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Research Article

Pyrido-pyrimido-thiadiazinones: green synthesis, molecular docking studies and biological investigation as obesity inhibitors

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Pages 1275-1286 | Received 28 Oct 2022, Accepted 13 Dec 2022, Published online: 23 Dec 2022

References

  • Costa G, Gidaro MC, Vullo D, et al. Active components of essential oils as anti-obesity potential drugs investigated by in silico techniques. JAgric Food Chem. 2016;64:5295–5300.
  • Sumaryada T, Simamora REM, Ambarsari L. Docking evaluation of catechin and its derivatives on fat mass and obesity-associated (FTO) protein for anti-obesity agent. J Appl Pharm Sci. 2018;8:63–68.
  • Gandhi SP, Lokhande KB, Swamy VK, et al. Computational data of phytoconstituents from Hibiscus rosa-sinensis on various anti-obesity targets. Data Br. 2019;24:103994.
  • Gomha SM, Riyadh SM. Cellulose sulfuric acid as an eco-friendly catalyst for novel one-pot synthesis of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5-ones. J Braz Chem Soc 2015;26:916–923.
  • Qurioga J, Hormaza A, Insuasty B, et al. Synthesis of pyrimido[4,5-b]quinolines in the reaction of 6-aminopyrimidines with dimedone and benzaldehydes. J Heterocycl Chem. 1998;35:231–233.
  • Gomha SM, Abdallah MA, Mourad MA, et al. Application of Mannich and Michael reactions in synthesis of pyridopyrimido[2,1-b][1,3,5]thiadiazinones and pyridopyrimido[2,1-b][1,3]thiazinones as anticancer agents. Heterocycles. 2016;92:688–699.
  • Nasr MN, Gineinah MM. Pyrido[2,3-d]pyrimidines and pyrimido[5′,4′:5,6]pyrido[2, 3-d]pyrimidines as new antiviral agents: synthesis and biological activity. Arch Pharm. 2002;335:289–295.
  • Taylor EC, Palmer DC, George TJ, et al. Synthesis and biological activity of L-5-deazafolic acid and L-deazaaminopterin: synthetic strategies to 5-deazapteridines. J Org Chem. 1983;48:4852–4860.
  • Nam G, Yoon CM, Kim E, et al. Syntheses and evaluation of pyrido[2,3-d]pyrimidine-2,4-diones as PDE IV inhibitors. Bioorg Med Chem Lett. 2011;5:611–614.
  • Pai SB, Liu SH, Zhu ZL, et al. Inhibition of hepatitis B virus by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyl uracil. Antimicrob Agents Chemother. 1996;40:380–386.
  • Huron DR, Corre ME, Kraker AJ, et al. A novel pyridopyrimidine inhibitor of Abl kinase is a picomolar inhibitor of Bcr-abl-driven K562 cells and Is effective against STI571-resistant Bcr-abl mutants. Clinical Cancer Res. 2003;9:1267–1273.
  • Smejkalova H, Erb TJ, Fuchs G. Methanol assimilation in methylobacterium extorquens AM1: demonstration of all enzymes and their regulation. PLoS ONE. 2010;5:e13001.
  • Erb TJ, Berg IA, Brecht V, et al. Synthesis of C5-dicarboxylic acids from C2-units involving crotonyl-CoA carboxylase/reductase: the ethylmalonyl-CoA pathway. Proc Natl Acad Sci USA. 2007;104:10631–10636.
  • Khomyakova M, Bukmez O, Thomas LK, et al. A methylaspartate cycle in haloarchaea. Science 2011;331:334–337.
  • Gangjee A, Vasudevan A, Queener SF, et al. 2,4-Diamino-5-deaza-6-substituted pyrido[2,3-d]pyrimidine antifolates as potent and selective nonclassical inhibitors of dihydrofolate reductases. J Med Chem. 1996;39:1438–1446.
  • Gangjee A, Adair OO, Pagley M, et al. N9-substituted 2,4-diaminoquinazolines: synthesis and biological evaluation of lipophilic inhibitors of pneumocystis carinii and toxoplasma gondii dihydrofolate reductase. J Med Chem 2008;51:6195–6200.
  • Chan DCM, Rosowsky A. Synthesis of the lipophilic antifolate piritrexim via a palladium(0)-catalyzed cross-coupling reaction. J Org Chem. 2005;70:1364–1368.
  • Tong L. Structure and function of biotin-dependent carboxylases. Cell Mol Life Sci. 2013;5:863–891.
  • Shivaiah K-K, Upton B, Nikolau BJ. Kinetic, structural, and mutational analysis of Acyl-CoA carboxylase from thermobifida fusca YX. Front Mol Biosci. 2021;7:615614.
  • Subramaniapillai SG. Mannich reaction: a versatile and convenient approach to bioactive skeletons. J Chem Sci 2013;125:467–482.
  • Roman G. Mannich bases in medicinal chemistry and drug design. Eur J Med Chem. 2015;89:743–816.
  • Mammadbayli EH, Hajiyeva GE, Ibrahimli SI, et al. Synthesis and antimicrobial activity of norbornene-containing Mannich bases. Russ J Appl Chem. 2019;92:1161–1169.
  • Afsah EMM, Kandil ED, Abdelmageed SM, et al. Synthesis of novel Mannich bases and hybrid Mannich bases related to isoindolin-1,3-dione. J Heterocycl Chem. 2020;57:346–354.
  • Banerjee D, Yogeeswari P, Bhat P, et al. Novel isatinyl thiosemicarbazones derivatives as potential molecule to combat HIV-TB co-infection. Eur J Med Chem. 2011;46:106–121.
  • Roman G. Anticancer activity of Mannich bases: a review of recent literature. ChemMedChem. 2022;17:e202200258.
  • Liu C, Zhou L, Jiang D, et al. Multicomponent reactions of Aldo-X bifunctional reagent α-oxoketene dithioacetals and indoles or amines: divergent synthesis of dihydrocoumarins, quinolines, furans, and pyrroles. Asian J Org Chem. 2016;5:367–372.
  • Cioc RC, Ruijter E, Orru RVA. Multicomponent reactions: advanced tools for sustainable organic synthesis. Green Chem. 2014;16:2958–2975.
  • Abu-Melha S, Muhammad ZA, Abouzid AS, et al. Multicomponent synthesis, DFT calculations and molecular docking studies of novel thiazolyl-pyridazinones as potential antimicrobial agents against antibiotic-resistant bacteria. J Mol Str. 2021;1234:130180.
  • Abu-Melha S, Gomha SM, Abouzied AS, et al. Microwave-assisted one pot three-component synthesis of novel bioactive thiazolyl-pyridazinediones as potential antimicrobial agents against antibiotic-resistant bacteria. Molecules. 2021;26:4260.
  • Alshabanah LA, Al-Mutabagani LA, Gomha SM, et al. Three-component synthesis of some new coumarin derivatives as anti-cancer agents. Front Chem. 2022;9:762248S.
  • Gomha SM, Kheder NA, Abdelhamid AO, et al. One pot single step synthesis and biological evaluation of some novel bis(1,3,4-thiadiazole) derivatives as potential cytotoxic agents. Molecules. 2016;21:1532.
  • Gomha SM, Edrees MM, Faty RAM, et al. Microwave-assisted one pot three-component synthesis of some novel pyrazole scaffolds as potent anticancer agents. Chem Central J. 2017;11:37.
  • Gu Y. Multicomponent reactions in unconventional solvents: state of the art. Green Chem. 2012;14:2091–2128.
  • Mohamed MAA, Abd Allah OA, Bekhit AA, et al. Synthesis and antidiabetic activity of novel triazole derivatives containing amino acids. J Heterocycl Chem. 2020;57:2365–2378.
  • Saadati MR, Maleki B, Tayebee R, et al. 6-methylguanamine-supported cofe2o4: an efficient catalyst for one-pot three-component synthesis of Isoxazol-5(4H)-One derivatives. Polycycl Aromat Compd. 2020;42:885–896.
  • Al-Shaal MG, Hausoul PJC, Palkovits R. Efficient, solvent-free hydrogenation of α-angelica lactone catalysed by Ru/C at atmospheric pressure and room temperature. Chem Commun. 2014;50:10206–10209.
  • Sheldon RA. Selective catalytic synthesis of fine chemicals: opportunities and trends. J Mol Catal A Chem. 1996;107:75–83.
  • Acharyulu PVR, Dubey PK, Prasada Reddy PVV, et al. Synthesis of new 4(3H)-quinazolinone derivatives under solvent-free conditions using PEG-400. Arkivoc. 2008;11:104–111.
  • Sayed AR, Gomha SM, Abdelrazek FM, et al. Design, efficient synthesis and molecular docking of some novel thiazolyl-pyrazole derivatives as anticancer agents. BMC Chem. 2019;13:1–13.
  • Metwally NH, Abdelrazek FM, Eldaly SM. Synthesis, molecular docking, and biological evaluation of some novel bis-heterocyclic compounds based N,N′-([1,1′-biphenyl]-4,4′-diyl)bis(2-cyanoacetamide) as potential anticancer agents. J Heterocycl Chem. 2018;55:2668–2682.
  • Gomha SM, Muhammad ZA, Abdel-aziz HM, et al. Green synthesis, molecular docking and anticancer activity of novel 1,4-dihydropyridine-3,5-dicarbohydrazones under grind-stone chemistry. Green Chem Lett Rev. 2020;13:6–17.
  • Gomha SM, Abdelrazek FM, Abdelrahman AH, et al. Synthesis of some novel thiazole, thiadiazole and 1,4-phenylene-bis-thiazole derivatives as potent antitumor agents. Heterocycles. 2016;92:954–967.
  • Gomha SM, Riyadh SM. Synthesis of triazolo[4,3-b][1,2,4,5]tetrazines and triazolo[3,4-b][1,3,4]thiadiazines using chitosan as ecofriendly catalyst under microwave irradiation. Arkivoc. 2009;xi:58–68.
  • Gomha SM, Muhammad ZA, Abdel-aziz MR, et al. One pot synthesis of new thiadiazolyl-pyridines as anticancer and antioxidant agents. J Heterocycl Chem. 2018;55:530–536.
  • Abbas EMH, Gomha SM, Farghaly TA. Multicomponent reactions for synthesis of bioactive polyheterocyclic ring systems under controlled microwave irradiation. Arab J Chem. 2014;7:623–629.
  • Gomha SM, Riyadh SM. Multicomponent synthesis of novel penta-heterocyclic ring systems incorporating benzopyranopyridines scaffold. Synthesis. 2014;46:258–262.
  • Abdelrazek FM, Gomha SM, Abdel-aziz HM, et al. Efficient synthesis and in silico study of some novel pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives. J Heterocycl Chem. 2020;57:1759–1769.
  • Abdelrazek FM, Gomha SM, Farghaly MS, et al. One-pot, three-component synthesis of pyrido[2,3-d]pyrimidinones using aluminate sulfonic acid nanocatalyst under grinding technique. Polycycl Arom Comp. 2021;41:1472–1482.
  • Abdelmonsef AH, Mosallam AM. Synthesis, in vitro biological evaluation and in silico docking studies of new quinazolin-2,4-dione analogues as possible anticarcinoma agents. J Heterocycl Chem. 2020;57:1637–1654.
  • El-Naggar M, Mohamed ME, Mosallam AM, et al. Synthesis, characterization, antibacterial activity, and computer-aided design of novel quinazolin-2,4-dione derivatives as potential inhibitors against vibrio cholerae. Evol Bioinform. 2020;16:1–13.
  • Rashdan HRM, Abdelmonsef AH. In silico study to identify novel potential thiadiazole-based molecules as anti-Covid-19 candidates by hierarchical virtual screening and molecular dynamics simulations. Struct Chem. 2022;33(5):1727–1739.
  • Rashdan HRM, El-Naggar M, Abdelmonsef AH. Synthesis, molecular docking studies and in silico admet screening of new heterocycles linked thiazole conjugates as potent anti-hepatic cancer agents. Molecules. 2021;26:1–17.
  • Abdelmonsef AH, et al. A search for antiinflammatory therapies: synthesis, in silico investigation of the mode of action, and in vitro analyses of new quinazolin-2,4-dione derivatives targeting phosphodiesterase-4 enzyme. J Heterocycl Chem. 2021;1:1–19.
  • Abdelmonsef AH. Computer-aided identification of lung cancer inhibitors through homology modeling and virtual screening. Egypt J Med Hum Genet. 2019;20(1):1–14.
  • Noser AA, Abdelmonsef AH, El-naggar M, et al. New amino acid Schiff bases as anticancer agents via potential mitochondrial complex I-associated hexokinase inhibition and targeting AMP-protein kinases / mTOR signaling pathway. Molecules. 2021;26:1–28.
  • Abdelmonsef AH, Mohamed ME, El-Naggar M, et al. Novel quinazolin-2,4-dione hybrid molecules as possible inhibitors against malaria: synthesis and in silico molecular docking studies. Front Mol Biosci. 2020;7:1–19.
  • Noser AA, Shehadi IA, Abdelmonsef AH, et al. Newly synthesized pyrazolinone chalcones as anticancer agents via inhibiting the PI3K/Akt/ERK1/2 signaling pathway. ACS Omega. 2022;7:25265–25277.
  • Hussein HM, El-Adasy A-BA, El-Saghier AM, et al. Synthesis, characterization, in silico molecular docking, and antibacterial activities of some new nitrogen-heterocyclic analogues based on a p- phenolic unit. RSC Adv. 2022;12:12607–12621.
  • Berman HM. The protein data bank. Nucleic Acids Res. 2000;28:235–242.
  • O’Boyle NM, Banck M, James CA, et al. Open Babel: an open chemical toolbox. J Cheminform. 2011;3:33.
  • Rappé K, Casewit CJ, Colwell KS, et al. UFF, a full periodic table force field for molecular mechanics and molecular dynamics simulations. J Am Chem Soc. 1992;114:10024.
  • Brooks R, Brooks CL, Mackerell AD, et al. CHARMM: molecular dynamics simulation package. J Comput Chem 2009;30:1545–1614.
  • Dallakyan S, Olson AJ. Small-molecule library screening by docking with PyRx. Chem Biol. 2015;1263:243–250.
  • Srinivasan K, Patole PS, Kaul CL, et al. Reversal glucose intolerance by pioglitazone in high fat diet-fed rats. Methods Find Exp Clin Pharmacol. 2004;26:327.
  • Bancroft JD, Layton C. The haemtoxylins and eosin. Bancroft’s theory and practice of histological techniques, expert consult: online and print, 7: Bancroft’s theory and practice of histological techniques 2013, p. 173.
  • Nassir F, Rector RS, Hammoud GM, et al. Pathogenesis and prevention of hepatic steatosis. Gastroenterol Hepatol. 2015;11:167.