Cyclooxygenase-1-selective inhibitors based on the (E)-2′- des -methyl-sulindac sulfide scaffold

Journal of Medicinal Chemistry

Volumn 55, Issue 5, 2012, Pages 2287-2300

  Liedtke, Andy J ^a   Crews, Brenda C ^a   Daniel, Cristina M ^a   Blobaum, Anna L ^a   Kingsley, Philip J ^a   Ghebreselasie, Kebreab ^a   Marnett, Lawrence J ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [1 [(1,1' BIPHENYL) 4 YLMETHYLENE] 5 FLUORO 1H INDEN 3 YL] N [(TRIFLUOROMETHYL)SULFONYL] ACETAMIDE; 2 [5 FLUORO 1 [(2 FLUOROBIPHENYL 4 YL) METHYLENE] 1H INDEN 3 YL]ACETIC ACID; 2 [5 FLUORO 1 [(4 METHYL 2 PHENYLPYRIMIDIN 5 YL)METHYLENE] 1H INDEN 3 YL]ACETIC ACID; 2 [5 FLUORO 1 [4 (6 FLUOROPYRIDIN 3 YL)BENZYLIDENE] 1H INDEN 3 YL]ACETIC ACID; 2 [5 FLUORO 1 [4 (METHYLTHIO)BENZYLIDENE] 1H INDEN 3 YL] 2 METHYLPROPANOIC ACID; CYCLOOXYGENASE 1; CYCLOOXYGENASE 1 INHIBITOR; ETHYL 2 [1 [(1,1' BIPHENYL) 4 YLMETHYLENE] 5 FLUORO 1H INDEN 3 YL] 2 METHYLPROPANOATE; ETHYL 2 [5 FLUORO 1 [[6 (4 FLUOROPHENYL)PYRIDIN 2 YL] METHYLENE] 1H INDEN 3 YL] 2 METHYL PROPANOATE; ISOPROPYL 2 [5 FLUORO 1 [4 (METHYLTHIO)BENZYLIDENE] 1H INDEN 3 YL]ACETATE; SODIUM 2 [1 [(1,1' BIPHENYL) 4 YLMETHYLENE] 5 METHOXY 1H INDEN 3 YL]ACETATE; SULINDAC SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CARCINOMA CELL; CELL PROLIFERATION; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME ACTIVITY; HUMAN; HUMAN CELL; OVARY CARCINOMA; TUMOR CELL;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MICE; SHEEP; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULINDAC;

EID: 84858036311     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201528b     Document Type: Article

References (87)

1. Blobaum, A. L.; Marnett, L. J. Structural and Functional Basis of Cyclooxygenase Inhibition J. Med. Chem. 2007, 50, 1425-1441
2. Vane, J. R. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs Nature (London), New Biol. 1971, 231, 232-235
3. Smith, J. B.; Willis, A. L. Aspirin selectively inhibits prostaglandin production in human platelets Nature (London), New Biol. 1971, 231, 235-237
4. Ferreira, S. H.; Moncada, S.; Vane, J. R. Indomethacin and aspirin abolish prostaglandin release from the spleen Nature (London), New Biol. 1971, 231, 237-239
5. Xie, W.; Chipman, J. G.; Robertson, D. L.; Erikson, R. L.; Simmons, D. L. Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 2692-2696
6. Fu, J. Y.; Masferrer, J. L.; Seibert, K.; Raz, A.; Needleman, P. The induction and suppression of prostaglandin H2 synthase (cyclooxygenase) in human monocytes J. Biol. Chem. 1990, 265, 16737-16740
7. Kujubu, D. A.; Fletcher, B. S.; Varnum, B. C.; Lim, R. W.; Herschman, H. R. TIS10, a phorbol ester tumor promoter-inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue J. Biol. Chem. 1991, 266, 12866-12872
8. Patel, C. K.; Sen, D. J. COX-1 and COX-2 inhibitors: Current status and future prospects over COX-3 inhibitors Int. J. Drug Dev. Res. 2009, 1, 136-145
9. Kawai, S.; Kojima, F.; Kusunoki, N. Recent advances in nonsteroidal anti-inflammatory drugs Allergol. Int. 2005, 54, 209-215
10. Al-Hourani, B. J.; Sharma, S. K.; Mane, J. Y.; Tuszynski, J.; Baracos, V.; Kniess, T.; Suresh, M.; Pietzsch, J.; Wuest, F. Synthesis and evaluation of 1,5-diaryl-substituted tetrazoles as novel selective cyclooxygenase-2 (COX-2) inhibitors Bioorg. Med. Chem. Lett. 2011, 21, 1823-1826
11. Pairet, M.; Churchill, L.; Trummlitz, G.; Engelhardt, G. Differential inhibition of cyclooxygenase-1 (COX-1) and -2 (COX-2) by NSAIDS: Consequences on anti-inflammatory activity versus gastric and renal safety Inflammopharmacology 1996, 4, 61-70
12. Prasit, P.; Riendeau, D. Selective cyclooxygenase-2 inhibitors Annu. Rep. Med. Chem. 1997, 32, 211-220
13. Talley, J. J. Selective inhibitors of cyclooxygenase-2 (COX-2) Prog. Med. Chem. 1999, 36, 201-234
14. Talley, J. J.; Bertenshaw, S. R.; Brown, D. L.; Carter, J. S.; Graneto, M. J.; Koboldt, C. M.; Masferrer, J. L.; Norman, B. H.; Rogier, D. J., Jr.; Zweifel, B. S.; Seibert, K. 4,5-Diaryloxazole inhibitors of cyclooxygenase-2 (COX-2) Med. Res. Rev. 1999, 19, 199-208
15. Chan, C. C.; Boyce, S.; Brideau, C.; Charleson, S.; Cromlish, W.; Ethier, D.; Evans, J.; Ford-Hutchinson, A. W.; Forrest, M. J.; Gauthier, J. Y.; Gordon, R.; Gresser, M.; Guay, J.; Kargman, S.; Kennedy, B.; Leblanc, Y.; Leger, S.; Mancini, J.; O'Neill, G. P.; Ouellet, M.; Patrick, D.; Percival, M. D.; Perrier, H.; Prasit, P.; Rodger, I.; Tagari, P.; Therien, M.; Vickers, P.; Visco, D.; Wang, Z.; Webb, J.; Wong, E.; Xu, L. J.; Young, R. N.; Zamboni, R.; Riendeau, D. Rofecoxib [Vioxx, MK-0966; 4-(4′-methylsulfonylphenyl)-3-phenyl-2-(5H)- furanone]: A potent and orally active cyclooxygenase-2 inhibitor. Pharmacological and biochemical profiles J. Pharmacol. Exp. Ther. 1999, 290, 551-560
16. Esser, R.; Berry, C.; Du, Z.; Dawson, J.; Fox, A.; Fujimoto, R. A.; Haston, W.; Kimble, E. F.; Koehler, J.; Peppard, J.; Quadros, E.; Quintavalla, J.; Toscano, K.; Urban, L.; van Duzer, J.; Zhang, X.; Zhou, S.; Marshall, P. J. Preclinical pharmacology of lumiracoxib: A novel selective inhibitor of cyclooxygenase-2 Br. J. Pharmacol. 2005, 144, 538-550
17. Marnett, L. J. The COXIB experience: A look in the rearview mirror Annu. Rev. Pharmacol. Toxicol. 2009, 49, 265-290
18. Rodriguez, L. A. G.; Tolosa, L. B. Risk of upper gastrointestinal complications among users of traditional NSAIDs and COXIBs in the general population Gastroenterology 2007, 132, 498-506
19. Hippisley-Cox, J.; Coupland, C.; Logan, R. Risk of adverse gastrointestinal outcomes in patients taking cyclo-oxygenase-2 inhibitors or conventional non-steroidal anti-inflammatory drugs: Population based nested case-control analysis BMJ [Br. Med. J.] 2005, 331, 1310-1312
20. Ott, E.; Nussmeier, N. A.; Duke, P. C.; Feneck, R. O.; Alston, R. P.; Snabes, M. C.; Hubbard, R. C.; Hsu, P. H.; Saidman, L. J.; Mangano, D. T. Efficacy and safety of the cyclooxygenase 2 inhibitors parecoxib and valdecoxib in patients undergoing coronary artery bypass surgery J. Thorac. Cardiovasc. Surg. 2003, 125, 1481-1492
21. Nussmeier, N. A.; Whelton, A. A.; Brown, M. T.; Langford, R. M.; Hoeft, A.; Parlow, J. L.; Boyce, S. W.; Verburg, K. M. Complications of the COX-2 inhibitors parecoxib and valdecoxib after cardiac surgery N. Engl. J. Med. 2005, 352, 1081-1091
22. Cannon, C. P.; Curtis, S. P.; FitzGerald, G. A.; Krum, H.; Kaur, A.; Bolognese, J. A.; Reicin, A. S.; Bombardier, C.; Weinblatt, M. E.; van der Heijde, D.; Erdmann, E.; Laine, L. Cardiovascular outcomes with etoricoxib and diclofenac in patients with osteoarthritis and rheumatoid arthritis in the multinational etoricoxib and diclofenac arthritis long-term (MEDAL) programme: A randomized comparison Lancet 2006, 368, 1771-1781
23. Blobaum, A. L.; Marnett, L. J. NSAID action and the foundations for cardiovascular toxicity Cardiotoxicity Non-Cardiovascular Drugs 2010, 257-285
24. Wallace, J. L.; McKnight, W.; Reuter, B. K.; Vergnolle, N. NSAID-induced gastric damage in rats: requirement for inhibition of both cyclooxygenase 1 and 2 Gastroenterology 2000, 119, 706-714
25. Kakuta, H.; Zheng, X.; Oda, H.; Harada, S.; Sugimoto, Y.; Sasaki, K.; Tai, A. Cyclooxygenase-1-Selective Inhibitors Are Attractive Candidates for Analgesics That Do Not Cause Gastric Damage. Design and in Vitro/in Vivo Evaluation of a Benzamide-Type Cyclooxygenase-1 Selective Inhibitor J. Med. Chem. 2008, 51, 2400-2411
26. Perrone, M. G.; Scilimati, A.; Simone, L.; Vitale, P. Selective COX-1 inhibition: A therapeutic target to be reconsidered Curr. Med. Chem. 2010, 17, 3769-3805
27. Aid, S.; Bosetti, F. Targeting cyclooxygenases-1 and -2 in neuroinflammation: Therapeutic implications Biochimie 2011, 93, 46-51
28. Simmons, D. L.; Botting, R. M.; Hla, T. Cyclooxygenase isozymes: The biology of prostaglandin synthesis and inhibition Pharmacol. Rev. 2004, 56, 387-437
29. Teismann, P.; Tieu, K.; Choi, D.-K.; Wu, D.-C.; Naini, A.; Hunot, S.; Vila, M.; Jackson-Lewis, V.; Przedborski, S. Cyclooxygenase-2 is instrumental in Parkinson's disease neurodegeneration Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5473-5478
30. Choi, S.-H.; Bosetti, F. Cyclooxygenase-1 null mice show reduced neuroinflammation in response to β-amyloid Aging 2009, 1, 234-244
31. McKee, A. C.; Carreras, I.; Hossain, L.; Ryu, H.; Klein, W. L.; Oddo, S.; LaFerla, F. M.; Jenkins, B. G.; Kowall, N. W.; Dedeoglu, A. Ibuprofen reduces Aβ, hyperphosphorylated tau and memory deficits in Alzheimer mice Brain Res. 2008, 1207, 225-236
32. Nomura, D. K.; Morrison, B. E.; Blankman, J. L.; Long, J. Z.; Kinsey, S. G.; Marcondes, M. C. G.; Ward, A. M.; Hahn, Y. K.; Lichtman, A. H.; Conti, B.; Cravatt, B. F. Endocannabinoid Hydrolysis Generates Brain Prostaglandins That Promote Neuroinflammation Science (Washington, DC, U.S.) 2011, 334, 809-813
33. Smith, C. J.; Zhang, Y.; Koboldt, C. M.; Muhammad, J.; Zweifel, B. S.; Shaffer, A.; Talley, J. J.; Masferrer, J. L.; Seibert, K.; Isakson, P. C. Pharmacological analysis of cyclooxygenase-1 in inflammation Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 13313-13318
34. Brenneis, C.; Maier, T. J.; Schmidt, R.; Hofacker, A.; Zulauf, L.; Jakobsson, P.-J.; Scholich, K.; Geisslinger, G. Inhibition of prostaglandin E2 synthesis by SC-560 is independent of cyclooxygenase 1 inhibition FASEB J. 2006, 20, 1352-1360
35. Daikoku, T.; Tranguch, S.; Trofimova, I. N.; Dinulescu, D. M.; Jacks, T.; Nikitin, A. Y.; Connolly, D. C.; Dey, S. K. Cyclooxygenase-1 Is Overexpressed in Multiple Genetically Engineered Mouse Models of Epithelial Ovarian Cancer Cancer Res. 2006, 66, 2527-2531
36. Gupta Rajnish, A.; Tejada Lovella, V.; Tong Beverly, J.; Das Sanjoy, K.; Morrow Jason, D.; Dey Sudhansu, K.; DuBois Raymond, N. Cyclooxygenase-1 is overexpressed and promotes angiogenic growth factor production in ovarian cancer Cancer Res. 2003, 63, 906-911
37. Kakuta, H.; Fukai, R.; Zheng, X.; Ohsawa, F.; Bamba, T.; Hirata, K.; Tai, A. Identification of urine metabolites of TFAP, a cyclooxygenase-1 inhibitor Bioorg. Med. Chem. Lett. 2010, 20, 1840-1843
38. Bhattacharyya, D. K.; Lecomte, M.; Dunn, J.; Morgans, D. J.; Smith, W. L. Selective inhibition of prostaglandin endoperoxide synthase-1 (cyclooxygenase-1) by valerylsalicylic acid Arch. Biochem. Biophys. 1995, 317, 19-24
39. Siqueira-Junior, J. M.; Peters, R. R.; de Brum-Fernandes, A. J.; Ribeiro-do-Valle, R. M. Effects of valeryl salicylate, a COX-1 inhibitor, on models of acute inflammation in mice Pharmacol. Res. 2003, 48, 437-443
40. Labayle, D.; Fischer, D.; Vielh, P.; Drouhin, F.; Pariente, A.; Bories, C.; Duhamel, O.; Trousset, M.; Attali, P. Sulindac causes regression of rectal polyps in familial adenomatous polyposis Gastroenterology 1991, 101, 635-639
41. Narisawa, T. An overview on chemoprevention of colorectal cancer Nihon Geka Gakkai zasshi 1998, 99, 362-367
42. Kashfi, K.; Rigas, B. Non-COX-2 targets and cancer: Expanding the molecular target repertoire of chemoprevention Biochem. Pharmacol. 2005, 70, 969-986
43. Piazza, G. A.; Keeton, A. B.; Tinsley, H. N.; Gary, B. D.; Whitt, J. D.; Mathew, B.; Thaiparambil, J.; Coward, L.; Gorman, G.; Li, Y.; Sani, B.; Hobrath, J. V.; Maxuitenko, Y. Y.; Reynolds, R. C. A novel sulindac derivative that does not inhibit cyclooxygenases but potently inhibits colon tumor cell growth and induces apoptosis with antitumor activity Cancer Prev. Res. (Philadelphia, PA, U. S.) 2009, 2, 572-580
44. Piazza, G. A.; Keeton, A. B.; Tinsley, H. N.; Whitt, J. D.; Gary, B. D.; Mathew, B.; Singh, R.; Grizzle, W. E.; Reynolds, R. C. NSAIDs: Old drugs reveal new anticancer targets Pharmaceuticals 2010, 3, 1652-1667
45. Wang, X.; Kingsley, P. J.; Marnett, L. J.; Eling, T. E. The role of NAG-1/GDF15 in the inhibition of intestinal polyps in APC/Min mice by sulindac Cancer Prev. Res. 2011, 4, 150-160
46. Steinbrink, S. D.; Pergola, C.; Buehring, U.; George, S.; Metzner, J.; Fischer, A. S.; Haefner, A.-K.; Wisniewska, J. M.; Geisslinger, G.; Werz, O.; Steinhilber, D.; Maier, T. J. Sulindac sulfide suppresses 5-lipoxygenase at clinically relevant concentrations Cell. Mol. Life Sci. 2010, 67, 797-806
47. Etienne, F.; Resnick, L.; Sagher, D.; Brot, N.; Weissbach, H. Reduction of Sulindac to its active metabolite, sulindac sulfide: Assay and role of the methionine sulfoxide reductase system Biochem. Biophys. Res. Commun. 2003, 312, 1005-1010
48. Walters, M. J.; Blobaum, A. L.; Kingsley, P. J.; Felts, A. S.; Sulikowski, G. A.; Marnett, L. J. The influence of double bond geometry in the inhibition of cyclooxygenases by sulindac derivatives Bioorg. Med. Chem. Lett. 2009, 19, 3271-3274
49. Prusakiewicz, J. J.; Felts, A. S.; Mackenzie, B. S.; Marnett, L. J. Molecular Basis of the Time-Dependent Inhibition of Cyclooxygenases by Indomethacin Biochemistry 2004, 43, 15439-15445
50. Alcalde, E.; Mesquida, N.; Frigola, J.; Lopez-Perez, S.; Merce, R. Indene-based scaffolds. Design and synthesis of novel serotonin 5-HT6 receptor ligands Org. Biomol. Chem. 2008, 6, 3795-3810
51. Felts, A. S.; Siegel, B. S.; Young, S. M.; Moth, C. W.; Lybrand, T. P.; Dannenberg, A. J.; Marnett, L. J.; Subbaramaiah, K. Sulindac Derivatives That Activate the Peroxisome Proliferator-activated Receptor gamma but Lack Cyclooxygenase Inhibition J. Med. Chem. 2008, 51, 4911-4919
52. Musser, J. H.; Kreft, A. F., III; Failli, A. A.; Demerson, C. A.; Shah, U. S.; Nelson, J. A. Substituted indole-, indene-, pyranoindole- and tetrahydrocarbazolealkanoic acid derivatives as inhibitors of PLA2 and lipoxygenase. 93-29199 5420289, 19930310, 1995.
53. Musso, D. L.; Cochran, F. R.; Kelley, J. L.; McLean, E. W.; Selph, J. L.; Rigdon, G. C.; Orr, G. F.; Davis, R. G.; Cooper, B. R.; Styles, V. L.; Thompson, J. B.; Hall, W. R. Indanylidenes. 1. Design and Synthesis of (E)-2-(4,6-Difluoro-1-indanylidene)acetamide, a Potent, Centrally Acting Muscle Relaxant with Antiinflammatory and Analgesic Activity J. Med. Chem. 2003, 46, 399-408
54. Romeiro Nelilma, C.; Leite Ramon, D. F.; Lima Lidia, M.; Cardozo Suzana, V. S.; de Miranda Ana, L. P.; Fraga Carlos, A. M.; Barreiro Eliezer, J. Synthesis, pharmacological evaluation and docking studies of new sulindac analogues Eur. J. Med. Chem. 2009, 44, 1959-1971
55. Jung, M.; Wahl, A. F.; Neupert, W.; Geisslinger, G.; Senter, P. D. Synthesis and activity of fluorinated derivatives of sulindac sulphide and sulindac Sulphone Pharm. Pharmacol. Commun. 2000, 6, 217-221
56. Felts, A. S.; Ji, C.; Stafford, J. B.; Crews, B. C.; Kingsley, P. J.; Rouzer, C. A.; Washington, M. K.; Subbaramaiah, K.; Siegel, B. S.; Young, S. M.; Dannenberg, A. J.; Marnett, L. J. Desmethyl Derivatives of Indomethacin and Sulindac as Probes for Cyclooxygenase-Dependent Biology ACS Chem. Biol. 2007, 2, 479-483
57. Broyles, D. A.; Carpenter, B. K. Factors affecting the selection of products from a photochemically generated singlet biradical Org. Biomol. Chem. 2005, 3, 1757-1767
58. Brewster, K.; Chittenden, R. A.; Pinder, R. M.; Skeels, M. Structure of the indene-3-acetic acids. II. Reformatskii reactions of 6-(benzyloxy)-, 5,6-dimethoxy-, and 6-methoxy-1-indanones J. Chem. Soc., Perkin Trans. 1 1972, 941-943
59. Peerboom, R. A. L.; de Koning, L. J.; Nibbering, N. M. M. On the stabilization of carbanions by adjacent phenyl, cyano, methoxycarbonyl, and nitro groups in the gas phase J. Am. Soc. Mass Spectrom. 1994, 5, 159-168
60. Peretto, I.; Radaelli, S.; Parini, C.; Zandi, M.; Raveglia, L. F.; Dondio, G.; Fontanella, L.; Misiano, P.; Bigogno, C.; Rizzi, A.; Riccardi, B.; Biscaioli, M.; Marchetti, S.; Puccini, P.; Catinella, S.; Rondelli, I.; Cenacchi, V.; Bolzoni, P. T.; Caruso, P.; Villetti, G.; Facchinetti, F.; Del Giudice, E.; Moretto, N.; Imbimbo, B. P. Synthesis and biological activity of flurbiprofen analogues as selective inhibitors of beta -amyloid1-42 secretion J. Med. Chem. 2005, 48, 5705-5720
61. Barreca, G.; Cannata, V. Stereoselective isomerization process for the preparation of cis-5-fluoro-2-methyl-1-[4-(methylthio)benzyliden]inden-3-acetic acid. 2000-677842 6355836, 20001003, 2002.
62. Liedtke, A. J.; Keck, P. R. W. E. F.; Lehmann, F.; Koeberle, A.; Werz, O.; Laufer, S. A. Arylpyrrolizines as Inhibitors of Microsomal Prostaglandin E2 Synthase-1 (mPGES-1) or as Dual Inhibitors of mPGES-1 and 5-Lipoxygenase (5-LOX) J. Med. Chem. 2009, 52, 4968-4972
63. Hutchinson, J. H.; Li, Y.; Arruda, J. M.; Baccei, C.; Bain, G.; Chapman, C.; Correa, L.; Darlington, J.; King, C. D.; Lee, C.; Lorrain, D.; Prodanovich, P.; Rong, H.; Santini, A.; Stock, N.; Prasit, P.; Evans, J. F. 5-Lipoxygenase-Activating Protein Inhibitors: Development of 3-[3- tert -Butylsulfanyl-1-[4-(6-methoxy-pyridin-3-yl)-benzyl]-5-(pyridin-2-ylmethoxy)-1 H -indol-2-yl]-2,2-dimethylpropionic Acid (AM103) J. Med. Chem. 2009, 52, 5803-5815
64. Bundgaard, H.; Nielsen, N. M. Ester prodrug derivatives of carboxylic acid drugs. 1987-DK104 8801615, 19870825, 1988.
65. Stock, N.; Munoz, B.; Wrigley, J. D. J.; Shearman, M. S.; Beher, D.; Peachey, J.; Williamson, T. L.; Bain, G.; Chen, W.; Jiang, X.; St-Jacques, R.; Prasit, P. The geminal dimethyl analogue of Flurbiprofen as a novel Abeta 42 inhibitor and potential Alzheimer's disease modifying agent Bioorg. Med. Chem. Lett. 2006, 16, 2219-2223
66. Hutchinson, D. K.; Bellettini, J. R.; Betebenner, D. A.; Bishop, R. D.; Borchardt, T. B.; Bosse, T. D.; Cink, R. D.; Flentge, C. A.; Gates, B. D.; Green, B. E.; Hinman, M. M.; Huang, P. P.; Klein, L. L.; Krueger, A. C.; Larson, D. P.; Leanna, M. R.; Liu, D.; Madigan, D. L.; McDaniel, K. F.; Randolph, J. T.; Rockway, T. W.; Rosenberg, T. A.; Stewart, K. D.; Stoll, V. S.; Wagner, R.; Yeung, M. C. Preparation of fused thiadiazinediones, particularly dioxothiadiazinylnaphthalenones, as antiviral agents for the treatment of infections involving RNA-containing viral species such as hepatitis B and C and HIV. 2004-925072 20050107364, 20040824, 2005.
67. Allegretti, M.; Bertini, R.; Cesta, M. C.; Bizzarri, C.; Di Bitondo, R.; Di Cioccio, V.; Galliera, E.; Berdini, V.; Topai, A.; Zampella, G.; Russo, V.; Di Bello, N.; Nano, G.; Nicolini, L.; Locati, M.; Fantucci, P.; Florio, S.; Colotta, F. 2-Arylpropionic CXC Chemokine Receptor 1 (CXCR1) Ligands as Novel Noncompetitive CXCL8 Inhibitors J. Med. Chem. 2005, 48, 4312-4331
68. Halder, S.; Satyam, A. Accidental discovery of a 'longer-range' vinylogous Pummerer-type lactonization: Formation of sulindac sulfide lactone from sulindac Tetrahedron Lett. 2011, 52, 1179-1182
69. Barreiro, E. J.; Lima, M. E. F. The synthesis and anti-inflammatory properties of a new sulindac analog synthesized from natural safrole J. Pharm. Sci. 1992, 81, 1219-1222
70. Piazza, G. A.; Rahm, A. L. K.; Krutzsch, M.; Sperl, G.; Paranka, N. S.; Gross, P. H.; Brendel, K.; Burt, R. W.; Alberts, D. S.; Pamukcu, R.; Ahnen, D. J. Antineoplastic drugs sulindac sulfide and sulfone inhibit cell growth by inducing apoptosis Cancer Res. 1995, 55, 3110-3116
71. Williams, C. S.; Goldman, A. P.; Sheng, H.; Morrow, J. D.; DuBois, R. N. Sulindac sulfide, but not sulindac sulfone, inhibits colorectal cancer growth Neoplasia (New York) 1999, 1, 170-176
72. Richter, M.; Weiss, M.; Weinberger, I.; Furstenberger, G. Marian, B. Growth inhibition and induction of apoptosis in colorectal tumor cells by cyclooxygenase inhibitors Carcinogenesis 2001, 22, 17-25
73. Tegeder, I.; Pfeilschifter, J.; Geisslinger, G. Cyclooxygenase- independent actions of cyclooxygenase inhibitors FASEB J. 2001, 15, 2057-2072
74. Kundu, N.; Fulton, A. M. Selective cyclooxygenase (COX)-1 or COX-2 inhibitors control metastatic disease in a murine model of breast cancer Cancer Res. 2002, 62, 2343-2346
75. Chen, G.; Fei, S. Non-steroidal anti-inflammatory drugs (NSAIDs) inhibiting the proliferation of human colorectal cancer cells Nanjing Yike Daxue Xuebao 2005, 25, 923-927
76. Daikoku, T.; Wang, D.; Tranguch, S.; Morrow, J. D.; Orsulic, S.; DuBois, R. N.; Dey, S. K. Cyclooxygenase-1 is a potential target for prevention and treatment of ovarian epithelial cancer Cancer Res. 2005, 65, 3735-3744
77. Mitchell, J. A.; Akarasereenont, P.; Thiemermann, C.; Flower, R. J.; Vane, J. R. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 11693-11697
78. Gierse, J. K.; McDonald, J. J.; Hauser, S. D.; Rangwala, S. H.; Koboldt, C. M.; Seibert, K. 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, 15810-15814
79. De Leval, X.; Delarge, J.; Devel, P.; Neven, P.; Michaux, C.; Masereel, B.; Pirotte, B.; David, J. L.; Henrotin, Y.; Dogne, J. M. Evaluation of classical NSAIDs and COX-2 selective inhibitors on purified ovine enzymes and human whole blood Prostaglandins, Leukotrienes Essent. Fatty Acids 2001, 64, 211-216
80. Kitamura, T.; Kawamori, T.; Uchiya, N.; Itoh, M.; Noda, T.; Matsuura, M.; Sugimura, T.; Wakabayashi, K. Inhibitory effects of mofezolac, a cyclooxygenase-1 selective inhibitor, on intestinal carcinogenesis Carcinogenesis 2002, 23, 1463-1466
81. Kino, Y.; Kojima, F.; Kiguchi, K.; Igarashi, R.; Ishizuka, B.; Kawai, S. Prostaglandin E2 production in ovarian cancer cell lines is regulated by cyclooxygenase-1, not cyclooxygenase-2 Prostaglandins, Leukotrienes Essent. Fatty Acids 2005, 73, 103-111
82. Li, W.; Xu, R.-j.; Lin, Z.-y.; Zhuo, G.-c.; Zhang, H.-h. Effects of a cyclooxygenase-1-selective inhibitor in a mouse model of ovarian cancer, administered alone or in combination with ibuprofen, a nonselective cyclooxygenase inhibitor Med. Oncol. (Totowa, NJ, U. S.) 2009, 26, 170-177
83. Picot, D.; Loll, P. J.; Garavito, R. M. The x-ray crystal structure of the membrane protein prostaglandin H2 synthase-1 Nature (London, United Kingdom) 1994, 367, 243-249
84. Harman, C. A.; Turman, M. V.; Kozak, K. R.; Marnett, L. J.; Smith, W. L.; Garavito, R. M. Structural Basis of Enantioselective Inhibition of Cyclooxygenase-1 by S-alpha -Substituted Indomethacin Ethanolamides J. Biol. Chem. 2007, 282, 28096-28105
85. Perissutti, E.; Fiorino, F.; Renner, C.; Severino, B.; Roviezzo, F.; Sautebin, L.; Rossi, A.; Cirino, G.; Santagada, V.; Caliendo, G. Synthesis of 2-Methyl-3-indolylacetic Derivatives as Anti-Inflammatory Agents That Inhibit Preferentially Cyclooxygenase 1 without Gastric Damage J. Med. Chem. 2006, 49, 7774-7780
86. Bikzhanova, G. A.; Toulokhonova, I. S.; Gately, S.; West, R. Novel silicon-containing drugs derived from the indomethacin scaffold: Synthesis, characterization and evaluation of biological activity Silicon Chem. 2007, 3, 209-217
87. Boltze, K. H.; Brendler, O.; Jacobi, H.; Opitz, W.; Raddatz, S.; Seidel, P. R.; Vollbrecht, D. Chemical structure and antiinflammatory activity in the group of substituted indole-3-acetic acids Arzneim.-Forsch. 1980, 30, 1314-1325