Novel derivatives of the benzo[b][1,6]naphthyridine system
An efficient synthesis of 2‐hydroxy‐6‐methylbenzo[b][1,6]naphthyridin‐1(2H)‐one was devised. The hydroxy group was alkylated, acylated and replaced by hydrogen. Electrophilic nitration, bromination and chlorosulfonation occurred readily in the 4‐position. From the last, various sulfonamide derivativ...
Saved in:
| Published in: | Journal of heterocyclic chemistry Vol. 43; no. 2; pp. 405 - 416 |
|---|---|
| Main Authors: | , |
| Format: | Journal Article |
| Language: | English |
| Published: |
Hoboken
Wiley-Blackwell
01-03-2006
Wiley‐Blackwell |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| Abstract | An efficient synthesis of 2‐hydroxy‐6‐methylbenzo[b][1,6]naphthyridin‐1(2H)‐one was devised. The hydroxy group was alkylated, acylated and replaced by hydrogen. Electrophilic nitration, bromination and chlorosulfonation occurred readily in the 4‐position. From the last, various sulfonamide derivatives were prepared. A selection of the products was screened by the National Cancer Institute. Cytotoxicities were generally low. |
|---|---|
| AbstractList | An efficient synthesis of 2‐hydroxy‐6‐methylbenzo[b][1,6]naphthyridin‐1(2H)‐one was devised. The hydroxy group was alkylated, acylated and replaced by hydrogen. Electrophilic nitration, bromination and chlorosulfonation occurred readily in the 4‐position. From the last, various sulfonamide derivatives were prepared. A selection of the products was screened by the National Cancer Institute. Cytotoxicities were generally low. |
| Author | Deady, Leslie W. Rogers, Michael L. |
| Author_xml | – sequence: 1 givenname: Leslie W. surname: Deady fullname: Deady, Leslie W. organization: Chemistry Department, La Trobe University, Victoria 3086, Australia – sequence: 2 givenname: Michael L. surname: Rogers fullname: Rogers, Michael L. organization: Chemistry Department, La Trobe University, Victoria 3086, Australia |
| BookMark | eNqFj01PwkAURScGEwFdu-0PsNA30-lMdWWQDwnBhRiIhEymnUdahJZ0GrT-ekswGleubm5yz01OizSyPENCrsHrgOfR7ibBssO58HzmUUrPSBNCn7kcQtYgzXpBXeB0cUFa1m7qCkyIJrmd5gfcOgaL9KDL9IDWyddOmaATYfaZL6PVEm6CVab3SZlURWrSDB1b2RJ3l-R8rbcWr76zTV4G_Vlv5E6eho-9-4kb0wCoK0xsAh1xFpkoBh0a6UsjjCck05IJX9NYGE51CEJDJHkgJAIykFGMMZiAtUn39BsXubUFrtW-SHe6qBR46qiujurqV70m7k7Ee7rF6r-5Go_6sz-0e6LT2vLjh9bFmwoEE1zNp0P10HtdjNn8WUn2BRGHb70 |
| CitedBy_id | crossref_primary_10_1007_s11164_013_1496_2 crossref_primary_10_1002_jccs_201600196 crossref_primary_10_1016_j_jphotochem_2023_114619 crossref_primary_10_1002_chin_200631132 |
| Cites_doi | 10.1080/00304940309355366 10.1081/SCC-120018934 10.1016/S0040-4039(00)97039-4 10.1021/ja01546a060 10.1002/jhet.5570380524 10.1139/v71-464 10.1080/10426500210275 10.1021/jo00900a018 10.1016/j.bmc.2004.11.007 10.2174/0929867033457647 10.1021/jm020420u 10.1080/00397919008052336 |
| ContentType | Journal Article |
| Copyright | Copyright © 2006 Journal of Heterocyclic Chemistry |
| Copyright_xml | – notice: Copyright © 2006 Journal of Heterocyclic Chemistry |
| DBID | BSCLL AAYXX CITATION |
| DOI | 10.1002/jhet.5570430222 |
| DatabaseName | Istex CrossRef |
| DatabaseTitle | CrossRef |
| DatabaseTitleList | |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1943-5193 |
| EndPage | 416 |
| ExternalDocumentID | 10_1002_jhet_5570430222 JHET5570430222 ark_67375_WNG_DCZXJ3WS_8 |
| Genre | article |
| GroupedDBID | --- -~X .GJ 05W 0R~ 1L6 1OB 1OC 31~ 33P 3EH 3SF 3WU 4.4 52U 52V 53G 5GY 6TJ 8-0 8-1 8UM 8WZ A00 A6W AABCJ AAESR AAEVG AAHHS AANLZ AAONW AASGY AAXRX AAYJJ AAZKR ABCUV ABDBF ABDPE ABJNI ABQWH ABXGK ACAHQ ACBWZ ACCFJ ACCZN ACFBH ACGFS ACGOF ACIWK ACMXC ACNCT ACPOU ACXBN ACXQS ADBBV ADBTR ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN AEEZP AEGXH AEIGN AEIMD AENEX AEQDE AEUQT AEUYR AFBPY AFFPM AFGKR AFPWT AFZJQ AHBTC AI. AIACR AITYG AIURR AIWBW AJBDE ALMA_UNASSIGNED_HOLDINGS ALUQN AMBMR AMYDB ASPBG ATUGU AVWKF AZFZN AZVAB BDRZF BFHJK BHBCM BMXJE BNHUX BOGZA BRXPI BSCLL BTSUX DCZOG DRFUL DRMAN DRSTM EBD EBS EJD ESX F5P FEDTE FUBAC G-S GODZA HF~ HGLYW HVGLF HZ~ KBYEO LATKE LEEKS LH4 LITHE LOXES LUTES LW6 LYRES MEWTI MRFUL MRMAN MRSTM MSFUL MSMAN MSSTM MXFUL MXMAN MXSTM MY~ NNB O66 O9- OIG P2W P4E PALCI QRW RIWAO RJQFR ROL RWI SAMSI SJN SUPJJ TN5 TUS VH1 WBFHL WBKPD WH7 WIH WIJ WIK WOHZO WXSBR WYISQ WYJ XV2 Y6R YCJ ZCG ZZTAW ~S- C3M G8K AAMNL AAYXX CITATION |
| ID | FETCH-LOGICAL-c2612-7dcd6ab53bdbc1a9d848d7d0783a8374a2c7d52a917a1b85678e1e318bcec1d63 |
| IEDL.DBID | 33P |
| ISSN | 0022-152X |
| IngestDate | Fri Nov 22 01:07:01 EST 2024 Sat Aug 24 00:55:02 EDT 2024 Wed Oct 30 09:55:57 EDT 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 2 |
| Language | English |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-c2612-7dcd6ab53bdbc1a9d848d7d0783a8374a2c7d52a917a1b85678e1e318bcec1d63 |
| Notes | istex:C35A02E37C07463E1A2E3FF7CB9ED0B5B0EF810C ark:/67375/WNG-DCZXJ3WS-8 ArticleID:JHET5570430222 |
| PageCount | 12 |
| ParticipantIDs | crossref_primary_10_1002_jhet_5570430222 wiley_primary_10_1002_jhet_5570430222_JHET5570430222 istex_primary_ark_67375_WNG_DCZXJ3WS_8 |
| PublicationCentury | 2000 |
| PublicationDate | 2006-03 March/April 2006 2006-03-00 |
| PublicationDateYYYYMMDD | 2006-03-01 |
| PublicationDate_xml | – month: 03 year: 2006 text: 2006-03 |
| PublicationDecade | 2000 |
| PublicationPlace | Hoboken |
| PublicationPlace_xml | – name: Hoboken |
| PublicationTitle | Journal of heterocyclic chemistry |
| PublicationYear | 2006 |
| Publisher | Wiley-Blackwell Wiley‐Blackwell |
| Publisher_xml | – name: Wiley-Blackwell – name: Wiley‐Blackwell |
| References | H. M. Faidallah, H. A. Albar, M. S. I. Makki and E. M. Sharshira, Phosphorus, Sulfur and Silicon, 177, 685 (2002). L. W. Deady, T. Rodemann, L. Zhuang, B. C. Baguley and W. A. Denny, J. Med. Chem., 46, 1049 (2003). L. W. Deady, S. M. Devine and M. L. Rogers, Org. Prep, and Proced. Int., 35, 627 (2003). L. W. Deady, M. L. Rogers, L. Zhuang, B. C. Baguley and W. A. Denny, Bioorg. Med. Chem., 13, 1341 (2005). D. E. Horning, G. Lacasse and J. M. Muchowski, Can. J. Chem., 49, 2785 (1971). J. N. Chatterjea, S. K. Mukherjee and C. Bhakta, J. Ind. Chem. Soc., 59, 707 (1982). J. Y. Q. Lai, Y. Ferguson and M. Jones, Synthetic Commun., 33, 3427 (2003). M. Kawase, T. Kitamura, M. Shimada and Y. Kikugawa, Synthetic Commun., 20, 887 (1990). S. L. Graham and T. H. Scholz, Tetrahedron Lett., 31, 6269 (1990). R. A. Henry, C. A. Heller and D. W. Moore, J. Org. Chem., 40, 1760 (1975). A. Scozzafava, T. Owa, A. Mastrolorenzo and C. T. Supuran, Curr. Med. Chem., 10, 925 (2003). M. M. Robison and B. L. Robison, J. Am. Chem. Soc., 80, 3443 (1958). Chem. Abstr., 128, 48150 (1997). L. W. Deady and T. Rodemann, J. Heterocyclic Chem., 38, 1185 (2001). 1990; 20 1990; 31 1982; 59 1997; 128 1971; 49 2002; 177 2003; 46 2003; 35 2001; 38 1958; 80 1975; 40 2003; 10 2005; 13 2003; 33 Horning (10.1002/jhet.5570430222-BIB6|cit6) 1971; 49 Deady (10.1002/jhet.5570430222-BIB3|cit3) 2005; 13 Deady (10.1002/jhet.5570430222-BIB1|cit1) 2001; 38 10.1002/jhet.5570430222-BIB19|cit20 Scozzafava (10.1002/jhet.5570430222-BIB10|cit10) 2003; 10 Chatterjea (10.1002/jhet.5570430222-BIB4|cit4) 1982; 59 Faidallah (10.1002/jhet.5570430222-BIB13|cit14) 2002; 177 10.1002/jhet.5570430222-BIB16|cit17 Deady (10.1002/jhet.5570430222-BIB8|cit8) 2003; 35 Robison (10.1002/jhet.5570430222-BIB5|cit5) 1958; 80 10.1002/jhet.5570430222-BIB15|cit16 Lai (10.1002/jhet.5570430222-BIB9|cit9) 2003; 33 10.1002/jhet.5570430222-BIB18|cit19 Deady (10.1002/jhet.5570430222-BIB2|cit2) 2003; 46 10.1002/jhet.5570430222-BIB11|cit11 (10.1002/jhet.5570430222-BIB11.2|cit12) 1997; 128 Henry (10.1002/jhet.5570430222-BIB7|cit7) 1975; 40 Graham (10.1002/jhet.5570430222-BIB14|cit15) 1990; 31 Kawase (10.1002/jhet.5570430222-BIB12|cit13) 1990; 20 10.1002/jhet.5570430222-BIB17|cit18 |
| References_xml | – volume: 31 start-page: 6269 year: 1990 publication-title: Tetrahedron Lett. – volume: 40 start-page: 1760 year: 1975 publication-title: J. Org. Chem. – volume: 20 start-page: 887 year: 1990 publication-title: Synthetic Commun. – volume: 59 start-page: 707 year: 1982 publication-title: J. Ind. Chem. Soc. – volume: 10 start-page: 925 year: 2003 publication-title: Curr. Med. Chem. – volume: 177 start-page: 685 year: 2002 publication-title: Phosphorus, Sulfur and Silicon – volume: 38 start-page: 1185 year: 2001 publication-title: J. Heterocyclic Chem. – volume: 33 start-page: 3427 year: 2003 publication-title: Synthetic Commun. – volume: 49 start-page: 2785 year: 1971 publication-title: Can. J. Chem. – volume: 35 start-page: 627 year: 2003 publication-title: Org. Prep, and Proced. Int. – volume: 13 start-page: 1341 year: 2005 publication-title: Bioorg. Med. Chem. – volume: 128 start-page: 48150 year: 1997 publication-title: Chem. Abstr. – volume: 46 start-page: 1049 year: 2003 publication-title: J. Med. Chem. – volume: 80 start-page: 3443 year: 1958 publication-title: J. Am. Chem. Soc. – ident: 10.1002/jhet.5570430222-BIB15|cit16 – ident: 10.1002/jhet.5570430222-BIB18|cit19 – volume: 35 start-page: 627 year: 2003 ident: 10.1002/jhet.5570430222-BIB8|cit8 publication-title: Org. Prep, and Proced. Int. doi: 10.1080/00304940309355366 contributor: fullname: Deady – ident: 10.1002/jhet.5570430222-BIB17|cit18 – volume: 33 start-page: 3427 year: 2003 ident: 10.1002/jhet.5570430222-BIB9|cit9 publication-title: Synthetic Commun. doi: 10.1081/SCC-120018934 contributor: fullname: Lai – volume: 31 start-page: 6269 year: 1990 ident: 10.1002/jhet.5570430222-BIB14|cit15 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)97039-4 contributor: fullname: Graham – volume: 80 start-page: 3443 year: 1958 ident: 10.1002/jhet.5570430222-BIB5|cit5 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja01546a060 contributor: fullname: Robison – volume: 38 start-page: 1185 year: 2001 ident: 10.1002/jhet.5570430222-BIB1|cit1 publication-title: J. Heterocyclic Chem. doi: 10.1002/jhet.5570380524 contributor: fullname: Deady – volume: 49 start-page: 2785 year: 1971 ident: 10.1002/jhet.5570430222-BIB6|cit6 publication-title: Can. J. Chem. doi: 10.1139/v71-464 contributor: fullname: Horning – ident: 10.1002/jhet.5570430222-BIB11|cit11 – volume: 128 start-page: 48150 year: 1997 ident: 10.1002/jhet.5570430222-BIB11.2|cit12 publication-title: Chem. Abstr. – volume: 177 start-page: 685 year: 2002 ident: 10.1002/jhet.5570430222-BIB13|cit14 publication-title: Phosphorus, Sulfur and Silicon doi: 10.1080/10426500210275 contributor: fullname: Faidallah – ident: 10.1002/jhet.5570430222-BIB19|cit20 – volume: 40 start-page: 1760 year: 1975 ident: 10.1002/jhet.5570430222-BIB7|cit7 publication-title: J. Org. Chem. doi: 10.1021/jo00900a018 contributor: fullname: Henry – ident: 10.1002/jhet.5570430222-BIB16|cit17 – volume: 13 start-page: 1341 year: 2005 ident: 10.1002/jhet.5570430222-BIB3|cit3 publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2004.11.007 contributor: fullname: Deady – volume: 10 start-page: 925 year: 2003 ident: 10.1002/jhet.5570430222-BIB10|cit10 publication-title: Curr. Med. Chem. doi: 10.2174/0929867033457647 contributor: fullname: Scozzafava – volume: 46 start-page: 1049 year: 2003 ident: 10.1002/jhet.5570430222-BIB2|cit2 publication-title: J. Med. Chem. doi: 10.1021/jm020420u contributor: fullname: Deady – volume: 59 start-page: 707 year: 1982 ident: 10.1002/jhet.5570430222-BIB4|cit4 publication-title: J. Ind. Chem. Soc. contributor: fullname: Chatterjea – volume: 20 start-page: 887 year: 1990 ident: 10.1002/jhet.5570430222-BIB12|cit13 publication-title: Synthetic Commun. doi: 10.1080/00397919008052336 contributor: fullname: Kawase |
| SSID | ssj0021377 |
| Score | 1.7604783 |
| Snippet | An efficient synthesis of 2‐hydroxy‐6‐methylbenzo[b][1,6]naphthyridin‐1(2H)‐one was devised. The hydroxy group was alkylated, acylated and replaced by... |
| SourceID | crossref wiley istex |
| SourceType | Aggregation Database Publisher |
| StartPage | 405 |
| Title | Novel derivatives of the benzo[b][1,6]naphthyridine system |
| URI | https://api.istex.fr/ark:/67375/WNG-DCZXJ3WS-8/fulltext.pdf https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fjhet.5570430222 |
| Volume | 43 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrZ3ZS8MwHMeDzgd98RbrRR9EfLCuR9K0vo0djj0UYZMNxwi5yjxoxy7Ev96kXTfmiyC-FApJKd_-kt_R5BMArmmMuMAOt7ATUgvK2LfCGCGLUeXPBJIxFLqU3WzjqBfU6hqTUyn2wuR8iGXBTY-MbL7WA5yySXkFDX0byum9BkhBTyctahZWuUK2icN7WqZcmqdX8MKVp-oVcB_bLf_ov-aXtrTEn-vxauZwGnv_8Kr7YHcRbZqV3DwOwIZMDsF2tTjk7Qg8ROlcfphC2eE8Q4BPzDQ2VVBoMpl8pX026Dt3_iCho6H6ouNX5emkmdOfj8Fzo96pNq3FcQoW15wwCwsufMqQxwTjDg1FAAOBhf6PR1WaCqnLsUAuVQkcdViAlBuTji6RMi65I3zvBJSSNJGnwPSQ4LbNpM0x1RFBGLhUNQ5CymPIODTAbSEmGeXUDJLzkV2ixSArMQxwk4m9bEfH73qxGUakGz2SWvWl1_K6bRIYAGYa__ZA0mrWO6vbs791Owc7ebFFrza7AKXpeCYvweZEzK4yC1PXdiv6Biy80Jc |
| link.rule.ids | 315,782,786,1408,27933,27934,46064,46488 |
| linkProvider | Wiley-Blackwell |
| linkToHtml | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrZ1ZS8NAEMcHrQ_64i3WMw8iPhhtkt0cvkltrVcRWrEoZdkr1IO09BDx07uT9KC-COJjYLOE2dn8Z2Z3fwtwwGMqVeBIO3AibhMd-3YUU2oLbvRMUR0ThaXsSi2oNsKLEmJyxmdhMj7EuOCGMyP9X-MEx4L06YQa-trS_RMkSBEPs5ZZmCO-cUc8xuHdj5MuJOqNiOFGqxojvE_BPf3RwZQyzaGRP6cj1lRyykv_8bHLsDgMOK3zzENWYEYnqzBfHN3ztgZn1faHfreUccWPlALes9qxZeJCS-jkq_0sms_Osd9MeKdlBrX7YsROWxkAeh0eyqV6sWIPb1SwJaLC7EBJ5XNBPaGEdHikQhKqQOFSHjeZKuGuDBR1ucnhuCNCapRMO1glFVJLR_neBuSSdqI3wfKokoWC0AUZcAwKotDlpnEYcRkTIUkejkbWZJ0MnMEyRLLL0BhsYow8HKbWHrfj3TfcbxZQ9li9ZBfFp8a191hjYR5IauTfOmTXlVJ98rj1t9f2Yb5Sv7tlt1fVm21YyGovuPlsB3L97kDvwmxPDfZSd_sGisrTsw |
| linkToPdf | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwrZ3JS8NAFMYfWkG9uIt1zUHEg9EsM1m8lS7WKkGw0qKUYbbgRlq6If71ziSmpV4E8RiYDOHLTL73XmZ-A3BMY8yFb3PTt0NqIhl7ZhhjbDKq_ExgGSOhS9n1ez9qB5WqxuSU8r0wGR9iUnDTMyP9XusJ3hPxxRQa-vosh-caIIVcnbTMwwJSwbjG57vu3STn0kC9HBiurKqd030s5-JHBzPGtKA1_pgNWFPHqa3-w7Ouwcp3uGmUsvGxDnMy2YClcn7K2yZcRt2xfDeEGojjlAE-MLqxoaJCg8nks_vEOk_2mddJaO9ZvdL-i7I6aWT45y14qFWb5br5fZ6CyTUozPQFFx5l2GWCcZuGIkCB8IX-kUdVnoqow32BHaoyOGqzACsfk7aukTIuuS08dxsKSTeRO2C4WHDLYtLiPtUhQRg4VDUOQspjxDgqwmkuJull2AySAZIdosUgUzGKcJKKPWlH-296tZmPSSu6IpXyY7vhtu5JUASUavxbh6RRrzanl7t_u-0IFu8qNXJ7Hd3swXJWeNErz_ahMOyP5AHMD8ToMB1sXxDZ0lk |
| 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=Novel+derivatives+of+the+benzo%5Bb%5D%5B1%2C6%5Dnaphthyridine+system&rft.jtitle=Journal+of+heterocyclic+chemistry&rft.au=Deady%2C+Leslie+W.&rft.au=Rogers%2C+Michael+L.&rft.date=2006-03-01&rft.pub=Wiley%E2%80%90Blackwell&rft.issn=0022-152X&rft.eissn=1943-5193&rft.volume=43&rft.issue=2&rft.spage=405&rft.epage=416&rft_id=info:doi/10.1002%2Fjhet.5570430222&rft.externalDBID=10.1002%252Fjhet.5570430222&rft.externalDocID=JHET5570430222 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0022-152X&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0022-152X&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0022-152X&client=summon |