daccf7c9aee7283307a888b4dd192a8c pmc_26479031.pdf c21a5d9ae8418c17b0f863d5cf05f07dd15ef4e6 pmc_26479031.pdf f815dec9850c8f210cc141dd5d1bbf044f3d98a211167e118c2d09addf09768f pmc_26479031.pdf Title: Multicomponent reaction-based synthesis and biological evaluation of tricyclic heterofused quinolines with multi-trypanosomatid activity Subject: European Journal of Medicinal Chemistry, 105 (2015) 120-137. doi:10.1016/j.ejmech.2015.10.007 Author: Ornella Di Pietro Creator: Elsevier Producer: Acrobat Distiller 8.1.0 (Windows) CreationDate: Tue Oct 27 08:31:20 2015 CET ModDate: Tue Oct 27 08:32:04 2015 CET Tagged: no UserProperties: no Suspects: no Form: none JavaScript: no Pages: 18 Encrypted: no Page size: 595.276 x 793.701 pts Page rot: 0 File size: 816721 bytes Optimized: yes PDF version: 1.7 name type encoding emb sub uni object ID ------------------------------------ ----------------- ---------------- --- --- --- --------- EGIKHK+AdvOT863180fb Type 1C WinAnsi yes yes no 1141 0 EGIKHL+AdvP4C4E59 Type 1C Custom yes yes yes 1146 0 EGIKHM+AdvTT5843c571 Type 1C WinAnsi yes yes no 1150 0 EGIKHN+AdvOTb92eb7df.I Type 1C WinAnsi yes yes no 1152 0 EGIKHO+AdvOTc4d0b532 Type 1C WinAnsi yes yes no 1155 0 EGIKHP+AdvOTb83ee1dd.B Type 1C WinAnsi yes yes no 1157 0 EGIKIA+AdvPS44A44B Type 1C WinAnsi yes yes no 1163 0 EGIKJB+AdvOT863180fb+fb Type 1C Custom yes yes yes 1159 0 EGIKJC+AdvP3F4C13 Type 1C WinAnsi yes yes no 1161 0 EGIKJD+AdvOTb0c9bf5d Type 1C WinAnsi yes yes no 1170 0 EGIKMD+AdvPSA35D Type 1C WinAnsi yes yes no 1174 0 EGIKPD+AdvP4C4E74 Type 1C Custom yes yes yes 796 0 EGIKPE+AdvPS40C6FB Type 1C WinAnsi yes yes no 797 0 EGILNP+AdvOTb92eb7df.I+fb Type 1C Custom yes yes yes 803 0 EGIMIL+AdvP4721B4 Type 1C WinAnsi yes yes no 814 0 EGIMIM+AdvOT404f8e91.BI Type 1C WinAnsi yes yes no 818 0 EGIMMM+AdvOT863180fb+20 Type 1C WinAnsi yes yes no 823 0 Jhove (Rel. 1.22.1, 2019-04-17) Date: 2020-08-10 13:43:41 CEST RepresentationInformation: pmc_26479031.pdf ReportingModule: PDF-hul, Rel. 1.12.1 (2019-04-17) LastModified: 2018-01-31 05:57:03 CET Size: 816721 Format: PDF Version: 1.7 Status: Well-Formed, but not valid SignatureMatches: PDF-hul ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - 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referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fne' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnf' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fnd' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'tbl2fng' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'bib14' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'bib56' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'bib57' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'bib58' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'bib59' cannot be found Offset: 777189 ID: PDF-HUL-122 ErrorMessage: edu.harvard.hul.ois.jhove.module.pdf.PdfInvalidException: Invalid indirect destination - referenced object 'bib50' cannot be found Offset: 777189 MIMEtype: application/pdf Profile: Linearized PDF PDFMetadata: Objects: 1267 FreeObjects: 1 IncrementalUpdates: 1 DocumentCatalog: PageLayout: SinglePage PageMode: UseOutlines Outlines: Item: Title: 4. Experimental part Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@6121c9d6 Children: Item: Title: 1. Introduction Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@87f383f Item: Title: 2. Results and discussion Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@4eb7f003 Children: Item: Title: 2.1. Design and synthesis of the target compounds Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@eafc191 Item: Title: 2.2. Biological profiling of the novel heterofused quinoline compounds and ring-open analogues Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@612fc6eb Children: Item: Title: 2.2.1. In vitro activity against T. brucei Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@1060b431 Item: Title: 2.2.2. Brain permeation Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@612679d6 Item: Title: 2.2.3. Cytotoxicity and acetylcholinesterase inhibitory activity Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@11758f2a Item: Title: 2.2.4. In vitro activity against T. cruzi and L. infantum Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@e720b71 Item: Title: 3. Conclusion Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@1b26f7b2 Item: Title: 4. Experimental part Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@491cc5c9 Children: Item: Title: 4.1. Chemistry. General methods Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@74ad1f1f Children: Item: Title: 4.1.1. 1-Benzyl-9-(tert-butoxycarbonylaminomethyl)-5-(4-chlorophenyl)-1,2,3,4-tetrahydro-2-oxobenzo[h][1,6]naphthyridine 8 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@6a1aab78 Item: Title: 4.1.2. N-{1-Benzyl-5-(4-chlorophenyl)-1,2,3,4-tetrahydro-2-oxobenzo[h][1,6]naphthyridin-9-yl}methanamine 9 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@462d5aee Item: Title: 4.1.3. N-{1-Benzyl-5-(4-chlorophenyl)-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-9-yl}methanamine 2 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@69b0fd6f Item: Title: 4.1.4. 4-{1-Benzyl-9-chloro-1,2,3,4-tetrahydro-2-oxobenzo[h][1,6]naphthyridin-5-yl}benzonitrile 13 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@757942a1 Item: Title: 4.1.5. 4-{1-Benzyl-9-chloro-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5-yl}benzylamine 3 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@4a87761d Item: Title: 4.1.6. 4-{1-(tert-Butoxycarbonyl)-8-chloro-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-4-yl}benzonitrile 22 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@66d1af89 Item: Title: 4.1.7. 4-{1-(tert-Butoxycarbonyl)-9-chloro-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5-yl}benzonitrile 23 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@8646db9 Item: Title: 4.1.8. 4-{1-(tert-Butoxycarbonyl)-10-chloro-2,3,4,5-tetrahydro-1H-azepino[3,2-c]quinolin-6-yl}benzonitrile 24 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@37374a5e Item: Title: 4.1.9. 4-{1-(tert-Butoxycarbonyl)-8-chloro-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5-yl}benzonitrile 25 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@4671e53b Item: Title: 4.1.10. 4-{8-Chloro-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-4-yl}benzonitrile 26 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@2db7a79b Item: Title: 4.1.11. 4-{9-Chloro-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5-yl}benzonitrile 27 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@6950e31 Item: Title: 4.1.12. 4-{10-Chloro-2,3,4,5-tetrahydro-1H-azepino[3,2-c]quinolin-6-yl}benzonitrile 28 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@b7dd107 Item: Title: 4.1.13. 4-{8-Chloro-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5-yl}benzonitrile 29 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@42eca56e Item: Title: 4.1.14. 4-{8-Chloro-2,3-dihydro-1H-pyrrolo[3,2-c]quinolin-4-yl}benzylamine 30 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@52f759d7 Item: Title: 4.1.15. 4-{9-Chloro-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5-yl}benzylamine 31 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@7cbd213e Item: Title: 4.1.16. 4-{10-Chloro-2,3,4,5-tetrahydro-1H-azepino[3,2-c]quinolin-6-yl}benzylamine 32 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@192d3247 Item: Title: 4.1.17. 4-{8-Chloro-1,2,3,4-tetrahydrobenzo[h][1,6]naphthyridin-5-yl}benzylamine 33 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@3ecd23d9 Item: Title: 4.1.18. 4-[3-(3-Aminopropyl)-7-chloroquinolin-2-yl]benzonitrile 35 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@569cfc36 Item: Title: 4.1.19. 4-{9-Chloro-3,4-dihydro-2H-pyrano[3,2-c]quinolin-5-yl}benzonitrile 38 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@43bd930a Item: Title: 4.1.20. 4-{9-Chloro-3,4-dihydro-2H-pyrano[3,2-c]quinolin-5-yl}benzylamine 39 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@33723e30 Item: Title: 4.1.21. 9-Chloro-5-(2-furyl)-3,4-dihydro-2H-pyrano[3,2-c]quinoline 42 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@64f6106c Item: Title: 4.1.22. 9-Chloro-3,4-dihydro-5-(2-thienyl)-2H-pyrano[3,2-c]quinoline 43 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@553a3d88 Item: Title: 4.1.23. N-(tert-butyldimethylsilyloxy)-N-[3-(6-chloro-2-(2-thienyl)quinolin-3-yl)propyl]-4-methylbenzenesulfonamide 46 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@7a30d1e6 Item: Title: 4.1.24. 3-[6-Chloro-2-(2-thienyl)quinolin-3-yl]propanenitrile 47 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@5891e32e Item: Title: 4.1.25. 3-[6-Chloro-2-(2-thienyl)quinolin-3-yl]propyl methanesulfonate 48 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@cb0ed20 Item: Title: 4.1.26. N-{3-[6-Chloro-2-(2-thienyl)quinolin-3-yl]propyl}pyrrolidine 49 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@8e24743 Item: Title: 4.1.27. N-{3-[6-Chloro-2-(2-thienyl)quinolin-3-yl]propyl}-N,N-diethylamine 50 Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@74a10858 Item: Title: 4.2. Biological assays Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@23fe1d71 Children: Item: Title: 4.2.1. T. brucei culturing and evaluation of trypanocidal activity Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@28ac3dc3 Item: Title: 4.2.2. T. cruzi and L. infantum culturing and evaluation of trypanocidal and leishmanicidal activity Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@32eebfca Item: Title: 4.2.3. Cytotoxic activity against rat skeletal myoblast L6 cells Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@4e718207 Item: Title: 4.2.4. Acetylcholinesterase inhibitory activity Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@1d371b2d Item: Title: 4.2.5. Determination of brain permeability: PAMPA-BBB assay Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@543c6f6d Item: Title: Acknowledgements Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@13eb8acf Item: Title: Appendix A. Supplementary material Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@51c8530f Item: Title: References Destination: edu.harvard.hul.ois.jhove.module.pdf.PdfSimpleObject@7403c468 Info: Title: Multicomponent reaction-based synthesis and biological evaluation of tricyclic heterofused quinolines with multi-trypanosomatid activity Author: Ornella Di Pietro Subject: European Journal of Medicinal Chemistry, 105 (2015) 120-137. doi:10.1016/j.ejmech.2015.10.007 Creator: Elsevier Producer: Acrobat Distiller 8.1.0 (Windows) CreationDate: Tue Oct 27 09:01:20 CET 2015 ModDate: Tue Oct 27 09:02:04 CET 2015 ID: 0xc83f97d9b61c8b420a15689e84019d27, 0xd5a3e1b5209c8f429d8c18ace9f16476 Filters: FilterPipeline: FlateDecode FilterPipeline: DCTDecode Images: Image: NisoImageMetadata: FormatName: image/jpg CompressionScheme: JPEG ImageWidth: 107 ImageHeight: 107 ColorSpace: RGB BitsPerSample: 8 BitsPerSampleUnit: integer Image: NisoImageMetadata: FormatName: image/jpg CompressionScheme: 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FontDescriptor: FontName: EGIKHM+AdvTT5843c571 Flags: Nonsymbolic FontBBox: -72, -208, 927, 875 FontFile3: true Encoding: WinAnsiEncoding XMP: application/pdf doi:10.1016/j.ejmech.2015.10.007 Multicomponent reaction-based synthesis and biological evaluation of tricyclic heterofused quinolines with multi-trypanosomatid activity Ornella Di Pietro Esther Vicente-García Martin C. Taylor Diana Berenguer Elisabet Viayna Anna Lanzoni Irene Sola Helena Sayago Cristina Riera Roser Fisa M. Victòria Clos Belén Pérez John M. Kelly Rodolfo Lavilla Diego Muñoz-Torrero Benzo[h][1,6]naphthyridines Pyrano[3,2-c]quinolines Povarov reaction Trypanocidal agents Leishmanicidal agents Brain permeability European Journal of Medicinal Chemistry, 105 (2015) 120-137. doi:10.1016/j.ejmech.2015.10.007 Elsevier Masson SAS journal European Journal of Medicinal Chemistry Copyright © 2015 The Authors. Published by Elsevier Masson SAS. 0223-5234 105 C 13 November 2015 2015-11-13 120-137 120 137 10.1016/j.ejmech.2015.10.007 http://dx.doi.org/10.1016/j.ejmech.2015.10.007 2010-04-23 true 10.1016/j.ejmech.2015.10.007 elsevier.com sciencedirect.com 6.4 10.1016/j.ejmech.2015.10.007 noindex 2010-04-23 true sciencedirect.com elsevier.com Elsevier 2015-10-27T13:01:20+05:30 2015-10-27T13:02:04+05:30 2015-10-27T13:02:04+05:30 True Acrobat Distiller 8.1.0 (Windows) uuid:7c938359-3d2c-4a03-873d-ea08ea501f0e uuid:018ad1e2-55f6-4f87-8d9b-a37ea31a0380 Pages: Page: Label: 120 Sequence: 1 Annotations: Annotation: Subtype: Link Rect: 32, 564, 32, 566 Annotation: Subtype: Link Rect: 120, 567, 124, 578 Destination: 1045 Annotation: Subtype: Link Rect: 130, 564, 130, 566 Annotation: Subtype: Link Rect: 242, 567, 247, 578 Destination: 1045 Annotation: Subtype: Link Rect: 253, 564, 253, 566 Annotation: Subtype: Link Rect: 337, 567, 341, 578 Destination: 1045 Annotation: Subtype: Link Rect: 347, 564, 347, 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