Araştırma Makalesi
BibTex RIS Kaynak Göster
Yıl 2023, Cilt: 10 Sayı: 3, 837 - 846, 30.08.2023
https://doi.org/10.18596/jotcsa.1269213

Öz

Proje Numarası

2021-1-TP2-4217

Kaynakça

  • 1. Muhammad M, Khan S, Shehzadi SA, Gul Z, Al-Saidi HM, Waheed Kamran A, Alhumaydhi FA. Recent advances in colorimetric and fluorescent chemosensors based on thiourea derivatives for metallic cations: A review. Dye Pigment. 2022 Sep;205:110477. Available from: <URL> 2. Nural Y, Karasu E, Keleş E, Aydıner B, Seferoğlu N, Efeoğlu Ç, Şahin E, Seferoğlu Z. Synthesis of novel acylthioureas bearing naphthoquinone moiety as dual sensor for high-performance naked-eye colorimetric and fluorescence detection of CN− and F− ions and its application in water and food samples. Dye Pigment. 2022 Feb;198:110006. Available from: <URL>
  • 3. Mitrea DG, Cîrcu V. Synthesis and characterization of novel acylthiourea compounds used in ions recognition and sensing in organic media. Spectrochim Acta Part A Mol Biomol Spectrosc. 2021 Sep;258:119860. Available from: <URL>
  • 4. Khan E, Khan S, Gul Z, Muhammad M. Medicinal Importance, Coordination Chemistry with Selected Metals (Cu, Ag, Au) and Chemosensing of Thiourea Derivatives. A Review. Crit Rev Anal Chem. 2020 Jun;51(8):1–23. Available from: <URL>
  • 5. Gemili M, Nural Y, Keleş E, Aydıner B, Seferoğlu N, Şahin E, Sarı H, Seferoğlu Z. Novel 1,4-naphthoquinone N-aroylthioureas: Syntheses, crystal structure, anion recognition properties, DFT studies and determination of acid dissociation constants. J Mol Liq. 2018 Nov;269:920–32. Available from: <URL>
  • 6. Huang X, Cao X, Wang W, Zhong H, Cao ZF. Investigation of removal of Ag(I) from aqueous solution by a novel chelating resin containing acyl and thiourea groups. J Dispers Sci Technol. 2019 Apr;40(4):477–86. Available from: <URL>
  • 7. Huang X, Cao X, Wang W, Zhong H, Cao Z. Preparation of a novel resin with acyl and thiourea groups and its properties for Cu(II) removal from aqueous solution. J Environ Manage. 2017 Dec;204:264–71. Available from: <URL>
  • 8. Zahra U, Saeed A, Abdul Fattah T, Flörke U, Erben MF. Recent trends in chemistry, structure, and various applications of 1-acyl-3-substituted thioureas: a detailed review. RSC Adv. 2022;12(20):12710–45. Available from: <URL>
  • 9. Saeed A, Mustafa MN, Zain-ul-Abideen M, Shabir G, Erben MF, Flörke U. Current developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3- (substituted)thioureas: advances Continue …. J Sulfur Chem. 2019 May;40(3):312–50. Available from: <URL>
  • 10. Nural Y, Gemili M, Seferoglu N, Sahin E, Ulger M, Sari H. Synthesis, crystal structure, DFT studies, acid dissociation constant, and antimicrobial activity of methyl 2-(4-chlorophenyl)-7a-((4-chlorophenyl)carbamothioyl)-1-oxo-5,5-diphenyl-3-thioxo-hexahydro-1H-pyrrolo[1,2-e]imidazole-6-carboxylate. J Mol Struct. 2018 May;1160:375–82. Available from: <URL>
  • 11. Nural Y, Gemili M, Yabalak E, Coen LM De, Ulger M. Green synthesis of highly functionalized octahydropyrrolo[3,4-c]pyrrole derivatives using subcritical water, and their anti(myco)bacterial and antifungal activity. ARKIVOC. 2018 Jun;2018(5):51–64. Available from: <URL>
  • 12. Arslan B, Binzet G. Synthesis, crystal structure analysis, DFT calculations, antioxidant and antimicrobial activity of N,N-di-2,4-dimethoxybenzyl-N’-2-nitrobenzoylthiourea. J Mol Struct. 2022 Nov;1267:133579. Available from: <URL>
  • 13. Erşen D, Ülger M, Mangelinckx S, Gemili M, Şahin E, Nural Y. Synthesis and anti(myco)bacterial activity of novel 5,5-diphenylpyrrolidine N-aroylthiourea derivatives and a functionalized hexahydro-1H-pyrrolo[1,2-c]imidazole. Med Chem Res. 2017 Sep;26(9):2152–60. Available from: <URL>
  • 14. Döndaş HA, Nural Y, Duran N, Kilner C. Synthesis, crystal structure and antifungal/antibacterial activity of some novel highly functionalized benzoylaminocarbothioyl pyrrolidines. Turkish J Chem. 2006;30(5):573–83. Available from: <URL> 15. Wang H, Zhai ZW, Shi YX, Tan CX, Weng JQ, Han L, Li BJ, Liu XH. Novel Trifluoromethylpyrazole Acyl Thiourea Derivatives: Synthesis, Antifungal Activity and Docking Study. Lett Drug Des Discov. 2019 Jun;16(7):785–91. Available from: <URL>
  • 16. Antypenko L, Meyer F, Kholodniak O, Sadykova Z, Jirásková T, Troianova A, Buhaiova V, Cao S, Kovalenko S, Garbe LA, Steffens KG. Novel acyl thiourea derivatives: Synthesis, antifungal activity, gene toxicity, drug-like and molecular docking screening. Arch Pharm (Weinheim). 2019 Feb;352(2):1800275. Available from: <URL>
  • 17. Kalaiyarasi A, Haribabu J, Gayathri D, Gomathi K, Bhuvanesh NSP, Karvembu R, Biju VM. Chemosensing, molecular docking and antioxidant studies of 8-aminoquinoline appended acylthiourea derivatives. J Mol Struct. 2019 Jun;1185:450–60. Available from: <URL>
  • 18. Arshad N, Saeed A, Perveen F, Ujan R, Farooqi SI, Ali Channar P, Shabir G, El-Seedi HR, Javed A, Yamin M, Bolte M, Hökelek T. Synthesis, X-ray, Hirshfeld surface analysis, exploration of DNA binding, urease enzyme inhibition and anticancer activities of novel adamantane-naphthyl thiourea conjugate. Bioorg Chem. 2021 Apr;109:104707. Available from: <URL>
  • 19. Zahra U, Zaib S, Saeed A, Rehman M ur, Shabir G, Alsaab HO, Khan I. New acetylphenol-based acyl thioureas broaden the scope of drug candidates for urease inhibition: synthesis, in vitro screening and in silico analysis. Int J Biol Macromol. 2022 Feb;198:157–67. Available from: <URL>
  • 20. Efeoglu C, Yetkin D, Nural Y, Ece A, Seferoğlu Z, Ayaz F. Novel urea-thiourea hybrids bearing 1,4-naphthoquinone moiety: Anti-inflammatory activity on mammalian macrophages by regulating intracellular PI3K pathway, and molecular docking study. J Mol Struct. 2022 Sep;1264:133284. Available from: <URL>
  • 21. Ahmed A, Shafique I, Saeed A, Shabir G, Saleem A, Taslimi P, Taskin Tok T, Kirici M, Üç EM, Hashmi MZ. Nimesulide linked acyl thioureas potent carbonic anhydrase I, II and α-glucosidase inhibitors: Design, synthesis and molecular docking studies. Eur J Med Chem Reports. 2022 Dec;6:100082. Available from: <URL>
  • 22. Ertano BY, Demir Y, Nural Y, Erdoğan O. Investigation of The Effect of Acylthiourea Derivatives on Diabetes‐Associated Enzymes. ChemistrySelect. 2022 Dec;7(46). Available from: <URL>
  • 23. Mustafa MN, Saeed A, Channar PA, Larik FA, Zain-ul abideen M, Shabir G, Abbas Q, Hassan M, Raza H, Seo SY. Synthesis, molecular docking and kinetic studies of novel quinolinyl based acyl thioureas as mushroom tyrosinase inhibitors and free radical scavengers. Bioorg Chem. 2019 Sep;90:103063. Available from: <URL>
  • 24. Al‐abbasi AA, Tahir MIM, Kayed SF, Kassim MB. Synthesis, characterisation and biological activities of mixed ligand oxovanadium (IV) complexes derived from N , N ‐diethyl‐ N ′‐ para ‐substituted‐benzoylthiourea and hydrotris(3,5‐dimethylpyrazolyl)borate. Appl Organomet Chem. 2022 Apr;36(4). Available from: <URL>
  • 25. Oyeka EE, Babahan I, Eboma B, Ifeanyieze KJ, Okpareke OC, Coban EP, Özmen A, Coban B, Aksel M, Özdemir N, Groutso TV, Ayogu JI, Yildiz U, Dinçer Bilgin M, Halil Biyik H, Schrage BR, Ziegler CJ, Asegbeloyin JN. Biologically active acylthioureas and their Ni(II) and Cu(II) Complexes: Structural, spectroscopic, anti-proliferative, nucleolytic and antimicrobial studies. Inorganica Chim Acta. 2021 Dec;528:120590. Available from: <URL>
  • 26. Le CD, Pham CT, Nguyen HH. Zinc(II) {2}-metallacoronates and {2}-metallacryptates based on dipicolinoylbis(N,N-diethylthiourea): Structures and biological activities. Polyhedron. 2019 Nov;173:114143. Available from: <URL>
  • 27. Alharbi W. Advancement and recent trends in seeking less toxic and more active anti-cancer drugs: Insights into thiourea based molecules. Main Gr Chem. 2022 Sep;21(3):885–901. Available from: <URL>
  • 28. Al-Riyahee A, Murad D, Shenta A. Electrochemical Studies Of Novel 3,4-Dichloro-N-((5-ChloroPyridin-2-yl)Carbamothioyl)Benzamide Based On Its Complexes With Copper(II), Cobalt(II), Nickel(II) and Zinc(II) ions. Egypt J Chem. 2021 Apr;64(8):4323–41. Available from: <URL>
  • 29. Ghazal K, Shoaib S, Khan M, Khan S, Rauf MK, Khan N, Badshah A, Tahir MN, Ali I, Rehman A ur. Synthesis, characterization, X-ray diffraction study, in-vitro cytotoxicity, antibacterial and antifungal activities of nickel(II) and copper(II) complexes with acyl thiourea ligand. J Mol Struct. 2019 Feb;1177:124–30. Available from: <URL>
  • 30. Gemili M, Sari H, Ulger M, Sahin E, Nural Y. Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives: Synthesis, characterization, physical parameters and biological activity. Inorganica Chim Acta. 2017 Jul;463:88–96. Available from: <URL>
  • 31. Zhang YM, Wei TB, Xian L, Gao LM. An Efficient Synthesis of Polymethylene-Bis-Aroyl Thiourea Derivatives Under The Condition of Phase-Transfer Catalysis. Phosphorus Sulfur Silicon Relat Elem. 2004 Oct;179(10):2007–13. Available from: <URL>
  • 32. Kurt G, Mercimek B. Synthesis and Characterization of N,N’-(propane-1,2 diyldicarbamothioyl)dibenzamide. Molbank. 2008 Nov;2008(3):M578. Available from: <URL>
  • 33. Abd Halim AN, Ngaini Z. Synthesis and characterization of halogenated bis(acylthiourea) derivatives and their antibacterial activities. Phosphorus Sulfur Silicon Relat Elem. 2017 Sep;192(9):1012–7. Available from: <URL>
  • 34. Abd Halim AN, Ngaini Z. Synthesis and Bacteriostatic Activities of Bis(thiourea) Derivatives with Variable Chain Length. J Chem. 2016;2016:1–7. Available from: <URL>
  • 35. Kurt G, Sevgi F, Mercimek B. Synthesis, characterization, and antimicrobial activity of new benzoylthiourea ligands. Chem Pap. 2009 Jan;63(5). Available from: <URL>
  • 36. Duan XE, Li R, Tong HB, Li YQ, Bai SD, Guo YJ, Liu DS. Synthesis and structural characterization of electrochemically reversible bisferrocenes containing bis(acyl-thiourea)s: enantiomers and conformers. New J Chem. 2017;41(9):3333–43. Available from: <URL>
  • 37. Károlyi BI, Bősze S, Orbán E, Sohár P, Drahos L, Gál E, Csámpai A. Acylated mono-, bis- and tris- Cinchona-Based Amines Containing Ferrocene or Organic Residues: Synthesis, Structure and in Vitro Antitumor Activity on Selected Human Cancer Cell Lines. Molecules. 2012 Feb;17(3):2316–29. Available from: <URL>
  • 38. Arafa WAA, Ghoneim AA, Mourad AK. N -Naphthoyl Thiourea Derivatives: An Efficient Ultrasonic-Assisted Synthesis, Reaction, and In Vitro Anticancer Evaluations. ACS Omega. 2022 Feb;7(7):6210–22. Available from: <URL>
  • 39. Maalik A, Hameed S, Bhatti HA, Rauf A, Bukhari SM, Fatima N, Rafique H, Mughal EU, Mumtaz A. Synthesis and Biological Screening of N,N’-bis Disubstituted Adipic Acid Thioureas. Curr Pharm Anal. 2018 Sep;14(6):618–21. Available from: <URL>
  • 40. Patujo J, Azeem M, Khan M, Muhammad H, Raheel A, Fatima S, Mirza B, Hussain Z, Badshah A. Assessing the biological potential of new symmetrical ferrocene based bisthiourea analogues. Bioorg Chem. 2021 Jan;106:104180. Available from: <URL>
  • 41. Mumtaz A, Saeed K, Mahmood A, Zaib S, Saeed A, Pelletier J, Sévigny J, Iqbal J. Bisthioureas of pimelic acid and 4-methylsalicylic acid derivatives as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP) and intestinal alkaline phosphatase (IAP): Synthesis and molecular docking studies. Bioorg Chem. 2020 Aug;101:103996. Available from: <URL>
  • 42. Ujan R, Channar PA, Bahadur A, Abbas Q, Shah M, Rashid SG, Iqbal S, Saeed A, Abd-Rabboh HSM, Raza H, Hassan M, Siyal AN, Mahesar PA, Lal B, Channar KA, Khan BA, Nawaz M, Rajoka MSR, et al. Synthesis, kinetics and biological assay of some novel aryl bis-thioureas: A potential drug candidates for Alzheimer’s disease. J Mol Struct. 2021 Dec;1246:131136. Available from: <URL>
  • 43. Koch KR, Hallale O, Bourne SA, Miller J, Bacsa J. Self-assembly of 2:2 metallomacrocyclic complexes of NiII and PdII with 3,3,3′,3′-tetraalkyl-1,1′-isophthaloylbis(thioureas). Crystal and molecular structures of cis-[Pd(L2-S,O)]2 and the adducts of the corresponding NiII complexes: [Ni(L1-S,O)(pyridine)2. J Mol Struct. 2001 Apr;561(1–3):185–96. Available from: <URL>
  • 44. Schwade VD, Kirsten L, Hagenbach A, Schulz Lang E, Abram U. Indium(III), lead(II), gold(I) and copper(II) complexes with isophthaloylbis(thiourea) ligands. Polyhedron. 2013 May;55:155–61. Available from: <URL>
  • 45. Nkabyo HA, Barnard I, Koch KR, Luckay RC. Recent advances in the coordination and supramolecular chemistry of monopodal and bipodal acylthiourea-based ligands. Coord Chem Rev. 2021 Jan;427:213588. Available from: <URL>
  • 46. Selvakumaran N, Bhuvanesh NSP, Karvembu R. Self-assembled Cu (II) and Ni (II) metallamacrocycles formed from 3, 3, 3′, 3′-tetrabenzyl-1, 1′-aroylbis (thiourea) ligands: DNA and protein binding studies, and cytotoxicity of trinuclear complexes. Dalt Trans. 2014;43(43):16395–410. Available from: <URL>
  • 47. Razak NHA, Tan LL, Hasbullah SA, Heng LY. Reflectance chemosensor based on bis-thiourea derivative as ionophore for copper(II) ion detection. Microchem J. 2020 Mar;153:104460. Available from: <URL>
  • 48. Hamedan NA, Hasan S, Zaki HM, Alias NZ. Colorimetric chemosensor of symmetrical benzoylthiourea derivatives as for detection of Cu 2+ in aqueous solution. IOP Conf Ser Mater Sci Eng. 2017 Feb;172:012038. Available from: <URL>
  • 49. Turanov AN, Karandashev VK, Proshin AN. Extraction properties of hexamethylene-1,6-bis[(N-benzoyl)thiourea] in hydrochloric acid solutions. Russ J Inorg Chem. 2006 Dec;51(12):1968–72. Available from: <URL>
  • 50. Manallack DT. The acid–base profile of a contemporary set of drugs: implications for drug discovery. SAR QSAR Environ Res. 2009 Oct;20(7–8):611–55. Available from: <URL>
  • 51. Alongi KS, Shields GC. Theoretical Calculations of Acid Dissociation Constants: A Review Article. In: Wheeler RABTAR in CC, editor. Elsevier; 2010. p. 113–38. Available from: <URL>
  • 52. Nural Y, Gemili M, Ulger M, Sari H, De Coen LM, Sahin E. Synthesis, antimicrobial activity and acid dissociation constants of methyl 5,5-diphenyl-1-(thiazol-2-yl)pyrrolidine-2-carboxylate derivatives. Bioorg Med Chem Lett. 2018 Mar;28(5):942–6. Available from: <URL> 53. Nural Y, Ozdemir S, Doluca O, Demir B, Yalcin MS, Atabey H, Kanat B, Erat S, Sari H, Seferoglu Z. Synthesis, biological properties, and acid dissociation constant of novel naphthoquinone–triazole hybrids. Bioorg Chem. 2020 Dec;105:104441. Available from: <URL>
  • 54. Nural Y, Ozdemir S, Yalcin MS, Demir B, Atabey H, Seferoglu Z, Ece A. New bis- and tetrakis-1,2,3-triazole derivatives: Synthesis, DNA cleavage, molecular docking, antimicrobial, antioxidant activity and acid dissociation constants. Bioorg Med Chem Lett. 2022 Jan;55:128453. Available from: <URL>
  • 55. Takács-Novák K, Tam KY. Multiwavelength spectrophotometric determination of acid dissociation constants: Part V: microconstants and tautomeric ratios of diprotic amphoteric drugs. Journal of pharmaceutical and biomedical analysis, 2000 Jan;21(6):1171-1182. Available from: <URL>
  • 56. Huang J, Yuan F, Zeng G, Li X, Gu Y, Sh, L, Liu W, Shi, Y. Influence of pH on heavy metal speciation and removal from wastewater using micellar-enhanced ultrafiltration. Chemosphere, 2017 April;173:199-206. Available from: <URL>
  • 57. İnci D. Equilibrıum studies on Ni(II) and Cu(II) complexes with 4,7-dİmethyl-1,10-phenanthrolİne and acidic amıno acids in aqueous solution. J Turkish Chem Soc Sect A Chem. 2020 Oct;7(3):775–88. Available from: <URL>
  • 58. Türkoǧlu G, Berber H, Özkütük M. Spectrophotometric determination of the acidity dissociation constants of symmetric Schiff base derivatives. Gazi Univ J Sci. 2014;27(2):771–83. Available from: <URL>
  • 59. Berber H, Ateş NA, Özkütük MY. Synthesis, Characterization And Spectroscoic Studies On Azo-Hydrazone Tautomerism And Acidity Constants Of Certain 4-(Phenyldıazenyl) Benzene-1,3-Diol Derivatives. Anadolu Üniversitesi Bilim Ve Teknol Derg - B Teor Bilim. 2016 Mar;4(1). Available from: <URL>
  • 60. Kim H s., Chung TD, Kim H. Voltammetric determination of the pKa of various acids in polar aprotic solvents using 1,4-benzoquinone. J Electroanal Chem. 2001 Feb;498(1–2):209–15. Available from: <URL>
  • 61. Doğan A, Başcı NE, Polat MB. Spectrophotometry, potentiometry and HPLC in determination of acidity constant for Cabergoline and Tadalafil. J Res Pharm. 2019 Feb;23(2):177–86. Available from: <URL>
  • 62. Koçak E, Doğan A, Altınöz S, Başçı NE, Çelebier M. Investigating the physicochemical properties of phenazopyridine hydrochloride using high-performance liquid chromatography and UV-Visible spectrophotometry. J Res Pharm. 2018 Jul;22(1):198–205. Available from: <URL>
  • 63. Mumcu A, Küçükbay H. Determination of p K a values of some novel benzimidazole salts by using a new approach with 1 H NMR spectroscopy. Magn Reson Chem. 2015 Dec;53(12):1024–30. Available from: <URL>
  • 64. Gans P, Sabatini A, Vacca A. Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAD suite of programs. Talanta. 1996 Oct;43(10):1739–53. Available from: <URL>
  • 65. Schröder B, Schröder U, Dietze F, Beyer L. Protonation, complexation and thermochemical behaviour of N-benzoylthiocarbamic-O-alkylester anions in solution. Inorg Chem Commun. 2001 Aug;4(8):398–401. Available from: <URL> 66. Ersen D, Gemili M, Sarı H, Nural Y. Acid Dissociation Constants of 5,5-Diphenylpyrrolidine N-Aroylthioureas and Stability Constants of their Pt(II) and Ni(II) Complexes in Acetonitrile-Water Hydroorganic Solvent. Celal Bayar Üniversitesi Fen Bilim Derg. 2017 Mar;3(1):125–38. Available from: <URL>
  • 67. Nural Y. Synthesis and Determination of Acid Dissociation Constants in Dimethyl Sulfoxide–Water Hydroorganic Solvent of 5,5-Diphenylpyrrolidine N-Aroylthiourea Derivatives. J Turkish Chem Soc Sect A Chem. 2017 Aug;841–54. Available from: <URL>
  • 68. Atabey H, Sari H, Al-Obaidi FN. Protonation Equilibria of Carminic Acid and Stability Constants of Its Complexes with Some Divalent Metal Ions in Aqueous Solution. J Solution Chem. 2012 Jun;41(5):793–803. Available from: <URL>

Synthesis and Determination of Acid Dissociation Constants of Bis-Acyl Thiourea Derivatives

Yıl 2023, Cilt: 10 Sayı: 3, 837 - 846, 30.08.2023
https://doi.org/10.18596/jotcsa.1269213

Öz

N,N'-((dodecane-1,12-diylbis(azanediyl))bis(carbonothioyl))bis(4-nitrobenzamide) 5 and N,N'-((dodecane-1,12-diylbis(azanediyl))bis(carbonothioyl))bis(3-nitrobenzamide) 6 as bis acyl thiourea derivatives were synthesized and their molecular structures were characterized using 1H NMR, 13C NMR, COSY, DEPT, HMQC, FT-IR, and HRMS techniques. The acid dissociation constants (pKa) of the bis-acyl thiourea derivatives 5, 6 were determined potentiometrically and spectrophotometrically. The pKa values of products 5, 6 were determined in 50% (v/v) dimethyl sulfoxide–water hydro-organic solvent in the presence of 0.1 molL1 ionic strength of NaCl and in the acidic medium at 25±0.1 °C, and two pKa values were calculated for each compound with the HYPERQUAD computer program using the data obtained from the potentiometric titrations performed. In addition, three pKa values for each compound were determined in the calculations using the HypSpec program from the data obtained from the spectrophotometric titrations performed under the conditions where the potentiometric titrations were performed. For compounds 5 and 6, spectrophotometrically, pKa1 was 3.56±0.08 and 3.87±0.01, respectively, pKa2 was 7.11±0.08 and 7.05±0.01, respectively, and pKa3 was 12.30±0.08 and 11.82±0.02, respectively. It can be said that pKa1, pKa2, and pKa3 values may belong to enol, enthiol, and NH, respectively. Moreover, for compounds 5 and 6, potentiometrically, pKa2 was 7.06±0.13 and 6.94±0.11, respectively, and pKa3 was 12.11±0.06 and 11.17±0.06, respectively, and it can be said that pKa2 and pKa3 values may belong to enthiol and NH, respectively. It is seen that the pKa values determined spectrophotometrically and potentiometrically are compatible with each other.

Destekleyen Kurum

Mersin University

Proje Numarası

2021-1-TP2-4217

Teşekkür

This work is a part of Şit Tiken’s master thesis and we are thankful to Mersin University (Project grant: 2021-1-TP2-4217)

Kaynakça

  • 1. Muhammad M, Khan S, Shehzadi SA, Gul Z, Al-Saidi HM, Waheed Kamran A, Alhumaydhi FA. Recent advances in colorimetric and fluorescent chemosensors based on thiourea derivatives for metallic cations: A review. Dye Pigment. 2022 Sep;205:110477. Available from: <URL> 2. Nural Y, Karasu E, Keleş E, Aydıner B, Seferoğlu N, Efeoğlu Ç, Şahin E, Seferoğlu Z. Synthesis of novel acylthioureas bearing naphthoquinone moiety as dual sensor for high-performance naked-eye colorimetric and fluorescence detection of CN− and F− ions and its application in water and food samples. Dye Pigment. 2022 Feb;198:110006. Available from: <URL>
  • 3. Mitrea DG, Cîrcu V. Synthesis and characterization of novel acylthiourea compounds used in ions recognition and sensing in organic media. Spectrochim Acta Part A Mol Biomol Spectrosc. 2021 Sep;258:119860. Available from: <URL>
  • 4. Khan E, Khan S, Gul Z, Muhammad M. Medicinal Importance, Coordination Chemistry with Selected Metals (Cu, Ag, Au) and Chemosensing of Thiourea Derivatives. A Review. Crit Rev Anal Chem. 2020 Jun;51(8):1–23. Available from: <URL>
  • 5. Gemili M, Nural Y, Keleş E, Aydıner B, Seferoğlu N, Şahin E, Sarı H, Seferoğlu Z. Novel 1,4-naphthoquinone N-aroylthioureas: Syntheses, crystal structure, anion recognition properties, DFT studies and determination of acid dissociation constants. J Mol Liq. 2018 Nov;269:920–32. Available from: <URL>
  • 6. Huang X, Cao X, Wang W, Zhong H, Cao ZF. Investigation of removal of Ag(I) from aqueous solution by a novel chelating resin containing acyl and thiourea groups. J Dispers Sci Technol. 2019 Apr;40(4):477–86. Available from: <URL>
  • 7. Huang X, Cao X, Wang W, Zhong H, Cao Z. Preparation of a novel resin with acyl and thiourea groups and its properties for Cu(II) removal from aqueous solution. J Environ Manage. 2017 Dec;204:264–71. Available from: <URL>
  • 8. Zahra U, Saeed A, Abdul Fattah T, Flörke U, Erben MF. Recent trends in chemistry, structure, and various applications of 1-acyl-3-substituted thioureas: a detailed review. RSC Adv. 2022;12(20):12710–45. Available from: <URL>
  • 9. Saeed A, Mustafa MN, Zain-ul-Abideen M, Shabir G, Erben MF, Flörke U. Current developments in chemistry, coordination, structure and biological aspects of 1-(acyl/aroyl)-3- (substituted)thioureas: advances Continue …. J Sulfur Chem. 2019 May;40(3):312–50. Available from: <URL>
  • 10. Nural Y, Gemili M, Seferoglu N, Sahin E, Ulger M, Sari H. Synthesis, crystal structure, DFT studies, acid dissociation constant, and antimicrobial activity of methyl 2-(4-chlorophenyl)-7a-((4-chlorophenyl)carbamothioyl)-1-oxo-5,5-diphenyl-3-thioxo-hexahydro-1H-pyrrolo[1,2-e]imidazole-6-carboxylate. J Mol Struct. 2018 May;1160:375–82. Available from: <URL>
  • 11. Nural Y, Gemili M, Yabalak E, Coen LM De, Ulger M. Green synthesis of highly functionalized octahydropyrrolo[3,4-c]pyrrole derivatives using subcritical water, and their anti(myco)bacterial and antifungal activity. ARKIVOC. 2018 Jun;2018(5):51–64. Available from: <URL>
  • 12. Arslan B, Binzet G. Synthesis, crystal structure analysis, DFT calculations, antioxidant and antimicrobial activity of N,N-di-2,4-dimethoxybenzyl-N’-2-nitrobenzoylthiourea. J Mol Struct. 2022 Nov;1267:133579. Available from: <URL>
  • 13. Erşen D, Ülger M, Mangelinckx S, Gemili M, Şahin E, Nural Y. Synthesis and anti(myco)bacterial activity of novel 5,5-diphenylpyrrolidine N-aroylthiourea derivatives and a functionalized hexahydro-1H-pyrrolo[1,2-c]imidazole. Med Chem Res. 2017 Sep;26(9):2152–60. Available from: <URL>
  • 14. Döndaş HA, Nural Y, Duran N, Kilner C. Synthesis, crystal structure and antifungal/antibacterial activity of some novel highly functionalized benzoylaminocarbothioyl pyrrolidines. Turkish J Chem. 2006;30(5):573–83. Available from: <URL> 15. Wang H, Zhai ZW, Shi YX, Tan CX, Weng JQ, Han L, Li BJ, Liu XH. Novel Trifluoromethylpyrazole Acyl Thiourea Derivatives: Synthesis, Antifungal Activity and Docking Study. Lett Drug Des Discov. 2019 Jun;16(7):785–91. Available from: <URL>
  • 16. Antypenko L, Meyer F, Kholodniak O, Sadykova Z, Jirásková T, Troianova A, Buhaiova V, Cao S, Kovalenko S, Garbe LA, Steffens KG. Novel acyl thiourea derivatives: Synthesis, antifungal activity, gene toxicity, drug-like and molecular docking screening. Arch Pharm (Weinheim). 2019 Feb;352(2):1800275. Available from: <URL>
  • 17. Kalaiyarasi A, Haribabu J, Gayathri D, Gomathi K, Bhuvanesh NSP, Karvembu R, Biju VM. Chemosensing, molecular docking and antioxidant studies of 8-aminoquinoline appended acylthiourea derivatives. J Mol Struct. 2019 Jun;1185:450–60. Available from: <URL>
  • 18. Arshad N, Saeed A, Perveen F, Ujan R, Farooqi SI, Ali Channar P, Shabir G, El-Seedi HR, Javed A, Yamin M, Bolte M, Hökelek T. Synthesis, X-ray, Hirshfeld surface analysis, exploration of DNA binding, urease enzyme inhibition and anticancer activities of novel adamantane-naphthyl thiourea conjugate. Bioorg Chem. 2021 Apr;109:104707. Available from: <URL>
  • 19. Zahra U, Zaib S, Saeed A, Rehman M ur, Shabir G, Alsaab HO, Khan I. New acetylphenol-based acyl thioureas broaden the scope of drug candidates for urease inhibition: synthesis, in vitro screening and in silico analysis. Int J Biol Macromol. 2022 Feb;198:157–67. Available from: <URL>
  • 20. Efeoglu C, Yetkin D, Nural Y, Ece A, Seferoğlu Z, Ayaz F. Novel urea-thiourea hybrids bearing 1,4-naphthoquinone moiety: Anti-inflammatory activity on mammalian macrophages by regulating intracellular PI3K pathway, and molecular docking study. J Mol Struct. 2022 Sep;1264:133284. Available from: <URL>
  • 21. Ahmed A, Shafique I, Saeed A, Shabir G, Saleem A, Taslimi P, Taskin Tok T, Kirici M, Üç EM, Hashmi MZ. Nimesulide linked acyl thioureas potent carbonic anhydrase I, II and α-glucosidase inhibitors: Design, synthesis and molecular docking studies. Eur J Med Chem Reports. 2022 Dec;6:100082. Available from: <URL>
  • 22. Ertano BY, Demir Y, Nural Y, Erdoğan O. Investigation of The Effect of Acylthiourea Derivatives on Diabetes‐Associated Enzymes. ChemistrySelect. 2022 Dec;7(46). Available from: <URL>
  • 23. Mustafa MN, Saeed A, Channar PA, Larik FA, Zain-ul abideen M, Shabir G, Abbas Q, Hassan M, Raza H, Seo SY. Synthesis, molecular docking and kinetic studies of novel quinolinyl based acyl thioureas as mushroom tyrosinase inhibitors and free radical scavengers. Bioorg Chem. 2019 Sep;90:103063. Available from: <URL>
  • 24. Al‐abbasi AA, Tahir MIM, Kayed SF, Kassim MB. Synthesis, characterisation and biological activities of mixed ligand oxovanadium (IV) complexes derived from N , N ‐diethyl‐ N ′‐ para ‐substituted‐benzoylthiourea and hydrotris(3,5‐dimethylpyrazolyl)borate. Appl Organomet Chem. 2022 Apr;36(4). Available from: <URL>
  • 25. Oyeka EE, Babahan I, Eboma B, Ifeanyieze KJ, Okpareke OC, Coban EP, Özmen A, Coban B, Aksel M, Özdemir N, Groutso TV, Ayogu JI, Yildiz U, Dinçer Bilgin M, Halil Biyik H, Schrage BR, Ziegler CJ, Asegbeloyin JN. Biologically active acylthioureas and their Ni(II) and Cu(II) Complexes: Structural, spectroscopic, anti-proliferative, nucleolytic and antimicrobial studies. Inorganica Chim Acta. 2021 Dec;528:120590. Available from: <URL>
  • 26. Le CD, Pham CT, Nguyen HH. Zinc(II) {2}-metallacoronates and {2}-metallacryptates based on dipicolinoylbis(N,N-diethylthiourea): Structures and biological activities. Polyhedron. 2019 Nov;173:114143. Available from: <URL>
  • 27. Alharbi W. Advancement and recent trends in seeking less toxic and more active anti-cancer drugs: Insights into thiourea based molecules. Main Gr Chem. 2022 Sep;21(3):885–901. Available from: <URL>
  • 28. Al-Riyahee A, Murad D, Shenta A. Electrochemical Studies Of Novel 3,4-Dichloro-N-((5-ChloroPyridin-2-yl)Carbamothioyl)Benzamide Based On Its Complexes With Copper(II), Cobalt(II), Nickel(II) and Zinc(II) ions. Egypt J Chem. 2021 Apr;64(8):4323–41. Available from: <URL>
  • 29. Ghazal K, Shoaib S, Khan M, Khan S, Rauf MK, Khan N, Badshah A, Tahir MN, Ali I, Rehman A ur. Synthesis, characterization, X-ray diffraction study, in-vitro cytotoxicity, antibacterial and antifungal activities of nickel(II) and copper(II) complexes with acyl thiourea ligand. J Mol Struct. 2019 Feb;1177:124–30. Available from: <URL>
  • 30. Gemili M, Sari H, Ulger M, Sahin E, Nural Y. Pt(II) and Ni(II) complexes of octahydropyrrolo[3,4-c]pyrrole N-benzoylthiourea derivatives: Synthesis, characterization, physical parameters and biological activity. Inorganica Chim Acta. 2017 Jul;463:88–96. Available from: <URL>
  • 31. Zhang YM, Wei TB, Xian L, Gao LM. An Efficient Synthesis of Polymethylene-Bis-Aroyl Thiourea Derivatives Under The Condition of Phase-Transfer Catalysis. Phosphorus Sulfur Silicon Relat Elem. 2004 Oct;179(10):2007–13. Available from: <URL>
  • 32. Kurt G, Mercimek B. Synthesis and Characterization of N,N’-(propane-1,2 diyldicarbamothioyl)dibenzamide. Molbank. 2008 Nov;2008(3):M578. Available from: <URL>
  • 33. Abd Halim AN, Ngaini Z. Synthesis and characterization of halogenated bis(acylthiourea) derivatives and their antibacterial activities. Phosphorus Sulfur Silicon Relat Elem. 2017 Sep;192(9):1012–7. Available from: <URL>
  • 34. Abd Halim AN, Ngaini Z. Synthesis and Bacteriostatic Activities of Bis(thiourea) Derivatives with Variable Chain Length. J Chem. 2016;2016:1–7. Available from: <URL>
  • 35. Kurt G, Sevgi F, Mercimek B. Synthesis, characterization, and antimicrobial activity of new benzoylthiourea ligands. Chem Pap. 2009 Jan;63(5). Available from: <URL>
  • 36. Duan XE, Li R, Tong HB, Li YQ, Bai SD, Guo YJ, Liu DS. Synthesis and structural characterization of electrochemically reversible bisferrocenes containing bis(acyl-thiourea)s: enantiomers and conformers. New J Chem. 2017;41(9):3333–43. Available from: <URL>
  • 37. Károlyi BI, Bősze S, Orbán E, Sohár P, Drahos L, Gál E, Csámpai A. Acylated mono-, bis- and tris- Cinchona-Based Amines Containing Ferrocene or Organic Residues: Synthesis, Structure and in Vitro Antitumor Activity on Selected Human Cancer Cell Lines. Molecules. 2012 Feb;17(3):2316–29. Available from: <URL>
  • 38. Arafa WAA, Ghoneim AA, Mourad AK. N -Naphthoyl Thiourea Derivatives: An Efficient Ultrasonic-Assisted Synthesis, Reaction, and In Vitro Anticancer Evaluations. ACS Omega. 2022 Feb;7(7):6210–22. Available from: <URL>
  • 39. Maalik A, Hameed S, Bhatti HA, Rauf A, Bukhari SM, Fatima N, Rafique H, Mughal EU, Mumtaz A. Synthesis and Biological Screening of N,N’-bis Disubstituted Adipic Acid Thioureas. Curr Pharm Anal. 2018 Sep;14(6):618–21. Available from: <URL>
  • 40. Patujo J, Azeem M, Khan M, Muhammad H, Raheel A, Fatima S, Mirza B, Hussain Z, Badshah A. Assessing the biological potential of new symmetrical ferrocene based bisthiourea analogues. Bioorg Chem. 2021 Jan;106:104180. Available from: <URL>
  • 41. Mumtaz A, Saeed K, Mahmood A, Zaib S, Saeed A, Pelletier J, Sévigny J, Iqbal J. Bisthioureas of pimelic acid and 4-methylsalicylic acid derivatives as selective inhibitors of tissue-nonspecific alkaline phosphatase (TNAP) and intestinal alkaline phosphatase (IAP): Synthesis and molecular docking studies. Bioorg Chem. 2020 Aug;101:103996. Available from: <URL>
  • 42. Ujan R, Channar PA, Bahadur A, Abbas Q, Shah M, Rashid SG, Iqbal S, Saeed A, Abd-Rabboh HSM, Raza H, Hassan M, Siyal AN, Mahesar PA, Lal B, Channar KA, Khan BA, Nawaz M, Rajoka MSR, et al. Synthesis, kinetics and biological assay of some novel aryl bis-thioureas: A potential drug candidates for Alzheimer’s disease. J Mol Struct. 2021 Dec;1246:131136. Available from: <URL>
  • 43. Koch KR, Hallale O, Bourne SA, Miller J, Bacsa J. Self-assembly of 2:2 metallomacrocyclic complexes of NiII and PdII with 3,3,3′,3′-tetraalkyl-1,1′-isophthaloylbis(thioureas). Crystal and molecular structures of cis-[Pd(L2-S,O)]2 and the adducts of the corresponding NiII complexes: [Ni(L1-S,O)(pyridine)2. J Mol Struct. 2001 Apr;561(1–3):185–96. Available from: <URL>
  • 44. Schwade VD, Kirsten L, Hagenbach A, Schulz Lang E, Abram U. Indium(III), lead(II), gold(I) and copper(II) complexes with isophthaloylbis(thiourea) ligands. Polyhedron. 2013 May;55:155–61. Available from: <URL>
  • 45. Nkabyo HA, Barnard I, Koch KR, Luckay RC. Recent advances in the coordination and supramolecular chemistry of monopodal and bipodal acylthiourea-based ligands. Coord Chem Rev. 2021 Jan;427:213588. Available from: <URL>
  • 46. Selvakumaran N, Bhuvanesh NSP, Karvembu R. Self-assembled Cu (II) and Ni (II) metallamacrocycles formed from 3, 3, 3′, 3′-tetrabenzyl-1, 1′-aroylbis (thiourea) ligands: DNA and protein binding studies, and cytotoxicity of trinuclear complexes. Dalt Trans. 2014;43(43):16395–410. Available from: <URL>
  • 47. Razak NHA, Tan LL, Hasbullah SA, Heng LY. Reflectance chemosensor based on bis-thiourea derivative as ionophore for copper(II) ion detection. Microchem J. 2020 Mar;153:104460. Available from: <URL>
  • 48. Hamedan NA, Hasan S, Zaki HM, Alias NZ. Colorimetric chemosensor of symmetrical benzoylthiourea derivatives as for detection of Cu 2+ in aqueous solution. IOP Conf Ser Mater Sci Eng. 2017 Feb;172:012038. Available from: <URL>
  • 49. Turanov AN, Karandashev VK, Proshin AN. Extraction properties of hexamethylene-1,6-bis[(N-benzoyl)thiourea] in hydrochloric acid solutions. Russ J Inorg Chem. 2006 Dec;51(12):1968–72. Available from: <URL>
  • 50. Manallack DT. The acid–base profile of a contemporary set of drugs: implications for drug discovery. SAR QSAR Environ Res. 2009 Oct;20(7–8):611–55. Available from: <URL>
  • 51. Alongi KS, Shields GC. Theoretical Calculations of Acid Dissociation Constants: A Review Article. In: Wheeler RABTAR in CC, editor. Elsevier; 2010. p. 113–38. Available from: <URL>
  • 52. Nural Y, Gemili M, Ulger M, Sari H, De Coen LM, Sahin E. Synthesis, antimicrobial activity and acid dissociation constants of methyl 5,5-diphenyl-1-(thiazol-2-yl)pyrrolidine-2-carboxylate derivatives. Bioorg Med Chem Lett. 2018 Mar;28(5):942–6. Available from: <URL> 53. Nural Y, Ozdemir S, Doluca O, Demir B, Yalcin MS, Atabey H, Kanat B, Erat S, Sari H, Seferoglu Z. Synthesis, biological properties, and acid dissociation constant of novel naphthoquinone–triazole hybrids. Bioorg Chem. 2020 Dec;105:104441. Available from: <URL>
  • 54. Nural Y, Ozdemir S, Yalcin MS, Demir B, Atabey H, Seferoglu Z, Ece A. New bis- and tetrakis-1,2,3-triazole derivatives: Synthesis, DNA cleavage, molecular docking, antimicrobial, antioxidant activity and acid dissociation constants. Bioorg Med Chem Lett. 2022 Jan;55:128453. Available from: <URL>
  • 55. Takács-Novák K, Tam KY. Multiwavelength spectrophotometric determination of acid dissociation constants: Part V: microconstants and tautomeric ratios of diprotic amphoteric drugs. Journal of pharmaceutical and biomedical analysis, 2000 Jan;21(6):1171-1182. Available from: <URL>
  • 56. Huang J, Yuan F, Zeng G, Li X, Gu Y, Sh, L, Liu W, Shi, Y. Influence of pH on heavy metal speciation and removal from wastewater using micellar-enhanced ultrafiltration. Chemosphere, 2017 April;173:199-206. Available from: <URL>
  • 57. İnci D. Equilibrıum studies on Ni(II) and Cu(II) complexes with 4,7-dİmethyl-1,10-phenanthrolİne and acidic amıno acids in aqueous solution. J Turkish Chem Soc Sect A Chem. 2020 Oct;7(3):775–88. Available from: <URL>
  • 58. Türkoǧlu G, Berber H, Özkütük M. Spectrophotometric determination of the acidity dissociation constants of symmetric Schiff base derivatives. Gazi Univ J Sci. 2014;27(2):771–83. Available from: <URL>
  • 59. Berber H, Ateş NA, Özkütük MY. Synthesis, Characterization And Spectroscoic Studies On Azo-Hydrazone Tautomerism And Acidity Constants Of Certain 4-(Phenyldıazenyl) Benzene-1,3-Diol Derivatives. Anadolu Üniversitesi Bilim Ve Teknol Derg - B Teor Bilim. 2016 Mar;4(1). Available from: <URL>
  • 60. Kim H s., Chung TD, Kim H. Voltammetric determination of the pKa of various acids in polar aprotic solvents using 1,4-benzoquinone. J Electroanal Chem. 2001 Feb;498(1–2):209–15. Available from: <URL>
  • 61. Doğan A, Başcı NE, Polat MB. Spectrophotometry, potentiometry and HPLC in determination of acidity constant for Cabergoline and Tadalafil. J Res Pharm. 2019 Feb;23(2):177–86. Available from: <URL>
  • 62. Koçak E, Doğan A, Altınöz S, Başçı NE, Çelebier M. Investigating the physicochemical properties of phenazopyridine hydrochloride using high-performance liquid chromatography and UV-Visible spectrophotometry. J Res Pharm. 2018 Jul;22(1):198–205. Available from: <URL>
  • 63. Mumcu A, Küçükbay H. Determination of p K a values of some novel benzimidazole salts by using a new approach with 1 H NMR spectroscopy. Magn Reson Chem. 2015 Dec;53(12):1024–30. Available from: <URL>
  • 64. Gans P, Sabatini A, Vacca A. Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAD suite of programs. Talanta. 1996 Oct;43(10):1739–53. Available from: <URL>
  • 65. Schröder B, Schröder U, Dietze F, Beyer L. Protonation, complexation and thermochemical behaviour of N-benzoylthiocarbamic-O-alkylester anions in solution. Inorg Chem Commun. 2001 Aug;4(8):398–401. Available from: <URL> 66. Ersen D, Gemili M, Sarı H, Nural Y. Acid Dissociation Constants of 5,5-Diphenylpyrrolidine N-Aroylthioureas and Stability Constants of their Pt(II) and Ni(II) Complexes in Acetonitrile-Water Hydroorganic Solvent. Celal Bayar Üniversitesi Fen Bilim Derg. 2017 Mar;3(1):125–38. Available from: <URL>
  • 67. Nural Y. Synthesis and Determination of Acid Dissociation Constants in Dimethyl Sulfoxide–Water Hydroorganic Solvent of 5,5-Diphenylpyrrolidine N-Aroylthiourea Derivatives. J Turkish Chem Soc Sect A Chem. 2017 Aug;841–54. Available from: <URL>
  • 68. Atabey H, Sari H, Al-Obaidi FN. Protonation Equilibria of Carminic Acid and Stability Constants of Its Complexes with Some Divalent Metal Ions in Aqueous Solution. J Solution Chem. 2012 Jun;41(5):793–803. Available from: <URL>
Toplam 64 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Analitik Kimya, Organik Kimyasal Sentez
Bölüm ARAŞTIRMA MAKALELERİ
Yazarlar

Çağla Efeoğlu 0000-0003-2794-8961

Şit Tiken 0000-0003-0214-5433

Hayati Sarı 0000-0002-9245-0871

Yahya Nural 0000-0002-5986-8248

Proje Numarası 2021-1-TP2-4217
Yayımlanma Tarihi 30 Ağustos 2023
Gönderilme Tarihi 22 Mart 2023
Kabul Tarihi 19 Haziran 2023
Yayımlandığı Sayı Yıl 2023 Cilt: 10 Sayı: 3

Kaynak Göster

Vancouver Efeoğlu Ç, Tiken Ş, Sarı H, Nural Y. Synthesis and Determination of Acid Dissociation Constants of Bis-Acyl Thiourea Derivatives. JOTCSA. 2023;10(3):837-46.