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Sugar modified pyrimido[4,5-b]indole nucleosides: synthesis and antiviral activity

. 2017 Sep 01 ; 8 (9) : 1856-1862. [epub] 20170825

Status PubMed-not-MEDLINE Language English Country Great Britain, England Media electronic-ecollection

Document type Journal Article

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).

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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

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