Discovery and SAR of novel [1,6]Naphthyridines as potent inhibitors of spleen tyrosine kinase (SYK)
The discovery of novel 5,7-disubstituted[1,6]naphthyridines as potent inhibitors of Spleen Tyrosine Kinase (SYK) is discussed. The SAR reveals the necessity for a 7-aryl group with preference towards para substitution and that this in combination with 5-aminoalkylamino substituents further improved...
Saved in:
Published in | Bioorganic & medicinal chemistry letters Vol. 13; no. 8; pp. 1415 - 1418 |
---|---|
Main Authors | , , , , , , , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Oxford
Elsevier Ltd
17.04.2003
Elsevier |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | The discovery of novel 5,7-disubstituted[1,6]naphthyridines as potent inhibitors of Spleen Tyrosine Kinase (SYK) is discussed. The SAR reveals the necessity for a 7-aryl group with preference towards
para substitution and that this in combination with 5-aminoalkylamino substituents further improved the potency of the compounds. The initial SAR as well as a survey of the other positions is discussed in detail.
Graphic |
---|---|
AbstractList | The discovery of novel 5,7-disubstituted[1,6]naphthyridines as potent inhibitors of Spleen Tyrosine Kinase (SYK) is discussed. The SAR reveals the necessity for a 7-aryl group with preference towards
para substitution and that this in combination with 5-aminoalkylamino substituents further improved the potency of the compounds. The initial SAR as well as a survey of the other positions is discussed in detail.
Graphic The discovery of novel 5,7-disubstituted[1,6]naphthyridines as potent inhibitors of Spleen Tyrosine Kinase (SYK) is discussed. The SAR reveals the necessity for a 7-aryl group with preference towards para substitution and that this in combination with 5-aminoalkylamino substituents further improved the potency of the compounds. The initial SAR as well as a survey of the other positions is discussed in detail. |
Author | Prokopowicz, Anthony S Winters, Michael P Jakes, Scott Cywin, Charles L Morwick, Tina M Soll, Richard M Hrapchak, Matt McNeil, Daniel W Goldberg, Daniel R Player, Mark R Kashem, Mohammed Rinker, James Zhao, Bao-Ping Gao, Amy Magolda, Ronald L DesJarlais, Renee L Bobko, Mark A |
Author_xml | – sequence: 1 givenname: Charles L surname: Cywin fullname: Cywin, Charles L email: ccywin@rdg.boehringer-ingelheim.com organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 2 givenname: Bao-Ping surname: Zhao fullname: Zhao, Bao-Ping organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 3 givenname: Daniel W surname: McNeil fullname: McNeil, Daniel W organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 4 givenname: Matt surname: Hrapchak fullname: Hrapchak, Matt organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 5 givenname: Anthony S surname: Prokopowicz fullname: Prokopowicz, Anthony S organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 6 givenname: Daniel R surname: Goldberg fullname: Goldberg, Daniel R organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 7 givenname: Tina M surname: Morwick fullname: Morwick, Tina M organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 8 givenname: Amy surname: Gao fullname: Gao, Amy organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 9 givenname: Scott surname: Jakes fullname: Jakes, Scott organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 10 givenname: Mohammed surname: Kashem fullname: Kashem, Mohammed organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 11 givenname: Ronald L surname: Magolda fullname: Magolda, Ronald L organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 12 givenname: Richard M surname: Soll fullname: Soll, Richard M organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 13 givenname: Mark R surname: Player fullname: Player, Mark R organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 14 givenname: Mark A surname: Bobko fullname: Bobko, Mark A organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 15 givenname: James surname: Rinker fullname: Rinker, James organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 16 givenname: Renee L surname: DesJarlais fullname: DesJarlais, Renee L organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 17 givenname: Michael P surname: Winters fullname: Winters, Michael P organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA |
BackLink | http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14640601$$DView record in Pascal Francis https://www.ncbi.nlm.nih.gov/pubmed/12668002$$D View this record in MEDLINE/PubMed |
BookMark | eNqFkFtrGzEQRkVJiC_NT2jRSyGGbDpaydrdpxDc5kJCCnEKLqUIrXaElTjaRdoE_O8rx6Z-7NMww_mGmTMiB771SMgnBmcMmPw6h0pCVlZicQJ8AmnEs8UHMmRCiowLmB6Q4T9kQEYxPiVIgBBHZMByKUuAfEjMNxdN-4ZhTbVv6PzigbaW-jRZ0d_sVP65192yX66Da5zHSHWkXduj76nzS1e7vg1xk4jdCtHTfh3amED67LyOSE_mv24nH8mh1auIx7s6Jj8vvz_OrrO7H1c3s4u7zPCK9Zm1umAFiAYrWUtesNQKJiznJa-rvDAlsDovSiuFASjrvLZY1HrKpYBCgOVjMt3uNemIGNCqLrgXHdaKgdpIU-_S1MaIAq7epalFyn3e5rrX-gWbfWpnKQFfdoCORq9s0N64uOeScpDAEne-5TB9-eYwqGgceoONC2h61bTuP6f8BRZXinY |
CitedBy_id | crossref_primary_10_1371_journal_pone_0049284 crossref_primary_10_1007_s10593_010_0457_6 crossref_primary_10_1016_j_bmcl_2016_08_070 crossref_primary_10_1039_C2MD20270K crossref_primary_10_1080_1062936X_2016_1209555 crossref_primary_10_1002_slct_202200288 crossref_primary_10_1016_j_bmc_2008_06_017 crossref_primary_10_3390_molecules28073139 crossref_primary_10_1007_s41061_020_00314_6 crossref_primary_10_1080_07391102_2016_1240108 crossref_primary_10_3390_molecules28041662 crossref_primary_10_1016_j_bmcl_2015_03_072 crossref_primary_10_1016_j_jmgm_2012_11_011 crossref_primary_10_1021_acsmedchemlett_9b00621 crossref_primary_10_1021_jm201271b crossref_primary_10_1517_13543776_2012_665878 crossref_primary_10_1007_s10311_015_0494_6 crossref_primary_10_1021_ci300227f crossref_primary_10_1016_j_compbiomed_2013_01_015 crossref_primary_10_1016_j_bmc_2005_05_033 crossref_primary_10_1007_s11302_008_9117_z crossref_primary_10_1016_j_bmcl_2008_09_106 crossref_primary_10_1016_j_drudis_2010_05_001 crossref_primary_10_1002_slct_202004462 crossref_primary_10_1016_j_ejmech_2013_04_070 crossref_primary_10_1021_jm8011036 crossref_primary_10_1016_j_tet_2009_11_115 crossref_primary_10_1517_13543770903059281 crossref_primary_10_1016_j_bmcl_2011_10_025 crossref_primary_10_1016_j_pupt_2007_06_002 crossref_primary_10_1016_j_tet_2009_09_082 crossref_primary_10_1517_13543770903207039 crossref_primary_10_1002_chin_200329125 crossref_primary_10_1039_D0RA08769F crossref_primary_10_1016_j_bmcl_2015_08_037 crossref_primary_10_3390_ph14101029 crossref_primary_10_1016_j_bmcl_2009_02_049 crossref_primary_10_1039_D2OB01216B crossref_primary_10_1517_14728222_9_5_901 |
Cites_doi | 10.1084/jem.184.1.71 10.1055/s-2000-6254 10.1016/S0021-9258(18)43936-1 10.1128/MCB.15.8.4149 10.1016/S0167-5699(99)01574-1 10.1016/S0161-5890(02)00068-8 10.1128/MCB.15.3.1582 |
ContentType | Journal Article |
Copyright | 2003 Elsevier Science Ltd 2003 INIST-CNRS |
Copyright_xml | – notice: 2003 Elsevier Science Ltd – notice: 2003 INIST-CNRS |
DBID | IQODW CGR CUY CVF ECM EIF NPM AAYXX CITATION |
DOI | 10.1016/S0960-894X(03)00163-X |
DatabaseName | Pascal-Francis Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef |
DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef |
DatabaseTitleList | MEDLINE |
Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: EIF name: MEDLINE url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/medline/basic-search sourceTypes: Index Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Medicine Anatomy & Physiology Chemistry |
EISSN | 1464-3405 |
EndPage | 1418 |
ExternalDocumentID | 10_1016_S0960_894X_03_00163_X 12668002 14640601 S0960894X0300163X |
Genre | Journal Article |
GroupedDBID | --- --K --M .HR .~1 0R~ 1B1 1RT 1~. 1~5 23N 4.4 457 4G. 53G 5GY 5VS 6TJ 7-5 71M 8P~ 9JM 9JN AABNK AACTN AAEDT AAEDW AAIAV AAIKJ AAKOC AALRI AAOAW AAQFI AAQXK AARLI AATCM AAXUO ABBQC ABFNM ABGSF ABJNI ABLVK ABMAC ABMZM ABTAH ABUDA ABXDB ABYKQ ABZDS ACDAQ ACGFS ACIUM ACNNM ACRLP ADBBV ADECG ADEZE ADMUD ADUVX AEBSH AEHWI AEKER AENEX AFFNX AFKWA AFTJW AFXIZ AFZHZ AGHFR AGRDE AGUBO AGYEJ AHHHB AIEXJ AIKHN AITUG AJBFU AJOXV AJRQY AJSZI ALCLG ALMA_UNASSIGNED_HOLDINGS AMFUW AMRAJ ANZVX ASPBG AVWKF AXJTR AZFZN BKOJK BLXMC BNPGV CS3 D0L DOVZS EBS EFJIC EFLBG EJD EO8 EO9 EP2 EP3 F5P FDB FEDTE FGOYB FIRID FLBIZ FNPLU FYGXN G-2 G-Q GBLVA HEA HMK HMO HMS HMT HVGLF HZ~ IHE J1W KOM LCYCR LZ2 M29 M2Z M34 M41 MO0 N9A O-L O9- OAUVE OGGZJ OZT P-8 P-9 P2P PC. Q38 R2- RIG ROL RPZ SAE SCB SCC SDF SDG SDP SES SEW SOC SPC SPCBC SPT SSH SSK SSP SSU SSZ T5K WUQ XFK XPP Y6R YK3 ZMT ZY4 ~02 ~G- ABPIF ABPTK IQODW AAXKI AKRWK CGR CUY CVF ECM EIF NPM AAYXX AFJKZ CITATION |
ID | FETCH-LOGICAL-c391t-ffa71704de96b6371a71414f3383b927c801b278f64c008b2bfe7ba53640740f3 |
IEDL.DBID | AIKHN |
ISSN | 0960-894X |
IngestDate | Thu Sep 26 18:55:59 EDT 2024 Sat Sep 28 08:38:12 EDT 2024 Sun Oct 22 16:05:09 EDT 2023 Fri Feb 23 02:24:00 EST 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 8 |
Keywords | Phosphorylation Enzyme Nitrogen heterocycle Transferases Enzyme inhibitor In vitro Diamine Signal transduction Structure activity relation Bicyclic compound Naphtyridine derivatives Chemical synthesis Protein-tyrosine kinase Aromatic amine |
Language | English |
License | CC BY 4.0 |
LinkModel | DirectLink |
MergedId | FETCHMERGED-LOGICAL-c391t-ffa71704de96b6371a71414f3383b927c801b278f64c008b2bfe7ba53640740f3 |
PMID | 12668002 |
PageCount | 4 |
ParticipantIDs | crossref_primary_10_1016_S0960_894X_03_00163_X pubmed_primary_12668002 pascalfrancis_primary_14640601 elsevier_sciencedirect_doi_10_1016_S0960_894X_03_00163_X |
PublicationCentury | 2000 |
PublicationDate | 2003-04-17 |
PublicationDateYYYYMMDD | 2003-04-17 |
PublicationDate_xml | – month: 04 year: 2003 text: 2003-04-17 day: 17 |
PublicationDecade | 2000 |
PublicationPlace | Oxford |
PublicationPlace_xml | – name: Oxford – name: England |
PublicationTitle | Bioorganic & medicinal chemistry letters |
PublicationTitleAlternate | Bioorg Med Chem Lett |
PublicationYear | 2003 |
Publisher | Elsevier Ltd Elsevier |
Publisher_xml | – name: Elsevier Ltd – name: Elsevier |
References | Rivera, Brugge (BIB4) 1995; 15 Oliver, Burg, Wilson, McLaughlin, Geahlen (BIB6) 1994; 269 BIB9 Turner, Schweighoffer, Colucci, Di Santo, Tybulewicz (BIB1) 2000; 21 Siraganian, Zhang, Suzuki, Sada (BIB2) 2001; 38 Brun, Gil, Mestres, Parra (BIB7) 2000 Ames, Dodds (BIB8) 1972 Taylor, Karas, Ram, Green, Seidel-Dugan (BIB3) 1995; 15 Zhang, Berenstein, Evans, Siraganian (BIB5) 1996; 184 BIB10 Ames (10.1016/S0960-894X(03)00163-X_BIB8) 1972 Turner (10.1016/S0960-894X(03)00163-X_BIB1) 2000; 21 Zhang (10.1016/S0960-894X(03)00163-X_BIB5) 1996; 184 Brun (10.1016/S0960-894X(03)00163-X_BIB7) 2000 Oliver (10.1016/S0960-894X(03)00163-X_BIB6) 1994; 269 Taylor (10.1016/S0960-894X(03)00163-X_BIB3) 1995; 15 Siraganian (10.1016/S0960-894X(03)00163-X_BIB2) 2001; 38 Rivera (10.1016/S0960-894X(03)00163-X_BIB4) 1995; 15 |
References_xml | – volume: 21 start-page: 148 year: 2000 ident: BIB1 publication-title: Immunology Today contributor: fullname: Tybulewicz – volume: 15 start-page: 4149 year: 1995 ident: BIB3 publication-title: Mol. Cell Biol. contributor: fullname: Seidel-Dugan – year: 1972 ident: BIB8 publication-title: J. Chem. Soc., Perkin Trans. 1, contributor: fullname: Dodds – volume: 15 start-page: 1582 year: 1995 ident: BIB4 publication-title: Mol. Cell. Biol. contributor: fullname: Brugge – ident: BIB10 – volume: 269 start-page: 29697 year: 1994 ident: BIB6 publication-title: J. Biol. Chem. contributor: fullname: Geahlen – volume: 38 start-page: 1229 year: 2001 ident: BIB2 publication-title: Molecular Immunology contributor: fullname: Sada – volume: 184 start-page: 71 year: 1996 ident: BIB5 publication-title: J. Exp. Med. contributor: fullname: Siraganian – ident: BIB9 – start-page: 273 year: 2000 ident: BIB7 publication-title: Synthesis contributor: fullname: Parra – volume: 184 start-page: 71 year: 1996 ident: 10.1016/S0960-894X(03)00163-X_BIB5 publication-title: J. Exp. Med. doi: 10.1084/jem.184.1.71 contributor: fullname: Zhang – year: 1972 ident: 10.1016/S0960-894X(03)00163-X_BIB8 publication-title: J. Chem. Soc., Perkin Trans. 1, 705, could be employed for the synthesis of III contributor: fullname: Ames – start-page: 273 year: 2000 ident: 10.1016/S0960-894X(03)00163-X_BIB7 publication-title: Synthesis doi: 10.1055/s-2000-6254 contributor: fullname: Brun – volume: 269 start-page: 29697 year: 1994 ident: 10.1016/S0960-894X(03)00163-X_BIB6 publication-title: J. Biol. Chem. doi: 10.1016/S0021-9258(18)43936-1 contributor: fullname: Oliver – volume: 15 start-page: 4149 year: 1995 ident: 10.1016/S0960-894X(03)00163-X_BIB3 publication-title: Mol. Cell Biol. doi: 10.1128/MCB.15.8.4149 contributor: fullname: Taylor – volume: 21 start-page: 148 year: 2000 ident: 10.1016/S0960-894X(03)00163-X_BIB1 publication-title: Immunology Today doi: 10.1016/S0167-5699(99)01574-1 contributor: fullname: Turner – volume: 38 start-page: 1229 year: 2001 ident: 10.1016/S0960-894X(03)00163-X_BIB2 publication-title: Molecular Immunology doi: 10.1016/S0161-5890(02)00068-8 contributor: fullname: Siraganian – volume: 15 start-page: 1582 year: 1995 ident: 10.1016/S0960-894X(03)00163-X_BIB4 publication-title: Mol. Cell. Biol. doi: 10.1128/MCB.15.3.1582 contributor: fullname: Rivera |
SSID | ssj0014044 |
Score | 1.9584938 |
Snippet | The discovery of novel 5,7-disubstituted[1,6]naphthyridines as potent inhibitors of Spleen Tyrosine Kinase (SYK) is discussed. The SAR reveals the necessity... |
SourceID | crossref pubmed pascalfrancis elsevier |
SourceType | Aggregation Database Index Database Publisher |
StartPage | 1415 |
SubjectTerms | Animals Biological and medical sciences Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Enzyme Precursors - antagonists & inhibitors Humans Inhibitory Concentration 50 Intracellular Signaling Peptides and Proteins Medical sciences Miscellaneous Naphthyridines - chemistry Naphthyridines - pharmacology Pharmacology. Drug treatments Protein-Tyrosine Kinases - antagonists & inhibitors Spleen - enzymology Structure-Activity Relationship Syk Kinase |
Title | Discovery and SAR of novel [1,6]Naphthyridines as potent inhibitors of spleen tyrosine kinase (SYK) |
URI | https://dx.doi.org/10.1016/S0960-894X(03)00163-X https://www.ncbi.nlm.nih.gov/pubmed/12668002 |
Volume | 13 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3fa9swED7aFLbCGFu6H9m6oIcxWpgb2VJk-TFkK9lK87Cs4DGGkWyJmraOabyHvOxv30l2GjoYgz1almT5PvnuO-ukA3ibM6qp1Dag0uqAm0gFCcfPvci1RPXHJPXHMZzPxeyCf07H6Q5MN3thXFhlp_tbne61dVcy6qQ5qstytHDkWyY8xWmKvIWlu7CH5ojzHuxNPp3N5neLCZz6nK6ufuAabDfytJ34wiPKjn0_Qfo3E_WoVisUnG0zXvzBQ709On0CjzsiSSbtWJ_Cjqn6cDCp0Im-WZN3xId2-n_mfXg43aR168OD8241_QDyD-UqdyGca6KqgiwmX8jSkgpLrsn38L34MVf1JQJ5WxYuOJ6oFamXyLEbUlaXpS5doh7XYlW7eAzSrPF1sCK5Kiu0jeRo8e3s-BlcnH78Op0FXdKFIGdJ2ATWKvTwKC9MIrRgcYiXKFXrXFmdRHGOJk1HsbSC58gfdKStibUaM7ciyKllz6FXLSvzEojUuTBICMeRlFyaRCWRTUQRWqGkNUoM4GQj56xuz9bItkFnCEzmgMkoyzwwWToAuUEjuzdJMtT__2o6vIfe9oEcB45e6QBetHBu7yB3cXT61f8_9TXs--A_dzZkfAi95vaneYMkptFD2D35FQ67qfobDgLqTw |
link.rule.ids | 315,786,790,4521,24144,27955,27956,45618,45712 |
linkProvider | Elsevier |
linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3fb9MwED6NITEkNEHHjzI2_IDQJpE1iV3Heaw6psLWPtBNCkKTZSe2FgFptIaHvvC3c3ZSqiEhJB7j2I7jc-6-iz_fAbzJaahDoW0QCqsDZmIVpAw_9yLXAtUfFaEPxzCd8ckV-5gNsy0Yr8_COFplp_tbne61dVcy6GZzUJflYO7At0hZhssUcQvN7sF9hwYcr-vk52-ehwsf42NIYe3AVd8c42m78IVHIT32vQTZ3wzUo1otcdpsm-_iDxTqrdHZY9jtYCQZtSN9Alum6sHeqEIX-vuKvCWe2On_mPdgZ7xO6taDB9NuL30P8tNymTsC54qoqiDz0SeysKTCkm_kS_SOX89UfYNivC0LR40naknqBSLshpTVTalLl6bHtVjWjo1BmhW-DlYkX8sKLSM5mn8-P34KV2fvL8eToEu5EOQ0jZrAWoX-XcgKk3LNaRLhJYuYdY6sTuMkR4Om40RYznJEDzrW1iRaDanbD2Shpc9gu1pU5gUQoXNuEA4OYyGYMKlKY5vyIrJcCWsU78PJep5l3UbWkBvKGQpGOsHIkEovGJn1QaylIe8sEYna_19ND-9Ib_NAhgNHn7QPz1txbu4gcnFg-uX_P_U17Ewupxfy4sPsfB8eehqgixKZvILt5vaHOUA40-hDv1x_ARev6yQ |
openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Discovery+and+SAR+of+novel+Naphthyridines+as+potent+inhibitors+of+spleen+tyrosine+kinase+%28SYK%29&rft.jtitle=Bioorganic+%26+medicinal+chemistry+letters&rft.au=Cywin%2C+Charles+L&rft.au=Zhao%2C+Bao-Ping&rft.au=McNeil%2C+Daniel+W&rft.au=Hrapchak%2C+Matt&rft.date=2003-04-17&rft.issn=0960-894X&rft.volume=13&rft.issue=8&rft.spage=1415&rft.epage=1418&rft_id=info:doi/10.1016%2FS0960-894X%2803%2900163-X&rft.externalDBID=n%2Fa&rft.externalDocID=10_1016_S0960_894X_03_00163_X |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0960-894X&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0960-894X&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0960-894X&client=summon |