Non-ulcerogenic pyrazolyl 2-hydroxychalcones and pyrazolylpyrazolines derived from naturally existing furochromone (khellin): semi-synthesis, docking study and anti-inflammatory activity

References

• Back M, Yin L, Ingelsson E. 2012. Cyclooxygenase-2 inhibitors and cardiovascular risk in a nation-wide cohort study after the withdrawal of rofecoxib. Eur Heart J. 33(15):1928–1933.
   PubMed Web of Science ®Google Scholar
• Badr JM, Hadad GM, Nahriry K, Hassanean HA. 2015. Validated HPLC method for simultaneous estimation of khellol glucoside, khellin and visnagin in Ammi visnaga L. fruits and pharmaceutical preparations. Nat Prod Res. 29(7):593–601.
   PubMed Web of Science ®Google Scholar
• Blobaum AL, Marnett LJ. 2007. Structural and functional basis of cyclooxygenase inhibition. J Med Chem. 50(7):1425–1441.
   PubMed Web of Science ®Google Scholar
• Dao-Tran T, Park H, Kim HP, Ecker GF, Thai KM. 2009. Inhibitory activity of prostaglandin E2 production by the synthetic 2'-hydroxychalcone analogues: synthesis and SAR study. Bioorg Med Chem Lett. 19(6):1650–1653.
   PubMed Web of Science ®Google Scholar
• David B, Wolfender JL, Dias DA. 2015. The pharmaceutical industry and natural products: historical status and new trends. Phytochem Rev. 14(2):299–315.
   Web of Science ®Google Scholar
• Day RO, Graham GG. 2013. Non-steroidal anti-inflammatory drugs (NSAIDs). BMJ. 346:f3195.
   PubMedGoogle Scholar
• Deshpande R, Bhagawan Raju M, Parameshwar S, Shanth Kumar SM, Appalaraju S, Manjunath S, Yelagatti SM. 2012. Microwave-assisted synthesis and pharmacological activity of pyrazolyl benzofuran deravatives. Chemistry. 2(3):115–120.
   Google Scholar
• Elattar KM, Fadda AA. 2016. Chemistry of antipyrine. Synth Commun. 46(19):1567–1594.
   Web of Science ®Google Scholar
• Forey A, Yonida M. 2002. Treating acute gouty arthritis with selective COX 2 inhibitors. BMJ. 325(7371):980–981.
   PubMedGoogle Scholar
• Günaydin K, Beyazit N. 2004. The chemical investigations on the ripe fruits of Ammi visnaga (Lam.) lamarck growing in turkey. Nat Prod Res. 18(2):169–175.
   PubMed Web of Science ®Google Scholar
• Hassan GS, Abou-Seri SM, Kamel G, Ali MM. 2014. Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: design, synthesis and evaluation as potential anti-inflammatory agents. Eur J Med Chem. 76:482–493.
   PubMed Web of Science ®Google Scholar
• Hassan GS, Soliman GA. 2010. Design, synthesis and anti-ulcerogenic effect of some of furo-salicylic acid derivatives on acetic acid-induced ulcerative colitis. Eur J Med Chem. 45(9):4104–4112.
   PubMed Web of Science ®Google Scholar
• Khalil N, Bishr M, Desouky S, Salama O. 2020. Ammi visnaga L., a potential medicinal plant: a review. Molecules. 25(2):301–318.
   PubMed Web of Science ®Google Scholar
• Kinghorn AD, Pan L, Fletcher JN, Chai H. 2011. The relevance of higher plants in lead compound discovery programs. J Nat Prod. 74(6):1539–1555.
   PubMed Web of Science ®Google Scholar
• Kingston DG. 2011. Modern natural products drug discovery and its relevance to biodiversity conservation. J Nat Prod. 74(3):496–511.
   PubMed Web of Science ®Google Scholar
• Matsui H, Shimokawa O, Kaneko T, Nagano Y, Rai K, Hyodo I. 2011. The pathophysiology of non-steroidal anti-inflammatory drug (NSAID)-induced mucosal injuries in stomach and small intestine. J Clin Biochem Nutr. 48(2):107–111.
   PubMed Web of Science ®Google Scholar
• Newman DJ, Cragg GM. 2012. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod. 75(3):311–335.
   PubMed Web of Science ®Google Scholar
• Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, et al. 1997. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1 H-pyrazol-1-yl]benzenesulfonamide (SC-58635, celecoxib). J Med Chem. 40(9):1347–1365.
   PubMed Web of Science ®Google Scholar
• Ragab FA, El-Said MK, Kenawy SAK. 1992. Synthesis and pharmacological activities of certain new pyrazole and chromone derivatives. Egypt J Pharm Sci. 33:83–97.
   Google Scholar
• Ragab FA, Hassan GS, Yossef HA, Hashem HA. 2007. Synthesis of 6- and 9-alkylaminomethyl furoflavones as gastroprotective agents. Eur J Med Chem. 42(8):1117–1127.
   PubMed Web of Science ®Google Scholar
• Ragab FA, Mohammed EI, Abdel Jaleel GA, Selim AAMA, Nissan YM. 2020. Synthesis of hydroxybenzofuranyl-pyrazolyl and Hydroxyphenyl-pyrazolyl chalcones and their corresponding pyrazoline derivatives as COX inhibitors, anti-inflammatory and gastroprotective agents. Chem Pharm Bull (Tokyo). 68(8):742–752.
   PubMed Web of Science ®Google Scholar
• Ren S-Z, Wang Z-C, Zhu X-H, Zhu D, Li Z, Shen F-Q, Duan Y-T, Cao H, Zhao J, Zhu H-L. 2018. Design and biological evaluation of novel hybrids of 1, 5-diarylpyrazole and chrysin for selective COX-2 inhibition. Bioorg Med Chem. 26(14):4264–4275.
   PubMed Web of Science ®Google Scholar
• Scannell JW, Blanckley A, Boldon H, Warrington B. 2012. Diagnosing the decline in pharmaceutical R&D efficiency. Nat Rev Drug Discov. 11(3):191–200.
   PubMed Web of Science ®Google Scholar
• Singh P, Anand A, Kumar V. 2014. Recent developments in biological activities of chalcones: a mini review. Eur J Med Chem. 85:758–777.
   PubMed Web of Science ®Google Scholar
• Spath E, Gruber W. 1938. Die konstitution des kellins (aus ammi visnaga) 1.Mitteil uber naturliche chromone. Ber Dtsch Chem Ges A/B. 71(1):106–113.
   Google Scholar
• Wang JL, Limburg D, Graneto MJ, Springer J, Hamper JR, Liao S, Pawlitz JL, Kurumbail RG, Maziasz T, Talley JJ, et al. 2010. The novel benzopyran class of selective cyclooxygenase-2 inhibitors. Part 2: the second clinical candidate having a shorter and favorable human half-life. Bioorg Med Chem Lett. 20(23):7159–7163.
   PubMed Web of Science ®Google Scholar
• Winter CA, Risley EA, Nuss GW. 1962. Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc Soc Exp Biol Med. 111:544–547.
   PubMed Web of Science ®Google Scholar
• Yogi P, Ashid M, Hussain N, Khanam R, Khan S, Joshi A. 2015. Synthesis of pyrazoles via Vilsmeier Haack reaction and their pyrazolone, thiazolidinedione derivative: a comparative study of conventional and microwave routes. Iran J Org Chem. 7(2):1515–1522.
   Google Scholar