메뉴 건너뛰기




Volumn 89, Issue , 2015, Pages 503-523

Development and evaluation of ST-1829 based on 5-benzylidene-2-phenylthiazolones as promising agent for anti-leukotriene therapy

Author keywords

5 Lipoxygenase; Anti leukotriene therapy; Hydroxythiazoles; Inflammation; Solubility; Structureeactivity relationship

Indexed keywords

5 ( 4 CHLOROBENZYL) 2,4 TOLYLTHIAZOL 4 OL; ARACHIDONATE 5 LIPOXYGENASE; ARACHIDONATE 5 LIPOXYGENASE INHIBITOR; LEUKOTRIENE RECEPTOR BLOCKING AGENT; OXYGENASE INHIBITOR; PLASMA PROTEIN; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; 5-(4-CHLOROBENZYL)-2-P-TOLYLTHIAZOL-4-OL; 5-(4-METHOXYBENZYLIDENE)-2-P-TOLYLTHIAZOL-4(5H)-ONE; LEUKOTRIENE; LIPOXYGENASE INHIBITOR;

EID: 84908456983     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.10.054     Document Type: Article
Times cited : (15)

References (50)
  • 3
    • 0242357690 scopus 로고    scopus 로고
    • The molecular biology and regulation of 5-lipoxygenase
    • O.P. Rådmark The molecular biology and regulation of 5-lipoxygenase Am. J. Respir. Crit. Care Med. 161 2000 S11 S15
    • (2000) Am. J. Respir. Crit. Care Med. , vol.161 , pp. 11-S15
    • Rådmark, O.P.1
  • 4
    • 30044446862 scopus 로고    scopus 로고
    • 5-lipoxygenase activating protein homodimer in human neutrophils: Evidence for a role in leukotriene synthesis
    • H. Plante S. Picard J. Mancini P. Borgeat 5-lipoxygenase activating protein homodimer in human neutrophils: evidence for a role in leukotriene synthesis Biochem. J. 393 2006 211 218
    • (2006) Biochem. J. , vol.393 , pp. 211-218
    • Plante, H.1    Picard, S.2    Mancini, J.3    Borgeat, P.4
  • 7
    • 0019311062 scopus 로고
    • Leukotriene B, a potent chemokinetic and aggregating substance released from polymorphonuclear leukocytes
    • A.W. Ford-Hutchinson M.A. Bray M.V. Doig M.E. Shipley M.J. Smith Leukotriene B, a potent chemokinetic and aggregating substance released from polymorphonuclear leukocytes Nature 286 1980 264 265
    • (1980) Nature , vol.286 , pp. 264-265
    • Ford-Hutchinson, A.W.1    Bray, M.A.2    Doig, M.V.3    Shipley, M.E.4    Smith, M.J.5
  • 8
    • 0023177955 scopus 로고
    • Leukotrienes and lipoxins: Structures, biosynthesis, and biological effects
    • B. Samuelsson S.E. Dahlen J.A. Lindgren C.A. Rouzer C.N. Serhan Leukotrienes and lipoxins: structures, biosynthesis, and biological effects Science 237 1987 1171 1176
    • (1987) Science , vol.237 , pp. 1171-1176
    • Samuelsson, B.1    Dahlen, S.E.2    Lindgren, J.A.3    Rouzer, C.A.4    Serhan, C.N.5
  • 10
    • 33750102847 scopus 로고    scopus 로고
    • Therapeutic options for 5-lipoxygenase inhibitors
    • O. Werz D. Steinhilber Therapeutic options for 5-lipoxygenase inhibitors Pharmacol. Ther. 112 2006 701 718
    • (2006) Pharmacol. Ther. , vol.112 , pp. 701-718
    • Werz, O.1    Steinhilber, D.2
  • 16
    • 84861185532 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of a class of 5-benzylidene-2-phenyl-thiazolinones as potent 5-lipoxygenase inhibitors
    • S. Barzen C.B. Rödl A. Lill D. Steinhilber H. Stark B. Hofmann Synthesis and biological evaluation of a class of 5-benzylidene-2-phenyl-thiazolinones as potent 5-lipoxygenase inhibitors Bioorg. Med. Chem. 20 2012 3575 3583
    • (2012) Bioorg. Med. Chem. , vol.20 , pp. 3575-3583
    • Barzen, S.1    Rödl, C.B.2    Lill, A.3    Steinhilber, D.4    Stark, H.5    Hofmann, B.6
  • 17
    • 0022002461 scopus 로고
    • Studies on thiazolin-4-one: Synthesis of some pyrano[2,3-b]thiazole derivatives
    • E.M. Zayed A.A.A. Elbannany S.A.S. Ghozlan Studies on thiazolin-4-one: synthesis of some pyrano[2,3-b]thiazole derivatives Pharmazie 40 1985 194 197
    • (1985) Pharmazie , vol.40 , pp. 194-197
    • Zayed, E.M.1    Elbannany, A.A.A.2    Ghozlan, S.A.S.3
  • 18
    • 0028031723 scopus 로고
    • Synthesis and biological evaluation of 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]oxazoles, -thiazoles, and -imidazoles: Novel dual 5-lipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity
    • P.C. Unangst D.T. Connor W.A. Cetenko R.J. Sorenson C.R. Kostlan J.C. Sircar C.D. Wright D.J. Schrier R.D. Dyer Synthesis and biological evaluation of 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]oxazoles, -thiazoles, and -imidazoles: novel dual 5-lipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity J. Med. Chem. 37 1994 322 328
    • (1994) J. Med. Chem. , vol.37 , pp. 322-328
    • Unangst, P.C.1    Connor, D.T.2    Cetenko, W.A.3    Sorenson, R.J.4    Kostlan, C.R.5    Sircar, J.C.6    Wright, C.D.7    Schrier, D.J.8    Dyer, R.D.9
  • 19
    • 33751066430 scopus 로고
    • Some observations concerning the lactonization of 3-aroylpropionic acids
    • A. Tsolomitis C. Sandris Some observations concerning the lactonization of 3-aroylpropionic acids J. Heterocycl. Chem. 20 1983 1545 1548
    • (1983) J. Heterocycl. Chem. , vol.20 , pp. 1545-1548
    • Tsolomitis, A.1    Sandris, C.2
  • 20
    • 0141832164 scopus 로고    scopus 로고
    • Synthesis of arylidene derivatives of N -unsubstituted pyrrolin-2-ones
    • A.Y. Egorova Synthesis of arylidene derivatives of N -unsubstituted pyrrolin-2-ones Russ. Chem. Bull. 51 2002 183 184
    • (2002) Russ. Chem. Bull. , vol.51 , pp. 183-184
    • Egorova, A.Y.1
  • 21
    • 0024588517 scopus 로고
    • Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety
    • J. DeRuiter B.E. Swearingen V. Wandrekar C.A. Mayfield Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety J. Med. Chem. 32 1989 1033 1038
    • (1989) J. Med. Chem. , vol.32 , pp. 1033-1038
    • Deruiter, J.1    Swearingen, B.E.2    Wandrekar, V.3    Mayfield, C.A.4
  • 24
    • 33644786846 scopus 로고    scopus 로고
    • Electronic effects of ring substituents on triplet benzylic biradicals
    • P.J. Wagner L. Wang Electronic effects of ring substituents on triplet benzylic biradicals Org. Lett. 8 2006 645 647
    • (2006) Org. Lett. , vol.8 , pp. 645-647
    • Wagner, P.J.1    Wang, L.2
  • 25
    • 0141747457 scopus 로고    scopus 로고
    • A practical synthesis of±,2-unsaturated imides, useful substrates for asymmetric conjugate addition reactions
    • E.N. Jacobsen S.N. Goodman A practical synthesis of ±, 2-unsaturated imides, useful substrates for asymmetric conjugate addition reactions Adv. Synth. Catal. 344 2002 953 956
    • (2002) Adv. Synth. Catal. , vol.344 , pp. 953-956
    • Jacobsen, E.N.1    Goodman, S.N.2
  • 26
    • 37049089175 scopus 로고
    • Synthesis and reactions of 5-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-4-ones
    • Y.S. Laxmi D.S. Iyengar Synthesis and reactions of 5-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-4-ones J. Chem. Soc. Perkin Trans. 1 1995 3043 3045
    • (1995) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 3043-3045
    • Laxmi, Y.S.1    Iyengar, D.S.2
  • 27
    • 9644268880 scopus 로고    scopus 로고
    • Simple microwave-assisted method for the synthesis of primary thioamides from nitriles
    • M.C. Bagley K. Chapaneri C. Glover E.A. Merritt Simple microwave-assisted method for the synthesis of primary thioamides from nitriles Synlett 14 2004 2615 2617
    • (2004) Synlett , vol.14 , pp. 2615-2617
    • Bagley, M.C.1    Chapaneri, K.2    Glover, C.3    Merritt, E.A.4
  • 28
    • 0001668869 scopus 로고
    • Umsetzungen mit Dicarbonsäure-dichloriden
    • J. Goerdeler H. Horstman Umsetzungen mit Dicarbonsäure-dichloriden Chem. Ber. 93 1960 671 678
    • (1960) Chem. Ber. , vol.93 , pp. 671-678
    • Goerdeler, J.1    Horstman, H.2
  • 29
    • 33846490748 scopus 로고
    • Reaktionen mit Acyl-isocyanaten
    • R. Neidlein Reaktionen mit Acyl-isocyanaten Arch. Pharm. 298 1965 124 130
    • (1965) Arch. Pharm. , vol.298 , pp. 124-130
    • Neidlein, R.1
  • 31
    • 84863216964 scopus 로고    scopus 로고
    • Structure-based design of rhodanine-based acylsulfonamid derivatives as antagonists of the anti-apoptotic Bcl-2 protein
    • H. Li J. Yang S. Ma C. Qiao Structure-based design of rhodanine-based acylsulfonamid derivatives as antagonists of the anti-apoptotic Bcl-2 protein Bioorg. Med. Chem. 20 2012 4194 4200
    • (2012) Bioorg. Med. Chem. , vol.20 , pp. 4194-4200
    • Li, H.1    Yang, J.2    Ma, S.3    Qiao, C.4
  • 33
    • 84862929061 scopus 로고    scopus 로고
    • A general and facile one-pot process of isothiocyanates from amines under aqueous conditions
    • X. Hu N. Sun B. Li J. Shao W. Mo B. Hu Z. Shen A general and facile one-pot process of isothiocyanates from amines under aqueous conditions Beilstein J. Org. Chem. 8 2012 61 70
    • (2012) Beilstein J. Org. Chem. , vol.8 , pp. 61-70
    • Hu, X.1    Sun, N.2    Li, B.3    Shao, J.4    Mo, W.5    Hu, B.6    Shen, Z.7
  • 35
    • 0033602270 scopus 로고    scopus 로고
    • Synthesis of novel 2-benzothiopyran and 3-benzothiepin derivatives and their stimulatory effect on bone formation
    • T. Oda K. Notoya M. Gotoh S. Taketomi Y. Fujisawa H. Makino T. Sohda Synthesis of novel 2-benzothiopyran and 3-benzothiepin derivatives and their stimulatory effect on bone formation J. Med. Chem. 42 1999 751 760
    • (1999) J. Med. Chem. , vol.42 , pp. 751-760
    • Oda, T.1    Notoya, K.2    Gotoh, M.3    Taketomi, S.4    Fujisawa, Y.5    Makino, H.6    Sohda, T.7
  • 36
    • 55349110319 scopus 로고    scopus 로고
    • Microwave-assisted esterification of diverse carboxylic acids and chiral amino acids
    • Q.-D. You Q. Yang X.-J. Wang Z.-Y. Li L. Sun Microwave-assisted esterification of diverse carboxylic acids and chiral amino acids Synth. Commun. 38 2008 4107 4115
    • (2008) Synth. Commun. , vol.38 , pp. 4107-4115
    • You, Q.-D.1    Yang, Q.2    Wang, X.-J.3    Li, Z.-Y.4    Sun, L.5
  • 39
    • 67849103989 scopus 로고    scopus 로고
    • Highly enantioselective and diastereoselective synthesis of chiral amino alcohols by ruthenium-catalyzed asymmetric hydrogenation of ±-amino aliphatic ketones
    • Q.-L. Zhou J.-H. Xie S. Liu W.-L. Kong W.-J. Bai X.-C. Wang L.-X. Wang Highly enantioselective and diastereoselective synthesis of chiral amino alcohols by ruthenium-catalyzed asymmetric hydrogenation of ±-amino aliphatic ketones J. Am. Chem. Soc. 131 2009 4222 4223
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 4222-4223
    • Zhou, Q.-L.1    Xie, J.-H.2    Liu, S.3    Kong, W.-L.4    Bai, W.-J.5    Wang, X.-C.6    Wang, L.-X.7
  • 43
    • 84874632186 scopus 로고    scopus 로고
    • Principles and applications of halogen bonding in medicinal chemistry and chemical biology
    • R. Wilcken M.O. Zimmermann A. Lange A.C. Joerger F.M. Boeckler Principles and applications of halogen bonding in medicinal chemistry and chemical biology J. Med. Chem. 56 2013 1363 1388
    • (2013) J. Med. Chem. , vol.56 , pp. 1363-1388
    • Wilcken, R.1    Zimmermann, M.O.2    Lange, A.3    Joerger, A.C.4    Boeckler, F.M.5
  • 44
    • 0032760203 scopus 로고    scopus 로고
    • Reversible ligand binding to human serum albumin: Theoretical and clinical aspects
    • H. Vorum Reversible ligand binding to human serum albumin: theoretical and clinical aspects Dan. Med. Bull. 46 1999 379 399
    • (1999) Dan. Med. Bull. , vol.46 , pp. 379-399
    • Vorum, H.1
  • 46
    • 77950571108 scopus 로고    scopus 로고
    • New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays
    • J.B. Baell G.A. Holloway New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays J. Med. Chem. 53 2010 2719
    • (2010) J. Med. Chem. , vol.53 , pp. 2719
    • Baell, J.B.1    Holloway, G.A.2
  • 47
    • 36148998726 scopus 로고    scopus 로고
    • Synthesis of ethyl 4-O-[4-(1,2,4-Oxadiazol-5-yl)phenyl]-alpha-D-mannopyranosides
    • D. Sinou J.V.d. Anjos S.J.d. Melo R.M. Srivastava Synthesis of ethyl 4-O-[4-(1,2,4-Oxadiazol-5-yl)phenyl]-alpha-D-mannopyranosides Lett. Org. Chem. 4 2007 393 397
    • (2007) Lett. Org. Chem. , vol.4 , pp. 393-397
    • Sinou, D.1    Anjos, S.J.D.2    Melo, R.M.3    Srivastava, R.M.4
  • 48
    • 0036464591 scopus 로고    scopus 로고
    • Activation of 5-lipoxygenase by cell stress is calcium independent in human polymorphonuclear leukocytes
    • O. Werz Activation of 5-lipoxygenase by cell stress is calcium independent in human polymorphonuclear leukocytes Blood 99 2002 1044 1052
    • (2002) Blood , vol.99 , pp. 1044-1052
    • Werz, O.1
  • 50
    • 0028961439 scopus 로고
    • Sequential induction of 5-lipoxygenase gene expression and activity in Mono Mac 6 cells by transforming growth factor beta and 1,25-dihydroxyvitamin D3
    • M. Brungs O. Rådmark B. Samuelsson D. Steinhilber Sequential induction of 5-lipoxygenase gene expression and activity in Mono Mac 6 cells by transforming growth factor beta and 1,25-dihydroxyvitamin D3 Proc. Natl. Acad. Sci. U. S. A. 92 1995 107 111
    • (1995) Proc. Natl. Acad. Sci. U. S. A. , vol.92 , pp. 107-111
    • Brungs, M.1    Rådmark, O.2    Samuelsson, B.3    Steinhilber, D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.