Unsymmetrical Thiourea Derivatives: Synthesis and Evaluation as Promising Antioxidant and Enzyme Inhibitors

References

• Tajbin R , SoniaZ, SauravHet al. In vitro antioxidant activity of Antidesma bunius leaf extracts. J. Pharmacogn. Phytochem.10(3), 1–6 (2021).
   Google Scholar
• Dontha S . A review on antioxidant methods. Asian J. Pharm. Clin. Res.9(2), 14–32 (2016).
   Google Scholar
• Liu X , JiaJ, JingXet al. Antioxidant activities of extracts from sarcocarp of Cotoneaster multiflorus. J. Chem.2018, 1–7 (2018).
   Web of Science ®Google Scholar
• Fritz KL , SeppanenCM, KurzerMSet al. The in vivo antioxidant activity of soybean isoflavones in human subjects. Nutr. Res.23(4), 479–487 (2003).
   Web of Science ®Google Scholar
• Oteiza PI , ErlejmanAG, VerstraetenSVet al. Flavonoid-membrane interactions: a protective role of flavonoids at the membrane surface. Clin. Dev. Immunol.12(1), 19–25 (2005).
   PubMedGoogle Scholar
• Hadjipavlou-Litina D , MagoulasGE, KrokidisMet al. Syntheses and evaluation of the antioxidant activity of acitretin analogs with amide bond (s) in the polyene spacer. Eur. J. Med. Chem.45(1), 298–310 (2010).
   PubMed Web of Science ®Google Scholar
• Ramarathnam N , OsawaT, OchiHet al. The contribution of plant food antioxidants to human health. Trends Food Sci. Technol.6(3), 75–82 (1995).
   Web of Science ®Google Scholar
• Krishnaiah D , SarbatlyR, NithyanandamR. A review of the antioxidant potential of medicinal plant species. Food Bioprod. Process89(3), 217–233 (2011).
   Web of Science ®Google Scholar
• Loncaric M , StrelecI, MoslavacTet al. Lipoxygenase inhibition by plant extracts. Biomolecules11(2), 152 (2021).
   PubMed Web of Science ®Google Scholar
• Newcomer ME , BrashAR. The structural basis for specificity in lipoxygenase catalysis. Protein Sci.24(3), 298–309 (2015).
   PubMed Web of Science ®Google Scholar
• Pallavi PC , SinghAK, SinghSet al. In silico structural and functional insights into the lipoxygenase enzyme of legume Cajanus cajan. Int. J. Recent. Innov. Trends Comput. Commun.5, 87–91 (2014).
   Google Scholar
• Srivastava P , VyasVK, VariyaBet al. Synthesis, anti-inflammatory, analgesic, 5-lipoxygenase (5-LOX) inhibition activities, and molecular docking study of 7-substituted coumarin derivatives. Bioorg. Chem.67, 130–138 (2016).
   PubMed Web of Science ®Google Scholar
• Kuhn H , WaltherM, KubanRJ. Mammalian arachidonate 15-lipoxygenases: structure, function, and biological implications. Prostaglandins Other Lipid Mediat.68, 263–290 (2002).
   PubMed Web of Science ®Google Scholar
• Pooryaghoobi N , BakavoliM, AlimardaniMet al. New Insight into the S.A.R. of Pyrimido [4,5-b][1,4]Benzothiazines as 15-lipoxygenase Inhibitors. Iran J. Basic. Med. Sci.16(6), 784 (2013).
   PubMed Web of Science ®Google Scholar
• Mahdavi M , ShiraziMS, TaherkhaniRet al. Synthesis, biological evaluation, and docking study of 3-aroyl-1-(4-sulfamoyl phenyl) thiourea derivatives as 15-lipoxygenase inhibitors. Eur. J. Med. Chem.82, 308–313 (2014).
   PubMed Web of Science ®Google Scholar
• Harrison R . Structure and function of xanthine oxidoreductase: where are we now?Free Radic. Biol. Med.33(6), 774–797 (2002).
   PubMed Web of Science ®Google Scholar
• George J , StruthersAD. The role of urate and xanthine oxidase inhibitors in cardiovascular disease. Cardiovasc. Drug Rev.26(1), 59–64 (2008).
   Google Scholar
• McCord JM . Oxygen-derived free radicals in postischemic tissue injury. NEJM312(3), 159–163 (1985).
   PubMed Web of Science ®Google Scholar
• Saavedra WF , PaolocciN, StJohn MEet al. Imbalance between xanthine oxidase and nitric oxide synthase signaling pathways underlies mechanoenergetic uncoupling in the failing heart. Circ. Res.90(3), 297–304 (2002).
   PubMed Web of Science ®Google Scholar
• Minhas KM , SaraivaRM, SchuleriKHet al. Xanthine oxidoreductase inhibition causes reverse remodeling in rats with dilated cardiomyopathy. Circ. Res.98(2), 271–279 (2006).
   PubMed Web of Science ®Google Scholar
• Sugumar D , SaravananJ, EmdormiRet al. An update on the role of Nrf2 and its activators in diseases associated with oxidative stress. Indian J. Pharm. Sci.82(2), 184–192 (2020).
   Web of Science ®Google Scholar
• Mohanta PK , DharS, SamalSKet al. 1-(Methyldithiocarbonyl) imidazole: a useful thiocarbonyl transfer reagent for synthesis of substituted thioureas. Tetrahedron56(4), 629–637 (2000).
   Web of Science ®Google Scholar
• Ngaini Z , WanZulkiplee WSH, WSHet al. One-pot multicomponent synthesis of thiourea derivatives in cyclotriphosphazenes moieties. J. Chem.2017, 1–7 (2017).
   Google Scholar
• Abd Halim AN , NgainiZ. Synthesis and bacteriostatic activities of bis (thiourea) derivatives with variable chain length. J. Chem.2016, 1–7 (2016).
   Web of Science ®Google Scholar
• Choi J , JeeJG. Repositioning of thiourea-containing drugs as tyrosinase inhibitors. Int. J. Mol. Sci.16(12), 28534–28548 (2015).
   PubMed Web of Science ®Google Scholar
• Taha M , AlshamraniFJ, RahimFet al. Synthesis of novel triazinoindole-based thiourea hybrid: a study on α-glucosidase inhibitors and their molecular docking. Molecules24(21), 3819 (2019).
   PubMed Web of Science ®Google Scholar
• Imran S , TahaM, IsmailNHet al. Synthesis, biological evaluation, and docking studies of novel thiourea derivatives of bisindolylmethane as carbonic anhydrase II inhibitor. Bioorg. Chem.62, 83–93 (2015).
   PubMed Web of Science ®Google Scholar
• Khan KM , NazF, TahaMet al. Synthesis and in vitro urease inhibitory activity of N,N‘-disubstituted thioureas. Eur. J. Med. Chem.74, 314–323 (2014).
   PubMed Web of Science ®Google Scholar
• Taha M , IsmailNH, JamilWet al. Synthesis and evaluation of unsymmetrical heterocyclic thioureas as potent β-glucuronidase inhibitors. Med. Chem. Res.24(8), 3166–3173 (2015).
   Web of Science ®Google Scholar
• Bano B , KhanKM, LodhiAet al. Synthesis, in vitro urease inhibitory activity, and molecular docking studies of thiourea and urea derivatives. Bioorg. Chem.80, 129–144 (2018).
   PubMed Web of Science ®Google Scholar
• Wahid S , JahangirS, VersianiMAet al. Atenolol thiourea hybrid as potent urease inhibitors: design, biology-oriented drug synthesis, inhibitory activity screening, and molecular docking studies. Bioorg. Chem.94, 103359 (2020).
   PubMed Web of Science ®Google Scholar
• Khan M , KhanKM, ParveenSet al. Syntheses, in vitro urease inhibitory activities of urea and thiourea derivatives of tryptamine, their molecular docking, and cytotoxic studies. Bioorg. Chem.83, 595–610 (2019).
   PubMed Web of Science ®Google Scholar
• Kilic A , BeyazsakalL, IşıkMet al. Mannich reaction derived novel boron complexes with amine-bis (phenolate) ligands: synthesis, spectroscopy and in vitro/in silico biological studies. J. Organomet. Chem.927, 121542 (2020).
   Web of Science ®Google Scholar
• Lolak N , AkocakS, DurgunMet al. Novel bis-ureido-substituted sulfaguanidines and sulfisoxazoles as carbonic anhydrase and acetylcholinesterase inhibitors. Mol. Divers27(4), 1735–1749 (2023).
   PubMed Web of Science ®Google Scholar
• Raziq N , SaeedM, AliMSet al. A new glycosidic antioxidant from Ranunculus muricatus L. (Ranunculaceae) exhibited lipoxygenase and xanthine oxidase inhibition properties. Nat. Prod. Res.31(11), 1251–1257 (2017).
   PubMed Web of Science ®Google Scholar
• Tappel AL . The mechanism of the oxidation of unsaturated fatty acids catalyzed by hematin compounds. Arch. Biochem. Biophys.44(2), 378–395 (1953).
   PubMed Web of Science ®Google Scholar
• Chan WS , WenPC, ChiangHC. Structure–activity relationship of caffeic acid analogs on xanthine oxidase inhibition. Anticancer Res.15(3), 703–707 (1995).
   PubMed Web of Science ®Google Scholar
• Van Hoorn DE , NijveldtRJ, Van LeeuwenPAet al. Accurate prediction of xanthine oxidase inhibition based on the structure of flavonoids. Eur. J. Pharmacol.451(2), 111–118 (2002).
   PubMed Web of Science ®Google Scholar
• Frisch MJ , TrucksGW, SchlegelHBet al. Gaussian 09, Revision. Gaussian, Inc., CT, USA (2009).
   Google Scholar
• Lee C , YangW, ParrRG. Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B37(2), 785 (1988).
   PubMed Web of Science ®Google Scholar
• Parr RG . Density functional theory of atoms and molecules. In: Horizons of Quantum Chemistry.Proceedings of the Third International Congress of Quantum Chemistry Held at Kyoto, Japan, Springer, Amsterdam, The Netherlands, 5–15 (1980).
   Google Scholar
• Raghavachari K . Perspective on ‘Density functional thermochemistry. III. The role of exact exchange,’ Becke AD (1993) J. Chem. Phys 98: 5648–5652. Theor. Chem. Acc.103, 361–363 (2000).
   Web of Science ®Google Scholar
• Petersson GA , Al-LahamMA. A complete basis set model chemistry. II. Open-shell systems and the total energies of the first-row atoms. J. Chem. Phys.94(9), 6081–6090 (1991).
   Web of Science ®Google Scholar
• Inc, C.C.G . Molecular operating environment (M.O.E.).Chemical Computing Group Inc., 1010 (2016).
   Google Scholar
• Demir Y , TokalıFS, KalayEet al. Synthesis and characterization of novel acyl hydrazones derived from vanillin as potential aldose reductase inhibitors. Mol. Divers27(4), 1713–1733 (2023).
   PubMed Web of Science ®Google Scholar
• Işık M , DemirY, DurgunMet al. Molecular docking and investigation of 4-(benzylideneamino)-and 4-(benzylamino)-benzenesulfonamide derivatives as potent AChE inhibitors. Chem. Pap.74(5), 1395–1405 (2020).
   Web of Science ®Google Scholar
• Türkeş C . A potential risk factor for paraoxonase 1: in silico and in-vitro analysis of the biological activity of proton-pump inhibitors. J. Pharm. Pharmacol.71(10), 1553–1564 (2019).
   PubMed Web of Science ®Google Scholar
• Samad A , AjmalA, MahmoodAet al. Identification of novel inhibitors for SARS-CoV-2 as therapeutic options using machine learning-based virtual screening, molecular docking, and MD simulation. Front Mol. Biosci.10, 1060076 (2023).
   PubMed Web of Science ®Google Scholar