Urease: a highly efficient biocatalyst for synthesis of polyhydroquinolines and polyhydroacridines from the ammonia formed in situ

Siddaiah V, Basha GM, Rao GP, Prasad UV, Rao RS (2012) PEG-mediated catalyst-free synthesis of hantzsch 1,4-dihydropyridines and polyhydroquinoline derivatives. Synth Commun 42:627–634. https://doi.org/10.1080/00397911.2010.528289 Jadhvar SC, Kasraliker HM, Goswami SV, Chakrawar AV, Bhusare SR (2017) One-pot synthesis and evaluation of anticancer activity of polyhydroquinoline derivatives catalyzed by [Msim]Cl. Res Chem Intermed 43:7211–7221. https://doi.org/10.1007/s11164-017-3069-2 Maleki A, Akbarzade AR, Bhat AR (2017) Green synthesis of polyhydroquinolines via MCR using Fe3O4/SiO2–OSO3H nanostructure catalyst and prediction of their pharmacological and biological activities by PASS. J Nanostruct Chem 7:309–316. https://doi.org/10.1007/s40097-017-0240-7 Hantzsch A (1881) Condensationsprodukte aus Aldehydammoniak und ketonartigen Verbindungen. Ber Dtsch Chem Ges 14:1637–1638 Hantzsch A (1882) Ueber die synthese pyridinartiger verbindungen aus acotessigäther und aldehydainmcniak. Justus Liebigs Ann Chem 215:1–82. https://doi.org/10.1002/jlac.18822150102 Ruijter E, Scheffelaar R, Orru RVA (2011) Multicomponent reaction design in the quest for molecular complexity and diversity. Angew Chemie Int Ed 50:6234–6246. https://doi.org/10.1002/anie.201006515 Choudhury P, Ghosh P, Basu B (2020) Amine-functionalized graphene oxide nanosheets (AFGONs): an efficient bifunctional catalyst for selective formation of 1,4-dihydropyridines, acridinediones and polyhydroquinolines. Mol Divers 24:283–294. https://doi.org/10.1007/s11030-019-09949-0 Chen Y, Zhang Z, Jiang W, Zhang M, Li Y (2019) RuIII@CMC/Fe3O4 hybrid: an efficient, magnetic, retrievable, self-organized nanocatalyst for green synthesis of pyranopyrazole and polyhydroquinoline derivatives. Mol Divers 23:421–442. https://doi.org/10.1007/s11030-018-9887-3 Ghorbani-Choghamarani A, Mohammadi M, Tamoradi T, Ghadermazi M (2019) Covalent immobilization of Co complex on the surface of SBA-15: green, novel and efficient catalyst for the oxidation of sulfides and synthesis of polyhydroquinoline derivatives in green condition. Polyhedron 158:25–35. https://doi.org/10.1016/j.poly.2018.10.054 Das SK, Mondal S, Chatterjee S, Bhaumik A (2018) N-rich porous organic polymer as heterogeneous organocatalyst for the one-pot synthesis of polyhydroquinoline derivatives through the hantzsch condensation reaction. ChemCatChem 10:2488–2495. https://doi.org/10.1002/cctc.201702013 Elhamifar D, Badin P, Karimipoor G (2017) Alkyl-imidazolium based organosilica supported Fe/porphyrin complex: as novel, highly efficient and reusable catalyst for the unsymmetrical Hantzsch reaction. J Colloid Interface Sci 499:120–127. https://doi.org/10.1016/j.jcis.2017.03.084 Karhale S, Bhenki C, Rashinkar G, Helavi V (2017) Covalently anchored sulfamic acid on cellulose as heterogeneous solid acid catalyst for the synthesis of structurally symmetrical and unsymmetrical 1,4-dihydropyridine derivatives. New J Chem 41:5133–5141. https://doi.org/10.1039/c7nj00685c Kardooni R, Kiasat AR, Motamedi H (2017) Designing of a novel dual-function silica-iron oxide hybrid based nanocomposite, Fe3O4@SiO2–PEG/NH2, and its application as an eco-catalyst for the solvent-free synthesis of polyhydroacridines and polyhydroquinolines. J Taiwan Inst Chem Eng 81:373–382. https://doi.org/10.1016/j.jtice.2017.10.013 Yaghoubi A, Dekamin MG, Karimi B (2017) Propylsulfonic acid-anchored isocyanurate-based periodic mesoporous organosilica (PMO-ICS-PrSO3H): a highly efficient and recoverable nanoporous catalyst for the one-pot synthesis of substituted polyhydroquinolines. Catal Lett 147:2656–2663. https://doi.org/10.1007/s10562-017-2159-5 Goli-Jolodar O, Shirini F, Seddighi M (2016) Introduction of a novel nanosized N-sulfonated Brönsted acidic catalyst for the promotion of the synthesis of polyhydroquinoline derivatives via Hantzsch condensation under solvent-free conditions. RSC Adv 6:26026–26037. https://doi.org/10.1039/c6ra04148e Zarnegar Z, Safari J, Kafroudi ZM (2015) Co3O4-CNT nanocomposites: a powerful, reusable, and stable catalyst for sonochemical synthesis of polyhydroquinolines. New J Chem 39:1445–1451. https://doi.org/10.1039/c4nj01588f Magyar Á, Hell Z (2019) An efficient one-pot four-component synthesis of 9-aryl-hexahydroacridine-1,8-dione derivatives in the presence of a molecular sieves supported iron catalyst. Catal Lett 149:2528–2534. https://doi.org/10.1007/s10562-019-02845-0 Madankumar N, Pitchumani K (2018) β-Cyclodextrin monosulphonic acid promoted multicomponent synthesis of 1,8-dioxodecahydroacridines in water. ChemistrySelect 3:10886–10891. https://doi.org/10.1002/slct.201802244 Zarei Z, Akhlaghinia B (2017) ZnII doped and immobilized on functionalized magnetic hydrotalcite (Fe3O4/HT-SMTU-ZnII): a novel, green and magnetically recyclable bifunctional nanocatalyst for the one-pot multi-component synthesis of acridinediones under solvent-free conditions. New J Chem 41:15485–15500. https://doi.org/10.1039/c7nj03281a Eidi E, Kassaee MZ, Nasresfahani Z (2015) Nanocrystalline TiO2, via green combustion synthesis, as an efficient and reusable catalyst for the preparation of 1,8-dioxooctahydroxanthenes and 1,8-dioxodecahydroacridines. Appl Organomet Chem 29:793–797. https://doi.org/10.1002/aoc.3370 Wohlgemuth R (2010) Biocatalysis-key to sustainable industrial chemistry. Curr Opin Biotechnol 21:713–724. https://doi.org/10.1016/j.copbio.2010.09.016 Tamaddon F, Ghazi S (2015) Urease: a highly biocompatible catalyst for switchable Biginelli reactionand synthesis of 1,4-dihydropyridines from the in situ formed ammonia. Catal Commun 72:63–67. https://doi.org/10.1016/j.catcom.2015.09.006 Tamaddon F, Arab D (2019) Urease covalently immobilized on cotton-derived nanocellulose-dialdehyde for urea detection and urea-based multicomponent synthesis of tetrahydro-pyrazolopyridines in water. RSC Adv 9:41893–41902. https://doi.org/10.1039/c9ra05240b Vargas AY, Rojas HA, Romanelli GP, Martínez JJ (2017) Synthesis of 1,4-dihydropyrimidines with immobilized urease: effect of method immobilization on magnetic supports. Green Process Synth 6:377–384. https://doi.org/10.1515/gps-2016-0143