Sugar modified pyrimido[4,5-b]indole nucleosides: synthesis and antiviral activity
Status PubMed-not-MEDLINE Language English Country Great Britain, England Media electronic-ecollection
Document type Journal Article
PubMed
30108897
PubMed Central
PMC6084004
DOI
10.1039/c7md00319f
PII: c7md00319f
Knihovny.cz E-resources
- Publication type
- Journal Article MeSH
Three types of sugar modified pyrimido[4,5-b]indole nucleosides (2'-deoxy-2'-fluororibo-, 2'-deoxy-2'-fluoroarabino- and arabinonucleosides) were synthesized by glycosylation of 4,6-dichloropyrimido[4,5-b]indole followed by modification of sugar moiety and introduction of substituents into position 4 by cross-coupling reactions or nucleophilic substitutions. Some 2'-fluororibo- and 2'-fluoroarabinonucleosides displayed interesting anti-HCV activities (IC50 = 1.6-20 μM) and the latter compounds also some anti-dengue activities (IC50 = 10.8-40 μM).
See more in PubMed
De Clercq E. J. Clin. Virol. 2004;30:115–133. PubMed
De Clercq E., Li G. Clin. Microbiol. Rev. 2016;29:695–747. PubMed PMC
Jordheim L. P., Durantel D., Zoulim F., Dumontet C. Nat. Rev. Drug Discovery. 2013;12:447–464. PubMed
Pradere U., Garnier-Amblard E. C., Coats S. J., Amblard F., Schinazi R. F. Chem. Rev. 2014;114:9154–9218. PubMed PMC
Sofia M. J., Bao D., Chang W., Du J., Nagarathnam D., Rachakonda S., Reddy P. G., Ross B. S., Wang P., Zhang H.-R., Bansal S., Espiritu C., Keilman M., Lam A. M., Steuer H. M. M., Niu C., Otto M. J., Furman P. A. J. Med. Chem. 2010;53:7202–7218. PubMed
Siegel D., Hui H. C., Doerffler E., Clarke M. O., Chun K., Zhang L., Neville S., Carra E., Lew W., Ross B., Wang Q., Wolfe L., Jordan R., Soloveva V., Knox J., Perry J., Perron M., Stray K. M., Barauskas O., Feng J. Y., Xu Y., Lee G., Rheingold A. L., Ray A. S., Bannister R., Strickley R., Swaminathan S., Lee W. A., Bavari S., Cihlar T., Lo M. K., Warren T. K., Mackman R. L. J. Med. Chem. 2017;60:1648–1661. PubMed
Bhakat S., Karubiu W., Jayaprakash V., Soliman M. E. S. Eur. J. Med. Chem. 2014;87:677–702. PubMed
Nauš P., Pohl R., Votruba I., Džubák P., Hajdúch M., Ameral R., Birkuš G., Wang T., Ray A. S., Mackman R., Cihlar T., Hocek M. J. Med. Chem. 2010;53:460–470. PubMed
Bourderioux A., Nauš P., Perlíková P., Pohl R., Pichová I., Votruba I., Džubák P., Konečný P., Hajdúch M., Stray K. M., Wang T., Ray A. S., Feng J. Y., Birkus G., Cihlar T., Hocek M. J. Med. Chem. 2011;54:5498–5507. PubMed
Nauš P., Caletková O., Konečný P., Džubák P., Bogdanová K., Kolář M., Vrbková J., Slavětínská L., Tloušt'ová E., Perlíková P., Hajdúch M., Hocek M. J. Med. Chem. 2014;57:1097–1110. PubMed
Tichý M., Pohl R., Xu H. Y., Chen Y.-L., Yokokawa F., Shi P.-Y., Hocek M. Bioorg. Med. Chem. 2012;20:6123–6133. PubMed
Tichý M., Pohl R., Tloušt'ová E., Weber J., Bahador G., Lee Y.-J., Hocek M. Bioorg. Med. Chem. 2013;21:5362–5372. PubMed
Tichý M., Smoleń S., Tloušt'ová E., Pohl R., Oždian T., Hejtmánková M., Lišková B., Gurská S., Džubák P., Hajdúch M., Hocek M. J. Med. Chem. 2017;60:2411–2424. PubMed
Nauš P., Perlíková P., Bourderioux A., Pohl R., Slavětínská L., Votruba I., Bahador G., Birkuš G., Cihlář T., Hocek M. Bioorg. Med. Chem. 2012;20:5202–5214. PubMed
Nauš P., Perlíková P., Pohl R., Hocek M. Collect. Czech. Chem. Commun. 2011;76:957–988.
Perlíková P., Eberlin L., Ménová P., Raindlová V., Slavětínská L., Tloušťová E., Bahador G., Lee Y.-J., Hocek M. ChemMedChem. 2013;8:832–846. PubMed
Perlíková P., Jornet Martínez N., Slavětínská L., Hocek M. Tetrahedron. 2012;68:8300–8310.
Rai K. R., Peterson B. L., Appelbaum F. R., Kolitz J., Elias L., Shepherd L., Hines J., Threatte G. A., Larson R. A., Cheson B. D., Schiffer C. A. N. Engl. J. Med. 2000;343:1750–1757. PubMed
Bonate P. L., Arthaud L., Cantrell W. R., Stephenson K., Secrist J. A., Weitman S. Nat. Rev. Drug Discovery. 2006;5:855–863. PubMed
Parker W. B., Shaddix S. C., Rose L. M., Shewach D. S., Hertel L. W., Secrist III J. A., Montgomery J. A., Bennett Jr. L. L. Mol. Pharmacol. 1999;55:515–520. PubMed
Tann C. H., Brodfuehrer P. R., Brundidge S. P., Sapino Jr. C., Howell H. G. J. Org. Chem. 1985;50:3644–3647.
Kim Y. A., Sharon A., Chu C. K., Rais R. H., Al Safarjalani O. N., Naguib F. N. M., el Kouni M. H. J. Med. Chem. 2008;51:3934–3945. PubMed
Mejdrová I., Chalupská D., Kögler M., Šála M., Plačková P., Baumlová A., Hřebabecký H., Procházková E., Dejmek M., Guillon R., Strunin D., Weber J., Lee G., Birkus G., Mertlíková-Kaiserová H., Boura E., Nencka R. J. Med. Chem. 2015;58:3767–3793. PubMed
Perron M., Stray K., Kinkade A., Theodore D., Lee G., Eisenberg E., Sangi M., Gilbert B. E., Jordan R., Piedra P. A., Toms G. L., Mackman R., Cihlar T. Antimicrob. Agents Chemother. 2016;60:1264–1273. PubMed PMC
Yang H., Robinson M., Corsa A. C., Peng B., Cheng G., Tian Y., Wang Y., Pakdaman R., Shen M., Qi X., Mo H., Tay C., Krawczyk S., Sheng X. C., Kim C. U., Yang C., Delaney W. E. Antimicrob. Agents Chemother. 2014;58:647–653. PubMed PMC
Tong X., Le Pogam S., Li L., Haines K., Piso K., Baronas V., Yan J.-M., So S.-S., Klumpp K., Nájera I. J. Infect. Dis. 2014;209:668–675. PubMed
Le Pogam S., Yan J. M., Chhabra M., Ilnicka M., Kang H., Kosaka A., Ali S., Chin D. J., Shulman N. S., Smith P., Klumpp K., Nájera I. Antimicrob. Agents Chemother. 2012;56:5494–5502. PubMed PMC
Appleby T. C., Perry J. K., Murakami E., Barauskas O., Feng J., Cho A., Fox D., Wetmore D. R., McGrath M. E., Ray A. S., Sofia M. J., Swaminathan S., Edwards T. E. Science. 2015;347:771–775. PubMed
Gerber P. R., Müller K. J. J. Comput.-Aided Mol. Des. 1995;9:251–268. PubMed
Riss T. L., Moravec R. A., Niles A. L., Duellman S., Benink H. A., Worzella T. J. and Minor L., Cell Viability Assays. 2013 May 1 [Updated 2016 Jul 1]. in: Assay Guidance Manual [Online], ed. G. S. Sittampalam, N. P. Coussens and H. Nelson, et al., Eli Lilly & Company and the National Center for Advancing Translational Sciences, Bethesda, MD, 2004. https://www.ncbi.nlm.nih.gov/books/NBK144065/ (accessed 10/12, 2016).
Moore M. J., Tannock I. F., Ernst D. S., Huan S., Murray N. J. Clin. Oncol. 1997;15:3441–3445. PubMed