substituted Hydroxydiphenylmenthyl-3,3,4-oxadiazoles. Jordan J Chem. 2007; 2(3): 211–218.
  • [29] Issa YM, Issa RM, Abdel-Latif SA, Abdel-Salam HA. Structural Studies of Cu(II) Chelates with Some Arylidene Derivatives of Benzilic Hydrazide. Monatsh Chem. 1998; 129(1): 19–29. [CrossRef]
  • [30] Issa RM, Abdel-Latif SA, Abdel-Salam HA. Synthesis and Characterization of New Cu(II) Complexes Derived from Benzilic and Mandelic Hydrazones. Synth React Inorg Met Chem. 2001; 31(1): 95–105. [CrossRef]
There are 29 citations in total.

Details

Primary Language English
Subjects Pharmaceutical Chemistry
Journal Section Articles
Authors

Özlen Güzel Akdemir

Kübra Demir-yazıcı

Publication Date June 27, 2025
Published in Issue Year 2021 Volume: 25 Issue: 3

Cite

APA Güzel Akdemir, Ö., & Demir-yazıcı, K. (2025). Benzilic acid based new 2-aryl-1,3-thiazolidin-4-one derivatives: Synthesis and anticancer activity. Journal of Research in Pharmacy, 25(3), 305-317. https://doi.org/10.29228/jrp.21
AMA Güzel Akdemir Ö, Demir-yazıcı K. Benzilic acid based new 2-aryl-1,3-thiazolidin-4-one derivatives: Synthesis and anticancer activity. J. Res. Pharm. June 2025;25(3):305-317. doi:10.29228/jrp.21
Chicago Güzel Akdemir, Özlen, and Kübra Demir-yazıcı. “Benzilic Acid Based New 2-Aryl-1,3-Thiazolidin-4-One Derivatives: Synthesis and Anticancer Activity”. Journal of Research in Pharmacy 25, no. 3 (June 2025): 305-17. https://doi.org/10.29228/jrp.21.
EndNote Güzel Akdemir Ö, Demir-yazıcı K (June 1, 2025) Benzilic acid based new 2-aryl-1,3-thiazolidin-4-one derivatives: Synthesis and anticancer activity. Journal of Research in Pharmacy 25 3 305–317.
IEEE Ö. Güzel Akdemir and K. Demir-yazıcı, “Benzilic acid based new 2-aryl-1,3-thiazolidin-4-one derivatives: Synthesis and anticancer activity”, J. Res. Pharm., vol. 25, no. 3, pp. 305–317, 2025, doi: 10.29228/jrp.21.
ISNAD Güzel Akdemir, Özlen - Demir-yazıcı, Kübra. “Benzilic Acid Based New 2-Aryl-1,3-Thiazolidin-4-One Derivatives: Synthesis and Anticancer Activity”. Journal of Research in Pharmacy 25/3 (June 2025), 305-317. https://doi.org/10.29228/jrp.21.
JAMA Güzel Akdemir Ö, Demir-yazıcı K. Benzilic acid based new 2-aryl-1,3-thiazolidin-4-one derivatives: Synthesis and anticancer activity. J. Res. Pharm. 2025;25:305–317.
MLA Güzel Akdemir, Özlen and Kübra Demir-yazıcı. “Benzilic Acid Based New 2-Aryl-1,3-Thiazolidin-4-One Derivatives: Synthesis and Anticancer Activity”. Journal of Research in Pharmacy, vol. 25, no. 3, 2025, pp. 305-17, doi:10.29228/jrp.21.
Vancouver Güzel Akdemir Ö, Demir-yazıcı K. Benzilic acid based new 2-aryl-1,3-thiazolidin-4-one derivatives: Synthesis and anticancer activity. J. Res. Pharm. 2025;25(3):305-17.