The patent review of the biological activity of tropane containing compounds

References

• Al-Hussain SA, Farghaly TA, Ibrahim MH, et al. The anti-breast cancer activity of indeno[1,2-b]pyridin-5-one and their hydrazonal precursors endowed with anti-CDK-2 enzyme activity. J Mol Struct. 2024;1295:136692. doi: 10.1016/j.molstruc.2023.136692
   Google Scholar
• Farghaly TA, Abbas EMH, Al‐Sheikh MA, et al. Synthesis of tricyclic and tetracyclic benzo[6,7]cycloheptane derivatives linked morpholine moiety as CDK2 inhibitors. Drug Dev Res. 2023;84:1127–1141. doi: 10.1002/ddr.22074
   PubMed Web of Science ®Google Scholar
• Song Y, Zhan P, Liu X. Heterocycle-thioacetic acid motif: a privileged molecular scaffold with potent, broad-ranging pharmacological activities. Curr Pharm Des. 2013;19(40):7141–7154. doi: 10.2174/13816128113199990505
   PubMed Web of Science ®Google Scholar
• Song Y, Zhan P, Zhang Q, et al. Privileged scaffolds or promiscuous binders: a glance of pyrrolo[2,1-f][1,2,4]triazines and related bridgehead nitrogen heterocycles in medicinal chemistry. Curr Pharm Des. 2013;19(8):1528–1548. doi: 10.2174/1381612811319080020
   PubMed Web of Science ®Google Scholar
• Song Y, Chen W, Kang D, et al. Old friends in new guise”: exploiting privileged structures for scaffold re-evolution/refining. Comb Chem High Throughput Screen. 2014;17(6):536–553.
   PubMed Web of Science ®Google Scholar
• Zhang L, Zhang G, Xu S, et al. Recent advances of quinones as a privileged structure in drug discovery. Eur J Med Chem. 2021;5(223):113632. doi:10.1016/j.ejmech.2021.113632
   Google Scholar
• Alqurashi RM, Farghaly TA, Sabour R, et al. Design, synthesis, antimicrobial screening and molecular modeling of novel 6,7 dimethylquinoxalin-2(1H)-one and thiazole derivatives targeting DNA gyrase enzyme. Bioorg Chem. 2023;134:106433. doi: 10.1016/j.bioorg.2023.106433
   PubMed Web of Science ®Google Scholar
• Khan I, Rehman W, Rahim F, et al. Synthesis, in vitro glucosidase inhibitory activity and molecular docking study of new Benzotriazole-Based Bis-Schiff Base Derivatives. Pharmaceuticals. 2023;16:17. doi: 10.3390/ph16010017
   Web of Science ®Google Scholar
• Kohnen-Johannsen KL, Kayser O. Tropane alkaloids: chemistry, pharmacology, biosynthesis and production. Molecules (Basel, Switzerland). 2019;24(4):796. doi: 10.3390/molecules24040796
   PubMed Web of Science ®Google Scholar
• Bedewitz MA, Jones AD, D’Auria JC, et al. Tropinone synthesis via an atypical polyketide synthase and P450-mediated cyclization. Nat Commun. 2018;9(1):5281. doi: 10.1038/s41467-018-07671-3
   PubMedGoogle Scholar
• Alsamarrai ASH. Synthesis of tropane derivatives. In: Alkaloids - their importance in nature and human life. Intech Open; 2019. doi: 10.5772/intechopen.83382.
   Google Scholar
• Grynkiewicz G, Gadzikowska M. Tropane alkaloids as medicinally useful natural products and their synthetic derivatives as new drugs. Pharmacol Rep. 2008;60:439–463.
   PubMed Web of Science ®Google Scholar
• Shim KH, Kang MJ, Sharma N, et al. Beauty of the beast: anticholinergic tropane alkaloids in therapeutics. Nat Prod Bioprospecting. 2022;12(33). doi: 10.1007/s13659-022-00357-w
   PubMedGoogle Scholar
• Wei W, Cherukupalli S, Jing L, et al. Fsp3: A new parameter for drug-likeness. Drug Discov Today. 2020;25(10):1839–1845. doi: 10.1016/j.drudis.2020.07.017
   PubMed Web of Science ®Google Scholar
• Willstaetter R. About the constitution of the split products of atropine and cocaine. Ber Dtsch Chem Ges. 1898;31:1534–1553. doi: 10.1002/cber.18980310245
   Google Scholar
• Hamilton DJ, Dekker T, Klein HF, et al. Escape from planarity in fragment-based drug discovery: a physicochemical and 3D property analysis of synthetic 3D fragment libraries. Drug Discov Today Technol. 2020;38:77–90. doi: 10.1016/j.ddtec.2021.05.001
   PubMedGoogle Scholar
• Krzyzanowski A, Pahl A, Grigalunas M, et al. Spacial Score─A Comprehensive Topological Indicator for Small-Molecule Complexity. J Med Chem. 2023;66(18):12739–12750. 28. doi: 10.1021/acs.jmedchem.3c00689
   PubMed Web of Science ®Google Scholar
• Willstaetter R, Mueller W. On the structure of ecgonine. Ber Dtsch Chem Ges. 1898;31:2655–2669. doi:10.1002/cber.18980310316
   Google Scholar
• Willstaetter R, Iglauer F. About oxymethylene tropinone. Ber Dtsch Chem Ges. 1900;33:359–365. doi:10.1002/cber.19000330151
   Google Scholar
• Kai G, Zhang A, Guo Y, et al. Enhancing the production of tropane alkaloids in transgenic anisodus acutangulus hairy root cultures by over-expressing tropinone reductase I and hyoscyamine-6β-hydroxylase. Mol Biosyst. 2012;8(11):2883–2890. doi: 10.1039/c2mb25208b
   PubMedGoogle Scholar
• Shi Z, Zou W, Zhu Z, et al. Tropane alkaloids (hyoscyamine, scopolamine and atropine) from genus Datura: extractions, contents, syntheses and effects. Ind Crops Prod. 2022;186:115283.
   Web of Science ®Google Scholar
• Zhou W, Wang C, Hao X, et al. A chromosome-level genome assembly of anesthetic drug–producing anisodus acutangulus provides insights into its evolution and the biosynthesis of tropane alkaloids. Plant Commun. 2023;100680. doi: 10.1016/j.xplc.2023.100680
   Google Scholar
• Kai G, Li L, Zhang L, et al. Protein and cDNA sequences of anisodus acutangulus tropinone reductase I gene and applications in preparing transgenic plants. Faming Zhuanli Shenqing, CN 101168740 A 20080430. 2008.
   Google Scholar
• Rudner B, Prapas AG. Aminotropanium compounds No Corporate Source data available. US 2948730 196008098. 1960.
   Google Scholar
• Li Q, Zhu T, Zhang R, et al. Molecular cloning and functional analysis of hyoscyamine 6β-hydroxylase (H6H) in the poisonous and medicinal plant datura innoxia mill. Plant Physiol Biochem. 2020;153:11–19. doi: 10.1016/j.plaphy.2020.04.021
   PubMed Web of Science ®Google Scholar
• Farghaly TA, Alsaedi AMR, Alenazi NA, et al. Anti-viral activity of thiazole derivatives: an updated patent review. Expert Opin Ther Patents. 2022;32(7):791–815. doi: 10.1080/13543776.2022.2067477
   PubMed Web of Science ®Google Scholar
• Behbehani H, Dawood KM, Farghaly TA. Biological Evaluation of Benzosuberones. Expert Opin Ther Patents. 2018;28(1):5–29. doi: 10.1080/13543776.2018.1389898
   PubMed Web of Science ®Google Scholar
• Dawood KM, Farghaly TA, Raslan MA. Heteroannulation Routes to Bioactive Pyrazolooxazines. J Current Organic Chemistry. 2020;24:1943–1975. doi:10.2174/1570179417999200628035124
   Web of Science ®Google Scholar
• Farghaly TA, Harras MF, Alsaedi AMR, et al. Antiviral activity of pyrimidine containing compounds: patent review. Mini-Rev Med Chem. 2023;23:821–851. doi: 10.2174/1389557523666221220142911
   PubMed Web of Science ®Google Scholar
• Farghaly TA, Dawood K. Inhibitory activities of pyrazolo-oxazine heterocyclic derivatives. Mini Rev Med Chem. 2022;22(9):1256–1267. doi:10.2174/1389557522666211229114446
   PubMed Web of Science ®Google Scholar
• Roy A, Roy M, Gacem A, et al. Role of bioactive compounds in the treatment of hepatitis: a review. Front Pharmacol. 2022;13:1051751. doi: 10.3389/fphar.2022.1051751
   PubMed Web of Science ®Google Scholar
• Farghaly TA, Alfaifi GH, Gomha SM. Recent literature on the synthesis of thiazole derivatives and their biological activities. Mini Rev Med Chem. 2024;24:196–251. doi:10.2174/1389557523666230726142459
   Google Scholar
• Farghaly TA, Alosaimy AM, Al-Qurashi NT, et al. The most recent compilation of reactions of enaminone derivatives with various amine derivatives to generate biologically active compounds. Mini Rev Med Chem. 2024;24: doi: 10.2174/1389557523666230913164038
   Google Scholar
• Farghaly TA, Alqurashi RM, Masaret GS, et al. Recent methods for the synthesis of quinoxaline derivatives and their biological activities. Mini Rev Med Chem. 2024;24: doi: 10.2174/0113895575264375231012115026
   Google Scholar
• Farghaly TA, Al-Hussain SA, Zaki MEA, et al. A review article on synthesis of different types of bioactive spiropyrazole derivatives. Polycycl Aromat Compd. 2023;43:5639–5734. doi: 10.1080/10406638.2022.2105911
   Google Scholar
• Teotino U, Belia DD. p-Phenylphenacyl dervatives of l-hy cscyamane anad di-tropylatropine, US 3,356,682. 1967.
   Google Scholar
• Liang ZJS. Ipratropium bromide aerosol composition and preparation method thereof. CN110302157B. 2023. https://patents.google.com/patent/CN110302157B/en
   Google Scholar
• Cameron IG, Tasko MPE. Nebulizer formulation of levalbuterol and ipratropium. CA2596215A1. 2006.
   Google Scholar
• Sung JC. PERRY JM, Tauber M. Improved stability of dry powders containing tiotropium and amino acid US20170304198A1. 2017.
   Google Scholar
• Banholzer R, Sieger P, Kulinna C, et al. Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions. US 6,777,423 B. 2004.
   Google Scholar
• Bundschuh D, Wollin S-L, Weimar C. Synergistic combination comprising roflumilast and an anticholinergic agent selected from ipratropium, oxitropium and tiotropium salts for the treatment of respiratory diseases. US20060189642A. 2006.
   Google Scholar
• Busch-Petersen J, Laine DI, Palovich MR, et al. Preparation of azoniabicyclooctanes as M3 muscarinic acetylcholine receptor antagonists. PCT Int. ApplWO 2007016639 A2 20070208. 2007.
   Google Scholar
• Busch-Petersen J, Laine DI, Palovich MR, et al. Preparation of 3-(arylethenyl)-8,8-dimethyl-8-azoniabicyclo[3.3.1]octanes as M3 muscarinic acetylcholine receptor antagonists. PCT Int. Appl., WO 2007016650 A2 20070208. 2007.
   Google Scholar
• Lain DI, Wan Z, Yan H, et al. Design, synthesis, and structure-activity relationship of tropane muscarinic acetylcholine receptor antagonists. J Med Chem. 2009;52:5241–5252. doi: 10.1021/jm900736e
   PubMed Web of Science ®Google Scholar
• Bream RN, Hayes D, Hulcoop DG, et al. Development of synthetic routes, via a tropinone intermediate, to a long-acting muscarinic antagonist for the treatment of respiratory disease. Org Process Res Dev. 2013;17:641–650. doi: 10.1021/op3002933
   Web of Science ®Google Scholar
• Xu R, Sim M-K, Go M-L. Synthesis and pharmacological characterization of O-alkynyloximes of Tropinone and N-methylpiperidinone as muscarinic agonists. J Med Chem. 1998;41(17):3220–3231. doi: 10.1021/jm9708588
   PubMed Web of Science ®Google Scholar
• Makings LR, Garcia-Guzman B, Miguel H, et al. Preparation of spiro condensed piperidines as modulators of muscarinic receptors MODULATORS of MUSCARINIC RECEPTORS, WO 2007/076070. PCT Int. Appl., WO 2007100670 A1 20070907. 2007.
   Google Scholar
• Drutu I, Garcia-Guzman B, Miguel M, et al. Muscarinic modulators based on 4-aminopiperidine, and their preparation, pharmaceutical compositions, and use as modulators of muscarinic receptors for treatment of CNS disorders. PCT Int. Appl., WO 2006105035 A2 20061005. 2006.
   Google Scholar
• Pandey G, Bagul TD. Sahoo AK. [3 + 2] cycloaddition of nonstabilized azomethine ylides. 7. Stereoselective synthesis of Epibatidine and Analogues. J Org Chem. 1998;63:760.
   PubMed Web of Science ®Google Scholar
• Yogeeswari P, Sriram D, Bal TR, et al. Epibatidine and its analogues as nicotinic acetylcholine receptor agonist: an update. Nat Prod Res. 2006;20(5):497–505. doi: 10.1080/14786410600604583
   PubMed Web of Science ®Google Scholar
• Badio B, Garraffo HM, Plummer CV, et al. Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine. Eur J Pharmacol. 1997;321:189–194. doi: 10.1016/S0014-2999(96)00939-9
   PubMed Web of Science ®Google Scholar
• Raâdl S, Hezky P, Hafner W, et al. Synthesis and binding studies of some epibatidine analogues. Bioorganic Med Chem Lett. 2000;10:55–58. doi: 10.1016/S0960-894X(99)00575-2
   PubMedGoogle Scholar
• Peters D, Olsen GM, Nielsen SF, et al. Preparation of 8-azabicyclo[3.2.1]oct-2-ene and -octane derivatives as cholinergic ligands at the nicotinic acetyl choline receptors (nAchr). PCT Int. Appl., WO 2000032600 A1 20000608. 2000.
   Google Scholar
• Bhatti BS, Clark TJ. Preparation of azabicycloalkanes as nicotinic cholinergic receptor agonists for treatment of central and autonomic nervous system disorders. PCT Int. Appl., WO 2002012245 A2 20020214. 2002.
   Google Scholar
• Bhatti BS, Clark TJ, Miller CH, et al. Preparation of 2-pyridylmethyl(ene)-7-azabicyclo[2.2.1]heptanes as nicotinic cholinergic receptor agonists for treatment of central and autonomic nervous system disorders. PCT Int. Appl., WO 2002004442 A2 20020117. 2002.
   Google Scholar
• Zheng G, Dwoskin LP, Deaciuc AG, et al. Synthesis and evaluation of a series of tropane analogues as novel vesicular monoamine transporter-2 ligands. Bioorganic Med Chem Lett. 2005;15(20):4463–4466. doi: 10.1016/j.bmcl.2005.07.032
   PubMed Web of Science ®Google Scholar
• Ji J, Li T, Lynch CL, et al. Fused bicycloheterocycle substituted azabicyclic alkane derivatives and their preparation, pharmaceutical compositions and use in the treatment of diseases. PCT Int. Appl., WO 2007137030 A2 20071129. 2007.
   Google Scholar
• Edink E, Akdemir A, Jansen C, et al. Structure-based design, synthesis and structure–activity relationships of dibenzosuberyl- and benzoate-substituted tropines as ligands for acetylcholine-binding protein. Bioorganic Med Chem Lett. 2012;22(3):1448–1454. doi: 10.1016/j.bmcl.2011.12.008
   PubMed Web of Science ®Google Scholar
• Kohnen-Johannsen L, Kayser O. Tropane alkaloids: chemistry, pharmacology. Biosynthesis Prod Kathrin Mol. 2019;24:796.
   Google Scholar
• Newman AH, Kline RH, Allen AC, et al. Novel 4‘4-substituted and 4’,4”-disubstituted 3a-(Diphenylmethoxy)tropane analogs as potent and selective dopamine uptake inhibitors. J Med Chem. 1995;38:3933–3940.
   PubMed Web of Science ®Google Scholar
• Jiang S, Chang AC, Abraham P, et al. SYNTHESIS and TRANSPORTER BINDING PROPERTIES of (R)-213,313- and (R).2~3o~-DIARYLTROPANES. Bioorganic Med Chem Lett. 1998;8:3689–3692. doi: 10.1016/S0960-894X(98)00673-8
   PubMed Web of Science ®Google Scholar
• Lomenzo SA, Izenwasser S, Katz JL, et al. The effects of alkyl substituents at the 6-position of cocaine analogues on dopamine transporter binding affinity and dopamine uptake inhibition. Med Chem Res. 1998;8:35–42.
   Web of Science ®Google Scholar
• Newman AH, Allen AC, Kline RH, et al. Preparation of 4’- and 4’,4’’-substituted-3α-(diphenylmethoxy)tropane analogs as cocaine therapeutics. U.S., US 5792775 A 19980811. 1998.
   Google Scholar
• Zhang Y, Joseph DB, Bowen WD, et al. Synthesis and biological evaluation of tropane-like 1-□2-[Bis(4-fluorophenyl)methoxy]ethyl□-4-(3-phenylpropyl)piperazine (GBR 12909) Analogues. J Med Chem. 2001;44:3937–3945. doi: 10.1021/jm0101592
   PubMed Web of Science ®Google Scholar
• Zou M-F, Kopajtic T, Katz JL, et al. Structure-Activity Relationship Comparison of (S)-2â-Substituted 3r-(Bis[4-fluorophenyl]methoxy)tropanes and (R)-2â-Substituted 3â-(3,4-Dichlorophenyl)tropanes at the Dopamine Transporter. J Med Chem. 2003;46:2908–2916. doi: 10.1021/jm0300375
   PubMed Web of Science ®Google Scholar
• Peters D, Brown DT, Egestad B, et al. Enantiomers of 3-heteroaryl-8H-8-azabicyclo(3.2.1)oct-2-ene and their preparation, pharmaceutical compositions, and use as monoamine neurotransmitter re-uptake inhibitors. PCT Int. Appl., WO 2006064031 A1 20060622. 2006.
   Google Scholar
• PETERS D, JONES D, Spencer N, et al. 8-azabicyclo[3.2.1]oct-2-ene derivatives and their use as monoamine neurotransmitter re-uptake inhibitors. Patent Appl. Publ. within the TVPP - United States, WO 2010/057848. 2009.
   Google Scholar
• Bockaert J, Claeysen S, Compan V, et al. 5-HT(4) receptors: history, molecular pharmacology and brain functions. Neuropharmacology. 2008;55(6):922–931. doi: 10.1016/j.neuropharm.2008.05.013
   PubMed Web of Science ®Google Scholar
• Stiedl O, Pappa E, Konradsson-Geuken Å, et al. The role of the serotonin receptor subtypes 5-HT1A and 5-HT7 and its interaction in emotional learning and memory. Front Pharmacol. 2015;6:162. doi: 10.3389/fphar.2015.00162
   PubMed Web of Science ®Google Scholar
• Chaomin H, Xiang M, Juan H, et al. Preparation method of tropisetron hydrochloride. CN110845493B. 2021.
   Google Scholar
• Längle UW, Wolf A, Cordier A. Enhancement of SDZ ICT 322-induced cataracts and skin changes in rats following vitamin E- and selenium-deficient diet. Arch Toxicol. 1997;71(5):283–289. doi:10.1007/s002040050388
   PubMed Web of Science ®Google Scholar
• Kostochka LM, Gan’shina TS, Mirzoyan RS, et al. Synthesis and antiserotoninergic activity of new tropane derivatives. Trans Khimiko-Farmatsevticheskii Zhurnal. 2010;44:6–9. doi: 10.1007/s11094-010-0494-6
   Google Scholar
• GILBERT, Adam, Matthew. ARYL-8-azabicyclo[3.2.1]octanes for the treatment of depression. Publ. of the Int.Appl.WO 02/096906. 2002.
   Google Scholar
• Gilbert AM, Stack GP. Preparation of 8-aza-bicyclo[3.2.1]octan-3-ol derivatives of 2,3-dihydro-1,4-benzodioxan and their 5-HT1A antagonist activity. PCT Int. Appl., WO 2002085900 A1 20021031. 2002.
   Google Scholar
• Stack GP, Gilbert AM, Tran M. Preparation of azabicyclylmethyl derivatives of 2,3-dihydro-1,4-dioxino-[2,3-f]quinoline as 5-HT1A antagonists. PCT Int. Appl., WO 2002088130 A1 20021107. 2002.
   Google Scholar
• Nenaydenko VG, Kabakov VY. Hydrogenated pyrido[4,3-b]indole derivatives useful in the treatment and prevention of neurodegenerative and other diseases, pharmaceutical composition and methods for the preparation and use thereof. PCT Int. Appl., WO 2011014098 A1 20110203. 2011.
   Google Scholar
• Hung DT, Protter AA, Chakravarty S, et al. Preparation of hexahydroiminocyclohept[b]indole derivatives and analogs for use as histamine receptor modulators. PCT Int. Appl., WO 2009120720 A1 20091001. 2009.
   Google Scholar
• Yang S-W; Ho G; Tulshian D, et al. Identification of 3-substituted N-benzhydryl-nortropane analogs as nociception receptor ligands for the management of cough and anxiety. Bioorg Med Chem Lett. 2009;19:2482–2486. doi: 10.1016/j.bmcl.2009.03.057
   PubMed Web of Science ®Google Scholar
• Takahashi H, Sugimoto Y, Yoshizumi T, et al. Preparation of cycloalkanopyridine derivatives as antagonists of nociceptin receptor. PCT Int. Appl., WO 2005085228 A1 20050915. 2005.
   Google Scholar
• Tulshian D, Ho GD, Ng FW. Preparation of azabicyclo[3.2.1]octanols and related compounds as superior agonists for nociceptin receptor ORL-1. PCT Int. Appl., WO 2003039469 A2 20030515. 2003.
   Google Scholar
• Ho GD, Tulshian D, Yang S-W. 3-Monosubstituted tropane derivatives as nociceptin receptor ligands. PCT Int. Appl., WO 2007053435 A1 20070510. 2007.
   Google Scholar
• Irwin KK, Renzette N, Kowalik TF, et al. Antiviral drug resistance as an adaptive process. Virus Evol. 2016;2(1):vew014. doi: 10.1093/ve/vew014
   PubMed Web of Science ®Google Scholar
• Dorr P, Westby M, Dobbs S, et al. Maraviroc (UK-427,857), a potent, orally bioavailable, and selective small-molecule inhibitor of chemokine receptor CCR5 with broad-spectrum anti-human immunodeficiency virus type 1 activity. Antimicrob Agents Chemother. 2005;49(11):4721–32. doi: 10.1128/AAC.49.11.4721-4732.2005
   PubMed Web of Science ®Google Scholar
• Tan Q, Zhu Y, Li J, et al. Structure of the CCR5 chemokine receptor-HIV entry inhibitor maraviroc complex. Science. 2013;341:1387–1390. doi: 10.1126/science.1241475
   PubMed Web of Science ®Google Scholar
• Pfizer Ltd. Preparation of imidazopyridine substituted tropane derivatives with CCR5 receptor antagonist activity for the treatment of HIV and inflammation. WO2005033107. 2005.
   Google Scholar
• Pfizer Ltd. 8-Azabicyclo[3.2.1]octane derivatives with an activity on chemokine CCR5 receptors and their preparation, pharmaceutical compositions and use for treatment of inflammatory diseases and infection caused by HIV and genetically related retroviruses. WO2006067584. 2006.
   Google Scholar
• Supuran CT. Therapeutic compounds: patent evaluation of WO2011011652A1. Expert Opin Ther Pat. 2011;21(9):1491–1495. doi: 10.1517/13543776.2011.584873
   PubMed Web of Science ®Google Scholar
• Armour DR, de Groot MJ, Price DA, et al. The discovery of tropane-derived CCR5 receptor antagonists chem. Chem Biol Drug Des. 2006;67(4):305–308. doi: 10.1111/j.1747-0285.2006.00376.x
   PubMed Web of Science ®Google Scholar
• Badger AM. Pharmaceutical compns. contg. azaspirane derivs. for treatment of human immunodeficiency virus infections. PCT Int. Appl., WO 9503048 A1 19950202. 1995.
   Google Scholar
• Badger AM. Pharmaceutical compositions containing azaspirane derivatives for treatment of human immunodeficiency virus infections. PCT Int. Appl. WO 9503047 A1 19950202. 1995.
   Google Scholar
• Özçelik B, Kartal M, Orhan I. Cytotoxicity, antiviral and antimicrobial activities of alkaloids, flavonoids, and phenolic acids. Pharm Biol. 2011;49(4):396–402. doi: 10.3109/13880209.2010.519390
   PubMed Web of Science ®Google Scholar
• Wei W, Kong N, Liu MZ, et al. Anisodamine potently inhibits SARS-CoV-2 infection in vitro and targets its main protease. Biochem Biophys Res Commun. 2022;616:8–13. doi: 10.1016/j.bbrc.2022.05.024
   PubMed Web of Science ®Google Scholar
• Steppeler F, Iwan D, Gaida R, et al. Chiral 2-azabicycloalkanes bearing 1,2,3-triazole, thiourea, and ebselen moieties - synthesis and biological activity. Biomed Pharmacother. 2023;164:114908. doi: 10.1016/j.biopha.2023.114908
   PubMed Web of Science ®Google Scholar
• Urban-Chmiel R, Marek A, Stępień-Pyśniak D, et al. Antibiotic Resistance in bacteria-A review. Antibiotics. 2022;11(8):1079. doi: 10.3390/antibiotics11081079
   Google Scholar
• Yanhong W, Da H, Huihui L, et al. Application of Retapamulin compound in preparation of anti-EV 71 virus medicine. CN113143923A. 2021.
   Google Scholar
• Prevet H, Moune M, Tanina A, et al. A fragment-based approach towards the discovery of N-substituted tropinones as inhibitors of mycobacterium tuberculosis transcriptional regulator EthR2. Eur J Med Chem. 2019;167:426–438. doi: 10.1016/j.ejmech.2019.02.023
   PubMed Web of Science ®Google Scholar
• Reddy BS, Reddy AB, Reddy GR, et al. Synthesis and antibacterial activity of novel [3-(4-substitutedphenylamino)- 8-azabicyclo [3.2.1] oct-8yl]-phenyl-methanone derivatives. J Korean Chem Soc. 2011;55(6):969–973. doi: 10.5012/jkcs.2011.55.6.969
   Google Scholar
• Arhin F, Be´langer O, Ciblat S, et al. A new class of small molecule RNA polymerase inhibitors with activity against Rifampicin-resistant Staphylococcus aureus1. Bioorg Med Chem. 2006;14:5812–5832. doi: 10.1016/j.bmc.2006.05.035
   PubMed Web of Science ®Google Scholar
• Piechowska K; Świtalska M; Cytarska J, et al. Discovery of tropinonethiazole derivatives as potent caspase 3/7 activators, and noncompetitive tyrosinase inhibitors with high antiproliferative activity: rational design, one-pot tricomponent synthesis, and lipophilicity determination. Eur J Med Chem. 2019;175:162–171. doi: 10.1016/j.ejmech.2019.05.006
   PubMed Web of Science ®Google Scholar
• Piechowska K, Mizerska-Kowalska M, Zdzisińska B, et al. Tropinone-derived alkaloids as potent anticancer agents: synthesis, tyrosinase inhibition, mechanism of action, DFT Calculation, and molecular docking studies. Int J Mol Sci. 2020;21(23):9050. doi: 10.3390/ijms21239050 28 PMID: 33260768; PMCID: PMC7731314.
   PubMed Web of Science ®Google Scholar
• Yin X-J, Geng C-A, Chen X-L, et al. Synthesis and cytotoxicity evaluation of tropinone derivatives. Nat Prod Bioprospect. 2017;7(2):215–223. doi: 10.1007/s13659-017-0124-z
   PubMedGoogle Scholar
• George RF, Samir N, Ayoub IM, et al. Synthesis, antiproliferative activity and 2D-QSAR study of some 8-alkyl-2,4-bisbenzylidene-3-nortropinones. Future Med Chem. 2018;10(24):2815–2833. doi: 10.4155/fmc-2018-0205
   PubMed Web of Science ®Google Scholar
• Chen J, Yin X, Geng C, et al. Tropinone derivatives useful in treatment of cancer and their preparation. Faming Zhuanli Shenqing, CN 105924436 A 20160907. 2016.
   Google Scholar
• Ishikawa F, Saito Y, Hashizume Y, et al. Preparation of 7H-pyrrolo[2,3-d]pyrimidine and 1H-pyrazolo[3,4-d]pyrimidine derivatives as agents for treating or controlling recurrence of acute myelogenous leukemia. PCT Int. Appl., WO 2014017659 A1 20140130. 2014.
   Google Scholar
• Borcherding DR, Gross A, Shum PW-K, et al. Preparation of pyrazolyl phenyl urea derivatives as inhibitors of p38 kinase and/or tumor necrosis factor (TNF) inhibitors for the treatment of inflammations. PCT Int. Appl., WO 2004100946 A1 20041125. 2004.
   Google Scholar
• Choi-Sledeski YM, Liang G, Shum PW-K. Tropinone benzylamines as β-tryptase inhibitors. From PCT Int. Appl., WO 2011087652 A1 20110721 2011.
   Google Scholar
• Liang G, Choi-Sledeski YM, Shum P, et al. A β-tryptase inhibitor with a tropanylamide scaffold to improve in vitro stability and to lower hERG channel binding affinity. Bioorg Med Chem Lett. 2012;22(4):1606–1610. doi: 10.1016/j.bmcl.2011.12.127
   PubMed Web of Science ®Google Scholar
• Esposito L, Cummings J, Hudson FM, et al. Bis(dihydroxyaryl) compounds, pharmaceutical compositions containing them, and methods for the treatment of amyloid diseases and synucleinopathies. PCT Int. Appl., WO 2008154083 A2 20081218. 2008.
   Google Scholar
• Esposito L, Cummings J, Hudson M, et al. Bis(dihydroxyaryl) compounds, pharmaceutical compositions containing them, and methods for the treatment of amyloid diseases and synucleinopathies. U.S. Pat. Appl. Publ., US 20070276034 A1 20071129. 2007.
   Google Scholar
• Baeschlin DK, Fenton G, Namoto K, et al. Azabicyclooctane compounds as DPP-IV inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases. PCT Int. Appl., WO 2007115821 A2 20071018. 2007.
   Google Scholar
• Zheng Q, Xie C, Li Z, et al. Tropinone derivative and its pharmacologically acceptable salt, preparation method and application for treating type II diabetes. Faming Zhuanli Shenqing, CN 102993197 A 20130327. 2013.
   Google Scholar
• Nagase T, Sasaki T, Takahashi T. Preparation of 4-sulfonylpiperidine derivatives as LCE inhibitors. PCT Int. Appl. WO 2009038021 A1 20090326. 2009.
   Google Scholar
• Aletru M, Braun A, Namane C, et al. Preparation of urea derivatives of tropane and their therapeutic application. PCT Int. Appl. WO 2008000951 A2 20080103. 2008.
   Google Scholar
• Guckian KM, Lin EY-S, Silvian L, et al. Design and synthesis of a series of meta aniline-based LFA-1 ICAM inhibitors. Bioorganic Med Chem Lett. 2008;18:5249–5251. doi: 10.1016/j.bmcl.2008.08.061
   PubMedGoogle Scholar
• Watson RJ, Allen DR, Birch HL, et al. Development of CXCR3 antagonists. Part 3: tropenyl and homotropenyl-piperidine urea derivatives. Bioorg Med Chem Lett. 2008;18(1):147–151. doi: 10.1016/j.bmcl.2007.10.109 1
   PubMed Web of Science ®Google Scholar
• Chowdhury S, Owens KN, Jason Herr RJ, et al. Phenotypic J optimization of urea-thiophene carboxamides to yield potent, well tolerated and orally active protective agents against aminoglycoside-induced hearing loss. J Med Chem. 2018;61(1):84–97. doi: 10.1021/acs.jmedchem.7b00932
   PubMed Web of Science ®Google Scholar
• Bezencon O, Boss C, Bur D, et al. Preparation of bicyclic five-membered heteroaryl derivatives and their use as renin inhibitors. PCT Int. Appl., WO 2006092268 A1 20060908. 2006.
   Google Scholar
• Braun A, Cornet B, Courtemanche G, et al. Preparation of aminotropane derivatives and their therapeutic applications. Fr. Demande, FR 2873693 A1 20060203. 2006.
   Google Scholar
• Patchett AA, Tata JR, Lu Z Preparation of bridged piperidines promoting release of growth hormone. From Brit. UK Pat. Appl., GB 2298647 A 19960911. 1996.
   Google Scholar
• Daniel DL, Daisuke RS, Priscilla VD, et al. Amidoalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists US20110124677A1. 2011.
   Google Scholar
• Najmi A, Javed SA, Al Bratty M, et al. Modern approaches in the discovery and development of plant-based natural products and their analogues as potential therapeutic agents. Molecules. 2022;27(2):349. doi: 10.3390/molecules27020349
   PubMed Web of Science ®Google Scholar
• Atanasov AG, Zotchev SB, Dirsch VM. International Natural Product Sciences Taskforce, supuran CT. Natural products in drug discovery: advances and opportunities. Nat Rev Drug Discov. 2021;20(3):200–216. doi: 10.1038/s41573-020-00114-z
   PubMed Web of Science ®Google Scholar
• Castagnolo D. Looking back and moving forward in medicinal chemistry. Nat Commun. 2023;14(1):4299. doi: 10.1038/s41467-023-39949-6
   PubMed Web of Science ®Google Scholar