메뉴 건너뛰기




Volumn 75, Issue 6, 2010, Pages 641-652

The novel ketoprofen amides - Synthesis and biological evaluation as antioxidants, lipoxygenase inhibitors and cytostatic agents

Author keywords

Amide; Antioxidant activity; Cytostatic activity; Ketoprofen derivatives; Soybean lipoxygenase

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2 (3 BENZOYLPHENYL) N (CYCLOHEXANEMETHYL)PROPANAMIDE; 2 (3 BENZOYLPHENYL) N CYCLOPENTYLPROPANAMIDE; 2 (3 BENZOYLPHENYL) N PHENETHYLPROPANAMIDE; 2 (3 BENZYLPHENYL) N (2 HYDROXYETHYL)PROPANAMIDE; 2 (3 BENZYLPHENYL) N (3 HYDROXYPROPYL)PROPANAMIDE; 2 (3 BENZYLPHENYL) N (CYCLOHEXANEMETHYL)PROPANAMIDE; 2 (3 BENZYLPHENYL) N CYCLOHEXYLPROPANAMIDE; 2 (3 BENZYLPHENYL) N CYCLOPENTYLPROPANAMIDE; 2 (3 BENZYLPHENYL) N ETHOXYPROPANAMIDE; 2 (3 BENZYLPHENYL) N METHOXYPROPANAMIDE; 2 (3 BENZYLPHENYL) N PHENETHYLPROPANAMIDE; 2 (3 BENZYLPHENYL) N,N BIS(3 HYDROXYETHYL)PROPANAMIDE; 2 (3 BENZYLPHENYL)PROPANAMIDE; 2 [3 [HYDROXY(PHENYL)METHYL]PHENYL] N PHENETHYL PROPANAMIDE; ANTIOXIDANT; KETOPROFEN DERIVATIVE; LIPOXYGENASE; N BENZHYDRYL 2 (3 BENZOYLPHENYL)PROPANAMIDE; N BENZHYDRYL 2 (3 BENZYLPHENYL)PROPANAMIDE; N BENZHYDRYL 2 [3 [HYDROXY(PHENYL)METHYL]PHENYL]PROPANAMIDE; N BENZYL 2 (3 BENZOYLPHENYL)PROPANAMIDE; N BENZYL 2 (3 BENZYLPHENYL)PROPANAMIDE; N BENZYL 2 [3 [HYDROXY(PHENYL)METHYL]PHENYL]PROPANAMIDE; N BENZYLOXY 2 (3 BENZYLPHENYL)PROPANAMIDE; N CYCLOHEXANEMETHYL 2 [3 [HYDROXY(PHENYL)METHYL]PHENYL]PROPANAMIDE; N CYCLOHEXYL 2 [3 [HYDROXY(PHENYL)METHYL]PHENYL]PROPANAMIDE; N CYCLOPENTYL 2 [3 [HYDROXY(PHENYL)METHYL]PHENYL]PROPANAMIDE; N HYDROXY 2 [3 [HYDROXY(PHENYL)METHYL]PHENYL]PROPANAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 77951959254     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2010.00963.x     Document Type: Article
Times cited : (26)

References (32)
  • 1
    • 0037221753 scopus 로고    scopus 로고
    • Ketoprofen 1-alkylazacycloalkan-2-one esters as dermal prodrugs: In vivo and in vitro evaluations
    • DOI 10.1081/DDC-120016726
    • Bonina F., Santagati N.A., Puglia C. (2003) Ketoprofen 1-alkylazacycloalkan-2-one esters as dermal prodrugs: in vivo and in vitro evaluations. Drug Dev Ind Pharm 29 : 181 190. (Pubitemid 36292941)
    • (2003) Drug Development and Industrial Pharmacy , vol.29 , Issue.2 , pp. 181-190
    • Bonina, F.1    Santagati, N.A.2    Puglia, C.3
  • 2
    • 0036675468 scopus 로고    scopus 로고
    • Oligoethylene ester derivatives of ketoprofen, naproxen and diclofenac as oral prodrugs: A pharmacological evaluation
    • Bonina F., Puglia C., Santagati N.A., Saija A., Tomaino A., Tita B. (2002) Oligoethylene ester derivatives of ketoprofen, naproxen and diclofenac as oral prodrugs: a pharmacological evaluation. Pharmazie 57 : 552 555.
    • (2002) Pharmazie , vol.57 , pp. 552-555
    • Bonina, F.1    Puglia, C.2    Santagati, N.A.3    Saija, A.4    Tomaino, A.5    Tita, B.6
  • 3
    • 0036909618 scopus 로고    scopus 로고
    • 1-Ethyl and 1-propylazacycloalkan-2-one ester prodrugs of ketoprofen: Synthesis, chemical stability, enzymatic hydrolysis, anti-inflammatory activity, and gastrointestinal toxicity
    • Bonina F.P., Puglia C., Ventura D., Santagati N.A., Saija A., Trombetta D. (2002) 1-Ethyl and 1-propylazacycloalkan-2-one ester prodrugs of ketoprofen. Synthesis, chemical stability, enzymatic hydrolysis, anti-inflammatory activity, and gastrointestinal toxicity. Arzneim Forsch 52 : 884 889. (Pubitemid 36033185)
    • (2002) Arzneimittel-Forschung/Drug Research , vol.52 , Issue.12 , pp. 884-889
    • Bonina, F.P.1    Puglia, C.2    Ventura, D.3    Santagati, N.A.4    Saija, A.5    Trombetta, D.6
  • 4
    • 0034681109 scopus 로고    scopus 로고
    • Biochemicaly based design of cyclooxygenase-2 (COX-2) inhibitors: Facile conversion of nonsteroidal antiinflamatory drugs to potent and highly selective COX-2 inhibitors
    • Kalgutkar A.S., Crews B.C., Rowlinson S.W., Marnett A.B., Kozak K.R., Remmel R.P., Marnett L.J. (2000) Biochemicaly based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflamatory drugs to potent and highly selective COX-2 inhibitors. Proc Natl Acad Sci USA 97 : 925 930.
    • (2000) Proc Natl Acad Sci USA , vol.97 , pp. 925-930
    • Kalgutkar, A.S.1    Crews, B.C.2    Rowlinson, S.W.3    Marnett, A.B.4    Kozak, K.R.5    Remmel, R.P.6    Marnett, L.J.7
  • 7
    • 0037138743 scopus 로고    scopus 로고
    • Nonsteroidal anti-inflammatory drugs as anticancer agents: Mechanistic, pharmacologic, and clinical issues
    • Thun M.J., Henley S.J., Patrono C. (2002) Nonsteroidal anti-inflammatory drugs as anticancer agents: mechanistic, pharmacologic, and clinical issues. J Natl Cancer Inst 94 : 252 266. (Pubitemid 34196319)
    • (2002) Journal of the National Cancer Institute , vol.94 , Issue.4 , pp. 252-266
    • Thun, M.J.1    Jane Henley, S.2    Patrono, C.3
  • 8
    • 0035135598 scopus 로고    scopus 로고
    • Growth inhibition and induction of apoptosis in colorectal tumor cells by cyclooxygenase inhibitors
    • Richter M., Weiss M., Weinberger I., Fürstenberger G., Marian B. (2001) Growth inhibition and induction of apoptosis in colorectal tumor cells by cyclooxygenase inhibitors. Carcinogenesis 22 : 17 25. (Pubitemid 32098139)
    • (2001) Carcinogenesis , vol.22 , Issue.1 , pp. 17-25
    • Richter, M.1    Weiss, M.2    Weinberger, I.3    Furstenberger, G.4    Marian, B.5
  • 9
    • 0036142033 scopus 로고    scopus 로고
    • Chemoprevention of colorectal cancer
    • DOI 10.1016/S0002-9270(01)03997-1, PII S0002927001039971
    • Gwyn K., Sinicrope F.A. (2002) Chemoprevention of colorectal cancer. Am J Gastroenterol 97 : 13 21. (Pubitemid 34059758)
    • (2002) American Journal of Gastroenterology , vol.97 , Issue.1 , pp. 13-21
    • Gwyn, K.1    Sinicrope, F.A.2
  • 10
    • 0036130051 scopus 로고    scopus 로고
    • NSAID inhibition of GI cancer growth: Clinical implications and molecular mechanisms of action
    • Husain S.S., Szabo I.L., Tarnawski A.S. (2002) NSAID inhibition of GI cancer growth: clinical implications and molecular mechanisms of action. Am J Gastroenterol 97 : 542 553.
    • (2002) Am J Gastroenterol , vol.97 , pp. 542-553
    • Husain, S.S.1    Szabo, I.L.2    Tarnawski, A.S.3
  • 11
  • 12
    • 0020613372 scopus 로고
    • Growth inhibition of transplantable murine colon adenocarcinoma 38 by indomethacin
    • Sato M., Narisawa T., Sano M., Takahashi T., Goto A. (1983) Growth inhibition of translatable murinecolon adrenocarcinoma 38 by indomethacin. J Cancer Res Clin Oncol 106 : 21 25. (Pubitemid 13040893)
    • (1983) Journal of Cancer Research and Clinical Oncology , vol.106 , Issue.1 , pp. 21-26
    • Sato, M.1    Narisawa, T.2    Sano, M.3
  • 13
    • 0030912730 scopus 로고    scopus 로고
    • Indomethacin enhances the cytotoxicity of VCR and ADR in human pulmonary adenocarcinoma cells
    • Kobayashi S., Okada S., Yoshida H., Fujimura S. (1997) Indomethacin enhances the cytotoxicity of VCR and ADR in human pulmonary adenocarcinoma cells. J Exp Med 181 : 361 370. (Pubitemid 27204692)
    • (1997) Tohoku Journal of Experimental Medicine , vol.181 , Issue.3 , pp. 361-370
    • Kobayashi, S.1    Okada, S.2    Yoshida, H.3    Fujimura, S.4
  • 14
    • 34247188972 scopus 로고    scopus 로고
    • Fenoprofen and ketoprofen amides as potential antitumor agents
    • DOI 10.1111/j.1747-0285.2007.00494.x
    • Marjanović M., Zorc B., Pejnović L., Zovko M., Kralj M. (2007) Fenoprofen and ketoprofen amides as potential antitumor agents. Chem Biol Drug Des 69 : 222 226. (Pubitemid 46608460)
    • (2007) Chemical Biology and Drug Design , vol.69 , Issue.3 , pp. 222-226
    • Marjanovic, M.1    Zorc, B.2    Pejnovic, L.3    Zovko, M.4    Kralj, M.5
  • 15
    • 43949118108 scopus 로고    scopus 로고
    • Novel lipophilic hydroxyurea derivatives: Synthesis, cytostatic and antiviral activity evaluations
    • DOI 10.1111/j.1747-0285.2008.00660.x
    • Wittine K., Benci K., Rajić Z., Zorc B., Kralj M., Marjanović M., Pavelić K., De Clercq E., Andrei G., Snoeck R., Balzarini J., Mintas M. (2008) The novel phosphoramidate prodrugs of NSAID 3-hydroxypropylamides: synthesis, cytostatic and antiviral activity evaluations. Eur J Med Chem 44 : 143 151. (Pubitemid 351704050)
    • (2008) Chemical Biology and Drug Design , vol.71 , Issue.6 , pp. 546-553
    • Perkovic, I.1    Butula, I.2    Zorc, B.3    Hock, K.4    Pavelic, S.K.5    Pavelic, K.6    Clercq, E.D.7    Balzarini, J.8    Mintas, M.9
  • 17
    • 0027165112 scopus 로고
    • Macromolecular prodrugs. I. Synthesis of nonsteroidal anti-inflammatory drug esters
    • Zorc B., Antolić S., Butula I. (1993) Macromolecular prodrugs. I. Synthesis of some non-steroidal anti-inflammatory drug esters. Acta Pharm 43 : 127 133. (Pubitemid 23255951)
    • (1993) Acta Pharmaceutica , vol.43 , Issue.2 , pp. 127-133
    • Zorc, B.1    Antolic, S.2    Butula, I.3
  • 18
    • 0000007332 scopus 로고    scopus 로고
    • Reaction with 1-benzotriazolecarboxylic acid chloride. VIII. Synthesis of N-hydroxyisocyanate derivatives
    • Butula I., Jadrijević Mladar Takač M. (2000) Reaction with 1-benzotriazolecarboxylic acid chloride. VIII. Synthesis of N-hydroxyisocyanate derivatives. Croat Chem Acta 73 : 569 574.
    • (2000) Croat Chem Acta , vol.73 , pp. 569-574
    • Butula, I.1    Jadrijević Mladar Takač, M.2
  • 19
    • 1542512213 scopus 로고    scopus 로고
    • The novel ketoprofenamides: Synthesis and spectroscopic characterization
    • Zovko M., Zorc B., Jadrijević-Mladar Takač M., Metelko B., Novak P. (2003) The novel ketoprofenamides - synthesis and spectroscopic characterization. Croat Chem Acta 76 : 335 341. (Pubitemid 38333499)
    • (2003) Croatica Chemica Acta , vol.76 , Issue.4 , pp. 335-341
    • Zovko, M.1    Zorc, B.2    Takac, M.J.-M.3    Metelko, B.4    Novak, P.5
  • 20
    • 0000342917 scopus 로고
    • Synthesis, conformational studies and enantioselective homogeneous catalytic hydrogenation with CRC-PHOS, and some congeners
    • Comisso G., Sega A., Šunjić V. (1981) Synthesis, conformational studies and enantioselective homogeneous catalytic hydrogenation with CRC-PHOS, and some congeners. Croat Chem Acta 54 : 375 395.
    • (1981) Croat Chem Acta , vol.54 , pp. 375-395
    • Comisso, G.1    Sega, A.2    Šunjić, V.3
  • 22
    • 0029115908 scopus 로고
    • Comparative study on the enantiomeric separation of several non-steroidal anti-inflammatory drugs on two cellulose-bases chiral stationary phases
    • Van Overbeke A., Baeyens W., Dewaele C. (1995) Comparative study on the enantiomeric separation of several non-steroidal anti-inflammatory drugs on two cellulose-bases chiral stationary phases. J Liq Chromatogr 18 : 2427 2443.
    • (1995) J Liq Chromatogr , vol.18 , pp. 2427-2443
    • Van Overbeke, A.1    Baeyens, W.2    Dewaele, C.3
  • 23
    • 34447268471 scopus 로고    scopus 로고
    • Synthesis and pharmacochemical evaluation of novel aryl-acetic acid inhibitors of lipoxygenase, antioxidants, and anti-inflammatory agents
    • DOI 10.1016/j.bmc.2007.06.001, PII S096808960700524X
    • Pontiki E., Hadjipavlou-Litina D. (2007) Synthesis and pharmacochemical evaluation of novel aryl-acetic acid inhibitors of lipoxygenase, antioxidants, and anti-inflammatory agents. Bioorg Med Chem 15 : 5819 5827. (Pubitemid 47043473)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.17 , pp. 5819-5827
    • Pontiki, E.1    Hadjipavlou-Litina, D.2
  • 24
    • 0032982508 scopus 로고    scopus 로고
    • Antioxidant activity applying an improved ABTS radical cation decolorization assay
    • DOI 10.1016/S0891-5849(98)00315-3, PII S0891584998003153
    • Re R., Pellegrini N., Proteggente A., Pannala A., Yang M., Rice-Evans C. (1999) Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med 26 : 1231 1237. (Pubitemid 29262709)
    • (1999) Free Radical Biology and Medicine , vol.26 , Issue.9-10 , pp. 1231-1237
    • Re, R.1    Pellegrini, N.2    Proteggente, A.3    Pannala, A.4    Yang, M.5    Rice-Evans, C.6
  • 25
    • 0035806018 scopus 로고    scopus 로고
    • Chemoselective control of hydrogenation among aromatic carbonyl and benzyl alcohol derivatives using Pd/C(en) catalyst
    • DOI 10.1016/S0040-4020(01)00421-5, PII S0040402001004215
    • Hattori K., Sajiki H., Hirota K. (2001) Chemoselective control of hydrofenation among aromatic carbonyl and benzyl alcohol derivatives using Pd/C(en) catalyst. Tetrahedron 57 : 4817 4824. (Pubitemid 32510924)
    • (2001) Tetrahedron , vol.57 , Issue.23 , pp. 4817-4824
    • Hattori, K.1    Sajiki, H.2    Hirota, K.3
  • 26
    • 0025317890 scopus 로고
    • Synthesis and structure-activity relationships of anti-inflammatory 9,10-dihydro-9-oxo-2-acridine-alkanoic acids and 4-(2-carboxyphenyl) aminobenzenealkanoic acids
    • Taraborewala R.B., Kauffman J.M. (1990) Synthesis and structure-activity relationships of anti-inflammatory 9,10-dihydro-9-oxo-2-acridine-alkanoic acids and 4-(2-carboxyphenyl)aminobenzenealkanoic acids. J Pharm Sci 79 : 173 178.
    • (1990) J Pharm Sci , vol.79 , pp. 173-178
    • Taraborewala, R.B.1    Kauffman, J.M.2
  • 27
    • 0025084538 scopus 로고
    • Oxygenation of biological membranes by the pure reticulocyte lipoxygenase
    • Kühn H., Belkner J., Wiesner R., Brash A.R. (1990) Oxygenation of biological membranes by the pure reticulocyte lipoxygenase. J Biol Chem 265 : 18351 18361. (Pubitemid 20382195)
    • (1990) Journal of Biological Chemistry , vol.265 , Issue.30 , pp. 18351-18361
    • Kuhn, H.1    Belkner, J.2    Wiesner, R.3    Brash, A.R.4
  • 28
    • 34247633701 scopus 로고    scopus 로고
    • Lipoxygenases superfamily (LOX): An interesting target for the development of inhibitors-promising drugs against cell differentiation, inflammation and carcinogenesis
    • Pontiki E., Hadjipavlou-Litina D. (2005) Lipoxygenases superfamily (LOX): an interesting target for the development of inhibitors-promising drugs against cell differentiation, inflammation and carcinogenesis. Curr Enz Inh 1 : 309 328.
    • (2005) Curr Enz Inh , vol.1 , pp. 309-328
    • Pontiki, E.1    Hadjipavlou-Litina, D.2
  • 29
    • 0028032010 scopus 로고
    • 5-Lipoxygenase and 12-lipoxygenase: Attractive targets for the development of novel antipsoriatic drugs
    • Muller K. (1994) 5-Lipoxygenase and 12-lipoxygenase: attractive targets for the development of novel antipsoriatic drugs. Arch Pharm 327 : 3 19. (Pubitemid 24035620)
    • (1994) Archiv der Pharmazie , vol.327 , Issue.1 , pp. 3-19
    • Muller, K.1
  • 30
    • 11344277432 scopus 로고    scopus 로고
    • Quantitative-structure activity relationships on lipoxygenase inhibitors
    • Pontiki E., Hadjipavlou-Litina D. (2002) Quantitative-structure activity relationships on lipoxygenase inhibitors. Internet Electron J Mol Des 1 : 134 141.
    • (2002) Internet Electron J Mol des , vol.1 , pp. 134-141
    • Pontiki, E.1    Hadjipavlou-Litina, D.2
  • 31
    • 1542751777 scopus 로고    scopus 로고
    • Review in quantitative structure activity relationships on lipoxygenase inhibitors
    • Pontiki E., Hadjipavlou-Litina D. (2003) Review in quantitative structure activity relationships on lipoxygenase inhibitors. Mini Rev Med Chem 3 : 487 499.
    • (2003) Mini Rev Med Chem , vol.3 , pp. 487-499
    • Pontiki, E.1    Hadjipavlou-Litina, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.