Racemic and chiral sulfoxides as potential prodrugs of 4-pyrone COX-2 inhibitors
The enantiomeric synthesis and profiling of sulfoxide-based prodrugs of potent COX-2 inhibitors discovered at Almirall are reported. The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the potent and...
Saved in:
| Published in | Bioorganic & medicinal chemistry letters Vol. 16; no. 13; pp. 3605 - 3608 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Oxford
Elsevier Ltd
01.07.2006
Elsevier |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | The enantiomeric synthesis and profiling of sulfoxide-based prodrugs of potent COX-2 inhibitors discovered at Almirall are reported.
The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the potent and selective sulfone-containing COX-2 inhibitors 1, 2, and 3. Sulfoxide derivatives 7 and 9 were shown to be rapidly transformed in vivo into the corresponding sulfone derivatives 1 and 3, after oral administration to rats. |
|---|---|
| AbstractList | The enantiomeric synthesis and profiling of sulfoxide-based prodrugs of potent COX-2 inhibitors discovered at Almirall are reported.
The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the potent and selective sulfone-containing COX-2 inhibitors 1, 2, and 3. Sulfoxide derivatives 7 and 9 were shown to be rapidly transformed in vivo into the corresponding sulfone derivatives 1 and 3, after oral administration to rats. The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the potent and selective sulfone-containing COX-2 inhibitors 1, 2, and 3. Sulfoxide derivatives 7 and 9 were shown to be rapidly transformed in vivo into the corresponding sulfone derivatives 1 and 3, after oral administration to rats. |
| Author | Caturla, Francisco Calaf, Elena Amat, Mercè Warrellow, Graham Reinoso, Raquel F. |
| Author_xml | – sequence: 1 givenname: Francisco surname: Caturla fullname: Caturla, Francisco email: jfcaturl@almirall.es organization: Department of Medicinal Chemistry, Almirall Prodesfarma S.A., Research Center, Cardener 68-74, 08024 Barcelona, Spain – sequence: 2 givenname: Mercè surname: Amat fullname: Amat, Mercè organization: Department of Biology, Almirall Prodesfarma S.A., Research Center, Cardener 68-74, 08024 Barcelona, Spain – sequence: 3 givenname: Raquel F. surname: Reinoso fullname: Reinoso, Raquel F. organization: Department of Biology, Almirall Prodesfarma S.A., Research Center, Cardener 68-74, 08024 Barcelona, Spain – sequence: 4 givenname: Elena surname: Calaf fullname: Calaf, Elena organization: Department of Biology, Almirall Prodesfarma S.A., Research Center, Cardener 68-74, 08024 Barcelona, Spain – sequence: 5 givenname: Graham surname: Warrellow fullname: Warrellow, Graham organization: Department of Medicinal Chemistry, Almirall Prodesfarma S.A., Research Center, Cardener 68-74, 08024 Barcelona, Spain |
| BackLink | http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17800256$$DView record in Pascal Francis https://www.ncbi.nlm.nih.gov/pubmed/16647258$$D View this record in MEDLINE/PubMed |
| BookMark | eNqFkMFq3DAQhkVJSTZpXqCHokt682YkS7IMuYSlaQuBlJBCbkKWxo0W29pIdmnePja7kFtzGvj5ZubnOyVHQxyQkM8M1gyYutyum951aw6g1lAu2QeyYkKJohQgj8gKagWFrsXjCTnNeQvABAhxTE6YUqLiUq_Ir3vrsA-O2sFT9xSS7Wieujb-Cx4ztZnu4ojDGOZ8l6JP059MY0tFsXtJcx26uXssOA3DU2jCGFP-RD62tst4fphn5PfNt4fNj-L27vvPzfVt4QSTY6FEW_mmLnXdumburD3jKKqmbKzSnAuLpRJaeMak9NZWDddOSsdbCRJFWZdn5Ov-7tzqecI8mj5kh11nB4xTNkoDr2oB74KsYprVWs0g34MuxZwTtmaXQm_Ti2FgFuFmaxbhZhFuoFyyeenL4frU9OjfVg6GZ-DiANjsbNcmO7iQ37hKA3C5fL_aczhL-xswmewCDg59SOhG42P4X49XP5KfAA |
| CitedBy_id | crossref_primary_10_1007_s00706_014_1321_7 crossref_primary_10_1080_15569543_2021_1996394 crossref_primary_10_1002_adsc_201301086 crossref_primary_10_1007_s00706_015_1589_2 crossref_primary_10_1002_ardp_201800248 crossref_primary_10_1016_j_compbiolchem_2018_07_005 crossref_primary_10_1007_s00706_016_1844_1 crossref_primary_10_1021_cr900147h crossref_primary_10_1002_jhet_80 crossref_primary_10_1007_s00044_010_9534_8 crossref_primary_10_1002_jhet_1743 crossref_primary_10_1002_jhet_79 crossref_primary_10_1080_17415993_2012_725247 crossref_primary_10_1016_j_tet_2023_133550 crossref_primary_10_1016_j_tetasy_2007_03_010 |
| Cites_doi | 10.1021/jm049882t 10.1016/S0960-894X(98)00495-8 10.1021/jm991106b 10.1038/nrd1225 10.1055/s-1984-30829 10.1016/j.bmcl.2004.01.048 10.1016/S0960-894X(01)00534-0 10.1002/anie.199526401 10.1021/jo00129a060 |
| ContentType | Journal Article |
| Copyright | 2006 Elsevier Ltd 2006 INIST-CNRS |
| Copyright_xml | – notice: 2006 Elsevier Ltd – notice: 2006 INIST-CNRS |
| DBID | IQODW CGR CUY CVF ECM EIF NPM AAYXX CITATION 7QO 8FD FR3 P64 7X8 |
| DOI | 10.1016/j.bmcl.2006.03.101 |
| DatabaseName | Pascal-Francis Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef Biotechnology Research Abstracts Technology Research Database Engineering Research Database Biotechnology and BioEngineering Abstracts MEDLINE - Academic |
| DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef Engineering Research Database Biotechnology Research Abstracts Technology Research Database Biotechnology and BioEngineering Abstracts MEDLINE - Academic |
| DatabaseTitleList | MEDLINE Engineering Research Database MEDLINE - Academic |
| 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 | 3608 |
| ExternalDocumentID | 10_1016_j_bmcl_2006_03_101 16647258 17800256 S0960894X06004197 |
| Genre | Journal Article |
| GroupedDBID | --- --K --M .~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 AARLI AATCM AAXUO ABBQC ABFNM ABGSF ABJNI ABLVK ABMAC ABUDA ABXDB ABYKQ ABZDS ACDAQ ACGFS ACIUM ACNNM ACRLP ADBBV ADECG ADEZE ADMUD ADUVX AEBSH AEHWI AEKER AENEX AFFNX AFKWA AFTJW AFXIZ AFZHZ AGHFR AGUBO AGYEJ AHHHB AIEXJ AIKHN AITUG AJBFU AJOXV AJRQY AJSZI ALCLG ALMA_UNASSIGNED_HOLDINGS AMFUW AMRAJ ANZVX AXJTR BKOJK BLXMC BNPGV CS3 D0L DOVZS EBS EFJIC EFLBG EJD EO8 EO9 EP2 EP3 F5P FDB FIRID FLBIZ FNPLU FYGXN G-Q HZ~ IHE J1W KOM LCYCR LZ2 M29 M2Z M34 M41 MO0 N9A O-L O9- OAUVE OGGZJ OZT P-9 P2P PC. Q38 RIG ROL RPZ SCC SDF SDG SDP SES SPC SPCBC SSH SSK SSP SSU SSZ T5K Y6R YK3 ZMT ~02 ~G- .HR AAQXK ABMZM ABPIF ABPTK ABTAH AGRDE ASPBG AVWKF AZFZN FEDTE FGOYB G-2 GBLVA HEA HMK HMO HMS HMT IQODW P-8 R2- SAE SCB SEW SOC SPT WUQ XFK XPP ZY4 AKRWK CGR CUY CVF ECM EIF NPM AAXKI AAYXX CITATION HVGLF 7QO 8FD FR3 P64 7X8 |
| ID | FETCH-LOGICAL-c415t-64f7db9389fcb1468d12e47b3ba68224ae36484d1155daa7b28c55c2f505e4393 |
| IEDL.DBID | .~1 |
| ISSN | 0960-894X |
| IngestDate | Fri Aug 16 22:28:29 EDT 2024 Sat Aug 17 03:40:54 EDT 2024 Thu Sep 12 16:56:25 EDT 2024 Thu May 23 23:09:30 EDT 2024 Sun Oct 22 16:06:31 EDT 2023 Fri Feb 23 02:23:04 EST 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 13 |
| Keywords | COX-2 Sulfoxides Prodrugs Rat Sulfone Cyclooxygenase 2 Cyclooxygenase 2 inhibitor Selectivity Racemic Structure activity relation Enantiomer Chemical synthesis Enzyme Rodentia Pyran derivatives Oral administration Enzyme inhibitor Prodrug Pyranone derivatives In vitro Non steroidal antiinflammatory agent In vivo Vertebrata Mammalia Animal Sulfoxide Oxidoreductases Fluorine Organic compounds |
| Language | English |
| License | CC BY 4.0 |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c415t-64f7db9389fcb1468d12e47b3ba68224ae36484d1155daa7b28c55c2f505e4393 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| PMID | 16647258 |
| PQID | 17181986 |
| PQPubID | 23462 |
| PageCount | 4 |
| ParticipantIDs | proquest_miscellaneous_68027940 proquest_miscellaneous_17181986 crossref_primary_10_1016_j_bmcl_2006_03_101 pubmed_primary_16647258 pascalfrancis_primary_17800256 elsevier_sciencedirect_doi_10_1016_j_bmcl_2006_03_101 |
| PublicationCentury | 2000 |
| PublicationDate | 2006-07-01 |
| PublicationDateYYYYMMDD | 2006-07-01 |
| PublicationDate_xml | – month: 07 year: 2006 text: 2006-07-01 day: 01 |
| PublicationDecade | 2000 |
| PublicationPlace | Oxford |
| PublicationPlace_xml | – name: Oxford – name: England |
| PublicationTitle | Bioorganic & medicinal chemistry letters |
| PublicationTitleAlternate | Bioorg Med Chem Lett |
| PublicationYear | 2006 |
| Publisher | Elsevier Ltd Elsevier |
| Publisher_xml | – name: Elsevier Ltd – name: Elsevier |
| References | Brunel, Diter, Duetsch, Kagan (bib6) 1995; 60 bib9 Di Furia, Modena, Seraglia (bib8) 1984 FitzGerald (bib1) 2003; 2 de Laslo, Visco, Agarwal, Chang, Chin, Croft, Forsyth, Fletcher, Frantz, Hacker, Hanlon, Harper, Kostura, Li, Luell, MacCoss, Mantlo, O’Neill, Orevillo, Pang, Parsons, Ronaldo, Sahly, Sidler, Widmer, O’Keefe (bib3) 1998; 8 Bolm, Bienewald (bib7) 1995; 34 Caturla Javaloyes, F.; Warrellow, G. WO Patent 04072058, 2004. Puig, Crespo, Godessart, Feixas, Ibarzo, Jiménez, Soca, Cardelús, Heredia, Miralpeix, Puig, Beleta, Huerta, López, Segarra, Ryder, Palacios, Feixas, Jiménez, Godessart, Puig, Soca, Crespo, Caturla, Jiménez, Godessart, Amat, Cárdenas, Soca, Beleta, Ryder, Crespo (bib2) 2000; 43 Patrignani, Panara, Greco, Fusco, Natoli, Iacobelli, Chipollone, Ganci, Crèminon, Maclouf, Patrono (bib11) 1994; 271 Moh, Choi, Lim, Lee, Shin, Choi, Koh, Chung (bib4) 2004; 14 Kagan (bib10) 1993 Feixas (10.1016/j.bmcl.2006.03.101_reference0025) 2001; 11 Di Furia (10.1016/j.bmcl.2006.03.101_bib8) 1984 Patrignani (10.1016/j.bmcl.2006.03.101_bib11) 1994; 271 Puig (10.1016/j.bmcl.2006.03.101_reference0015) 2000; 43 Kagan (10.1016/j.bmcl.2006.03.101_bib10) 1993 Caturla (10.1016/j.bmcl.2006.03.101_bib2c) 2004; 47 Brunel (10.1016/j.bmcl.2006.03.101_bib6) 1995; 60 Moh (10.1016/j.bmcl.2006.03.101_bib4) 2004; 14 FitzGerald (10.1016/j.bmcl.2006.03.101_bib1) 2003; 2 Bolm (10.1016/j.bmcl.2006.03.101_bib7) 1995; 34 10.1016/j.bmcl.2006.03.101_bib5 de Laslo (10.1016/j.bmcl.2006.03.101_bib3) 1998; 8 |
| References_xml | – volume: 60 start-page: 8086 year: 1995 ident: bib6 publication-title: J. Org. Chem. contributor: fullname: Kagan – start-page: 203 year: 1993 end-page: 226 ident: bib10 publication-title: Catalytic Asymmetric Synthesis contributor: fullname: Kagan – volume: 8 start-page: 2689 year: 1998 ident: bib3 publication-title: Bioorg. Med. Chem. Lett. contributor: fullname: O’Keefe – volume: 34 start-page: 2640 year: 1995 ident: bib7 publication-title: Angew. Chem., Int. Ed. Engl. contributor: fullname: Bienewald – ident: bib9 – volume: 14 start-page: 1757 year: 2004 ident: bib4 publication-title: Bioorg. Med. Chem. Lett. contributor: fullname: Chung – start-page: 325 year: 1984 ident: bib8 publication-title: Synthesis contributor: fullname: Seraglia – volume: 2 start-page: 879 year: 2003 ident: bib1 publication-title: Nat. Rev. Drug Discov. contributor: fullname: FitzGerald – volume: 271 start-page: 1705 year: 1994 ident: bib11 publication-title: J. Pharmacol. Exp. Ther. contributor: fullname: Patrono – volume: 43 start-page: 214 year: 2000 ident: bib2 publication-title: J. Med. Chem. contributor: fullname: Crespo – volume: 47 start-page: 3874 year: 2004 ident: 10.1016/j.bmcl.2006.03.101_bib2c publication-title: J. Med. Chem. doi: 10.1021/jm049882t contributor: fullname: Caturla – volume: 8 start-page: 2689 year: 1998 ident: 10.1016/j.bmcl.2006.03.101_bib3 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/S0960-894X(98)00495-8 contributor: fullname: de Laslo – volume: 271 start-page: 1705 year: 1994 ident: 10.1016/j.bmcl.2006.03.101_bib11 publication-title: J. Pharmacol. Exp. Ther. contributor: fullname: Patrignani – volume: 43 start-page: 214 year: 2000 ident: 10.1016/j.bmcl.2006.03.101_reference0015 publication-title: J. Med. Chem. doi: 10.1021/jm991106b contributor: fullname: Puig – ident: 10.1016/j.bmcl.2006.03.101_bib5 – volume: 2 start-page: 879 year: 2003 ident: 10.1016/j.bmcl.2006.03.101_bib1 publication-title: Nat. Rev. Drug Discov. doi: 10.1038/nrd1225 contributor: fullname: FitzGerald – start-page: 325 year: 1984 ident: 10.1016/j.bmcl.2006.03.101_bib8 publication-title: Synthesis doi: 10.1055/s-1984-30829 contributor: fullname: Di Furia – volume: 14 start-page: 1757 year: 2004 ident: 10.1016/j.bmcl.2006.03.101_bib4 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/j.bmcl.2004.01.048 contributor: fullname: Moh – start-page: 203 year: 1993 ident: 10.1016/j.bmcl.2006.03.101_bib10 contributor: fullname: Kagan – volume: 11 start-page: 2687 year: 2001 ident: 10.1016/j.bmcl.2006.03.101_reference0025 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/S0960-894X(01)00534-0 contributor: fullname: Feixas – volume: 34 start-page: 2640 year: 1995 ident: 10.1016/j.bmcl.2006.03.101_bib7 publication-title: Angew. Chem., Int. Ed. Engl. doi: 10.1002/anie.199526401 contributor: fullname: Bolm – volume: 60 start-page: 8086 year: 1995 ident: 10.1016/j.bmcl.2006.03.101_bib6 publication-title: J. Org. Chem. doi: 10.1021/jo00129a060 contributor: fullname: Brunel |
| SSID | ssj0014044 |
| Score | 1.941485 |
| Snippet | The enantiomeric synthesis and profiling of sulfoxide-based prodrugs of potent COX-2 inhibitors discovered at Almirall are reported.
The preparation of the... The preparation of the sulfoxide analogues 7, 8, and 9 and their enantiomerically pure forms is discussed as well as their ability to act as prodrugs of the... |
| SourceID | proquest crossref pubmed pascalfrancis elsevier |
| SourceType | Aggregation Database Index Database Publisher |
| StartPage | 3605 |
| SubjectTerms | Animals Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents COX-2 Crystallography, X-Ray Cyclooxygenase 1 - drug effects Cyclooxygenase 2 - drug effects Cyclooxygenase 2 Inhibitors - chemical synthesis Cyclooxygenase 2 Inhibitors - chemistry Cyclooxygenase 2 Inhibitors - pharmacology Drug Evaluation, Preclinical Humans Male Medical sciences Models, Molecular Molecular Structure Pharmacology. Drug treatments Prodrugs Prodrugs - chemical synthesis Prodrugs - chemistry Prodrugs - pharmacology Rats Rats, Wistar Stereoisomerism Structure-Activity Relationship Sulfones - chemical synthesis Sulfones - chemistry Sulfones - pharmacology Sulfoxides Sulfoxides - chemical synthesis Sulfoxides - chemistry Sulfoxides - pharmacology |
| Title | Racemic and chiral sulfoxides as potential prodrugs of 4-pyrone COX-2 inhibitors |
| URI | https://dx.doi.org/10.1016/j.bmcl.2006.03.101 https://www.ncbi.nlm.nih.gov/pubmed/16647258 https://search.proquest.com/docview/17181986 https://search.proquest.com/docview/68027940 |
| Volume | 16 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lb9QwEB5VRQIkhMqWxwJdfEBckNnNy7GPq1WrBdSCgEp7i2zHboPaJNrsSvTCb2cmD6oe2kOv1sS2ZqyZz_E3MwDv0yBwwijFQ6VnnApycSWl4d5aGYhUh0pSvvPxiViexl9WyWoHFkMuDNEqe9_f-fTWW_cj016b07oopj8JfEsVr2aCikYpyiiPMRjhmf709z_Ng6rHtCWkUJiTdJ8403G8zKW96B8kIhq7LTg9qXWDKvNdr4vbwWgblI724GmPJtm82_Az2HHlCPbnJd6kL6_YB9byO9sf5yN4tBh6u43g4XH_pL4P339oSwR5psuc2fNijfM12wtf_Sly1zDdsLraEKUIx8nbrrdnDas8i3l9ta5KxxbfVjxkRXlemIJa9zyH06PDX4sl79sscIvRe8NF7NPcKEQu3hrKxMqD0MWpiYwWxDHVLhKxjHPEjkmudWpCaZPEhh7Bk0M8E72A3RLXewVMOJ0iIpS5pnsNmttqH0gTWK_bFhRj-DjoN6u7ahrZQDP7nZE1qC2myGYRjY0hGUyQ3TgTGbr7O7-b3LDX9VKpbDHeGN4NBsxQ8fREoktXbRuUQMSj5B0SQuJFXsWzMbzsLH89u6BS_Il8fc9tv4HH3f8d4gK_hd3NeusOEPFszKQ90hN4MP_8dXnyD1cv_eU |
| link.rule.ids | 315,786,790,4521,24144,27957,27958,45620,45714 |
| linkProvider | Elsevier |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lb9QwEB6VIlEkhGBLYXm0PiAuyOzm5djHakW1QLcgaKW9RbZj06A2iTa7Er3w25nJg6qH9sB1NLGtGWv8Of5mBuBtGgROGKV4qPSUU0EurqQ03FsrA5HqUEnKd16ciPlZ_HmZLLdgNuTCEK2yj_1dTG-jdS-Z9Nac1EUx-UHgW6p4ORVUNEql9-A-wXnq3_Dhzz-eB5WPaWtIoTYn9T5zpiN5mUt70b9IRCS77XR6VOsGbea7Zhe3o9H2VDp6Ao97OMkOuxU_hS1XjmD3sMSr9OUVe8dagmf753wEO7OhudsIHiz6N_Vd-PZdW2LIM13mzJ4XKxyv2Vz46neRu4bphtXVmjhFKKdwu9r8bFjlWczrq1VVOjb7uuQhK8rzwhTUu-cZnB19PJ3Ned9ngVs8vtdcxD7NjULo4q2hVKw8CF2cmshoQSRT7SIRyzhH8JjkWqcmlDZJbOgRPTkENNEebJc43wtgwukUIaHMNV1s0N9W-0CawHrd9qAYw_vBvlndldPIBp7Zr4y8QX0xRTaNSDaGZHBBdmNTZBjv7_xu_4a_rqdKZQvyxnAwODBDw9MbiS5dtWlQAyGPkndoCIk3eRVPx_C88_z16IJq8Sfy5X8u-wB25qeL4-z408mXV_Cw-9lDxODXsL1ebdwbhD9rs99u778kqf93 |
| 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=Racemic+and+chiral+sulfoxides+as+potential+prodrugs+of+4-pyrone+COX-2+inhibitors&rft.jtitle=Bioorganic+%26+medicinal+chemistry+letters&rft.au=Caturla%2C+Francisco&rft.au=Amat%2C+Merc%C3%A8&rft.au=Reinoso%2C+Raquel+F.&rft.au=Calaf%2C+Elena&rft.date=2006-07-01&rft.pub=Elsevier+Ltd&rft.issn=0960-894X&rft.eissn=1464-3405&rft.volume=16&rft.issue=13&rft.spage=3605&rft.epage=3608&rft_id=info:doi/10.1016%2Fj.bmcl.2006.03.101&rft.externalDocID=S0960894X06004197 |
| 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 |