تحضير وتشخيص والفعالية المضادة للأكسدة لمشتقات 1-(2-فيوريل) ثايويوريا ودراسة النمذجة الجزيئية لها كمثبطات قوية لانزيم اليوريز
محتوى المقالة الرئيسي
الملخص
يتضمن هذا العمل تحضير ثلاثة عشر مركبا من 1-(2-فيوريل) كمشتقات للثايويوريا 1-13 بوساطة تحويل المركب كلوريد 2-فيوريل الى ايزوثايوسيانيت الفيوريل بواسطة مفاعلته مع ايزوثايوسيانات البوتاسيوم باستعمال الاسيتون الجاف كمذيب في وقت تصعيد قليل نسبيا ومن ثم تم إضافة مجموعة من الامينات (امينات أولية، امينات ثانوية) الى وسط التفاعل بصورة مستقلة للحصول على مشتق الثايويريا المطلوب. تم تشخيص المركبات طيفيا بواسطة تقنيات (الاشعة تحت الحمراء، الرنين النووي المغناطيسي البروتوني والرنين النووي المغناطيسي الكاربوني). تم تقييم فعالية بعض المركبات كمضادات للأكسدة وذلك بطريقة اقتناص الجذور الحرة المتولدة من المركب (2,2-ثنائي فنيل-1-بكرل هيدرازيل) (DPPH) وقياسها طيفيا. كذلك تم دراسة النمذجة الجزيئية لجميع المركبات نظريا كمثبطات لانزيم اليوريز Bacillus pasteurii ذي الرقم (4UBP) وذلك باستخدام البرنامج الحاسوبي Autodock 4.2.6.
Received 13/09/2022
Revised 10/02/2023
Accepted 12/02/2023
Published 20/06/2023
تفاصيل المقالة
هذا العمل مرخص بموجب Creative Commons Attribution 4.0 International License.
كيفية الاقتباس
المراجع
Özgeriş B. Design, synthesis, characterization, and biological evaluation of nicotinoyl thioureas as antimicrobial and antioxidant agents. J Antibiot. 2021 Jan 14 [cited 2022 Aug 22]; 74(4): 233–43. https://doi.org/10.1038/s41429-020-00399-7.
Wang H, Zhai ZW, Shi YX, Tan CX, Weng JQ, Han L, et al. Novel Trifluoromethylpyrazole Acyl Thiourea Derivatives: Synthesis, Antifungal Activity and Docking Study. Lett Drug Des Discov. 2018 Jul 5; 16(7): 785–91. https://doi.org/10.2174/1570180815666180704103047.
Zahra U, Zaib S, Saeed A, Rehman M ur, Shabir G, Alsaab HO, et al. 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 15; 198: 157–67. https://doi.org/10.1016/J.IJBIOMAC.2021.12.064.
Min LJ, Zhai ZW, Shi YX, Han L, Tan CX, Weng JQ, et al. Synthesis and biological activity of acyl thiourea containing difluoromethyl pyrazole motif. Phosphorus Sulfur Silicon Relat Elem. 2019 Jan 2 [cited 2022 Aug 21]; 195(1): 22–8. https://doi.org/10.1080/10426507.2019.1633530
Aziz H, Saeed A, Khan MA, Afridi S, Jabeen F. Synthesis, characterization, antimicrobial, antioxidant and computational evaluation of N-acyl-morpholine-4-carbothioamides. Mol Divers. 2020 Feb 25 [cited 2022 Aug 22];25(2):763–76. https://doi.org/10.1007/S11030-020-10054-W.
Ghazal K, Shoaib S, Khan M, Khan S, Rauf MK, Khan N, et al. 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 5; 1177: 124–30. https://doi.org/10.1016/J.MOLSTRUC.2018.09.028.
Jeyalakshmi K, Haribabu J, Balachandran C, Narmatha E, Bhuvanesh NSP, Aoki S, et al. Highly active copper(I) complexes of aroylthiourea ligands against cancer cells-synthetic and biological studies. New J Chem. 2019; 43(7): 3188–98. https://doi.org/10.1039/c8nj04246b.
Mitrea DG, Cîrcu V. Synthesis and characterization of novel acylthiourea compounds used in ions recognition and sensing in organic media. Spectrochim Acta A Mol Biomol Spectrosc. 2021 Sep 5; 258: 1-8. https://doi.org/10.1016/j.saa.2021.119860.
Hakeem HS, Abbas NK. Preparing and studying structural and optical properties of Pb1-xCdxS nanoparticles of solar cells applications. Baghdad Sci J. 2021; 18(3): 640–8. https://doi.org/10.21123/BSJ.2021.18.3.0640.
Shanan ZJ, Majed MD, Ali HMJ. Effect of the concentration of copper on the properties of Copper Sulfide nanostructure. Baghdad Sci J. 2022; 19(1): 225–32. https://doi.org/10.21123/BSJ.2022.19.1.0225.
Al-Amily DH, Hassan M. Design, synthesis, and docking study of acyl thiourea derivatives as possible histone deacetylase inhibitors with a novel zinc binding group. Sci Pharm. 2019 Dec 1; 87(4): 28-43 https://doi.org/10.3390/scipharm87040028.
Saeed A, Ashraf S, Shabir G, Hökelek T, Flörke U, Mukhtar A, et al. Synthesis, X-Ray crystallography and HF/DFT analysis of N(diethylcarbamothioyl) furan-2-carboxamide, analyzed by experimental and theoretical methods. J Mol Struct. 2022 Nov 15; 1268: 133721. https://doi.org/10.1016/J.MOLSTRUC.2022.133721.
Mustafa MN, Saeed A, Channar PA, Larik FA, Zain-ul abideen M, Shabir G, et al. Synthesis, molecular docking and kinetic studies of novel quinolinyl based acyl thioureas as mushroom tyrosinase inhibitors and free radical scavengers. Bioorg Chem. 2019 Sep 1; 90: 103063. https://doi.org/10.1016/j.bioorg.2019.103063.
O’Boyle NM, Banck M, James CA, Morley C, Vandermeersch T, Hutchison GR. Open Babel: An Open chemical toolbox. J Cheminform . 2011 Oct 7 [cited 2022 Apr 20]; 3(10): 1–14. https://doi.org/10.1186/1758-2946-3-33/TABLES/2
Benini S, Rypniewski WR, Wilson KS, Miletti S, Ciurli S, Mangani S. The complex of Bacillus pasteurii urease with acetohydroxamate anion from X-ray data at 1.55 Å resolution. J Biol Inorg Chem [Internet]. 2000 [cited 2022 Mar 29]; 5(1): 110–8. https://doi.org/10.1007/S007750050014.
Schrödinger LLC. The PyMOL Molecular Graphics System, Version 2.5.2. 2021. https://pymol.org/2/support.html?#citing
Sanner MF. Python: a programming language for software integration and development. J Mol Graph Model 1999 [cited 2022 Mar 29]; 17(1): 57–61. Https://pubmed.ncbi.nlm.nih.gov/10660911/
Adasme MF, Linnemann KL, Bolz SN, Kaiser F, Salentin S, Haupt VJ, et al. PLIP 2021: Expanding the scope of the protein-ligand interaction profiler to DNA and RNA. Nucleic Acids Res. 2021 Jul 2; 49(W1): W530–4. https://doi.org/10.1093/NAR/GKAB294.
Stierand K, Maaß PC, Rarey M. Molecular complexes at a glance: automated generation of two-dimensional complex diagrams. Bioinformatics. 2006 Jul 15 [cited 2022 Aug 17]; 22(14): 1710–6. https://doi.org/10.1093/BIOINFORMATICS/BTL150.
Schöning K, Schöning-Stierand S, Diedrich K, Ehrt C, Flachsenberg F, Graef J, et al. ProteinsPlus: a comprehensive collection of web-based molecular modeling tools. Nucleic Acids Res . 2022 Jul 5 [cited 2022 Aug 17]; 50(W1): W611–5. https://doi.org/10.1093/NAR/GKAC305.
Solomons TWG, Fryhle CB, Snyder SA. Organic Chemistry. 4th ed. USA: Wiley; 2007. 792–794 p.
Zahra U, Saeed A, Fattah TA, Fï U, Erben MF. Recent trends in chemistry, structure, and various applications of 1-acyl-3-substituted thioureas: a detailed review. RSC Adv. 2022 Apr 26; 12(20): 12710–45. https://doi.org/10.1039/d2ra01781d.
Gandhaveeti R, Konakanchi R, Jyothi P, Bhuvanesh NSP, Anandaram S. Unusual coordination mode of aroyl/acyl thiourea ligands and their π-arene ruthenium (II) piano-stool complexes: Synthesis, molecular geometry, theoretical studies and biological applications. Appl Organomet Chem. 2019 May 1; 33(5): 1-13. https://doi.org/10.1002/aoc.4899.
Pavia DL, Lampman GM, Kriz GS, Vyvyan JR. Introduction to spectroscopy. 4th ed. Brooks/ Cole; 2009. 2–7 p.
Singh G, Rani S. Organosilatranes with Acylthiourea Derivatives – Metal-Ion Binding, Substituent-Dependent Sensitivity, and Prospects for the Fabrication of Magnetic Hybrids. Eur J Inorg Chem. 2016 Jun 1; 2016(18): 3000–11. https://doi.org/10.1002/ejic.201600204.
Al-Jeilawi UH, Al-Majidi SM, Al-Saadie KA. Synthesis, Characterization and Evaluation the Corrosion Inhibition for Carbon Steel in H2SO4 Solution of Several New Thiourea Derivatives. J Thi-Qar Sci. 2013 Dec; 8(5): 1–18.
Zhang Y, Zhang X, Qiao L, Ding Z, Hang X, Qin B, et al. Synthesis, structures, drug-likeness, in vitro evaluation and in silico docking on novel N-benzoyl-N′-phenyl thiourea derivatives. J Mol Struct. 2019 Jan 15; 1176: 335–45. https://doi.org/10.1016/j.molstruc.2018.08.069.
Phongpaichit S, Nikom J, Rungjindamai N, Sakayaroj J, Hutadilok-Towatana N, Rukachaisirikul V, et al. Biological activities of extracts from endophytic fungi isolated from Garcinia plants. FEMS Immunol Med Microbiol . 2007 Dec 1 [cited 2022 Jul 27]; 51(3): 517–25. https://doi.org/10.1111/J.1574-695X.2007.00331.X.
Huong DQ, Bay M van, Nam PC. Antioxidant activity of thiourea derivatives: An experimental and theoretical study. J Mol Liq. 2021 Oct 15; 340: 117149. https://doi.org/10.1016/J.MOLLIQ.2021.117149.