Convenient synthesis of ibuprofen and naproxen aminoacyl, dipeptidoyl and ester derivatives

Chemical Biology and Drug Design

Volumn 73, Issue 6, 2009, Pages 618-626

  Katritzky, Alan R ^a   Jishkariani, Davit ^a   Narindoshvili, Tamari ^a  

^a University of Florida ^*  (United States)

Author keywords

Amino acids; Ibuprofen; Naproxen; Non steroidal anti inflammatory drugs; Prodrugs

Indexed keywords

AMINE; DIPEPTIDE DERIVATIVE; ESTER DERIVATIVE; IBUPROFEN DERIVATIVE; NAPROXEN DERIVATIVE; PRODRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONJUGATE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS;

AMINO ACIDS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; DIPEPTIDES; ESTERS; IBUPROFEN; NAPROXEN; PRODRUGS; STIGMASTEROL;

EID: 65649086724     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00811.x     Document Type: Article

References (52)

1. Clinard F., Sgro C., Bardou M., Dumas M., Hillon P., Bonithon-Kopp C. (2001) Non-steroidal anti-inflammatory drug prescribing patterns in general practice: comparison of a general practitioner-based survey and a pharmacy-based survey in France. Pharmacoepidemiol Drug Saf 10 : 329 338.
2. Dubois R.W., Melmed G.Y., Henning J.M., Laine L. (2004) Guidelines for the appropriate use of non-steroidal anti-inflammatory drugs, cyclo-oxygenase-2-specific inhibitors and proton pump inhibitors in patients requiring chronic anti-inflammatory therapy. Aliment Pharmacol Ther 19 : 197 208.
3. Weber A.A., Yildirim H., Schrör K. (2000) Cyclooxygenase-independent inhibition of smooth muscle cell mitogenesis by ibuprofen. Eur J Pharmacol 389 : 67 69.
4. Sandrini G., Ruiz L., Capararo M., Garofoli F., Beretta A., Nappi G. (1992) Central analgesic activity of ibuprofen. A neurophysiological study in humans. Int J Clin Pharmacol Res 12 : 197 204.
5. Sanyal A.K., Roy D., Chowdhury B., Banerjee A.B. (1993) Ibuprofen, a unique anti-inflammatory compound with antifungal activity against dermatophytes. Lett Appl Microbiol 17 : 109 111.
6. Gabriel S.E., Jaakkimainen L., Bombardier C. (1991) Risk for serious gastrointestinal complications related to use of nonsteroidal anti-inflammatory drugs. A meta-analysis. Ann Intern Med 115 : 787 796.
7. Hernández-Diaz S., Rodriguez L.A.G. (2000) Association between nonsteroidal anti-inflammatory drugs and upper gastrointestinal tract bleeding/perforation: an overview of epidemiologic studies published in the 1990s. Arch Intern Med 160 : 2093 2099.
8. Garcia Rodriguez L.A., Jick H. (1994) Risk of upper gastrointestinal bleeding and perforation associated with individual non-steroidal anti-inflammatory drugs. Lancet 343 : 769 772.
9. Smalley W.E., Ray W.A., Daugherty J.R., Griffin M.R. (1995) Nonsteroidal anti-inflammatory drugs and the incidence of hospitalizations for peptic ulcer disease in elderly persons. Am J Epidemiol 141 : 539 545.
10. Ofman J.J., MacLean C.H., Straus W.L., Morton S.C., Berger M.L., Roth E.A., Shekelle P. (2002) A metaanalysis of severe upper gastrointestinal complications of nonsteroidal antiinflammatory drugs. J Rheumatol 29 : 804 812.
11. Smalley W.E., Griffin M.R., Fought R.L., Ray W.A. (1996) Excess costs from gastrointestinal disease associated with nonsteroidal anti-inflammatory drugs. J Gen Intern Med 11 : 461 469.
12. Rahme E., Joseph L., Kong S.X., Watson D.J., LeLorier J. (2000) Gastrointestinal health care resource use and costs associated with nonsteroidal antiinflammatory drugs versus acetaminophen: retrospective cohort study of an elderly population. Arthritis Rheum 43 : 917 924.
13. Mukherjee D., Nissen S.E., Topol E.J. (2001) Risk of cardiovascular events associated with selective COX-2 inhibitors. JAMA 286 : 954 959.
14. Graham D.J., Campen D., Hui R., Spence M., Cheetham C., Levy G., Shoor S., Ray W.A. (2005) Risk of acute myocardial infarction and sudden cardiac death in patients treated with cyclo-oxygenase 2 selective and non-selective non-steroidal anti-inflammatory drugs: nested case-control study. Lancet 365 : 475 481.
15. Couzin J. (2005) Drug safety: FDA panel urges caution on many anti-inflammatory drugs. Science 307 : 1183 1185.
16. Hart F.D., Huskisson E.C. (1984) Nonsteroidal anti-inflammatory drugs. Current status and rational therapeutic use. Drugs 27 : 232 255.
17. Griffin M.R., Scheiman J.M. (2001) Prospects for changing the burden of nonsteroidal anti-inflammatory drug toxicity. Am J Med 110 : 33S 37S.
18. Zhao X., Tao X., Wei D., Song Q. (2006) Pharmacological activity and hydrolysis behavior of novel ibuprofen glucopyranoside conjugates. Eur J Med Chem 41 : 1352 1358.
19. Nielsen N.M., Bundgaard H. (1988) Glycolamide esters as biolabile prodrugs of carboxylic acid agents: synthesis, stability, bioconversion, and physicochemical properties. J Pharm Sci 77 : 285 298.
20. Bundgaard H., Nielsen N.M. (1987) Esters of N,N-disubstituted 2-hydroxyacetamides as a novel highly biolabile prodrug type for carboxylic acid agents. J Med Chem 30 : 451 454.
21. Otis M.F., Levesque L., Marceau F., Lacroix J., Gaudreault R.C. (1992) Synthesis and pharmacological evaluation of amide derivatives of nonsteroidal anti-inflammatory drugs. Inflammopharmacology 1 : 201 212.
22. Lane M.E., Levis K., McDonald G.S.A., Corrigan O.I. (2006) Comparative assessment of two indices of drug induced permeability changes in the perfused rat intestine. Int J Pharm 312 : 196 199.
23. Kwapiszewski W., Krupinska J., Koziej P., Stephanus R. (1985) Synthesis and preliminary pharmacological testing of novel 2-(4-isobutylphenyl)propionic acid derivatives. Acta Pol Pharm 42 : 545 549.
24. Shanbhag V.R., Crider A.M., Gokhale R., Harpalani A., Dick R.M. (1992) Ester and amide prodrugs of ibuprofen and naproxen: synthesis, anti-inflammatory activity, and gastrointestinal toxicity. J Pharm Sci 81 : 149 154.
25. Levit G.L., Anikina L.V., Vikharev Y.B., Demin A.M., Safin V.A., Matveeva T.V., Krasnov V.P. (2002) Synthesis and antiinflammatory and analgesic activity of naproxen amides with amino acids derivatives. Pharm Chem J 36 : 232 236.
26. Lolli M.L., Cena C., Medana C., Lazzarato L., Morini G., Coruzzi G., Manarini S., Fruttero R., Gasco A. (2001) A new class of ibuprofen derivatives with reduced gastrotoxicity. J Med Chem 44 : 3463 3468.
27. Song N., Li Y.X., Sun X., Qu F. (2004) Synthesis of (+/-)ibuprofen sugar derivatives. Yao Xue Xue Bao 39 : 105 109.
28. Zhao X., Chen D., Gao P., Ding P., Li K. (2005) Synthesis of ibuprofen eugenol ester and its microemulsion formulation for parenteral delivery. Chem Pharm Bull 53 : 1246 1250.
29. Zhao X.L., Chen D.W., Gao P., Luo Y.F., Li K.X. (2005) Synthesis, properties and microemulsion formulation of ibuprofen eugenol ester. Pharmazie 60 : 883 887.
30. Chang S.Y., Park S.B., Jung J.H., Shon S.I., Yoon H.J. (1997) Ibuprofen heterocyclic esters as dermal prodrugs. In vitro evaluation. STP Pharma Sci 7 : 315 319.
31. Murtha J.L., Ando H.Y. (1994) Synthesis of the cholesteryl ester prodrugs cholesteryl ibuprofen and cholesteryl flufenamate and their formulation into phospholipid microemulsions. J Pharm Sci 83 : 1222 1228.
32. Davaran S., Rashidi M.R., Hanaee J., Hamidi A.A., Hashemi M. (2006) Synthesis and hydrolytic behavior of ibuprofen prodrugs and their PEGylated derivatives. Drug Deliv 13 : 383 387.
33. Ranatunge R.R., Augustyniak M.E., Dhawan V., Ellis J.L., Garvey D.S., Janero D.R., Letts L.G., Richardson S.K., Shumway M.J., Trocha A.M., Young D.V., Zemtseva I.S. (2006) Synthesis and anti-inflammatory activity of a series of N-substituted naproxen glycolamides: nitric oxide-donor naproxen prodrugs. Bioorg Med Chem 14 : 2589 2599.
34. Cheng Z. (2003) Preparation of naproxen esters as prodrugs for treatment of skin, Application: CN Patent No. 2002-134982 1410413.
35. Tammara V.K., Narurkar M.M., Crider A.M., Khan M.A. (1993) Synthesis and evaluation of morpholinoalkyl ester prodrugs of indomethacin and naproxen. Pharm Res 10 : 1191 1199.
36. Ranucci E., Sartore L., Peroni I., Latini R., Bernasconi R., Ferruti P. (1994) Pharmacokinetic results on naproxen prodrugs based on poly(ethyleneglycol)s. J Biomater Sci Polym Ed 6 : 141 147.
37. Allegretti M., Bertini R., Cesta M.C., Bizzarri C., Di Bitondo R., Di Cioccio V. et al. (2005) 2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors. J Med Chem 48 : 4312 4331.
38. Levit G.L., Koroleva M.A., Krasnov V.P. (1998) Synthesis of 2-arylpropionamides. Russ J Org Chem 34 : 346 350.
39. Bhuniya S., Seo Y.J., Kim B.H. (2006) (S)-(+)-Ibuprofen-based hydrogelators: an approach toward anti-inflammatory drug delivery. Tetrahedron Lett 47 : 7153 7156.
40. Siskou I.C., Rekka E.A., Kourounakis A.P., Chrysselis M.C., Tsiakitzis K., Kourounakis P.N. (2007) Design and study of some novel ibuprofen derivatives with potential nootropic and neuroprotective properties. Bioorg Med Chem 15 : 951 961.
41. Hall S.D., Xiaotao Q. (1994) The role of coenzyme A in the biotransformation of 2-arylpropionic acids. Chem Biol Interact 90 : 235 251.
42. Katritzky A.R., He H.-Y., Suzuki K. (2000) N-Acylbenzotriazoles: neutral acylating reagents for the preparation of primary, secondary, and tertiary amides. J Org Chem 65 : 8210 8213.
43. Katritzky A.R., Hoffmann S., Suzuki K. (2004) N-acylation of sulfonamides using N-acylbenzotriazoles. ARKIVOC 12 : 14 22.
44. Katritzky A.R., Narindoshvili T., Draghici B., Angrish P. (2008) Regioselective syntheses of β-N-linked glycoaminoacids and glycopeptides. J Org Chem 73 : 511 516.
45. Katritzky A.R., Yang H., Zhang S., Wang M. (2002) An efficient conversion of carboxylic acids into Weinreb amides. ARKIVOC 11 : 39 44.
46. Katritzky A.R., Meher N.K., Singh S.K. (2005) γ,δ-Unsaturated β-diketones by acylation of ketones. J Org Chem 70 : 7792 7794.
47. Katritzky A.R., Abdel-Fattah A.A.A., Wang M. (2003) Efficient conversion of sulfones into β-keto sulfones by N-acylbenzotriazoles. J Org Chem 68 : 1443 1446.
48. Katritzky A.R., Suzuki K., Singh S.K., He H.-Y. (2003) Regiospecific C-acylation of pyrroles and indoles using N-acylbenzotriazoles. J Org Chem 68 : 5720 5723.
49. Katritzky A.R., Suzuki K., Singh S.K. (2004) C-Acylation of 2-methylfuran and thiophene using N-acylbenzotriazoles. Croatica Chem Acta 77 : 175 178.
50. Katritzky A.R., Angrish P., Narindoshvili T. (2007) Chiral O-(Z-α-aminoacyl) sugars: convenient building blocks for glycopeptide libraries. Bioconjug Chem 18 : 994 998.
51. Franssen E.J.F., Koiter J., Kuipers C.A.M., Bruins A.P., Moolenaar F., De Zeeuw D. et al. (1992) Low molecular weight proteins as carriers for renal drug targeting. Preparation of drug-protein conjugates and drug-spacer derivatives and their catabolism in renal cortex homogenates and lysosomal lysates. J Med Chem 35 : 1246 1259.
52. Bellucci G., Berti G., Bianchini R., Vecchiani S. (1988) Enantioface differentiating additions of protected hexoses to prochiral ketenes. Synthesis of optically active α-arylpropanoic acids. Gazz Chim Ital 118 : 451 456.