Novel sulindac derivatives: synthesis, characterisation, evaluation of antioxidant, analgesic, anti-inflammatory, ulcerogenic and COX-2 inhibition activity

References

• Robert A, Nezamis JE, Lancaster C, et al. Mild irritants prevent gastric necrosis through “adaptive cytoprotection mediated by prostaglandins”. Am J Physiol 1983;245:G113–21.
   PubMed Web of Science ®Google Scholar
• Khatri CK, Indalkar KS, Patil CR, et al. Novel 2-phenyl-4,5,6,7-tetrahydro[b]benzothiophene analogues as selective COX-2 inhibitors: Design, synthesis, anti-inflammatory evaluation, and molecular docking studies. Bioorg Med Chem Lett 2017;27:1721–6.
   PubMed Web of Science ®Google Scholar
• Abdelgawad MA, Bakr RB, Azouz AA. Novel pyrimidine-pyridine hybrids: synthesis, cyclooxygenase inhibition, anti-inflammatory activity and ulcerogenic liability. Bioorg Chem 2018;77:339–48.
   PubMed Web of Science ®Google Scholar
• Banerjee AG, Das N, Shengule SA, et al. Synthesis, characterization, evaluation and molecular dynamics studies of 5, 6-diphenyl-1,2,4-triazin-3(2H)-one derivatives bearing 5-substituted 1,3,4-oxadiazole as potential anti-inflammatory and analgesic agents. Eur J Med Chem 2015;101:81–95.
   PubMed Web of Science ®Google Scholar
• Chandrashekharappa S, Venugopala KN, Tratrat C, et al. Efficient synthesis and characterization of novel indolizines: exploration of in vitro COX-2 inhibitory activity and molecular modelling studies. New J Chem 2018;42:4893–901.
   Web of Science ®Google Scholar
• Banerjee AG, Das N, Shengule SA, et al. Design, synthesis, evaluation and molecular modelling studies of some novel 5,6-diphenyl-1,2,4-triazin-3(2H)-ones bearing five-member heterocyclic moieties as potential COX-2 inhibitors: a hybrid pharmacophore approach. Bioorg Chem 2016;69:102–20.
   PubMed Web of Science ®Google Scholar
• Bhat MA, Ahmed AF, Wen ZH, et al. Synthesis, anti-inflammatory and neuroprotective activity of pyrazole and pyrazolo[3,4-d]pyridazine bearing 3,4,5- trimethoxyphenyl. Med Chem Res 2017;26:1557–66.
   Web of Science ®Google Scholar
• Bhat MA, Al-Omar MA, Ansari MA, et al. Design and synthesis of N-arylphthalimides as inhibitors of glucocorticoid-induced TNF receptor-related protein, proinflammatory mediators, and cytokines in carrageenan-induced lung inflammation. J Med Chem 2015;58:8850–67.
   PubMed Web of Science ®Google Scholar
• Romeiro NC, Leite RD, Lima LM, et al. Synthesis, pharmacological evaluation and docking studies of new sulindac analogues. Eur J Med Chem 2009;44:1959–71.
   PubMedGoogle Scholar
• Fogli S, Banti I, Stefanelli F, et al. Therapeutic potential of sulindac hydroxamic acid against human pancreatic and colonic cancer cells. Eur J Med Chem 2010;45:5100–7.
   PubMed Web of Science ®Google Scholar
• Mathew B, Hobrath JV, Connelly MC, et al. Diverse amide analogs of sulindac for cancer treatment and prevention. Bioorg Med Chem Lett 2017;27:4614–21.
   PubMed Web of Science ®Google Scholar
• Mathew B, Snowden TS, Connelly MC, et al. A small diversity library of α-methyl amide analogs of sulindac for probing anticancer structure-activity relationships. Bioorg Med Chem Lett 2018;28:2136–42.
   PubMed Web of Science ®Google Scholar
• Liedtke AJ, Crews BC, Daniel CM, et al. Cyclooxygenase-1-selective inhibitors based on the (E)-2'-des-methyl-sulindac sulfide scaffold. J Med Chem 2012;55:2287–300.
   PubMed Web of Science ®Google Scholar
• Felts AS, Siegel BS, Young SM, et al. Sulindac derivatives that activate the peroxisome proliferator-activated receptor gamma but lack cyclooxygenase inhibition. J Med Chem 2008;51:4911–9.
   PubMed Web of Science ®Google Scholar
• Amir M, Kumar S. Anti-inflammatory and gastro sparing activity of some new indomethacin derivatives. Arch Pharm 2005;338:24–31.
   PubMed Web of Science ®Google Scholar
• Bhat MA, Al-Omar MA, Raish M, et al. Indole derivatives as cyclooxygenase inhibitors: synthesis, biological evaluation and docking studies. Molecules 2018;23:1250.
   PubMed Web of Science ®Google Scholar
• Furness B, Hannaford AH, Smith PWG, Tatchell AR, Vogels Text book of practical organic chemistry. 5th ed. London: Addison Wesely Longman, Inc.; 1998:1077‒78.
   Google Scholar
• Braca A, De Tommasi N, Di Bari L, et al. Antioxidant principles from Bauhinia tarapotensis. J Nat Prod 2001;64:892–5.
   PubMed Web of Science ®Google Scholar
• Loux JJ, De Palma PD, Yankell SL. Antipyretic testing of aspirin in rats. Toxicol Appl Pharmacol 1972;22:672–‒5.
   PubMed Web of Science ®Google Scholar
• D’Amour FE, Smith DL. A method for determining loss of pain sensation. J Pharmacol Exp Ther 1941;72:74–9.
   Google Scholar
• Turner RA. Analgesic. In: Turner RA, ed. Screening methods in pharmacology. London: Academic Press; 1965.
   Google Scholar
• Winter CA, Risley EA, Nuss GW. Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc Soc Exp Biol Med 1962;111:544–7.
   PubMed Web of Science ®Google Scholar
• Yu C, Mei XT, Zheng YP, Xu DH. Gastroprotective effect of taurine zinc solid dispersions against absolute ethanol-induced gastric lesions is mediated by enhancement of antioxidant activity and endogenous PGE2 production and attenuation of NO production. Eur J Pharmacol 2014;740:329–36.
   PubMed Web of Science ®Google Scholar
• Bhargava KP, Gupta MB, Tangri KK. Mechanism of ulcerogenic activity of indomethacin and oxyphenbutazone. Eur J Pharmacol 1973;22:191–5.
   PubMed Web of Science ®Google Scholar
• Utley HG, Bernheim F, Hochstein P. Effect of sulfhydryl reagents on peroxidation in microsomes. Arch Biochem Biophy 1967;118:29–32.
   Web of Science ®Google Scholar
• Sedlak J, Lindsay RH. Estimation of total, protein-bound, and nonprotein sulfhydryl groups in tissue with Ellman's reagent. Anal Biochem 1968;25:192–205.
   PubMed Web of Science ®Google Scholar
• Karber G. Beitrag zur kollektiven Behandlung pharmakologischer Reihenversuche. Arch Exptl Pathol Pharmakol 1931;162:480–3.
   Google Scholar
• Kim HJ, Kim KW, Yu BP, et al. The effect of age on cyclooxygenase-2 gene expression: NF-kappaB activation and IkappaBalpha degradation. Free Radic Biol Med 2000;28:683–92.
   PubMed Web of Science ®Google Scholar
• Kim SH, Hong KO, Chung WY, et al. Abrogation of cisplatin-induced hepatotoxicity in mice by xanthorrhizol is related to its effect on the regulation of gene transcription. Toxicol Appl Pharmacol 2004;196:346–55.
   PubMed Web of Science ®Google Scholar
• Ashraf NM, Krishnagopal A, Hussain A, et al. Engineering of serine protease for improved thermostability and catalytic activity using rational design. Int J Biol Macromol 2019;126:229–37.
   PubMed Web of Science ®Google Scholar