2,557
Views
8
CrossRef citations to date
0
Altmetric
RESEARCH PAPER

Synthesis and anti-rheumatoid arthritis activities of 3-(4-aminophenyl)-coumarin derivatives

, , , ORCID Icon &
Pages 450-461 | Received 12 Nov 2020, Accepted 05 Jan 2021, Published online: 08 Feb 2021

References

  • Smolen JS, Aletaha D, Koeller M, et al. New therapies for treatment of rheumatoid arthritis. Lancet 2007;370:1861–74.
  • Mcinnes IB, Schett G. Pathogenetic insights from the treatment of rheumatoid arthritis. Lancet 2017;389:2328–37.
  • Firestein GS. Evolving concepts of rheumatoid arthritis. Nature 2003;423:356–61.
  • Schett G, Gravallese E. Bone erosion in rheumatoid arthritis: mechanisms, diagnosis and treatment. Nat Rev Rheumatol 2012;8:656–64.
  • Bartok B, Firestein GS. Fibroblast-like synoviocytes: key effector cells in rheumatoid arthritis. Immunol Rev 2010;233:233–55.
  • Bugatti S, Codullo V, Caporali R, Montecucco C. B cells in rheumatoid arthritis. Autoimmun Rev 2007;7:137–42.
  • Marston B, Palanichamy A, Anolik JH. B cells in the pathogenesis and treatment of rheumatoid arthritis. Curr Opin Rheumatol 2010;22:307–15.
  • Weyand CM, Seyler TM, Goronzy JJ. B cells in rheumatoid synovitis. Arthritis Res Ther 2005;7:S9.
  • Noss EH, Brenner MB. The role and therapeutic implications of fibroblast-like synoviocytes in inflammation and cartilage erosion in rheumatoid arthritis. Immunol Rev 2008;223:252–70.
  • Wienecke T. Paracetamol versus nonsteroidal anti-inflammatory drugs for rheumatoid arthritis. Cochrane DB Syst Rev 2004;1:CD003789.
  • Spies CM, Bijlsma JWJ, Burmester G-R, Buttgereit F. Pharmacology of glucocorticoids in rheumatoid arthritis. Curr Opin Pharmacol 2010;10:302–7.
  • Kremer JM, Alarcón GS, Lightfoot RW, et al. Methotrexate for rheumatoid arthritis. Suggested guidelines for monitoring liver toxicity. American College of Rheumatology. Arthritis Rheum 1994;37:316–28.
  • Atzeni F, Benucci M, Sallì S, et al. Different effects of biological drugs in rheumatoid arthritis. Autoimmun Rev 2013;12:575–9.
  • Feldmann M, Maini RN. Anti-TNF alpha therapy of rheumatoid arthritis: what have we learned? Annu Rev Immunol 2001;19:163–96.
  • Peng X-M, Damu GLV, Zhou C-H. Current developments of coumarin compounds in medicinal chemistry. Curr Pharm Des 2013;19:3884–930.
  • Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN. Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities. Curr Pharm Des 2004;10:3813–33.
  • Menezes JC, Diederich M. Translational role of natural coumarins and their derivatives as anticancer agents. Future Med Chem 2019;11:1057–82.
  • Wei Y, Peng W, Wang D, Hao SH, et al. Design, synthesis, antifungal activity, and 3D-QSAR of coumarin derivatives. J Pestic Sci 2018;43:88–95.
  • Kostova I, Bhatia S, Grigorov P, et al. Coumarins as antioxidants. Curr Med Chem 2011;18:3929–51.
  • Najafi Z, Mahdavi M, Saeedi M, et al. Novel tacrine-coumarin hybrids linked to 1,2,3-triazole as anti-Alzheimer’s compounds: in vitro and in vivo biological evaluation and docking study. Bioorg Chem 2019;83:303–16.
  • Kontogiorgis CA, Hadjipavlou-Litina DJ. Synthesis and antiinflammatory activity of coumarin derivatives. J Med Chem 2005;48:6400–8.
  • Arora RK, Kaur N, Bansal Y, Bansal G. Novel coumarin-benzimidazole derivatives as antioxidants and safer anti-inflammatory agents. Acta Pharm Sin B 2014;4:368–75.
  • Bansal Y, Sethi P, Bansal G. Coumarin: a potential nucleus for anti-inflammatory molecules. Med Chem Res 2013;22:3049–60.
  • Pan R, Gao XH, Li Y, et al. Anti-arthritic effect of scopoletin, a coumarin compound occurring in Erycibe obtusifolia Benth stems, is associated with decreased angiogenesis in synovium. Fundam Clin Pharmacol 2010;24:477–90.
  • Yao R, Fu Y, Li S, et al. Regulatory effect of daphnetin, a coumarin extracted from Daphne odora, on the balance of Treg and Th17 in collagen-induced arthritis. Eur J Pharmacol 2011;670:286–94.
  • Cheng JF, Chen M, Wallace D, et al. Discovery and structure-activity relationship of coumarin derivatives as TNF-alpha inhibitors. Bioorg Med Chem Lett 2004;14:2411–5.
  • Sahu D, Raghav SK, Gautam H, Das HR. A novel coumarin derivative, 8-methoxy chromen-2-one alleviates collagen induced arthritis by down regulating nitric oxide, NFκB and proinflammatory cytokines. Int Immunopharmacol 2015;29:891–900.
  • Berrino E, Milazzo L, Micheli L, et al. Synthesis and evaluation of carbonic anhydrase inhibitors with carbon monoxide releasing properties for the management of rheumatoid arthritis. J Med Chem 2019;62:7233–49.
  • Bua S, Lucarini L, Micheli L, et al. Bioisosteric development of multitarget nonsteroidal anti-inflammatory drug-carbonic anhydrases inhibitor hybrids for the management of rheumatoid arthritis. J Med Chem 2020;63:2325–42.
  • Menicatti M, Pallecchi M, Bua S, et al. Resolution of co-eluting isomers of anti-inflammatory drugs conjugated to carbonic anhydrase inhibitors from plasma in liquid chromatography by energy-resolved tandem mass spectrometry. J Enzyme Inhib Med Chem 2018;33:671–9.
  • Supuran CT. Coumarin carbonic anhydrase inhibitors from natural sources. J Enzyme Inhib Med Chem 2020;35:1462–70.
  • Bua S, Di Cesare Mannelli L, Vullo D, et al. Design and synthesis of novel nonsteroidal anti-inflammatory drugs and carbonic anhydrase inhibitors hybrids (NSAIDs-CAIs) for the treatment of rheumatoid arthritis. J Med Chem 2017;60:1159–70.
  • Di Cesare Mannelli L, Bani D, Bencini A, et al. Therapeutic effects of the superoxide dismutase mimetic compound MnIIMe2DO2A on experimental articular pain in rats. Mediators Inflammation 2013;2013:905360.
  • Hu Y-H, Yang J, Zhang Y, et al. Synthesis and biological evaluation of 3-(4-aminophenyl)-coumarin derivatives as potential anti-Alzheimer’s disease agents. J Enzyme Inhib Med Chem 2019;34:1083–92.
  • Liu Y, Pan YF, Xue Y-Q, et al. uPAR promotes tumor-like biologic behaviors of fibroblast-like synoviocytes through PI3K/Akt signaling pathway in patients with rheumatoid arthritis. Cell Mol Immunol 2018;15:171–81.
  • Firestein GS, Zvaifler NJ. How important are T cells in chronic rheumatoid synovitis?: II. T cell-independent mechanisms from beginning to end. Arthritis Rheum 2002;46:298–308.
  • Feldmann M, Brennan FM, Maini RN. Role of cytokines in rheumatoid arthritis. Annu Rev Immunol 1996;14:397–440.
  • McInnes IB, Schett G. Cytokines in the pathogenesis of rheumatoid arthritis. Nat Rev Immunol 2007;7:429–42.
  • Maini RN, Taylor PC. Anti-cytokine therapy for rheumatoid arthritis. Annu Rev Med 2000;51:207–29.
  • Dinarello CA. Interleukin-1. Cytokine Growth Factor Rev 1997;8:253–65.
  • Dinarello CA. Biologic basis for interleukin-1 in disease. Blood 1996;87:2095–147.
  • Schett G, Dayer J-M, Manger B. Interleukin-1 function and role in rheumatic disease. Nat Rev Rheumatol 2016;12:14–24.
  • Genovese MC, Becker J-C, Schiff M, et al. Abatacept for rheumatoid arthritis refractory to tumor necrosis factor alpha inhibition. N Engl J Med 2005;353:1114–23.
  • Kollias G, Douni E, Kassiotis G, Kontoyiannis D. On the role of tumor necrosis factor and receptors in models of multiorgan failure, rheumatoid arthritis, multiple sclerosis and inflammatory bowel disease. Immunol Rev 1999;169:175–94.
  • Palladino MA, Bahjat FR, Theodorakis EA, Moldawer LL. Anti-TNF-alpha therapies: the next generation. Nat Rev Drug Discov 2003;2:736–46.
  • Katsikis PD, Chu CQ, Brennan FM, et al. Immunoregulatory role of interleukin 10 in rheumatoid arthritis. J Exp Med 1994;179:1517–27.
  • Moore KW, O’Garra A, de Waal Malefyt R, et al. Interleukin-10. Annu Rev Immunol 1993;11:165–90.
  • Bissantz C, Kuhn B, Stahl M. A medicinal chemist’s guide to molecular interactions. J Med Chem 2010;53:5061–84.
  • Baker RG, Hayden MS, Ghosh S. NF-κB, inflammation, and metabolic disease. Cell Metab 2011;13:11–22.
  • Lin X, Wang M, Zhang J, Xu R. p38 MAPK: a potential target of chronic pain. Curr Med Chem 2014;21:4405–18.
  • Tian W, Zhang Z, Cohen DM. MAPK signaling and the kidney. Am J Physiol Renal Physiol 2000;279:F593–604.
  • Dent P, Yacoub A, Fisher PB, et al. MAPK pathways in radiation responses. Oncogene 2003;22:5885–96.
  • He Y-H, Zhou J, Wang Y-S, et al. Anti-inflammatory and anti-oxidative effects of cherries on Freund’s adjuvant-induced arthritis in rats. Scandinavian J Rheumatol 2006;35:356–8.
  • Guo W-Y, Chen L-Z, Shen B-N, et al. Synthesis and in vitro and in vivo anti-inflammatory activity of novel 4-ferrocenylchroman-2-one derivatives. J Enzyme Inhib Med Chem 2019;34:1678–89.
  • Maresca M, Micheli L, Cinci L, et al. Pain relieving and protective effects of Astragalus hydroalcoholic extract in rat arthritis models. J Pharm Pharmacol 2017;69:1858–70.
  • Wang S, Wang Y, Liu X, et al. Anti-inflammatory and anti-arthritic effects of taraxasterol on adjuvant-induced arthritis in rats. J Ethnopharmacol 2016;187:42–8.
  • Wang X, He X, Zhang C-F, et al. Anti-arthritic effect of berberine on adjuvant-induced rheumatoid arthritis in rats. Biomed Pharmacother 2017;89:887–93.