{"entity": "journal", "iuid": "d20e2df118cb4699858cbe10e7f21e18", "timestamp": "2026-07-13T09:07:22.337Z", "links": {"self": {"href": "https://publications.scilifelab.se/journal/J.%20Org.%20Chem..json"}, "display": {"href": "https://publications.scilifelab.se/journal/J.%20Org.%20Chem."}}, "title": "J. Org. Chem.", "issn": "1520-6904", "issn-l": "0022-3263", "publications_count": 6, "publications": [{"entity": "publication", "iuid": "5500537f43cc47dfa49d211fd8bed226", "links": {"self": {"href": "https://publications.scilifelab.se/publication/5500537f43cc47dfa49d211fd8bed226.json"}, "display": {"href": "https://publications.scilifelab.se/publication/5500537f43cc47dfa49d211fd8bed226"}}, "title": "Effect of the Aza-N-Bridge and Push-Pull Moieties: A Comparative Study between BODIPYs and Aza-BODIPYs.", "authors": [{"family": "Sch\u00e4fer", "given": "Clara", "initials": "C"}, {"family": "Mony", "given": "J\u00fcrgen", "initials": "J"}, {"family": "Olsson", "given": "Thomas", "initials": "T"}, {"family": "B\u00f6rjesson", "given": "Karl", "initials": "K", "orcid": "0000-0001-8533-201X", "researcher": {"href": "https://publications.scilifelab.se/researcher/cc22ad4eb905493e9ae51616b197edd4.json"}}], "type": "journal article", "published": "2022-03-04", "journal": {"title": "J. Org. Chem.", "issn": "1520-6904", "volume": "87", "issue": "5", "pages": "2569-2579", "issn-l": "0022-3263"}, "abstract": "In the field of fluorescent dyes, difluoroboron-dipyrromethenes (BODIPY) have a highly respected position. To predict their photophysical properties prior to synthesis and therefore to successfully design molecules specifically for one's needs, a solid structure-function understanding based on experimental observations is vital. This work delivers a photophysical evaluation of BODIPY and aza-BODIPY derivatives equipped with different electron-withdrawing/-donating substituents. Using combinatorial chemistry, pyrroles substituted with electron-donating/-withdrawing substituents were condensed together in two different manners, thus providing two sets of molecules. The only difference between the two sets is the bridging unit providing a so far lacking comparison between BODIPYs and aza-BODIPYs structural homologues. Replacing the meso-methine bridge with an aza-N bridge results in a red-shifted transition and considerably different, temperature-activated, excited-state relaxation pathways. The effect of electron-donating units on the absorption but not emission for BODIPYs was suppressed compared to aza-BODIPYs. This result could be evident in a substitution pattern-dependent Stokes shift. The outlook of this study is a deeper understanding of the structure-optics relationship of the (aza)-BODIPY-dye class, leading to an improvement in the de novo design of tailor-made molecules for future applications.", "doi": "10.1021/acs.joc.1c02525", "pmid": "35188769", "labels": {"Swedish NMR Centre": null}, "xrefs": [{"db": "pmc", "key": "PMC8902755"}], "notes": [], "created": "2022-04-25T12:01:39.846Z", "modified": "2025-10-17T13:03:54.931Z"}, {"entity": "publication", "iuid": "67c04459d0924d4283e17a0e296b0df2", "links": {"self": {"href": "https://publications.scilifelab.se/publication/67c04459d0924d4283e17a0e296b0df2.json"}, "display": {"href": "https://publications.scilifelab.se/publication/67c04459d0924d4283e17a0e296b0df2"}}, "title": "Pyridine-Fused 2-Pyridones via Povarov and A 3 Reactions: Rapid Generation of Highly Functionalized Tricyclic Heterocycles Capable of Amyloid Fibril Binding.", "authors": [{"family": "Singh", "given": "Pardeep", "initials": "P"}, {"family": "Adolfsson", "given": "Dan E", "initials": "DE"}, {"family": "\u00c5d\u00e9n", "given": "J\u00f6rgen", "initials": "J"}, {"family": "Cairns", "given": "Andrew G", "initials": "AG"}, {"family": "Bartens", "given": "Christian", "initials": "C"}, {"family": "Br\u00e4nnstr\u00f6m", "given": "Kristoffer", "initials": "K"}, {"family": "Olofsson", "given": "Anders", "initials": "A"}, {"family": "Almqvist", "given": "Fredrik", "initials": "F", "orcid": "0000-0003-4646-0216", "researcher": {"href": "https://publications.scilifelab.se/researcher/7468f9e036444b41a4558368d15e83d8.json"}}], "type": "journal article", "published": "2019-04-05", "journal": {"volume": "84", "issn": "1520-6904", "issue": "7", "pages": "3887-3903", "title": "J. Org. Chem.", "issn-l": "0022-3263"}, "abstract": "We here describe the use of three-component reactions to synthesize tricyclic pyridine ring-fused 2-pyridones. The developed protocols have a wide substrate scope and allow for the installation of diverse chemical functionalities on the tricyclic central fragment. Several of these pyridine-fused rigid polyheterocycles are shown to bind to A\u03b2 and \u03b1-synuclein fibrils, which are associated with neurodegenerative diseases.", "doi": "10.1021/acs.joc.8b03015", "pmid": "30862161", "labels": {"Cryo-EM": "Service", "Swedish NMR Centre": "Service"}, "xrefs": [], "notes": [], "created": "2019-12-20T16:14:56.606Z", "modified": "2025-10-17T13:03:58.043Z"}, {"entity": "publication", "iuid": "1581d756b302407c91822ab83dbd8b05", "links": {"self": {"href": "https://publications.scilifelab.se/publication/1581d756b302407c91822ab83dbd8b05.json"}, "display": {"href": "https://publications.scilifelab.se/publication/1581d756b302407c91822ab83dbd8b05"}}, "title": "NMR Determination of the Binding Constant of Ionic Species: A Caveat.", "authors": [{"family": "Schulz", "given": "Nils", "initials": "N"}, {"family": "Schindler", "given": "Severin", "initials": "S"}, {"family": "Huber", "given": "Stefan M", "initials": "SM", "orcid": "0000-0002-4125-159X", "researcher": {"href": "https://publications.scilifelab.se/researcher/4eae78fc256f4ea5bfd16f1e34e02f63.json"}}, {"family": "Erdelyi", "given": "Mate", "initials": "M", "orcid": "0000-0003-0359-5970", "researcher": {"href": "https://publications.scilifelab.se/researcher/f772b571449e417ca6fda2eee361a0c3.json"}}], "type": "journal article", "published": "2018-09-21", "journal": {"title": "J. Org. Chem.", "issn": "1520-6904", "volume": "83", "issue": "18", "pages": "10881-10886", "issn-l": "0022-3263"}, "abstract": "Determination of the dissociation constant of ionic complexes with the standard NMR titration and NMR dilution techniques may yield a severely compromised result, due to the typically unconsidered chemical shift alteration induced by the gradual change of the ionic strength during the experiment. We show that the reliability of an NMR titration experiment is markedly improved upon keeping the overall ionic strength constant.", "doi": "10.1021/acs.joc.8b01567", "pmid": "30110550", "labels": {"Swedish NMR Centre": "Service"}, "xrefs": [], "notes": [], "created": "2023-05-31T16:33:22.436Z", "modified": "2025-10-17T13:03:58.515Z"}, {"entity": "publication", "iuid": "07f943c602224528812fe68f04e4fa03", "links": {"self": {"href": "https://publications.scilifelab.se/publication/07f943c602224528812fe68f04e4fa03.json"}, "display": {"href": "https://publications.scilifelab.se/publication/07f943c602224528812fe68f04e4fa03"}}, "title": "Photochemically Induced Aryl Azide Rearrangement: Solution NMR Spectroscopic Identification of the Rearrangement Product", "authors": [{"family": "Andersson", "given": "Hanna", "initials": "H"}, {"family": "Gr\u00e4fenstein", "given": "J\u00fcrgen", "initials": "J"}, {"family": "Isobe", "given": "Minoru", "initials": "M"}, {"family": "Erd\u00e9lyi", "given": "M\u00e1t\u00e9", "initials": "M"}, {"family": "Sydnes", "given": "Magne O", "initials": "MO"}], "type": "journal-article", "published": "2017-02-03", "journal": {"volume": "82", "issn": "1520-6904", "issue": "3", "pages": "1812-1816", "title": "J. Org. Chem.", "issn-l": "0022-3263"}, "abstract": null, "doi": "10.1021/acs.joc.6b02555", "pmid": "28068094", "labels": {"Swedish NMR Centre": "Service"}, "xrefs": [], "notes": [], "created": "2017-11-03T16:52:26.456Z", "modified": "2025-10-17T13:04:00.037Z"}, {"entity": "publication", "iuid": "0a8b27e8804347b39d0f2955765605c6", "links": {"self": {"href": "https://publications.scilifelab.se/publication/0a8b27e8804347b39d0f2955765605c6.json"}, "display": {"href": "https://publications.scilifelab.se/publication/0a8b27e8804347b39d0f2955765605c6"}}, "title": "On-Water Synthesis of Biaryl Sulfonyl Fluorides.", "authors": [{"family": "Chinthakindi", "given": "Praveen K", "initials": "PK"}, {"family": "Kruger", "given": "Hendrik G", "initials": "HG"}, {"family": "Govender", "given": "Thavendran", "initials": "T"}, {"family": "Naicker", "given": "Tricia", "initials": "T"}, {"family": "Arvidsson", "given": "Per I", "initials": "PI", "orcid": "0000-0002-9453-6812", "researcher": {"href": "https://publications.scilifelab.se/researcher/ae064b90b750457e80e974947f2dfc7a.json"}}], "type": "journal article", "published": "2016-03-18", "journal": {"volume": "81", "issn": "1520-6904", "issue": "6", "pages": "2618-2623", "title": "J. Org. Chem.", "issn-l": "0022-3263"}, "abstract": "Herein, we report an efficient, ligand-free, and additive-free Suzuki-Miyaura coupling that is compatible with the aromatic sulfonyl fluoride functional group. The protocol proceeds at room temperature, on water, and offers facile access to a wide range of biaryl sulfonyl fluorides as bioorthogonal \"click\" reagents.", "doi": "10.1021/acs.joc.5b02770", "pmid": "26900892", "labels": {"Drug Discovery and Development": "Collaborative"}, "xrefs": [], "notes": [], "created": "2017-05-03T12:59:34.036Z", "modified": "2025-10-17T13:05:09.356Z"}, {"entity": "publication", "iuid": "6be2c429bb0046c6925861734bae9e0f", "links": {"self": {"href": "https://publications.scilifelab.se/publication/6be2c429bb0046c6925861734bae9e0f.json"}, "display": {"href": "https://publications.scilifelab.se/publication/6be2c429bb0046c6925861734bae9e0f"}}, "title": "Effect of a Bromo Substituent on the Glutathione Peroxidase Activity of a Pyridoxine-like Diselenide.", "authors": [{"family": "Singh", "given": "Vijay P", "initials": "VP"}, {"family": "Poon", "given": "Jia-Fei", "initials": "JF"}, {"family": "Butcher", "given": "Ray J", "initials": "RJ"}, {"family": "Lu", "given": "Xi", "initials": "X"}, {"family": "Mestres", "given": "Gemma", "initials": "G"}, {"family": "Ott", "given": "Marjam Karlsson", "initials": "MK"}, {"family": "Engman", "given": "Lars", "initials": "L"}], "type": "journal article", "published": "2015-08-07", "journal": {"volume": "80", "issn": "1520-6904", "issue": "15", "pages": "7385-7395", "title": "J. Org. Chem.", "issn-l": "0022-3263"}, "abstract": "In search for better mimics of the glutathione peroxidase enzymes, pyridoxine-like diselenides 6 and 11, carrying a 6-bromo substituent, were prepared. Reaction of 2,6-dibromo-3-pyridinol 5 with sodium diselenide provided 6 via aromatic nucleophilic substitution of the 2-bromo substituent. LiAlH4 caused reduction of all four ester groups and returned 11 after acidic workup. The X-ray structure of 6 showed that the dipyridyl diselenide moiety was kept in an almost planar, transoid conformation. According to NBO-analysis, this was due to weak intramolecular Se\u00b7\u00b7\u00b7O (1.1 kcal/mol) and Se\u00b7\u00b7\u00b7N-interactions (2.5 kcal/mol). That the 6-bromo substituent increased the positive charge on selenium was confirmed by NPA-analysis and seen in calculated and observed (77)Se NMR-shifts. Diselenide 6 showed a more than 3-fold higher reactivity than the corresponding des-bromo compound 3a and ebselen when evaluated in the coupled reductase assay. Experiments followed for longer time (2 h) confirmed that diselenide 6 is a better GPx-catalyst than 11. On the basis of (77)Se-NMR experiments, a catalytic mechanism for diselenide 6 was proposed involving selenol, selenosulfide and seleninic acid intermediates. At low concentration (10 \u03bcM) where it showed only minimal toxicity, it could scavenge ROS produced by MNC- and PMNC-cells more efficiently than Trolox.", "doi": "10.1021/acs.joc.5b00797", "pmid": "26133764", "labels": {"BioMaterial Interactions (BioMat)": null}, "xrefs": [], "notes": [], "created": "2017-05-02T12:58:50.287Z", "modified": "2017-05-30T13:23:06.256Z"}], "created": "2017-05-09T09:12:02.789Z", "modified": "2020-11-27T13:14:04.368Z"}