Synthesis and SAR of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones as 5-HT2C receptor agonists
A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT2C agonism with excellent selectivity over the closely related 5-HT2A and 5-HT2B receptors. Compounds such as 38 and 44 were shown to be effective in reducing food inta...
Saved in:
| Published in | Bioorganic & medicinal chemistry letters Vol. 23; no. 1; pp. 330 - 335 |
|---|---|
| Main Authors | , , , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
01.01.2013
Elsevier |
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT2C agonism with excellent selectivity over the closely related 5-HT2A and 5-HT2B receptors. Compounds such as 38 and 44 were shown to be effective in reducing food intake in an acute rat feeding model.
A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT2C agonism with excellent selectivity over the closely related 5-HT2A and 5-HT2B receptors. Compounds such as 38 and 44 were shown to be effective in reducing food intake in an acute rat feeding model. |
|---|---|
| AbstractList | A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT(2C) agonism with excellent selectivity over the closely related 5-HT(2A) and 5-HT(2B) receptors. Compounds such as 38 and 44 were shown to be effective in reducing food intake in an acute rat feeding model. A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT2C agonism with excellent selectivity over the closely related 5-HT2A and 5-HT2B receptors. Compounds such as 38 and 44 were shown to be effective in reducing food intake in an acute rat feeding model. (C) 2012 Elsevier Ltd. All rights reserved. A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT₂C agonism with excellent selectivity over the closely related 5-HT₂A and 5-HT₂B receptors. Compounds such as 38 and 44 were shown to be effective in reducing food intake in an acute rat feeding model. A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT2C agonism with excellent selectivity over the closely related 5-HT2A and 5-HT2B receptors. Compounds such as 38 and 44 were shown to be effective in reducing food intake in an acute rat feeding model. A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT2C agonism with excellent selectivity over the closely related 5-HT2A and 5-HT2B receptors. Compounds such as 38 and 44 were shown to be effective in reducing food intake in an acute rat feeding model. |
| Author | Miller, Keith J. Wu, Ginger Rohrbach, Kenneth W. Zhang, Ge Qu, Qinling Feng, Jianxin Hung, Chen-Pin Fevig, John M. Cullen, Mary Jane Malmstrom, Sarah E. Gan, Jinping Keim, William J. Pelleymounter, Mary Ann Robl, Jeffrey A. Rossi, Karen A. Ung, Thao |
| Author_xml | – sequence: 1 givenname: John M. surname: Fevig fullname: Fevig, John M. email: john.fevig@bms.com – sequence: 2 givenname: Jianxin surname: Feng fullname: Feng, Jianxin – sequence: 3 givenname: Karen A. surname: Rossi fullname: Rossi, Karen A. – sequence: 4 givenname: Keith J. surname: Miller fullname: Miller, Keith J. – sequence: 5 givenname: Ginger surname: Wu fullname: Wu, Ginger – sequence: 6 givenname: Chen-Pin surname: Hung fullname: Hung, Chen-Pin – sequence: 7 givenname: Thao surname: Ung fullname: Ung, Thao – sequence: 8 givenname: Sarah E. surname: Malmstrom fullname: Malmstrom, Sarah E. – sequence: 9 givenname: Ge surname: Zhang fullname: Zhang, Ge – sequence: 10 givenname: William J. surname: Keim fullname: Keim, William J. – sequence: 11 givenname: Mary Jane surname: Cullen fullname: Cullen, Mary Jane – sequence: 12 givenname: Kenneth W. surname: Rohrbach fullname: Rohrbach, Kenneth W. – sequence: 13 givenname: Qinling surname: Qu fullname: Qu, Qinling – sequence: 14 givenname: Jinping surname: Gan fullname: Gan, Jinping – sequence: 15 givenname: Mary Ann surname: Pelleymounter fullname: Pelleymounter, Mary Ann – sequence: 16 givenname: Jeffrey A. surname: Robl fullname: Robl, Jeffrey A. |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23177783$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkV-LEzEUxYOsuN3VL-CDzuOKTc2_zkzAl6WoFRYEuwuCSMhk7uymTJOapEq_vbe07qP4koSb3z059-SCnIUYgJCXnM044_W79azbuHEmGBdYmDHNn5AJV7WiUrH5GZkwXTPaavXtnFzkvGaMK6bUM3IuJG-appUTslntQ3mA7HNlQ1-trr9WcajEVE6lnSpaoCT7sO9TpHxJt_uU4hi_S7xxP3yOP3c-xNEHOr_S3fINRX-ok6s5Xd6KRZXAwbbEVNn7GHwu-Tl5Otgxw4vTfknuPn64XSzpzZdPnxfXN9TJlhUK2oFulZZd39WDmEMNXFjVDei6540CWwvXaq66FicFblvR89Yhgw-2tpGX5Oqou03oEXIxG58djKMNEHfZcKFYq3XNNaLiiLoUc04wmG3yG5v2hjNziNmszSFmc4j5UMOYsenVSX_XbaB_bPmbKwLtEfgNXRyy8xAcPGKMMcmFqJsGTzVf-GKLj2ERd6Fg69v_b0X69ZEebDT2Pvls7lZodY6fLXGtkXh_JAAD_-UhmZNm7_F_iumj_9eofwBdi7dv |
| CitedBy_id | crossref_primary_10_1002_ejoc_202201267 crossref_primary_10_2174_1568026619666190709101449 crossref_primary_10_1134_S1070428014090139 crossref_primary_10_1002_ajoc_201700377 crossref_primary_10_1021_acs_joc_0c01059 crossref_primary_10_1021_acs_orglett_8b04117 crossref_primary_10_1016_j_tet_2023_133491 crossref_primary_10_1016_S1875_5364_17_30070_5 crossref_primary_10_5937_arhfarm1703165R crossref_primary_10_1039_C7RA13627G crossref_primary_10_1039_C4NJ01718H crossref_primary_10_1002_ange_201303207 crossref_primary_10_1002_anie_201303207 |
| Cites_doi | 10.1038/nrd2136 10.1124/mi.5.5.8 10.1021/jm0612968 10.1016/S0079-6468(07)00006-9 10.1124/jpet.107.133348 10.1016/S0889-8529(03)00074-4 10.1021/jm0709034 10.1038/oby.2008.537 10.2165/00003495-200565100-00006 10.1046/j.1467-789x.2000.00011.x 10.1007/BF02244883 10.1007/s002130050952 10.1016/S0028-3908(97)00038-5 10.1038/374542a0 10.1007/s11883-007-0061-0 10.1161/01.CIR.102.23.2836 10.1016/S0040-4039(00)85909-2 10.1021/jm990388c |
| ContentType | Journal Article |
| Copyright | 2012 Elsevier Ltd Copyright © 2012 Elsevier Ltd. All rights reserved. |
| Copyright_xml | – notice: 2012 Elsevier Ltd – notice: Copyright © 2012 Elsevier Ltd. All rights reserved. |
| DBID | FBQ 1KM BLEPL DTL GKMDS CGR CUY CVF ECM EIF NPM AAYXX CITATION 7X8 |
| DOI | 10.1016/j.bmcl.2012.10.091 |
| DatabaseName | AGRIS Index Chemicus Web of Science Core Collection Science Citation Index Expanded Web of Science - Science Citation Index Expanded - 2013 Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef MEDLINE - Academic |
| DatabaseTitle | Web of Science MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef MEDLINE - Academic |
| DatabaseTitleList | MEDLINE Web of Science 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: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database – sequence: 3 dbid: FBQ name: AGRIS url: http://www.fao.org/agris/Centre.asp?Menu_1ID=DB&Menu_2ID=DB1&Language=EN&Content=http://www.fao.org/agris/search?Language=EN sourceTypes: Publisher |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Medicine Anatomy & Physiology Chemistry |
| EISSN | 1464-3405 |
| EndPage | 335 |
| ExternalDocumentID | 10_1016_j_bmcl_2012_10_091 23177783 000312267700061 US201500131506 S0960894X12013820 |
| Genre | Journal Article |
| GroupedDBID | --- --K --M .~1 0R~ 1B1 1RT 1~. 1~5 23N 4.4 457 4G. 5GY 5VS 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 ABMZM ABUDA ABXDB ABYKQ ABZDS ACDAQ ACGFS ACIUM ACRLP ADBBV ADECG ADEZE ADUVX AEBSH AEHWI AEKER AENEX 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 GBLVA IHE J1W KOM LCYCR LZ2 M29 M2Z M34 M41 MO0 N9A O-L O9- OAUVE OGGZJ OZT P-8 P-9 P2P PC. Q38 RIG ROL RPZ SCC SDF SDG SDP SES SPC SPCBC SSH SSK SSP SSU SSZ T5K YK3 ZMT ~02 ~G- .HR 53G 6TJ AAQXK ABPIF ABPTK ABTAH ACNNM ADMUD AFFNX AGRDE ASPBG AVWKF AZFZN FBQ FEDTE FGOYB G-2 HEA HMK HMO HMS HMT HVGLF HZ~ R2- SAE SCB SEW SOC SPT WUQ XFK XPP Y6R ZY4 1KM AAXKI AKRWK BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED CGR CUY CVF ECM EIF NPM AAYXX AFJKZ CITATION 7X8 |
| ID | FETCH-LOGICAL-c380t-e9ce98493bdb6f25e6e12a4bf177d174ea62c8914b8340e1a82d18c12aece8a73 |
| IEDL.DBID | AIKHN |
| ISICitedReferencesCount | 14 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000312267700061 |
| ISSN | 0960-894X |
| IngestDate | Fri Aug 16 21:15:36 EDT 2024 Thu Sep 26 16:02:01 EDT 2024 Sat Sep 28 07:59:43 EDT 2024 Fri Oct 11 20:28:12 EDT 2024 Tue Sep 17 22:28:15 EDT 2024 Wed Dec 27 19:20:22 EST 2023 Fri Feb 23 02:27:43 EST 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 1 |
| Keywords | Serotonin Obesity 5-HT2c receptor agonist LORCASERIN MICE FENFLURAMINE DISCOVERY |
| Language | English |
| License | Copyright © 2012 Elsevier Ltd. All rights reserved. |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c380t-e9ce98493bdb6f25e6e12a4bf177d174ea62c8914b8340e1a82d18c12aece8a73 |
| Notes | http://dx.doi.org/10.1016/j.bmcl.2012.10.091 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0002-7072-7614 |
| PMID | 23177783 |
| PQID | 1240899619 |
| PQPubID | 23479 |
| PageCount | 6 |
| ParticipantIDs | webofscience_primary_000312267700061CitationCount fao_agris_US201500131506 crossref_primary_10_1016_j_bmcl_2012_10_091 proquest_miscellaneous_1240899619 pubmed_primary_23177783 webofscience_primary_000312267700061 elsevier_sciencedirect_doi_10_1016_j_bmcl_2012_10_091 |
| PublicationCentury | 2000 |
| PublicationDate | 2013-01-01 2013 2013-Jan-01 2013-01-00 20130101 |
| PublicationDateYYYYMMDD | 2013-01-01 |
| PublicationDate_xml | – month: 01 year: 2013 text: 2013-01-01 day: 01 |
| PublicationDecade | 2010 |
| PublicationPlace | OXFORD |
| PublicationPlace_xml | – name: OXFORD – name: England |
| PublicationTitle | Bioorganic & medicinal chemistry letters |
| PublicationTitleAbbrev | BIOORG MED CHEM LETT |
| PublicationTitleAlternate | Bioorg Med Chem Lett |
| PublicationYear | 2013 |
| Publisher | Elsevier Ltd Elsevier |
| Publisher_xml | – name: Elsevier Ltd – name: Elsevier |
| References | Cooke, Bloom, Neff, Aronne (b0025) 2006; 5 Foxcroft, Milne (b0015) 2000; 1 b0150 Thomsen, Grottick, Menzaghi, Reyes-Saldana, Espitia, Yuskin, Whelan, Martin, Morgan, Chen, Al-Shamma, Smith, Chalmers, Behan, Smith, Prosser, Donahue, Morgan, Anderson, Shanahan, Smith, Smith, Tsai, Schultz, Gilson, Estrada, Chen, Park, Prieto, Gallardo, Sengupta, Dosa, Covel, Ren, Webb, Beeley, Martin, Morgan, Espitia, Saldana, Bjenning, Whelan, Grottick, Menzaghi, Thomsen (b0085) 2008; 325 Bromidge, Dabbs, Davies, Davies, Duckworth, Forbes, Gaster, Ham, Jones, King, Mulholland, Saunders, Wyman, Blaney, Clarke, Blackburn, Holland, Kennett, Lightowler, Middlemiss, Trail, Riley, Wood (b0145) 2000; 43 Wacker, Miller, Miller, Monck, Kennett (b0040) 2008; 11 Still, Gennari (b0135) 1983; 24 Ogden, Carroll, Flegal (b0010) 2003; 32 Fitzgerald, Burn, Brown, Patterson, Corjay, Valentine, Sun, Link, Abbaszade, Hollis, Largent, Hartig, Hollis, Meunier, Robichaud, Robertson, Rothman, Baumann, Savage, Rauser, McBride, Hufeisen, Roth (b0110) 2000; 57 . Walsh, Smith, Oldman, Williams, Goodall, Cowen (b0060) 1994; 116 229th ACS National Meeting, San Diego, CA; American Chemical Society: Washington, DC, 2005; MEDI-283. Kennett, Wood, Bright, Trail, Riley, Holland, Avenell, Stean, Upton, Bromidge, Forbes, Brown, Middlemiss, Blackburn (b0065) 1997; 36 Lee, T.; Robichaud, A. J.; Chen, W.; Lu, Y.; Dowdell, S.; Boyle, K. E.; Mitchell, I. S.; Fevig, J. M.; Wexler, R. R.; Miller, K. J.; Largent, B. L.; Rohrbach, K. W.; Devenny, J. J.; McElroy, J. F. Tecott, Sun, Akana, Strack, Lowenstein, Dallman, Julius, Vickers, Clifton, Dourish, Tecott (b0070) 1995; 374 Ioannides-Demos, Proietto, McNeil (b0020) 2005; 65 Wacker, Varnes, Malmstrom, Cao, Hung, Ung, Wu, Zhang, Zuvich, Thomas, Keim, Cullen, Rohrbach, Qu, Narayanan, Rossi, Janovitz, Lehman-McKeeman, Malley, Devenny, Pelleymounter, Miller, Robl (b0130) 2007; 50 Smith, SR (WOS:000263788700013) 2009; 17 Wacker, DA (WOS:000244895900028) 2007; 50 Thomsen, WJ (WOS:000255013800027) 2008; 325 Rothman, RB (WOS:000165607000008) 2000; 102 Lee, T. (000312267700061.7) 2005 Wacker, DA (WOS:000257329700002) 2008; 11 Ogden, CL (WOS:000187610100002) 2003; 32 WALSH, AES (WOS:A1994PF52600020) 1994; 116 Ioannides-Demos, LL (WOS:000230826200006) 2005; 65 Neff, Lisa M (MEDLINE:18377785) 2007; 9 Monck, NJT (WOS:000311286000007) 2008; 46 Miller, KJ (WOS:000232796800006) 2005; 5 TECOTT, LH (WOS:A1995QR06900052) 1995; 374 Bromidge, SM (WOS:000086055900009) 2000; 43 Fitzgerald, LW (WOS:000084580300010) 2000; 57 Smith, BM (WOS:000252519600012) 2008; 51 Kennett, GA (WOS:A1997XG56400023) 1997; 36 Foxcroft, D R (MEDLINE:12119985) 2000; 1 Vickers, SP (WOS:000080110300014) 1999; 143 Cooke, D (WOS:000241753000015) 2006; 5 STILL, WC (WOS:A1983RK55600006) 1983; 24 Wacker (10.1016/j.bmcl.2012.10.091_b0045) 2008; 11 Walsh (10.1016/j.bmcl.2012.10.091_b0060) 1994; 116 Smith (10.1016/j.bmcl.2012.10.091_b0095) 2009; 17 Rothman (10.1016/j.bmcl.2012.10.091_b0120) 2000; 102 Tecott (10.1016/j.bmcl.2012.10.091_b0075) 1995; 374 Ioannides-Demos (10.1016/j.bmcl.2012.10.091_b0020) 2005; 65 Kennett (10.1016/j.bmcl.2012.10.091_b0065) 1997; 36 Miller (10.1016/j.bmcl.2012.10.091_b0050) 2005; 5 Ogden (10.1016/j.bmcl.2012.10.091_b0010) 2003; 32 Cooke (10.1016/j.bmcl.2012.10.091_b0030) 2006; 5 Monck (10.1016/j.bmcl.2012.10.091_b0055) 2008; 46 10.1016/j.bmcl.2012.10.091_b0125 10.1016/j.bmcl.2012.10.091_b0105 10.1016/j.bmcl.2012.10.091_b0005 Vickers (10.1016/j.bmcl.2012.10.091_b0080) 1999; 143 Thomsen (10.1016/j.bmcl.2012.10.091_b0090) 2008; 325 Still (10.1016/j.bmcl.2012.10.091_b0135) 1983; 24 Neff (10.1016/j.bmcl.2012.10.091_b0035) 2007; 9 Wacker (10.1016/j.bmcl.2012.10.091_b0130) 2007; 50 Foxcroft (10.1016/j.bmcl.2012.10.091_b0015) 2000; 1 Smith (10.1016/j.bmcl.2012.10.091_b0100) 2008; 51 Bromidge (10.1016/j.bmcl.2012.10.091_b0145) 2000; 43 Fitzgerald (10.1016/j.bmcl.2012.10.091_b0115) 2000; 57 |
| References_xml | – volume: 11 start-page: 438 year: 2008 ident: b0040 publication-title: Curr. Opin. Drug Discovery Dev. contributor: fullname: Kennett – volume: 325 start-page: 577 year: 2008 ident: b0085 publication-title: J. Pharmacol. Exp. Ther. contributor: fullname: Thomsen – volume: 24 start-page: 4405 year: 1983 ident: b0135 publication-title: Tetrahedron Lett. contributor: fullname: Gennari – volume: 5 start-page: 919 year: 2006 ident: b0025 publication-title: Nat. Rev. Drug Disc. contributor: fullname: Aronne – volume: 65 start-page: 1391 year: 2005 ident: b0020 publication-title: Drugs contributor: fullname: McNeil – volume: 36 start-page: 609 year: 1997 ident: b0065 publication-title: Neuropharmacology contributor: fullname: Blackburn – volume: 57 start-page: 75 year: 2000 ident: b0110 publication-title: Mol. Pharmacol. contributor: fullname: Roth – volume: 50 start-page: 1365 year: 2007 ident: b0130 publication-title: J. Med. Chem. contributor: fullname: Robl – volume: 32 start-page: 741 year: 2003 ident: b0010 publication-title: Endocrinol. Metab. Clin. North Am. contributor: fullname: Flegal – volume: 374 start-page: 542 year: 1995 ident: b0070 publication-title: Nature contributor: fullname: Tecott – volume: 1 start-page: 121 year: 2000 ident: b0015 publication-title: Obes. Rev. contributor: fullname: Milne – volume: 43 start-page: 1123 year: 2000 ident: b0145 publication-title: J. Med. Chem. contributor: fullname: Wood – volume: 116 start-page: 120 year: 1994 ident: b0060 publication-title: Psychopharmacology contributor: fullname: Cowen – ident: b0150 – volume: 57 start-page: 75 year: 2000 ident: WOS:000084580300010 article-title: Possible role of valvular serotonin 5-HT2B receptors in the cardiopathy associated with fenfluramine publication-title: MOLECULAR PHARMACOLOGY contributor: fullname: Fitzgerald, LW – volume: 374 start-page: 542 year: 1995 ident: WOS:A1995QR06900052 article-title: EATING DISORDER AND EPILEPSY IN MICE LACKING 5-HT2C SEROTONIN RECEPTORS publication-title: NATURE contributor: fullname: TECOTT, LH – volume: 11 start-page: 438 year: 2008 ident: WOS:000257329700002 article-title: Agonists of the serotonin 5-HT2C receptor: Preclinical and clinical progression in multiple diseases publication-title: CURRENT OPINION IN DRUG DISCOVERY & DEVELOPMENT contributor: fullname: Wacker, DA – volume: 1 start-page: 121 year: 2000 ident: MEDLINE:12119985 article-title: Orlistat for the treatment of obesity: rapid review and cost-effectiveness model. publication-title: Obesity reviews : an official journal of the International Association for the Study of Obesity contributor: fullname: Foxcroft, D R – volume: 143 start-page: 309 year: 1999 ident: WOS:000080110300014 article-title: Reduced satiating effect of d-fenfluramine in serotonin 5-HT2C receptor mutant mice publication-title: PSYCHOPHARMACOLOGY contributor: fullname: Vickers, SP – volume: 5 start-page: 919 year: 2006 ident: WOS:000241753000015 article-title: The obesity pipeline: current strategies in the development of anti-obesity drugs publication-title: NATURE REVIEWS DRUG DISCOVERY doi: 10.1038/nrd2136 contributor: fullname: Cooke, D – volume: 24 start-page: 4405 year: 1983 ident: WOS:A1983RK55600006 article-title: DIRECT SYNTHESIS OF Z-UNSATURATED ESTERS - A USEFUL MODIFICATION OF THE HORNER-EMMONS OLEFINATION publication-title: TETRAHEDRON LETTERS contributor: fullname: STILL, WC – volume: 5 start-page: 282 year: 2005 ident: WOS:000232796800006 article-title: Serotonin 5-HT2C receptor agonists: For the treatment of obesity publication-title: MOLECULAR INTERVENTIONS doi: 10.1124/mi.5.5.8 contributor: fullname: Miller, KJ – volume: 50 start-page: 1365 year: 2007 ident: WOS:000244895900028 article-title: Discovery of (R)-9-ethyl-1,3,4,10b-tetrahydro-7-trifluoromethylpyrazino[2,1-a]isoindol-6(2H)-one, a selective, orally active agonist of the 5-HT2C receptor publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm0612968 contributor: fullname: Wacker, DA – volume: 46 start-page: 281 year: 2008 ident: WOS:000311286000007 article-title: 5-HT2C Ligands: Recent Progress publication-title: PROGRESS IN MEDICINAL CHEMISTRY, VOL 46 doi: 10.1016/S0079-6468(07)00006-9 contributor: fullname: Monck, NJT – volume: 65 start-page: 1391 year: 2005 ident: WOS:000230826200006 article-title: Pharmacotherapy for obesity publication-title: DRUGS contributor: fullname: Ioannides-Demos, LL – volume: 36 start-page: 609 year: 1997 ident: WOS:A1997XG56400023 article-title: SB 242084, a selective and brain penetrant 5-HT2C receptor antagonist publication-title: NEUROPHARMACOLOGY contributor: fullname: Kennett, GA – volume: 325 start-page: 577 year: 2008 ident: WOS:000255013800027 article-title: Lorcaserin, a novel selective human 5-Hydroxytryptamine(2C) agonist: In vitro and in vivo pharmacological characterization publication-title: JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS doi: 10.1124/jpet.107.133348 contributor: fullname: Thomsen, WJ – volume: 32 start-page: 741 year: 2003 ident: WOS:000187610100002 article-title: Epidemiologic trends in overweight and obesity publication-title: ENDOCRINOLOGY AND METABOLISM CLINICS OF NORTH AMERICA doi: 10.1016/S0889-8529(03)00074-4 contributor: fullname: Ogden, CL – volume: 51 start-page: 305 year: 2008 ident: WOS:000252519600012 article-title: Discovery and structure-activity relationship of (1R)-8-chloro-2,3,4,5-tetrahydro-1-methyl-1H-3-benzazepine (lorcaserin), a selective serotonin 5-HT2C receptor agonist for the treatment of obesity publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm0709034 contributor: fullname: Smith, BM – volume: 102 start-page: 2836 year: 2000 ident: WOS:000165607000008 article-title: Evidence for possible involvement of 5-HT2B receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications publication-title: CIRCULATION contributor: fullname: Rothman, RB – volume: 43 start-page: 1123 year: 2000 ident: WOS:000086055900009 article-title: Biarylcarbamoylindolines are novel and selective 5-HT2C receptor inverse agonists: Identification of 5-methyl-1-[[2-[(2-methyl-3-pyridyl)oxy]-5-pyridyl]carbamoyl]-6-trifluoromethylindoline (SB-243213) as a potential antidepressant/anxiolytic agent publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: Bromidge, SM – volume: 116 start-page: 120 year: 1994 ident: WOS:A1994PF52600020 article-title: M-CHLOROPHENYLPIPERAZINE DECREASES FOOD-INTAKE IN A TEST MEAL publication-title: PSYCHOPHARMACOLOGY contributor: fullname: WALSH, AES – start-page: MEDI year: 2005 ident: 000312267700061.7 publication-title: 229TH ACS NATIONAL M contributor: fullname: Lee, T. – volume: 17 start-page: 494 year: 2009 ident: WOS:000263788700013 article-title: Lorcaserin (APD356), a Selective 5-HT2C Agonist, Reduces Body Weight in Obese Men and Women publication-title: OBESITY doi: 10.1038/oby.2008.537 contributor: fullname: Smith, SR – volume: 9 start-page: 454 year: 2007 ident: MEDLINE:18377785 article-title: Pharmacotherapy for obesity. publication-title: Current atherosclerosis reports contributor: fullname: Neff, Lisa M – volume: 5 start-page: 282 year: 2005 ident: 10.1016/j.bmcl.2012.10.091_b0050 publication-title: Mol. Interventions doi: 10.1124/mi.5.5.8 contributor: fullname: Miller – volume: 11 start-page: 438 year: 2008 ident: 10.1016/j.bmcl.2012.10.091_b0045 publication-title: Curr. Opin. Drug Discovery Dev. contributor: fullname: Wacker – volume: 17 start-page: 494 year: 2009 ident: 10.1016/j.bmcl.2012.10.091_b0095 publication-title: Obesity doi: 10.1038/oby.2008.537 contributor: fullname: Smith – volume: 65 start-page: 1391 year: 2005 ident: 10.1016/j.bmcl.2012.10.091_b0020 publication-title: Drugs doi: 10.2165/00003495-200565100-00006 contributor: fullname: Ioannides-Demos – volume: 51 start-page: 305 year: 2008 ident: 10.1016/j.bmcl.2012.10.091_b0100 publication-title: J. Med. Chem. doi: 10.1021/jm0709034 contributor: fullname: Smith – volume: 57 start-page: 75 year: 2000 ident: 10.1016/j.bmcl.2012.10.091_b0115 publication-title: Mol. Pharmacol. contributor: fullname: Fitzgerald – ident: 10.1016/j.bmcl.2012.10.091_b0125 – volume: 1 start-page: 121 year: 2000 ident: 10.1016/j.bmcl.2012.10.091_b0015 publication-title: Obes. Rev. doi: 10.1046/j.1467-789x.2000.00011.x contributor: fullname: Foxcroft – volume: 116 start-page: 120 year: 1994 ident: 10.1016/j.bmcl.2012.10.091_b0060 publication-title: Psychopharmacology doi: 10.1007/BF02244883 contributor: fullname: Walsh – volume: 143 start-page: 309 year: 1999 ident: 10.1016/j.bmcl.2012.10.091_b0080 publication-title: Psychopharmacology doi: 10.1007/s002130050952 contributor: fullname: Vickers – volume: 32 start-page: 741 year: 2003 ident: 10.1016/j.bmcl.2012.10.091_b0010 publication-title: Endocrinol. Metab. Clin. North Am. doi: 10.1016/S0889-8529(03)00074-4 contributor: fullname: Ogden – volume: 50 start-page: 1365 year: 2007 ident: 10.1016/j.bmcl.2012.10.091_b0130 publication-title: J. Med. Chem. doi: 10.1021/jm0612968 contributor: fullname: Wacker – volume: 5 start-page: 919 year: 2006 ident: 10.1016/j.bmcl.2012.10.091_b0030 publication-title: Nat. Rev. Drug Disc. doi: 10.1038/nrd2136 contributor: fullname: Cooke – volume: 36 start-page: 609 year: 1997 ident: 10.1016/j.bmcl.2012.10.091_b0065 publication-title: Neuropharmacology doi: 10.1016/S0028-3908(97)00038-5 contributor: fullname: Kennett – volume: 374 start-page: 542 year: 1995 ident: 10.1016/j.bmcl.2012.10.091_b0075 publication-title: Nature doi: 10.1038/374542a0 contributor: fullname: Tecott – ident: 10.1016/j.bmcl.2012.10.091_b0105 – volume: 46 start-page: 281 year: 2008 ident: 10.1016/j.bmcl.2012.10.091_b0055 publication-title: Prog. Med. Chem. doi: 10.1016/S0079-6468(07)00006-9 contributor: fullname: Monck – volume: 9 start-page: 454 year: 2007 ident: 10.1016/j.bmcl.2012.10.091_b0035 publication-title: Curr. Atheroscler. Rep. doi: 10.1007/s11883-007-0061-0 contributor: fullname: Neff – volume: 102 start-page: 2836 year: 2000 ident: 10.1016/j.bmcl.2012.10.091_b0120 publication-title: Circulation doi: 10.1161/01.CIR.102.23.2836 contributor: fullname: Rothman – volume: 24 start-page: 4405 year: 1983 ident: 10.1016/j.bmcl.2012.10.091_b0135 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)85909-2 contributor: fullname: Still – ident: 10.1016/j.bmcl.2012.10.091_b0005 – volume: 43 start-page: 1123 year: 2000 ident: 10.1016/j.bmcl.2012.10.091_b0145 publication-title: J. Med. Chem. doi: 10.1021/jm990388c contributor: fullname: Bromidge – volume: 325 start-page: 577 year: 2008 ident: 10.1016/j.bmcl.2012.10.091_b0090 publication-title: J. Pharmacol. Exp. Ther. doi: 10.1124/jpet.107.133348 contributor: fullname: Thomsen |
| SSID | ssj0014044 |
| Score | 2.1752672 |
| Snippet | A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT2C agonism with excellent... A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT₂C agonism with excellent... A series of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones is described, several examples of which exhibit potent 5-HT(2C) agonism with excellent... |
| Source | Web of Science |
| SourceID | proquest crossref pubmed webofscience fao elsevier |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 330 |
| SubjectTerms | 5-HT2c receptor agonist agonistic behavior agonists Animals Chemistry Chemistry, Medicinal Chemistry, Organic food intake Half-Life Heterocyclic Compounds, 3-Ring - chemical synthesis Heterocyclic Compounds, 3-Ring - chemistry Heterocyclic Compounds, 3-Ring - pharmacokinetics Humans Isoquinolines - chemical synthesis Isoquinolines - chemistry Isoquinolines - pharmacokinetics Life Sciences & Biomedicine Male Obesity Pharmacology & Pharmacy Physical Sciences Pyrroles - chemical synthesis Pyrroles - chemistry Pyrroles - pharmacokinetics Rats Rats, Sprague-Dawley Receptor, Serotonin, 5-HT2A - chemistry Receptor, Serotonin, 5-HT2A - metabolism Receptor, Serotonin, 5-HT2B - chemistry Receptor, Serotonin, 5-HT2B - metabolism Receptor, Serotonin, 5-HT2C - chemistry Receptor, Serotonin, 5-HT2C - metabolism receptors Science & Technology Serotonin Serotonin 5-HT2 Receptor Agonists - chemical synthesis Serotonin 5-HT2 Receptor Agonists - chemistry Serotonin 5-HT2 Receptor Agonists - pharmacokinetics Structure-Activity Relationship |
| Title | Synthesis and SAR of 2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-ones as 5-HT2C receptor agonists |
| URI | https://dx.doi.org/10.1016/j.bmcl.2012.10.091 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000312267700061 https://www.ncbi.nlm.nih.gov/pubmed/23177783 https://search.proquest.com/docview/1240899619 |
| Volume | 23 |
| WOS | 000312267700061 |
| WOSCitedRecordID | wos000312267700061 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3db9MwED9tnQS8IOiAhY_JSBMCUa_xR-r4saqYAmh7oKtUCaHITpypSE2rJnvoC3875zSpQBoI8RrbsZNfcvc73_kO4CwvMpvrnFGlbUhlHGZUy4zRmCmbo8KyYZNt__JqlMzkp3k0P4BJdxbGh1W2sn8n0xtp3V4Ztm9zuF4shlNPvmMt54x7bxtHu_0I1ZGUPTgaf_ycXO2dCTJsarr6_tQPaM_O7MK87DLzHgjGz32Ql2Z_0k-HhVndxULvVFiNcrp4BA9bVknGu4U_hgNX9uF4XKJFvdySN6SJ82w20Ptwf9LVeOvDvcvWtX4My-m2RDJYLSpiypxMx1_IqiB8IAbCDCStXY1iaZtvVpQldL3dbPB2XwW2ZN8WFa52UfryPzR6q23yjvoKAMRUJKLJNZ8QfMVujdY9MTcrn6q3egKziw_Xk4S2tRhoJuKwpk5nTsdSC-vP7fHIjRzjRtqCKZWjVePMiGexZtLGQoaOmZjnLM6wD04QGyWeQq_EuU-AjFyUo91duMJpqY3RJuTWikwIZbQzPID3HQLpepdyI-1i0b6nHq_U4-WvIV4BRB1I6W8fToo64a_jThDR1NygLE1nU-53fnzuoSgcBfC6gzlFPLwHxZRudVulzCeEQwuR6QCe7fDfLxGJslIqFgGc_fpB7Nu99cmQ7CrV8MYA2L90m7SZ2n2Ggvr5fz7rC3jAmyoefufoJfTqza17hVyqtqdweP6DnbZ_zE8UWhbg |
| link.rule.ids | 315,786,790,4043,4521,24144,27954,27955,27956,45618,45712 |
| linkProvider | Elsevier |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV3fb9MwELZGJzFeEHTAwk8jTQhETWPHqe3HqmLK2NoH2kqVELLsxJmK1LRqsof-95zTpAJpIMRrbMdOvuTuO9_5DqHzLE9tpjJKhLIh4TJMieIpJZIKm4HCsmGdbX88GSRz_mURL47QqD0L48MqG9m_l-m1tG6u9Ju32d8sl_2pJ99S8QVl3tvGwG4_5rGgrIOOh5dXyeTgTOBhXdPV9yd-QHN2Zh_mZVep90BQ9skHeSn6J_10Lzfru1jonQqrVk4Xj9DDhlXi4X7hj9GRK7rodFiARb3a4Xe4jvOsN9C76GTU1njrovvjxrV-ilbTXQFksFyW2BQZng6_4nWOWS_qRabHSeUqEEu7bLsmNCGb3XYLt_sWQUv6fVnCapeFL_9D4vfKJh-IrwCATYljkszYCMMrdhuw7rG5WftUveUTNL_4PBslpKnFQNJIhhVxKnVKchVZf26PxW7gKDPc5lSIDKwaZwYslYpyKyMeOmoky6hMoQ9MII2InqJOAXOfITxwcQZ2d-5yp7gyRpmQWRulUSSMcoYF6GOLgN7sU27oNhbth_Z4aY-XvwZ4BShuQdK_fTgadMJfx50BotrcgCzV8ynzOz8-91AcDgL0toVZAx7eg2IKt74tNfUJ4cBCpCpAz_b4H5YIRFkIIaMAnf_6QRzavfVJgewKUfPGANF_6TZqMrX7DAXV8_981jfoJJmNr_X15eTqBXrA6ooefhfpJepU21v3CnhVZV83_81Pw-UY0A |
| 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=Synthesis+and+SAR+of+2%2C3%2C3a%2C4-tetrahydro-1H-pyrrolo%5B3%2C4-c%5Disoquinolin-5%289bH%29-ones+as+5-HT%E2%82%82C+receptor+agonists&rft.jtitle=Bioorganic+%26+medicinal+chemistry+letters&rft.au=Fevig%2C+John+M&rft.au=Feng%2C+Jianxin&rft.au=Rossi%2C+Karen+A&rft.au=Miller%2C+Keith+J&rft.date=2013&rft.pub=Elsevier+Ltd&rft.issn=0960-894X&rft.eissn=1464-3405&rft.volume=23&rft.issue=1&rft.spage=330&rft.epage=335&rft_id=info:doi/10.1016%2Fj.bmcl.2012.10.091&rft.externalDocID=US201500131506 |
| 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 |