Asymmetric synthesis and biological evaluation of the enantiomeric isomers of the immunosuppressive FTY720-phosphate
[Display omitted] A practical asymmetric synthesis of both enantiomers of the immunosuppressive FTY720-phosphate ( 2) was accomplished, and the enantiomers were pharmacologically evaluated. Several lipases showed considerable activity and enantioselectivity for O-acylation of N-acetyl FTY720 ( 3) or...
Saved in:
Published in | Bioorganic & medicinal chemistry Vol. 13; no. 2; pp. 425 - 432 |
---|---|
Main Authors | , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
Oxford
Elsevier Ltd
17.01.2005
Elsevier Science |
Subjects | |
Online Access | Get full text |
Cover
Loading…
Abstract | [Display omitted]
A practical asymmetric synthesis of both enantiomers of the immunosuppressive FTY720-phosphate (
2) was accomplished, and the enantiomers were pharmacologically evaluated. Several lipases showed considerable activity and enantioselectivity for
O-acylation of
N-acetyl FTY720 (
3) or
N-benzyloxycarbonyl FTY720 (
7) in combination with vinyl acetate or benzyl vinyl carbonate as the acyl donors. The synthesis using the lipase-catalyzed acylation as the key step produced the enantiomerically pure (>99.5% ee) enantiomers of
2 in multigram quantities. (
S)-Isomer of
2 had more potent binding affinities to S1P
1,3,4,5 and inhibitory activity on lymphocyte migration toward S1P than (
R)-
2, suggesting that (
S)-isomer of
2 is responsible for the immunosuppressive activity after administration of
1. Severe bradycardia was observed in anesthetized rats when (
S)-
2 was administered intravenously, while (
R)-
2 had no clear effect on heart rate up to 0.3
mg/kg. |
---|---|
AbstractList | A practical asymmetric synthesis of both enantiomers of the immunosuppressive FTY720-phosphate (2) was accomplished, and the enantiomers were pharmacologically evaluated. Several lipases showed considerable activity and enantioselectivity for O-acylation of N-acetyl FTY720 (3) or N-benzyloxycarbonyl FTY720 (7) in combination with vinyl acetate or benzyl vinyl carbonate as the acyl donors. The synthesis using the lipase-catalyzed acylation as the key step produced the enantiomerically pure (>99.5% ee) enantiomers of 2 in multigram quantities. (S)-Isomer of 2 had more potent binding affinities to S1P(1,3,4,5) and inhibitory activity on lymphocyte migration toward S1P than (R)-2, suggesting that (S)-isomer of 2 is responsible for the immunosuppressive activity after administration of 1. Severe bradycardia was observed in anesthetized rats when (S)-2 was administered intravenously, while (R)-2 had no clear effect on heart rate up to 0.3 mg/kg. A practical asymmetric synthesis of both enantiomers of the immunosuppressive FTY720-phosphate (2) was accomplished, and the enantiomers were pharmacologically evaluated. Several lipases showed considerable activity and enantioselectivity for O-acylation of N-acetyl FTY720 (3) or N-benzyloxycarbonyl FTY720 (7) in combination with vinyl acetate or benzyl vinyl carbonate as the acyl donors. The synthesis using the lipase-catalyzed acylation as the key step produced the enantiomerically pure (>99.5% ee) enantiomers of 2 in multigram quantities. (S)-Isomer of 2 had more potent binding affinities to S1P(1,3,4,5) and inhibitory activity on lymphocyte migration toward S1P than (R)-2, suggesting that (S)-isomer of 2 is responsible for the immunosuppressive activity after administration of 1. Severe bradycardia was observed in anesthetized rats when (S)-2 was administered intravenously, while (R)-2 had no clear effect on heart rate up to 0.3 mg/kg. [Display omitted] A practical asymmetric synthesis of both enantiomers of the immunosuppressive FTY720-phosphate ( 2) was accomplished, and the enantiomers were pharmacologically evaluated. Several lipases showed considerable activity and enantioselectivity for O-acylation of N-acetyl FTY720 ( 3) or N-benzyloxycarbonyl FTY720 ( 7) in combination with vinyl acetate or benzyl vinyl carbonate as the acyl donors. The synthesis using the lipase-catalyzed acylation as the key step produced the enantiomerically pure (>99.5% ee) enantiomers of 2 in multigram quantities. ( S)-Isomer of 2 had more potent binding affinities to S1P 1,3,4,5 and inhibitory activity on lymphocyte migration toward S1P than ( R)- 2, suggesting that ( S)-isomer of 2 is responsible for the immunosuppressive activity after administration of 1. Severe bradycardia was observed in anesthetized rats when ( S)- 2 was administered intravenously, while ( R)- 2 had no clear effect on heart rate up to 0.3 mg/kg. |
Author | Adachi, Kunitomo Sato, Noriko Mitsutomi, Naoko Chiba, Kenji Takeda, Shuzo Sugahara, Kunio Tomatsu, Ayumi Chino, Masao Tanaka, Yoshihito Maeda, Yasuhiro Kiuchi, Masatoshi |
Author_xml | – sequence: 1 givenname: Masatoshi surname: Kiuchi fullname: Kiuchi, Masatoshi email: kiuchi.masatoshi@ms.m-pharma.co.jp – sequence: 2 givenname: Kunitomo surname: Adachi fullname: Adachi, Kunitomo – sequence: 3 givenname: Ayumi surname: Tomatsu fullname: Tomatsu, Ayumi – sequence: 4 givenname: Masao surname: Chino fullname: Chino, Masao – sequence: 5 givenname: Shuzo surname: Takeda fullname: Takeda, Shuzo – sequence: 6 givenname: Yoshihito surname: Tanaka fullname: Tanaka, Yoshihito – sequence: 7 givenname: Yasuhiro surname: Maeda fullname: Maeda, Yasuhiro – sequence: 8 givenname: Noriko surname: Sato fullname: Sato, Noriko – sequence: 9 givenname: Naoko surname: Mitsutomi fullname: Mitsutomi, Naoko – sequence: 10 givenname: Kunio surname: Sugahara fullname: Sugahara, Kunio – sequence: 11 givenname: Kenji surname: Chiba fullname: Chiba, Kenji |
BackLink | http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16384316$$DView record in Pascal Francis https://www.ncbi.nlm.nih.gov/pubmed/15598563$$D View this record in MEDLINE/PubMed |
BookMark | eNp9kEtr3DAURkVJSSaPH9BN8abdearXyDJdhZC0hUA36SIroZGvOhpsydW1B-bfV2amZFcQkq50vitxrslFTBEI-cDomlGmvuzX28GtOaWy1GtK9TuyYlLJWoiWXZAVbZWuqW7VFblG3FNKuWzZJblim02rN0qsyHSPx2GAKQdX4TFOO8CAlY1dtQ2pT7-Ds30FB9vPdgopVslXhakg2ljqAZZcwGWD_-7CMMwx4TyOGRDDAaqnl9eG03rcJRx3doJb8t7bHuHuvN6QX0-PLw_f6-ef33483D_XTspmql3XeeW59FqC7soQ3ErKtedbDtI50E2ZPbeq0VJZJRlXbqNa0YmGSW3FDfl86jvm9GcGnMwQ0EHf2whpRqMaIbmSqoDsBLqcEDN4M-Yw2Hw0jJpFtdmbotosqpejorpkPp6bz9sBurfE2W0BPp0Bi8Wizza6gG-cEloKtjz-9cRBUXEIkA26ANFBFzK4yXQp_OcbfwE275_j |
CitedBy_id | crossref_primary_10_1177_1177391X0700100002 crossref_primary_10_1039_C4RA02401J crossref_primary_10_1002_ejoc_201101703 crossref_primary_10_5059_yukigoseikyokaishi_72_808 crossref_primary_10_5059_yukigoseikyokaishi_69_904 crossref_primary_10_1016_j_tetasy_2006_10_007 crossref_primary_10_1152_ajpcell_00606_2008 crossref_primary_10_1093_intimm_dxq036 crossref_primary_10_1016_j_bmc_2015_01_014 crossref_primary_10_1016_j_intimp_2010_10_005 crossref_primary_10_1016_j_tetlet_2011_08_100 crossref_primary_10_1016_j_bmc_2006_10_060 crossref_primary_10_1016_j_pharmthera_2005_05_002 crossref_primary_10_1248_cpb_c14_00462 crossref_primary_10_1016_j_ejphar_2011_05_071 crossref_primary_10_1248_yakushi_129_655 crossref_primary_10_1517_14728222_12_8_1009 crossref_primary_10_1021_ml100301k crossref_primary_10_3390_ph5050514 crossref_primary_10_1016_j_tetasy_2008_12_020 crossref_primary_10_2177_jsci_32_92 crossref_primary_10_1038_s41429_020_0351_0 crossref_primary_10_1016_j_apradiso_2015_04_010 crossref_primary_10_1016_j_tet_2012_06_090 crossref_primary_10_1021_np2000528 crossref_primary_10_1016_j_pharmthera_2007_04_006 crossref_primary_10_1254_fpj_139_265 crossref_primary_10_1016_j_tet_2011_02_028 crossref_primary_10_2492_inflammregen_31_167 crossref_primary_10_1248_bpb_b22_00304 crossref_primary_10_1016_j_tetlet_2005_11_092 crossref_primary_10_1016_j_tetlet_2005_05_127 crossref_primary_10_1016_j_tetlet_2014_05_047 crossref_primary_10_1016_j_transproceed_2004_12_286 crossref_primary_10_1248_bpb_31_1177 crossref_primary_10_1016_j_bmc_2011_12_049 crossref_primary_10_1016_j_tet_2008_01_086 crossref_primary_10_4155_fmc_12_25 crossref_primary_10_4236_pp_2013_48090 crossref_primary_10_1016_j_ejmech_2012_02_022 crossref_primary_10_1016_j_bmcl_2006_10_014 crossref_primary_10_1165_rcmb_2009_0223OC crossref_primary_10_2492_inflammregen_30_542 crossref_primary_10_1016_j_bmc_2014_05_035 crossref_primary_10_6061_clinics_2013_07_21 crossref_primary_10_2492_inflammregen_30_419 crossref_primary_10_1039_b402985m crossref_primary_10_4049_jimmunol_178_6_3437 crossref_primary_10_1002_cmdc_200600195 crossref_primary_10_4236_pp_2013_48089 crossref_primary_10_1124_dmd_110_035907 |
Cites_doi | 10.1016/S0008-6363(03)00260-8 10.1021/jm000173z 10.1074/jbc.C200176200 10.1016/j.bmc.2004.07.020 10.1126/science.1070238 10.1016/0960-894X(95)00127-F 10.1038/nature02284 10.1074/jbc.M311743200 10.1034/j.1600-6143.2003.00130.x 10.1038/nrm1103 10.1016/S0040-4020(01)88237-5 10.1246/cl.1984.265 10.1021/jm960391l 10.4049/jimmunol.160.11.5493 10.4049/jimmunol.160.10.5037 10.1016/S1388-1981(02)00176-2 10.1016/S0040-4020(01)92279-3 10.1021/ja00229a041 10.1358/dof.1997.022.01.391380 10.1016/j.bmcl.2004.04.070 10.1016/S0960-894X(97)10188-3 10.1021/ja00055a004 |
ContentType | Journal Article |
Copyright | 2004 Elsevier Ltd 2005 INIST-CNRS |
Copyright_xml | – notice: 2004 Elsevier Ltd – notice: 2005 INIST-CNRS |
DBID | IQODW CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 |
DOI | 10.1016/j.bmc.2004.10.008 |
DatabaseName | Pascal-Francis Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef MEDLINE - Academic |
DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef MEDLINE - Academic |
DatabaseTitleList | MEDLINE - Academic 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 | 1464-3391 |
EndPage | 432 |
ExternalDocumentID | 10_1016_j_bmc_2004_10_008 15598563 16384316 S0968089604007837 |
Genre | Journal Article |
GroupedDBID | --- --K --M .~1 0R~ 1B1 1RT 1~. 1~5 23N 4.4 457 4G. 53G 5GY 5VS 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 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 DOVZS DU5 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 UPT WUQ XPP YK3 ZMT ~02 ~G- AALMO ABFLS ABPIF ABPTK ADALY IPNFZ IQODW AAXKI AKRWK CGR CUY CVF ECM EIF NPM AAYXX AFJKZ CITATION 7X8 |
ID | FETCH-LOGICAL-c447t-cddf6f24f84e8de8d32a4028f2b2e4cce874ccf2a67846a64126c5693d37148a3 |
IEDL.DBID | .~1 |
ISSN | 0968-0896 |
IngestDate | Thu Aug 15 23:13:44 EDT 2024 Thu Sep 26 17:59:01 EDT 2024 Sat Sep 28 07:45:38 EDT 2024 Fri Nov 25 01:06:23 EST 2022 Fri Feb 23 02:34:39 EST 2024 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 2 |
Keywords | Immunosuppressant Asymmetric synthesis Lipase Sphingosine-1-phosphate Rat Arrhythmia Enzyme Toxicity Rodentia Triacylglycerol lipase Cardiovascular disease Esterases Biological activity Carboxylic ester hydrolases Vertebrata Bradycardia Mammalia Animal Organic phosphate Hydrolases S configuration Immunosuppressive agent Lymphocyte Enzymatic reaction Biological receptor |
Language | English |
License | CC BY 4.0 |
LinkModel | DirectLink |
MergedId | FETCHMERGED-LOGICAL-c447t-cddf6f24f84e8de8d32a4028f2b2e4cce874ccf2a67846a64126c5693d37148a3 |
Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
PMID | 15598563 |
PQID | 67342646 |
PQPubID | 23479 |
PageCount | 8 |
ParticipantIDs | proquest_miscellaneous_67342646 crossref_primary_10_1016_j_bmc_2004_10_008 pubmed_primary_15598563 pascalfrancis_primary_16384316 elsevier_sciencedirect_doi_10_1016_j_bmc_2004_10_008 |
PublicationCentury | 2000 |
PublicationDate | 2005-01-17 |
PublicationDateYYYYMMDD | 2005-01-17 |
PublicationDate_xml | – month: 01 year: 2005 text: 2005-01-17 day: 17 |
PublicationDecade | 2000 |
PublicationPlace | Oxford |
PublicationPlace_xml | – name: Oxford – name: England |
PublicationTitle | Bioorganic & medicinal chemistry |
PublicationTitleAlternate | Bioorg Med Chem |
PublicationYear | 2005 |
Publisher | Elsevier Ltd Elsevier Science |
Publisher_xml | – name: Elsevier Ltd – name: Elsevier Science |
References | Kiuchi, Adachi, Kohara, Teshima, Masubuchi, Mishina, Fujita (bib23) 1998; 8 Wang, Lalonde, Momongan, Bergbreiter, Wong (bib17) 1988; 110 Yanagawa, Sugahara, Kataoka, Kawaguchi, Masubuchi, Chiba (bib6) 1998; 160 Terradas, Teston-Henry, Fitzpatrick, Klibanov (bib18) 1993; 115 Pozo, Pulido, Gotor (bib19) 1992; 48 Ohmori, Yatomi, Osada, Kazama, Takafuta, Ikeda, Ozaki (bib9) 2003; 58 Spiegel, Milstien (bib7) 2003; 4 English, Brindley, Spiegel, Garcia (bib8) 2002; 1582 Budde, Schmouder, Nashan, Brunkhorst, Lucker, Mayer, Brookman, Nedelman, Skerjanec, Bohler, Neumayer (bib13) 2003; 3 Kiuchi, Adachi, Kohara, Minoguchi, Hanano, Aoki, Mishina, Arita, Nakao, Ohtsuki, Hoshino, Teshima, Chiba, Sasaki, Fujita (bib2) 2000; 43 Tedesco-Silva, Mourad, Kahan, Boira, Weimar, Mulgaonkar, Nashan, Madsen, Charpentier, Pellet, Vanrenterghem (bib4) 2004; 77 Brinkmann, Davis, Heise, Albert, Cottens, Hof, Bruns, Prieschl, Baumruker, Hiestand, Foster, Zollinger, Lynch (bib11) 2002; 277 Moris, Gotor (bib20) 1992; 48 Adachi, Kohara, Nakao, Arita, Chiba, Mishina, Sasaki, Fujita (bib1) 1995; 5 Fujita, Hirose, Yoneta, Sasaki, Inoue, Kiuchi, Hirase, Chiba, Sakamoto, Arita (bib15) 1996; 39 Sanna, Liao, Jo, Alfonso, Ahn, Peterson, Webb, Lefebvre, Chun, Gray, Rosen (bib14) 2004; 279 Hale, Yan, Neway, Hajdu, Bergstrom, Milligan, Shei, Chrebet, Thornton, Card, Rosenbach, Rosen, Mandala (bib16) 2004; 12 Chiba, Yanagawa, Masubuchi, Kataoka, Kawaguchi, Ohtsuki, Hoshino (bib5) 1998; 160 bib25 Mandala, Hajdu, Bergstrom, Quackenbush, Xie, Milligam, Thornton, Shei, Card, Keohane, Rosenbach, Hale, Lynch, Rupprecht, Parsons, Rosen (bib10) 2002; 296 Matloubian, Lo, Cinamon, Lesneski, Xu, Brinkmann, Allende, Proia, Cyster (bib12) 2004; 427 Chiba, Adachi (bib3) 1997; 22 bib22 Mukaiyama, Ohshima, Murakami (bib21) 1984 Hale, Doherty, Toth, Mills, Hajdu, Keohane, Rosenbach, Milligan, Shei, Chrebet, Bergstrom, Card, Forrest, Sun, West, Xie, Nomura, Rosen, Mandala (bib24) 2004; 14 Terradas (10.1016/j.bmc.2004.10.008_bib18) 1993; 115 Budde (10.1016/j.bmc.2004.10.008_bib13) 2003; 3 Sanna (10.1016/j.bmc.2004.10.008_bib14) 2004; 279 Hale (10.1016/j.bmc.2004.10.008_bib24) 2004; 14 Chiba (10.1016/j.bmc.2004.10.008_bib5) 1998; 160 Spiegel (10.1016/j.bmc.2004.10.008_bib7) 2003; 4 Chiba (10.1016/j.bmc.2004.10.008_bib3) 1997; 22 Tedesco-Silva (10.1016/j.bmc.2004.10.008_bib4) 2004; 77 Fujita (10.1016/j.bmc.2004.10.008_bib15) 1996; 39 Wang (10.1016/j.bmc.2004.10.008_bib17) 1988; 110 Mandala (10.1016/j.bmc.2004.10.008_bib10) 2002; 296 Adachi (10.1016/j.bmc.2004.10.008_bib1) 1995; 5 Kiuchi (10.1016/j.bmc.2004.10.008_bib2) 2000; 43 Mukaiyama (10.1016/j.bmc.2004.10.008_bib21) 1984 Kiuchi (10.1016/j.bmc.2004.10.008_bib23) 1998; 8 Yanagawa (10.1016/j.bmc.2004.10.008_bib6) 1998; 160 Brinkmann (10.1016/j.bmc.2004.10.008_bib11) 2002; 277 Matloubian (10.1016/j.bmc.2004.10.008_bib12) 2004; 427 Pozo (10.1016/j.bmc.2004.10.008_bib19) 1992; 48 Moris (10.1016/j.bmc.2004.10.008_bib20) 1992; 48 Ohmori (10.1016/j.bmc.2004.10.008_bib9) 2003; 58 English (10.1016/j.bmc.2004.10.008_bib8) 2002; 1582 Hale (10.1016/j.bmc.2004.10.008_bib16) 2004; 12 |
References_xml | – volume: 77 start-page: 1826 year: 2004 end-page: 1833 ident: bib4 article-title: FTY720, a novel immunomodulator: efficacy and safety results from the first phase 2A study in de novo renal transplantation publication-title: Transplantation contributor: fullname: Vanrenterghem – volume: 160 start-page: 5037 year: 1998 end-page: 5044 ident: bib5 article-title: FTY720, a novel immunosuppressant, induces sequestration of circulating mature lymphocytes by acceleration of lymphocyte homing in rats. I. FTY720 selectively decreases the number of circulating mature lymphocytes by acceleration of lymphocyte homing publication-title: J. Immunol. contributor: fullname: Hoshino – volume: 4 start-page: 397 year: 2003 end-page: 407 ident: bib7 article-title: Sphingosine-1-phosphate: an enigmatic signalling lipid publication-title: Nat. Rev. Mol. Cell Biol. contributor: fullname: Milstien – volume: 48 start-page: 6477 year: 1992 end-page: 6484 ident: bib19 article-title: Vinyl carbonates as novel alkoxycarbonylation reagents in enzymatic synthesis of carbonates publication-title: Tetrahedron contributor: fullname: Gotor – volume: 427 start-page: 355 year: 2004 end-page: 360 ident: bib12 article-title: Lymphocyte egress from thymus and peripheral lymphoid organs is dependent on S1P receptor 1 publication-title: Nature contributor: fullname: Cyster – volume: 3 start-page: 846 year: 2003 end-page: 854 ident: bib13 article-title: Pharmacodynamics of single doses of the novel immunosuppressant FTY720 in stable renal transplant patients publication-title: Am. J. Transplant. contributor: fullname: Neumayer – volume: 277 start-page: 21453 year: 2002 end-page: 21457 ident: bib11 article-title: The immune modulator FTY720 Targets sphingosine 1-phosphate receptors publication-title: J. Biol. Chem. contributor: fullname: Lynch – volume: 39 start-page: 4451 year: 1996 end-page: 4459 ident: bib15 article-title: Potent immunosuppressants, 2-alkyl-2-aminopropane-1,3-diols publication-title: J. Med. Chem. contributor: fullname: Arita – start-page: 265 year: 1984 end-page: 266 ident: bib21 article-title: 2-Benzyloxy-1-propene: a novel protective reagent of hydroxyl groups publication-title: Chem. Lett. contributor: fullname: Murakami – volume: 115 start-page: 390 year: 1993 end-page: 396 ident: bib18 article-title: Marked dependence of enzyme prochiral selectivity on the solvent publication-title: J. Am. Chem. Soc. contributor: fullname: Klibanov – ident: bib22 – volume: 48 start-page: 9869 year: 1992 end-page: 9876 ident: bib20 article-title: Lipase-mediated alkoxycarbonylation of nucleosides with oxime carbonates publication-title: Tetrahedron contributor: fullname: Gotor – volume: 14 start-page: 3501 year: 2004 end-page: 3505 ident: bib24 article-title: Selecting against S1P3 enhances the acute cardiovascular tolerability of 3-( publication-title: Bioorg. Med. Chem. Lett. contributor: fullname: Mandala – volume: 1582 start-page: 228 year: 2002 end-page: 239 ident: bib8 article-title: Lipid mediators of angiogenesis and the signalling pathways they initiate publication-title: Biochim. Biophys. Acta contributor: fullname: Garcia – volume: 110 start-page: 7200 year: 1988 end-page: 7205 ident: bib17 article-title: Lipase-catalyzed irreversible transesterifications using enol esters as acylating reagents: preparative enantio- and regioselective syntheses of alcohols, glycerol derivatives, sugars, and organometallics publication-title: J. Am. Chem. Soc. contributor: fullname: Wong – volume: 22 start-page: 18 year: 1997 end-page: 22 ident: bib3 article-title: FTY720, immunosuppressant publication-title: Drugs Future contributor: fullname: Adachi – volume: 5 start-page: 853 year: 1995 end-page: 856 ident: bib1 article-title: Design, synthesis, and structure–activity relationships of 2-substituted-2-amino-1,3-propanediols: discovery of a novel immunosuppressant, FTY720 publication-title: Bioorg. Med. Chem. Lett. contributor: fullname: Fujita – volume: 43 start-page: 2946 year: 2000 end-page: 2961 ident: bib2 article-title: Synthesis and immunosuppressive activity of 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols publication-title: J. Med. Chem. contributor: fullname: Fujita – volume: 279 start-page: 13839 year: 2004 end-page: 13848 ident: bib14 article-title: Sphingosine-1-phosphate (S1P) receptor subtypes S1P publication-title: J. Biol. Chem. contributor: fullname: Rosen – volume: 8 start-page: 101 year: 1998 end-page: 106 ident: bib23 article-title: Synthesis and biological evaluation of 2,2-disubstituted 2-aminoethanols: analogues of FTY720 publication-title: Bioorg. Med. Chem. Lett. contributor: fullname: Fujita – volume: 12 start-page: 4803 year: 2004 end-page: 4807 ident: bib16 article-title: Synthesis, stereochemical determination and biochemical characterization of the enantiomeric phosphate esters of the novel immunosuppressive agent FTY720 publication-title: Bioorg. Med. Chem. contributor: fullname: Mandala – volume: 58 start-page: 170 year: 2003 end-page: 177 ident: bib9 article-title: Sphingosine 1-phosphate induces contraction of coronary artery smooth muscle cells via S1P publication-title: Cardiovasc. Res. contributor: fullname: Ozaki – ident: bib25 – volume: 160 start-page: 5493 year: 1998 end-page: 5499 ident: bib6 article-title: FTY720, a novel immunosuppressant, induces sequestration of circulating mature lymphocytes by acceleration of lymphocyte homing in rats. II. FTY720 prolongs skin allograft survival by decreasing T cell infiltration into grafts but not cytokine production in vivo publication-title: J. Immunol. contributor: fullname: Chiba – volume: 296 start-page: 346 year: 2002 end-page: 349 ident: bib10 article-title: Alteration of lymphocyte trafficking by sphingosine-1-phosphate receptor agonists publication-title: Science contributor: fullname: Rosen – volume: 58 start-page: 170 year: 2003 ident: 10.1016/j.bmc.2004.10.008_bib9 article-title: Sphingosine 1-phosphate induces contraction of coronary artery smooth muscle cells via S1P2 publication-title: Cardiovasc. Res. doi: 10.1016/S0008-6363(03)00260-8 contributor: fullname: Ohmori – volume: 43 start-page: 2946 year: 2000 ident: 10.1016/j.bmc.2004.10.008_bib2 article-title: Synthesis and immunosuppressive activity of 2-substituted 2-aminopropane-1,3-diols and 2-aminoethanols publication-title: J. Med. Chem. doi: 10.1021/jm000173z contributor: fullname: Kiuchi – volume: 277 start-page: 21453 year: 2002 ident: 10.1016/j.bmc.2004.10.008_bib11 article-title: The immune modulator FTY720 Targets sphingosine 1-phosphate receptors publication-title: J. Biol. Chem. doi: 10.1074/jbc.C200176200 contributor: fullname: Brinkmann – volume: 12 start-page: 4803 year: 2004 ident: 10.1016/j.bmc.2004.10.008_bib16 article-title: Synthesis, stereochemical determination and biochemical characterization of the enantiomeric phosphate esters of the novel immunosuppressive agent FTY720 publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2004.07.020 contributor: fullname: Hale – volume: 296 start-page: 346 year: 2002 ident: 10.1016/j.bmc.2004.10.008_bib10 article-title: Alteration of lymphocyte trafficking by sphingosine-1-phosphate receptor agonists publication-title: Science doi: 10.1126/science.1070238 contributor: fullname: Mandala – volume: 5 start-page: 853 year: 1995 ident: 10.1016/j.bmc.2004.10.008_bib1 article-title: Design, synthesis, and structure–activity relationships of 2-substituted-2-amino-1,3-propanediols: discovery of a novel immunosuppressant, FTY720 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/0960-894X(95)00127-F contributor: fullname: Adachi – volume: 427 start-page: 355 year: 2004 ident: 10.1016/j.bmc.2004.10.008_bib12 article-title: Lymphocyte egress from thymus and peripheral lymphoid organs is dependent on S1P receptor 1 publication-title: Nature doi: 10.1038/nature02284 contributor: fullname: Matloubian – volume: 279 start-page: 13839 year: 2004 ident: 10.1016/j.bmc.2004.10.008_bib14 article-title: Sphingosine-1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate publication-title: J. Biol. Chem. doi: 10.1074/jbc.M311743200 contributor: fullname: Sanna – volume: 3 start-page: 846 year: 2003 ident: 10.1016/j.bmc.2004.10.008_bib13 article-title: Pharmacodynamics of single doses of the novel immunosuppressant FTY720 in stable renal transplant patients publication-title: Am. J. Transplant. doi: 10.1034/j.1600-6143.2003.00130.x contributor: fullname: Budde – volume: 4 start-page: 397 year: 2003 ident: 10.1016/j.bmc.2004.10.008_bib7 article-title: Sphingosine-1-phosphate: an enigmatic signalling lipid publication-title: Nat. Rev. Mol. Cell Biol. doi: 10.1038/nrm1103 contributor: fullname: Spiegel – volume: 48 start-page: 6477 year: 1992 ident: 10.1016/j.bmc.2004.10.008_bib19 article-title: Vinyl carbonates as novel alkoxycarbonylation reagents in enzymatic synthesis of carbonates publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)88237-5 contributor: fullname: Pozo – start-page: 265 year: 1984 ident: 10.1016/j.bmc.2004.10.008_bib21 article-title: 2-Benzyloxy-1-propene: a novel protective reagent of hydroxyl groups publication-title: Chem. Lett. doi: 10.1246/cl.1984.265 contributor: fullname: Mukaiyama – volume: 39 start-page: 4451 year: 1996 ident: 10.1016/j.bmc.2004.10.008_bib15 article-title: Potent immunosuppressants, 2-alkyl-2-aminopropane-1,3-diols publication-title: J. Med. Chem. doi: 10.1021/jm960391l contributor: fullname: Fujita – volume: 77 start-page: 1826 year: 2004 ident: 10.1016/j.bmc.2004.10.008_bib4 article-title: FTY720, a novel immunomodulator: efficacy and safety results from the first phase 2A study in de novo renal transplantation publication-title: Transplantation contributor: fullname: Tedesco-Silva – volume: 160 start-page: 5493 year: 1998 ident: 10.1016/j.bmc.2004.10.008_bib6 article-title: FTY720, a novel immunosuppressant, induces sequestration of circulating mature lymphocytes by acceleration of lymphocyte homing in rats. II. FTY720 prolongs skin allograft survival by decreasing T cell infiltration into grafts but not cytokine production in vivo publication-title: J. Immunol. doi: 10.4049/jimmunol.160.11.5493 contributor: fullname: Yanagawa – volume: 160 start-page: 5037 year: 1998 ident: 10.1016/j.bmc.2004.10.008_bib5 article-title: FTY720, a novel immunosuppressant, induces sequestration of circulating mature lymphocytes by acceleration of lymphocyte homing in rats. I. FTY720 selectively decreases the number of circulating mature lymphocytes by acceleration of lymphocyte homing publication-title: J. Immunol. doi: 10.4049/jimmunol.160.10.5037 contributor: fullname: Chiba – volume: 1582 start-page: 228 year: 2002 ident: 10.1016/j.bmc.2004.10.008_bib8 article-title: Lipid mediators of angiogenesis and the signalling pathways they initiate publication-title: Biochim. Biophys. Acta doi: 10.1016/S1388-1981(02)00176-2 contributor: fullname: English – volume: 48 start-page: 9869 year: 1992 ident: 10.1016/j.bmc.2004.10.008_bib20 article-title: Lipase-mediated alkoxycarbonylation of nucleosides with oxime carbonates publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)92279-3 contributor: fullname: Moris – volume: 110 start-page: 7200 year: 1988 ident: 10.1016/j.bmc.2004.10.008_bib17 article-title: Lipase-catalyzed irreversible transesterifications using enol esters as acylating reagents: preparative enantio- and regioselective syntheses of alcohols, glycerol derivatives, sugars, and organometallics publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00229a041 contributor: fullname: Wang – volume: 22 start-page: 18 year: 1997 ident: 10.1016/j.bmc.2004.10.008_bib3 article-title: FTY720, immunosuppressant publication-title: Drugs Future doi: 10.1358/dof.1997.022.01.391380 contributor: fullname: Chiba – volume: 14 start-page: 3501 year: 2004 ident: 10.1016/j.bmc.2004.10.008_bib24 article-title: Selecting against S1P3 enhances the acute cardiovascular tolerability of 3-(N-benzyl)aminopropylphosphonic acid S1P receptor agonists publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/j.bmcl.2004.04.070 contributor: fullname: Hale – volume: 8 start-page: 101 year: 1998 ident: 10.1016/j.bmc.2004.10.008_bib23 article-title: Synthesis and biological evaluation of 2,2-disubstituted 2-aminoethanols: analogues of FTY720 publication-title: Bioorg. Med. Chem. Lett. doi: 10.1016/S0960-894X(97)10188-3 contributor: fullname: Kiuchi – volume: 115 start-page: 390 year: 1993 ident: 10.1016/j.bmc.2004.10.008_bib18 article-title: Marked dependence of enzyme prochiral selectivity on the solvent publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00055a004 contributor: fullname: Terradas |
SSID | ssj0002491 |
Score | 2.0804121 |
Snippet | [Display omitted]
A practical asymmetric synthesis of both enantiomers of the immunosuppressive FTY720-phosphate (
2) was accomplished, and the enantiomers... A practical asymmetric synthesis of both enantiomers of the immunosuppressive FTY720-phosphate (2) was accomplished, and the enantiomers were pharmacologically... |
SourceID | proquest crossref pubmed pascalfrancis elsevier |
SourceType | Aggregation Database Index Database Publisher |
StartPage | 425 |
SubjectTerms | Animals Asymmetric synthesis Biological and medical sciences Cell Line Cell Movement - drug effects Fingolimod Hydrochloride Humans Immunomodulators Immunosuppressant Immunosuppressive Agents - chemical synthesis Immunosuppressive Agents - metabolism Immunosuppressive Agents - pharmacology Lipase Lymphocytes - drug effects Medical sciences Mice Models, Chemical Molecular Structure Pharmacology. Drug treatments Propylene Glycols - chemical synthesis Propylene Glycols - metabolism Propylene Glycols - pharmacology Protein Binding Rats Rats, Sprague-Dawley Receptors, Lysosphingolipid - metabolism Sphingosine - analogs & derivatives Sphingosine-1-phosphate Stereoisomerism |
Title | Asymmetric synthesis and biological evaluation of the enantiomeric isomers of the immunosuppressive FTY720-phosphate |
URI | https://dx.doi.org/10.1016/j.bmc.2004.10.008 https://www.ncbi.nlm.nih.gov/pubmed/15598563 https://search.proquest.com/docview/67342646 |
Volume | 13 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Ba9swFH6UDrbBGFu6ddnWTIexw8BNbMuWfAxhId1oL2uhOxnZkqgLsU2VFHLpb997sk3ooTsMTDCKRIw_ofcp-t73AL6KUqvEcBXoLLEBz3QSSGORyFEN1aQwOJEoUfj8Il1d8Z_XyfUBLIZcGJJV9mt_t6b71bpvmfZvc9pW1fQ3km85k2QuQnEupoxyjsEI5_Tpw17mgdsLXzUPOwfUezjZ9BqvYu1dDPmpF3jJp2LTq1Y5fGO2K3XxNBf1MWn5Bl73ZJLNu-d9CwemHsHRvMaN9HrHvjEv7_T_m4_gxWIo7TaC5-f9ifoRbOZut15TWa2SuV2NdNBVjqlas86eiTBke0tw1liGfZgh_Qxl7tO4ytGNG76rKOWkcdu209jeG7a8_CNw_9jeNK69QXL7Dq6WPy4Xq6CvxBCUnItNUGptUxtxK7mRGq84UrjxlDYqIsPL0kiBnzZSGPp4qlIeRmmZpFmsyRBQqvg9HNZNbT4AE9IQ58sKXcTcijhLrUh4GCpTzkRk4zF8HzDI285wIx-UaLc5AkaFMzk1IWBj4ANK-aNZk2NA-NewySNE9z-EqxF5A4zhywBxjtDQGYqqTbN1JIMjDok9jjvk92PJ6j5J44__90yf4KV3hZ2FQSg-w-HmbmtOkO9siomf0BN4Nj_7tbr4CzAsAAg |
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/eLvHCXMwnV3Pa9swFH50HayDMbZ0P7IfrQ5jh4Gb2JYt-RjCQrY1vSyF7mRkS6IexDZTMshlf_vek21CD91hYIyRJWz8Cb1P1qfvAXwQpVaJ4SrQWWIDnukkkMYikaMcqklhsCPRRuHVVbq85l9vkpsjmA97YUhW2Y_93ZjuR-u-ZNJ_zUlbVZPvSL7lVJK5CMW5WDyAh0TnKX_DxZ-DzgPnFz5tHtYOqPqwtOlFXsXG2xjyC6_wkvcFpyetcvjJbJfr4n4y6oPS4hk87dkkm3Uv_ByOTD2C01mNM-nNnn1kXt_pf5yP4GQ-5HYbwaNVv6R-CtuZ2282lFerZG5fIx90lWOq1qzzZyIQ2cETnDWWYR1mSEBDW_epXeXowg33Ktpz0rhd24lsfxu2WP8QOIFsbxvX3iK7fQHXi8_r-TLoUzEEJediG5Ra29RG3EpupMYjjhTOPKWNisjwsjRS4NlGCmMfT1XKwygtkzSLNTkCShW_hOO6qc1rYEIaIn1ZoYuYWxFnqRUJD0NlyqmIbDyGTwMGeds5buSDFO1njoBR5kxORQjYGPiAUn6n2-QYEf7V7OwOoocH4XBE5gBjOB8gzhEaWkRRtWl2jnRwRCKxxqsO-UNb8rpP0vjN_73TOZws16vL_PLL1be38NhbxE7DIBTv4Hj7a2feI_nZFme-c_8FBhYBmg |
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=Asymmetric+synthesis+and+biological+evaluation+of+the+enantiomeric+isomers+of+the+immunosuppressive+FTY720-phosphate&rft.jtitle=Bioorganic+%26+medicinal+chemistry&rft.au=Kiuchi%2C+Masatoshi&rft.au=Adachi%2C+Kunitomo&rft.au=Tomatsu%2C+Ayumi&rft.au=Chino%2C+Masao&rft.date=2005-01-17&rft.pub=Elsevier+Ltd&rft.issn=0968-0896&rft.eissn=1464-3391&rft.volume=13&rft.issue=2&rft.spage=425&rft.epage=432&rft_id=info:doi/10.1016%2Fj.bmc.2004.10.008&rft.externalDocID=S0968089604007837 |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0968-0896&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0968-0896&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0968-0896&client=summon |