{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,11]],"date-time":"2026-07-11T11:48:19Z","timestamp":1783770499387,"version":"3.55.0"},"reference-count":15,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2024,3,1]],"date-time":"2024-03-01T00:00:00Z","timestamp":1709251200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Saxony-Anhalt"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The synthesis of a novel disorazole C1 analogue is described, and its biological activity as a cytotoxic compound is reported. Based on our convergent and flexible route to the disorazole core, we wish to report a robust strategy to synthesize a non-symmetrical disorazole in which we couple one half of the molecule containing the naturally occurring oxazole heterocycle and the second half of the disorazole macrocycle containing a thiazole heterocycle. This resulted in a very unusual non-symmetrical disorazole C1 analogue containing two different heterocycles, and its biological activity was studied. This provided exciting information about SAR (structure-activity-relationship) for this highly potent class of antitumor compounds.<\/jats:p>","DOI":"10.3390\/molecules29051123","type":"journal-article","created":{"date-parts":[[2024,3,4]],"date-time":"2024-03-04T04:36:21Z","timestamp":1709526981000},"page":"1123","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Synthesis of a Non-Symmetrical Disorazole C1-Analogue and Its Biological Activity"],"prefix":"10.3390","volume":"29","author":[{"given":"Luca","family":"Lizzadro","sequence":"first","affiliation":[{"name":"Medicinal Chemistry and Chemical Biology Laboratory, School of Pharmacy, University of California San Francisco, 600 16th St., San Francisco, CA 94158, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Oliver","family":"Spie\u00df","sequence":"additional","affiliation":[{"name":"Chemisches Institut, Otto-von-Guericke-Universit\u00e4t, Universit\u00e4tsplatz 2, 39106 Magdeburg, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Silke","family":"Reinecke","sequence":"additional","affiliation":[{"name":"Helmholtz-Zentrum f\u00fcr Infektionsforschung GmbH, Inhoffenstra\u00dfe 7, 38124 Braunschweig, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7284-8671","authenticated-orcid":false,"given":"Marc","family":"Stadler","sequence":"additional","affiliation":[{"name":"Helmholtz-Zentrum f\u00fcr Infektionsforschung GmbH, Inhoffenstra\u00dfe 7, 38124 Braunschweig, Germany"},{"name":"Institute of Microbiology, Technische Universit\u00e4t Braunschweig, Spielmannstra\u00dfe 7, 38106 Braunschweig, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dieter","family":"Schinzer","sequence":"additional","affiliation":[{"name":"Chemisches Institut, Otto-von-Guericke-Universit\u00e4t, Universit\u00e4tsplatz 2, 39106 Magdeburg, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,3,1]]},"reference":[{"key":"ref_1","unstructured":"(2024, February 07). Jahresbericht GBF 2001. Available online: https:\/\/www.helmholtz-hzi.de\/fileadmin\/user_upload\/Infothek\/Ueber_das_HZI\/Jahresberichte\/Ergebnisberichte\/Annual_Report_2001.pdf."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"31","DOI":"10.7164\/antibiotics.48.31","article-title":"Disorazole A1, an Efficient Inhibitor of Eukariotic Organisms Isolated from Myxobacteria","volume":"48","author":"Irschik","year":"1995","journal-title":"J. Antibiot."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1276","DOI":"10.1039\/c001260m","article-title":"Myxobacterial secondary metabolites: Bioactivities and modes-of-action","volume":"27","author":"Weissman","year":"2010","journal-title":"Nat. Prod. 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Spectr."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Bold, C.P., and Altmann, K.-H. (2024). The Chemistry of Disorazoles and Structure-Activity Relationships: An Update. Tetrahedron, in press.","DOI":"10.1016\/j.tet.2024.133908"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"869","DOI":"10.1016\/j.drudis.2013.11.004","article-title":"Antibody-drug conjugates: Current status and future directions","volume":"19","author":"Perez","year":"2014","journal-title":"Drug Discov. Today"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"4543","DOI":"10.1021\/acs.orglett.1c01123","article-title":"Total Synthesis of (\u2212)-Disorazole C1","volume":"23","author":"Lizzadro","year":"2021","journal-title":"Org. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Lizzadro, L., Spie\u00df, O., Collisi, W., Stadler, L., and Schinzer, D. (2022). 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