RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2025; 57(02): 389-396
DOI: 10.1055/s-0043-1775411
DOI: 10.1055/s-0043-1775411
paper
Special Topic Dedicated to Prof. H. Ila
Facile Synthesis of New Antiviral Fluoro-Quinazolines Enabled by Merging Domino Reactions
S.B.T. gratefully acknowledges the financial support by the grant from Deutsche Forschungsgemeinschaft TS 87/28-1.
In honor of Professor H. Ila’s 80th anniversary
Abstract
Quinazolines, particularly fluoro-quinazolines, represent important structural motifs in bioactive molecules and pharmaceuticals. Despite several known synthetic routes, the efficient synthesis of fluorine-containing quinazolines remains a challenge. Herein, the straightforward and sustainable synthesis of fluorine-substituted quinazolines using domino sequences is reported. The obtained novel fluoro-quinazoline compounds exhibit significant in vitro activity against human cytomegalovirus (HCMV), expanding the library of potential antiviral drug compounds. Our finding outlays the synthetic toolkit for fluoro-quinazolines and introduces new agents for HCMV therapy.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775411.
- Supporting Information
Publikationsverlauf
Eingereicht: 05. Juni 2024
Angenommen nach Revision: 18. September 2024
Artikel online veröffentlicht:
12. November 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1a Marzaro G, Guiotto A, Chilin A. Expert Opin. Ther. Pat. 2012; 22: 223
- 1b Shagufta Ahmad I. MedChemComm 2017; 8: 871
- 2a Held FE, Guryev AA, Fröhlich T, Hampel F, Kahnt A, Hutterer C, Steingruber M, Bahsi H, von Bojničić-Kninski C, Mattes DS, Foertsch TC, Nesterov-Mueller A, Marschall M, Tsogoeva SB. Nat. Commun. 2017; 8: 15071
- 2b Xie D, Shi J, Zhang A, Lei Z, Zu G, Fu Y, Gan X, Yin L, Song B, Hu D. Bioorg. Chem. 2018; 80: 433
- 2c Piotrowska DG, Andrei G, Schols D, Snoeck R, Łysakowska M. Eur. J. Med. Chem. 2017; 126: 84
- 3 Baba A, Kawamura N, Makino H, Ohta Y, Taketomi S, Sohda T. J. Med. Chem. 1996; 39: 5176
- 4 Dutta A, Sarma D. Tuberculosis (Edinb) 2020; 124: 101986
- 5 Siegel-Lakhai WS, Beijnen JH, Schellens JH. M. Oncologist 2005; 10: 579
- 6 Murthy Boddapati SN, Babu Bollikolla H, Geetha Bhavani K, Singh Saini H, Ramesh N, Babu Jonnalagadda S. Arab. J. Chem. 2023; 16: 105190
- 7 Griess P. J. Prakt. Chem. 1869; 369
- 8 Von Niementowski S. J. Prakt. Chem. 1895; 51: 564
- 9a Hao Z, Zhou X, Ma Z, Zhang C, Han Z, Lin J, Lu GL. J. Org. Chem. 2022; 87: 12596
- 9b Sikari R, Chakraborty G, Guin AK, Paul ND. J. Org. Chem. 2021; 86: 279
- 9c Luo R, Luo N, Zhong Y, Shui H, Ouyang L. Synthesis 2022; 54: 2876
- 9d Yu Y, Zhang G, Wang Z, Chen W, He C. Synthesis 2020; 53: 1356
- 10a Bhanage B, Deshmukh D. Synlett 2018; 29: 979
- 10b Phan NT. S, Nguyen TT, Nguyen KX, Nguyen DK, Pham PH, Le HV. Synlett 2020; 31: 1112
- 10c Bera MK, Samanta SK. Synthesis 2023; 55: 2561
- 11 Reisenbauer JC, Paschke A.-SK, Krizic J, Botlik BB, Finkelstein P, Morandi B. Org. Lett. 2023; 25: 8419
- 12 Meanwell NA. J. Med. Chem. 2018; 61: 5822
- 13 Berrino E, Michelet B, Martin-Mingot A, Carta F, Supuran CT, Thibaudeau S. Angew. Chem. Int. Ed. 2021; 60: 23068
- 14 Böhm H.-J, Banner D, Bendels S, Kansy M, Kuhn B, Müller K, Obst-Sander U, Stahl M. ChemBioChem 2004; 5: 637
- 15 Saha A, Acharya BN, Parida M, Saxena N, Rajaiya J, Dash PK. Viruses 2023; 15: 2194
- 16 Kettle JG, Bagal SK, Bickerton S, Bodnarchuk MS, Boyd S, Breed J, Carbajo RJ, Cassar DJ, Chakraborty A, Cosulich S, Cumming I, Davies M, Davies NL, Eatherton A, Evans L, Feron L, Fillery S, Gleave ES, Goldberg FW, Hanson L, Harlfinger S, Howard M, Howells R, Jackson A, Kemmitt P, Lamont G, Lamont S, Lewis HJ, Liu L, Niedbala MJ, Phillips C, Polanski R, Raubo P, Robb G, Robinson DM, Ross S, Sanders MG, Tonge M, Whiteley R, Wilkinson S, Yang J, Zhang W. J. Med. Chem. 2022; 65: 6940
- 17 Liang T, Neumann CN, Ritter T. Angew. Chem. Int. Ed. 2013; 52: 8214
- 18 Grau BW, Bönisch S, Neuhauser A, Hampel F, Görling A, Tsogoeva SB. ChemCatChem 2019; 11: 3982
- 19 Wedemann L, Flomm FJ, Bosse JB. Mol. Microbiol. 2022; 117: 1317
- 20 Crumpacker Clyde S. N. Engl. J. Med. 1996; 335: 721
- 21 Komatsu TE, Pikis A, Naeger LK, Harrington PR. Antiviral Res. 2014; 101: 12
- 22 Bogner E, Egorova A, Makarov V. Viruses 2021; 13: 474
- 23 Marschall M, Freitag M, Weiler S, Sorg G, Stamminger T. Antimicrob. Agents Chemother. 2000; 44: 1588
- 24 Wangen C, Raithel A, Tillmanns J, Gege C, Herrmann A, Vitt D, Kohlhof H, Marschall M, Hahn F. Antiviral Res. 2024; 221: 105769
- 25 Repetto G, del Peso A, Zurita JL. Nat. Protoc. 2008; 3: 1125
- 26 Gualandi A, Canestrari P, Emer E, Cozzi PG. Adv. Synth. Catal. 2014; 356: 528
- 27 Grau D, Grau BW, Hampel F, Tsogoeva SB. Chem. Eur. J. 2018; 24: 6551
- 28 Aldoshin AS, Tabolin AA, Ioffe SL, Nenajdenko VG. Eur. J. Org. Chem. 2018; 3816