Design, synthesis and structure–activity relationship studies of novel and diverse cyclooxygenase-2 inhibitors as anti-inflammatory drugs

References

• Funk CD, Funk LB, Kennedy ME, et al. Human platelet/erythroleukemia cell prostaglandin G/H synthase: cDNA cloning, expression, and gene chromosomal assignment. FASEB J 1991;5:2304–12
   PubMed Web of Science ®Google Scholar
• Patrignani P, Panara MR, Greco A, et al. Biochemical and pharmacological characterization of the cyclooxygenase activity of human blood prostaglandin endoperoxide synthases. J Pharmacol Exp Ther 1994;271:1705–12
   PubMed Web of Science ®Google Scholar
• Smith WL, Garavito RM, DeWitt DL. Prostaglandin endoperoxide H synthase (cyclooxygenase)-1 and -2. J Biol Chem 1996;271:33157–60
   PubMed Web of Science ®Google Scholar
• Simmons DL, Botting RM, Hla T. Cyclooxygenase isozymes: the biology of prostaglandin synthesis and inhibition. Pharmacol Rev 2004;56:387–437. [Review]
   PubMed Web of Science ®Google Scholar
• Zeilhofer HU. Prostanoids in nociception and pain. Biochem Pharmacol 2007;73:165–74
   PubMed Web of Science ®Google Scholar
• Kojima F, Kapoor M, Kawai S, Crofford LJ. New insights into eicosanoid biosynthetic pathways: implication for arthritis. Expert Rev Clin Immunol 2006;2:277–91. [Review]
   PubMedGoogle Scholar
• Kang RY, Freire-Moar J, Sigal E, Chu C-Q. Expression of cyclooxygenase-2 in human and an animal model of rheumatoid arthritis. Br J Rheumatol 1996;35:711–18
   PubMedGoogle Scholar
• Blatteis CM. Endotoxic fever: new concepts of its regulation suggest new approaches to its management. Pharmacol Ther 2006;111:194–223. [Review]
   PubMed Web of Science ®Google Scholar
• Ivanov AI, Pero RS, Scheck AC, Romanovsky AA. Prostaglandin E2-synthesizing enzymes in fever: differential transcriptional regulation. Am J Physiol Regul Integr Comp Physiol 2002;283:R1104–17
   PubMed Web of Science ®Google Scholar
• Romanovsky AA, Almeida MC, Aronoff DM, et al. Fever and hypothermia in systemic inflammation: recent discoveries and revisions. Front Biosci 2005;10:2193–216
   PubMed Web of Science ®Google Scholar
• Steiner AA, Ivanov AI, Serrats J, et al. Cellular and molecular bases of the initiation of fever. PLoS Biol 2006;4:1517–24
   Web of Science ®Google Scholar
• Li S, Wang Y, Matsumura K, et al. The febrile response to lipopolysaccharide is blocked in cyclooxygenase-2−/–, but not in cyclooxygenase-1−/– mice. Brain Res 1999;825:86–94
   PubMed Web of Science ®Google Scholar
• Vane JR, Botting RM. The mechanism of action of aspirin. Thromb Res. 2003;110:255–8 . [Review]
   PubMed Web of Science ®Google Scholar
• Burian M, Geisslinger G. COX-dependent mechanisms involved in the antinociceptive action of NSAIDs at central and peripheral sites. Pharmacol Ther 107;2005:139–54. [Review]
   PubMed Web of Science ®Google Scholar
• Laine L. GI risk and risk factors of NSAIDs. J Cardiovasc Pharmacol 2006;47(Suppl. 1):S60–6
   PubMed Web of Science ®Google Scholar
• Radi ZA, Khan NK. Effects of cyclooxygenase inhibition on the gastrointestinal tract. Exp Toxicol Pathol 2006;58:163–73
   PubMed Web of Science ®Google Scholar
• Warner TD, Giuliano F, Vojnovic I, et al. Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis. Proc Natl Acad Sci USA 1999;96:7563–8
   PubMed Web of Science ®Google Scholar
• Hla T, Neilson K. Human cyclooxygenase-2 cDNA. Proc Natl Acad Sci USA. 1992;89:7384–8
   PubMed Web of Science ®Google Scholar
• O’Neill GP, Ford-Hutchinson AW. Expression of mRNA for cyclooxygenase-1 and cyclooxygenase-2 in human tissues. FEBS Lett 1993;330:156–60
   PubMed Web of Science ®Google Scholar
• Beiche F, Scheuerer S, Brune K, et al. Up-regulation of cyclooxygenase-2 mRNA in the rat spinal cord following peripheral inflammation. FEBS Lett 1996;390:165–9
   PubMed Web of Science ®Google Scholar
• Steer SA, Corbett JA. The role and regulation of COX-2 during viral infection. Viral Immunol 2003;16:447–60. [Review]
   PubMed Web of Science ®Google Scholar
• Duque J, Díaz-Muñoz MD, Fresno M, Iñiguez MA. Up-regulation of cyclooxygenase-2 by interleukin-1β in colon carcinoma cells. Cell Signal 2006;18:1262–9
   PubMed Web of Science ®Google Scholar
• Kelley DJ, Mestre JR, Subbaramaiah K, et al. Benzo[a]pyrene up-regulates cyclooxygenase-2 gene expression in oral epithelial cells. Carcinogenesis 1997;18:795–9
   PubMed Web of Science ®Google Scholar
• Kiritoshi S, Nishikawa T, Sonoda K, et al. Reactive oxygen species from mitochondria induce cyclooxygenase-2 gene expression in human mesangial cells. Potential role in diabetic nephropathy. Diabetes 2003;52:2570–7
   Google Scholar
• Hayashi S, Sumi Y, Ueno N, et al. Discovery of a novel COX-2 inhibitor as an orally potent anti-pyretic and anti-inflammatory drug: design, synthesis, and structure–activity relationship. Biochem Pharmacol 2011;82:755–68
   PubMed Web of Science ®Google Scholar
• Kowalski ML, Makowska J. Use of nonsteroidal anti-inflammatory drugs in patients with aspirin hypersensitivity. Safety of cyclo-oxygenase-2 inhibitors. Treat Respir Med 2006;5:399–406
   PubMedGoogle Scholar
• Sánchez-Borges M. NSAID hypersensitivity (respiratory, cutaneous, and generalized anaphylactic symptoms). Med Clin North Am 2010;94:853–64
   PubMed Web of Science ®Google Scholar
• Harrington LS, Lucas R, McMaster SK, et al. COX-1, and not COX-2 activity, regulates airway function: relevance to aspirin-sensitive asthma. FASEB J 2008;22:4005–10
   PubMed Web of Science ®Google Scholar
• Reddy BS, Rao CV. Novel approaches for colon cancer prevention by cyclooxygenase-2 inhibitors. J Environ Pathol Toxicol Oncol 2002;21:155–64
   PubMedGoogle Scholar
• Tsuji M, Kawano S, DuBois RN. Cyclooxygenase-2 expression in human colon cancer cells increases metastatic potential. Proc Natl Acad Sci USA 1997;94:3336–40
   PubMed Web of Science ®Google Scholar
• Wu K, Nie Y, Guo C, et al. Molecular basis of therapeutic approaches to gastric cancer. J Gastroenterol Hepatol 2009;24:37–41
   PubMed Web of Science ®Google Scholar
• Jüttner S, Cramer T, Wessler S, et al. Helicobacter pylori stimulates host cyclooxygenase-2 gene transcription: critical importance of MEK/ERK-dependent activation of USF1/-2 and CREB transcription factors. Cell Microbiol 2003;5:821–34
   PubMed Web of Science ®Google Scholar
• Ku GY, Ilson DH. Esophagogastric cancer: targeted agents. Cancer Treat Rev 2010;36:235–48
   PubMed Web of Science ®Google Scholar
• Saadi A, Shannon NB, Lao-Sirieix P, et al. Stromal genes discriminate preinvasive from invasive disease, predict outcome, and highlight inflammatory pathways in digestive cancers. Proc Natl Acad Sci USA 2010;107:2177–82
   PubMed Web of Science ®Google Scholar
• Lee JL, Mukhtar H, Bickers DR, et al. Cyclooxygenases in the skin: pharmacological and toxicological implications. Toxicol Appl Pharmacol 2003;192:294–306
   PubMed Web of Science ®Google Scholar
• Camp WL, Turnham JW, Athar M, Elmets CA. New agents for prevention of ultraviolet-induced nonmelanoma skin cancer. Semin Cutan Med Surg 2011;30:6–13
   PubMed Web of Science ®Google Scholar
• Mao Y, Poschke I, Wennerberg E, et al. Melanoma-educated CD14+ cells acquire a myeloid-derived suppressor cell phenotype through COX-2-dependent mechanisms. Cancer Res 2013;73:3877–87
   PubMed Web of Science ®Google Scholar
• Krysan K, Reckamp KL, Sharma S, Dubinett SM. The potential and rationale for COX-2 inhibitors in lung cancer. Anti-Cancer Agents Med Chem 2006;6:209–20
   PubMedGoogle Scholar
• Yuan A, Yu C-J, Shun C-T, et al. Total cyclooxygenase-2 mRNA levels correlate with vascular endothelial growth factor mRNA levels, tumor angiogenesis and prognosis in non-small cell lung cancer patients. Int J Cancer 2005;115:545–55
   PubMed Web of Science ®Google Scholar
• Sato M, Shames DS, Hasegawa Y. Emerging evidence of epithelial-to-mesenchymal transition in lung carcinogenesis. Respirology 2012;17:1048–59
   PubMed Web of Science ®Google Scholar
• Kew MC. Hepatitis B virus x protein in the pathogenesis of hepatitis B virus-induced hepatocellular carcinoma. J Gastroenterol Hepatol 2011;26(Suppl. 1):144–52
   PubMed Web of Science ®Google Scholar
• Fernández-Martínez A, Mollá B, Mayoral R, et al. Cyclo-oxygenase 2 expression impairs serum-withdrawal-induced apoptosis in liver cells. Biochem J 2006;398:371–80
   PubMed Web of Science ®Google Scholar
• Li G, Han C, Xu L, et al. Cyclooxygenase-2 prevents Fas-induced liver injury through up-regulation of epidermal growth factor receptor. Hepatology 2009;50:834–43
   PubMed Web of Science ®Google Scholar
• Zhao Q-T, Yue S-Q, Cui Z, et al. Potential involvement of the cyclooxygenase-2 pathway in hepatocellular carcinoma-associated angiogenesis. Life Sci 2007;80:484–92
   PubMed Web of Science ®Google Scholar
• Mohammed A, Qian L, Janakiram NB, et al. Atorvastatin delays progression of pancreatic lesions to carcinoma by regulating PI3/AKT signaling in p48Cre/+ LSL-KrasG12D/+ mice. Int J Cancer 2012;131:1951–62
   PubMed Web of Science ®Google Scholar
• Kokawa A, Kondo H, Gotoda T, et al. Increased expression of cyclooxygenase-2 in human pancreatic neoplasms and potential for chemoprevention by cyclooxygenase inhibitors. Cancer 2001;91:333–8
   PubMed Web of Science ®Google Scholar
• Niijima M, Yamaguchi T, Ishihara T, et al. Immunohistochemical analysis and in situ hybridization of cyclooxygenase-2 expression in intraductal papillary-mucinous tumors of the pancreas. Cancer 2002;94:1565–73
   PubMed Web of Science ®Google Scholar
• Hayashi N, Yamamoto H, Hiraoka N, et al. Differential expression of cyclooxygenase-2 (COX-2) in human bile duct epithelial cells and bile duct neoplasm. Hepatology 2001;34:638–50
   PubMed Web of Science ®Google Scholar
• Kawamoto T, Shoda J, Asano T, et al. Expression of cyclooxygenase-2 in the subserosal layer correlates with postsurgical prognosis of pathological tumor stage 2 carcinoma of the gallbladder. Int J Cancer 2002;98:427–34
   PubMed Web of Science ®Google Scholar
• Shirahama T, Arima J, Akiba S, Sakakura C. Relation between cyclooxygenase-2 expression and tumor invasiveness and patient survival in transitional cell carcinoma of the urinary bladder. Cancer 2001;92:188–93
   PubMed Web of Science ®Google Scholar
• Hu M, Peluffo G, Chen H, et al. Role of COX-2 in epithelial–stromal cell interactions and progression of ductal carcinoma in situ of the breast. Proc Natl Acad Sci USA 2009;106:3372–7
   PubMed Web of Science ®Google Scholar
• Barnes NLP, Warnberg F, Farnie G, et al. Cyclooxygenase-2 inhibition: effects on tumour growth, cell cycling and lymphangiogenesis in a xenograft model of breast cancer. Br J Cancer 2007;96:575–82
   PubMed Web of Science ®Google Scholar
• Jain S, Chakraborty G, Kundu GC. The crucial role of cyclooxygenase-2 in osteopontin-induced protein kinase C α/c-Src/IκB kinase α/β-dependent prostate tumor progression and angiogenesis. Cancer Res 2006;66:6638–48
   PubMed Web of Science ®Google Scholar
• Badawi AF. The role of prostaglandin synthesis in prostate cancer. BJU Int 2000;85:451–62
   PubMed Web of Science ®Google Scholar
• Lee S, Kim J-H, Kim H, et al. Activation of the interleukin-32 pro-inflammatory pathway in response to human papillomavirus infection and over-expression of interleukin-32 controls the expression of the human papillomavirus oncogene. Immunology 2010;132:410–20
   Web of Science ®Google Scholar
• Kim YB, Kim GE, Cho NH, et al. Overexpression of cyclooxygenase-2 is associated with a poor prognosis in patients with squamous cell carcinoma of the uterine cervix treated with radiation and concurrent chemotherapy. Cancer 2002;95:531–9
   PubMed Web of Science ®Google Scholar
• Uddin S, Ahmed M, Hussain A, et al. Cyclooxygenase-2 inhibition inhibits PI3K/AKT kinase activity in epithelial ovarian cancer. Int J Cancer 2010;126:382–94
   PubMed Web of Science ®Google Scholar
• Xin B, Yokoyama Y, Shigeto T, et al. Inhibitory effect of meloxicam, a selective cyclooxygenase-2 inhibitor, and ciglitazone, a peroxisome proliferator-activated receptor gamma ligand, on the growth of human ovarian cancers. Cancer 2007;110:791–800
   PubMed Web of Science ®Google Scholar
• Murono S, Inoue H, Tanabe T, et al. Induction of cyclooxygenase-2 by Epstein–Barr virus latent membrane protein 1 is involved in vascular endothelial growth factor production in nasopharyngeal carcinoma cells. Proc Natl Acad Sci USA 2001;98:6905–10
   PubMed Web of Science ®Google Scholar
• Urade M. Cyclooxygenase (COX)-2 as a potent molecular target for prevention and therapy of oral cancer. Jpn Dent Sci Rev 2008;44:57–65
   Google Scholar
• Iwata C, Kano MR, Komuro A, et al. Inhibition of cyclooxygenase-2 suppresses lymph node metastasis via reduction of lymphangiogenesis. Cancer Res 2007;67:10181–9
   PubMed Web of Science ®Google Scholar
• Liu H, Yang Y, Xiao J, et al. Inhibition of cyclooxygenase-2 suppresses lymph node metastasis via VEGF-C. Anat Rec 2009;292:1577–83
   Google Scholar
• Tomozawa S, Tsuno NH, Sunami E, et al. Cyclooxygenase-2 overexpression correlates with tumour recurrence, especially haematogenous metastasis, of colorectal cancer. Br J Cancer 2000;83:324–8
   PubMed Web of Science ®Google Scholar
• Tomozawa S, Nagawa H, Tsuno N, et al. Inhibition of haematogenous metastasis of colon cancer in mice by a selective COX-2 inhibitor, JTE-522. Br J Cancer 1999;81:1274–9
   PubMed Web of Science ®Google Scholar
• Chen J-H, Wu C-W, Kao H-L, et al. Effects of COX-2 inhibitor on growth of human gastric cancer cells and its relation to hepatocyte growth factor. Cancer Lett 2006;239:263–70
   PubMed Web of Science ®Google Scholar
• Kobayashi H, Gonda T, Uetake H, et al. JTE-522, a selective COX-2 inhibitor, interferes with the growth of lung metastases from colorectal cancer in rats due to inhibition of neovascularization: a vascular cast model study. Int J Cancer 2004;112:920–6
   PubMed Web of Science ®Google Scholar
• Yao M, Lam EC, Kelly CR, et al. Cyclooxygenase-2 selective inhibition with NS-398 suppresses proliferation and invasiveness and delays liver metastasis in colorectal cancer. Br J Cancer 2004;90:712–19
   PubMed Web of Science ®Google Scholar
• Nagatsuka I, Yamada N, Shimizu S, et al. Inhibitory effect of a selective cyclooxygenase-2 inhibitor on liver metastasis of colon cancer. Int J Cancer 2002;100:515–19
   PubMed Web of Science ®Google Scholar
• Chen W-S, Wei S-J, Liu JM, et al. Tumor invasiveness and liver metastasis of colon cancer cells correlated with cyclooxygenase-2 (COX-2) expression and inhibited by a COX-2-selective inhibitor, etodolac. Int J Cancer 2001;91:894–9
   PubMed Web of Science ®Google Scholar
• Mougiakakos D, Johansson CC, Trocme E, et al. Intratumoral forkhead box P3-positive regulatory T cells predict poor survival in cyclooxygenase-2-positive uveal melanoma. Cancer 2010;116:2224–33
   Google Scholar
• Kim H-S, Kim M-J, Kim EJ, et al. Berberine-induced AMPK activation inhibits the metastatic potential of melanoma cells via reduction of ERK activity and COX-2 protein expression. Biochem Pharm 2012;83:385–94
   PubMed Web of Science ®Google Scholar
• Said N, Theodorescu D. Permissive role of endothelin receptors in tumor metastasis. Life Sci 2012;91:522–7
   PubMed Web of Science ®Google Scholar
• Valsecchi ME, Pomerantz SC, Jaslow R, Tester W. Reduced risk of bone metastasis for patients with breast cancer who use COX-2 inhibitors. Clin Breast Cancer 2009;9:225–30
   PubMed Web of Science ®Google Scholar
• Ono K, Akatsu T, Murakami T, et al. Involvement of cyclo-oxygenase-2 in osteoclast formation and bone destruction in bone metastasis of mammary carcinoma cell lines. J Bone Miner Res 2002;17:774–81
   PubMed Web of Science ®Google Scholar
• Wu KK. Differential cyclooxygenase-2 transcriptional control in proliferating versus quiescent fibroblasts. Prostaglandins Other Lipid Mediat 2007;83:175–81
   PubMed Web of Science ®Google Scholar
• Denkert C, Winzer K-J, Müller B-M, et al. Elevated expression of cyclooxygenase-2 is a negative prognostic factor for disease free survival and overall survival in patients with breast carcinoma. Cancer 2003;97:2978–87
   PubMed Web of Science ®Google Scholar
• Ali-Fehmi R, Che M, Khalifeh I, et al. The effect of cyclooxygenase-2 expression on tumor vascularity in advanced stage ovarian serous carcinoma. Cancer 2003;98:1423–9
   PubMed Web of Science ®Google Scholar
• Dormond O, Foletti A, Paroz C, Rüegg C. NSAIDs inhibit αVβ3 integrin-mediated and Cdc42/Rac-dependent endothelial-cell spreading, migration and angiogenesis. Nat Med 2001;7:1041–7
   PubMed Web of Science ®Google Scholar
• Connolly EM, Harmey JH, O'Grady T, et al. Cyclo-oxygenase inhibition reduces tumour growth and metastasis in an orthotopic model of breast cancer. Br J Cancer 2002;87:231–7
   PubMed Web of Science ®Google Scholar
• Rozic JG, Chakraborty C, Lala PK. Cyclooxygenase inhibitors retard murine mammary tumor progression by reducing tumor cell migration, invasiveness and angiogenesis. Int J Cancer 2001;93:497–506
   PubMed Web of Science ®Google Scholar
• Chang S-H, Liu CH, Conway R, et al. Role of prostaglandin E2-dependent angiogenic switch in cyclooxygenase 2-induced breast cancer progression. Proc Natl Acad Sci USA 2004;101:591–6
   PubMed Web of Science ®Google Scholar
• Farooqui M, Li Y, Rogers T, et al. COX-2 inhibitor celecoxib prevents chronic morphine-induced promotion of angiogenesis, tumour growth, metastasis and mortality, without compromising analgesia. Br J Cancer 2007;97:1523–31
   PubMed Web of Science ®Google Scholar
• Oshima H, Oshima M. Mouse models of gastric tumors: Wnt activation and PGE2 induction. Pathol Int 2010;60:599–607
   PubMed Web of Science ®Google Scholar
• Qualtrough D, Kaidi A, Chell S, et al. Prostaglandin F2α stimulates motility and invasion in colorectal tumor cells. Int J Cancer 2007;121:734–40
   PubMed Web of Science ®Google Scholar
• Sales KJ, Maldonado-Pérez D, Grant V, et al. Prostaglandin F2α-F-prostanoid receptor regulates CXCL8 expression in endometrial adenocarcinoma cells via the calcium–calcineurin–NFAT pathway. Biochim Biophys Acta 2009;1793:1917–28
   PubMed Web of Science ®Google Scholar
• Sakai H, Suzuki T, Takahashi Y, et al. Upregulation of thromboxane synthase in human colorectal carcinoma and the cancer cell proliferation by thromboxane A2. FEBS Lett 2006;580:3368–74
   PubMed Web of Science ®Google Scholar
• Nie D, Lamberti M, Zacharek A, et al. Thromboxane A2 regulation of endothelial cell migration, angiogenesis, and tumor metastasis. Biochem Biophys Res Commun 2000;267:245–51
   PubMed Web of Science ®Google Scholar
• Cline SD, Riggins JN, Tornaletti S, et al. Malondialdehyde adducts in DNA arrest transcription by T7 RNA polymerase and mammalian RNA polymerase II. Proc Natl Acad Sci USA 2004;101:7275–80
   PubMed Web of Science ®Google Scholar
• Mao H, Schnetz-Boutaud NC, Weisenseel JP, et al. Duplex DNA catalyzes the chemical rearrangement of a malondialdehyde deoxyguanosine adduct. Proc Natl Acad Sci USA 1999;96:6615–20
   PubMed Web of Science ®Google Scholar
• Flockhart RJ, Diffey BL, Farr PM, et al. NFAT regulates induction of COX-2 and apoptosis of keratinocytes in response to ultraviolet radiation exposure. FASEB J 2008;22:4218–27
   PubMed Web of Science ®Google Scholar
• Fritsche E, Schäfer C, Calles C, et al. Lightening up the UV response by identification of the arylhydrocarbon receptor as a cytoplasmatic target for ultraviolet B radiation. Proc Natl Acad Sci USA 2007;104:8851–6
   PubMed Web of Science ®Google Scholar
• Zhou H, Ivanov VN, Gillespie J, et al. Mechanism of radiation-induced bystander effect: role of the cyclooxygenase-2 signaling pathway. Proc Natl Acad Sci USA 2005;102:14641–6
   PubMed Web of Science ®Google Scholar
• Hussain M, Javeed A, Ashraf M, et al. Non-steroidal anti-inflammatory drugs, tumour immunity and immunotherapy. Pharmacol Res 2012;66:7–18
   PubMed Web of Science ®Google Scholar
• White WB, Faich G, Borer JS, Makuch RW. Cardiovascular thrombotic events in arthritis trials of the cyclooxygenase-2 inhibitor celecoxib. Am J Cardiol 2003;92:411–18
   PubMed Web of Science ®Google Scholar
• Hinz B, Renner B, Brune K. Drug insight: cyclo-oxygenase-2 inhibitors—a critical appraisal. Nat Clin Pract Rhum 2007;3:552–60
   PubMedGoogle Scholar
• Oitate M, Hirota T, Murai T, et al. Covalent binding of rofecoxib, but not other cyclooxygenase-2 inhibitors, to allysine aldehyde in elastin of human arota. Drug Metab Dispos 2007;35:1846–52
   PubMed Web of Science ®Google Scholar
• Chenevard R, Hürlimann D, Béchir M, et al. Selective COX-2 inhibition improves endothelial function in coronary artery disease. Circulation J Am Heart Assoc 2003;107:405–9
   PubMed Web of Science ®Google Scholar
• Höcherl K, Dreher F, Kurtz A, Bucher M. Cyclooxygenase-2 inhibition attenuates lipopolysaccharide-induced cardiovascular failure. Hypertension J Am Heart Assoc 2002;40:947–53
   Google Scholar
• Limongelli V, Bonomi M, Marinelli L, et al. Molecular basis of cyclooxygenase enzymes (COXs) selective inhibition. Proc Natl Acad Sci USA 2010;107:5411–16
   PubMed Web of Science ®Google Scholar
• Rimon G, Sidhu RS, Lauver DA, et al. Coxibs interfere with the action of aspirin by binding tightly to one monomer of cyclooxygenase-1. Proc Natl Acad Sci USA 2010;107:28–33
   PubMed Web of Science ®Google Scholar
• Kurumbail RG, Stevens AM, Gierse JK, et al. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 1996;384:644–8
   PubMed Web of Science ®Google Scholar
• Gierse JK, McDonald JJ, Hauser SD, et al. A single amino acid difference between cyclooxygenase-1 (COX-1) and -2 (COX-2) reverses the selectivity of COX-2 specific inhibitors. J Biol Chem 1996;271:15810–14
   PubMed Web of Science ®Google Scholar
• Luong C, Miller A, Barnett J, et al. Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2. Nat Struct Biol 1996;3:927–33
   PubMedGoogle Scholar
• Hayashi S, Ueno N, Murase A, et al. Novel acid-type cyclooxygenase-2 inhibitors: design, synthesis, and structure–activity relationship for anti-inflammatory drug. Eur J Med Chem 2012;50:179–95
   PubMed Web of Science ®Google Scholar
• Katritzky AR, Akutagawa K. Carbon dioxide: a reagent for the protection of nucleophilic centres and the simultaneous activation of alternative locations to electrophilic attack part I. A new synthetic method for the 2-substitution of 1-unsubstituted indoles. Tetrahedron Lett 1985;26:5935–8
   Web of Science ®Google Scholar
• Baciocchi E, Muraglia E. Mn(III)-promoted homolytic methylmalonylation of pyrrole and indole derivatives. A simple route to α-methyl-2-pyrrole- and α-methyl-3-indoleacetic acids. J Org Chem 1993;58:7610–12
   Web of Science ®Google Scholar
• Artis DR, Cho I-S, Muchowski JM. Radical-based syntheses of 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid (ketorolac). Can J Chem 1992;70:1838–42
   Web of Science ®Google Scholar
• Nahm S, Weinreb SM. N-Methoxy-N-methylamides as effective acylating agents. Tetrahedron Lett 1981;22:3815–18
   Web of Science ®Google Scholar
• Moyer MP, Shiurba JF, Raporport H. Metal–halogen exchange of bromoindoles. A route to substituted indoles. J Org Chem 1986;51:5106–10
   Web of Science ®Google Scholar
• Frye SV, Johnson MC, Valvano NL. Synthesis of 2-aminobenzophenones via rapid halogen–lithium exchange in the presence of a 2-amino-N-methoxy-N-methylbenzamide. J Org Chem 1991;56:3750–2
   Web of Science ®Google Scholar
• Giordano C, Coppi, L. Br3− vs Br2: opposite diastereoselectivity in the bromination of enantiomerically pure ketals. J Org Chem 1992;57:2765–6
   Web of Science ®Google Scholar
• Bellucci G, Bianchini R, Vecchiani S. Comparison of molecular bromine and tribromide ion as brominating reagents. 2. Kinetic and product investigation of the bromination of 3-substituted cylohexenes. J Org Chem 1986;51:4224–32
   Google Scholar
• Riendeau D, Percival MD, Boyce S, et al. Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX-2 inhibitor. Br J Pharmacol 1997;121:105–17
   PubMed Web of Science ®Google Scholar
• Moore PF, Larson DL, Otterness IG, et al. Tenidap, a structurally novel drug for the treatment of arthritis: antiinflammatory and analgesic properties. Inflammation Res 1996;45:54–61
   PubMed Web of Science ®Google Scholar
• Winter CA, Risley EA, Nuss GV. 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
• Lombardino JG, Otterness IG, Wiseman EH. Acidic anti-inflammatory agents-correlations of some physical, pharmacological and clinical data. Arzneim Forsch 1975;25:1629–35
   PubMed Web of Science ®Google Scholar
• Gracia Leme J, Hamamura L, Leite MP, Rocha e Silva M. Pharmacological analysis of the acute inflammatory process induced in the rat’s paw by local injection of carrageenin and by heating. Br J Pharmacol 1973;48:88–96
   PubMed Web of Science ®Google Scholar
• Opas EE, Dallob A, Herold E, et al. Pharmacological modulation of eicosanoid levels and hyperalgesia in yeast-induced inflammation. Biochem Pharmacol 1987;36:547–51
   PubMed Web of Science ®Google Scholar
• Patel BA, Ziegler CB, Cortese NA, et al. Palladium-catalyzed vinylic substitution reactions with carboxylic acid derivatives. J Org Chem 1977;42:3903–7
   Web of Science ®Google Scholar
• Carling RW, Leeson PD, Moore KW, et al. 3-Nitro-3,4-dihydro-2(1H)-quinolones. Excitatory amino acid antagonists acting at glycine-site NMDA and (RS)-α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors. J Med Chem 1993;36:3397–408
   PubMed Web of Science ®Google Scholar
• Xie WL, Chipman JG, Robertson DL, et al. Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing. Proc Natl Acad Sci USA 1991;88:2692–6
   PubMed Web of Science ®Google Scholar
• Sugimoto Y, Narumiya S, Ichikawa A. Distribution and function of prostanoid receptors: studies from knockout mice. Prog Lipid Res 2000;39:289–314
   PubMed Web of Science ®Google Scholar
• Romano M, Faggioni R, Sironi M, et al. Carrageenan-induced acute inflammation in the mouse air pouch synovial model. Role of tumour necrosis factor. Mediat Inflamm 1997;6:32–8
   PubMed Web of Science ®Google Scholar
• Padi SSV, Jain NK, Singh S, Kulkarni SK. Pharmacological profile of paracoxib: a novel, potent injectable selective cyclooxygenase-2 inhibitor. Eur J Pharmacol 2004;491:69–76
   PubMed Web of Science ®Google Scholar
• Posadas I, Bucci M, Roviezzo F, et al. Carrageenan-induced mouse paw oedema is biphasic, age-weight dependent and displays differential nitric oxide cyclooxygenase-2 expression. Br J Pharmacol 2004;142:331–8
   PubMed Web of Science ®Google Scholar
• Claudino RF, Kassuya CAL, Ferreira J, Calixto JB. Pharmacological and molecular characterization of the mechanisms involved in prostaglandin E2-induced mouse paw edema. J Pharmacol Exp Ther 2006;318:611–18
   PubMed Web of Science ®Google Scholar