Dapson in Heterocyclic Chemistry, Part V: Synthesis, Molecular Docking and Anticancer Activity of Some Novel Sulfonylbiscompounds Carrying Biologically Active Dihydropyridine, Dihydroisoquinoline, 1,3-Dithiolan, 1,3-Dithian, Acrylamide, Pyrazole, Pyrazolopyrimidine and Benzochromenemoieties

dc.AffiliationOctober University for modern sciences and Arts (MSA)
dc.contributor.authorMohammed Ghorab, Mostafa
dc.contributor.authorSulaiman Al-Said, Mansour
dc.contributor.authorMohammed Nissan, Yassin
dc.date.accessioned2019-10-21T08:03:12Z
dc.date.available2019-10-21T08:03:12Z
dc.date.issued2012
dc.descriptionMSA Google Scholar
dc.description.abstractN,N′-(4,4′-Sulfonylbis(4,1-phenylene))bis(2-cyanoacetamid) 2 was utilized as a key intermediate for the synthesis of novel dihydropyridines 3, 4, 8, dihydroisoquinolines 5–7, dithiolan 10, dithian 11, acrylamide 12, benzochromenes 17 and 18 and chromenopyridones 19 and 20. Compound 2 was the starting material in the synthesis of the acrylamide derivative 14, the pyrazole derivative 15 and the pyrazolopyrimidine derivative 16. All the synthesized compounds were evaluated for their in vitro anticancer activity against human breast cancer cell line (MCF7). Compound 19 showed the best cytotoxic activity with IC50 value 19.36 μM. In addition, molecular docking study of the synthesized compounds on the active sites of farnesyltransferase and arginine methyltransferase was performed in order to give a suggestion about the mechanism of action of their cytotoxic activity.en_US
dc.description.sponsorshipChemical and Pharmaceutical Bulletinen_US
dc.description.urihttps://www.scimagojr.com/journalsearch.php?q=22769&tip=sid&clean=0
dc.identifier.citation1) Dominguez J. N., Leon C., Rodrigues J., Gamboa de Dominguez N., Gut J., Rosenthal P. J., Eur. J. Med. Chem., 44, 1457–1462 (2009). 2) Szilágyi G., Somorai T., Bozó É., Langó J., Nagy G., Reiter J., Janáky J., Andrási F., Eur. J. Med. Chem., 25, 95–101 (1990). 3) Gautam N., Goyal K., Saini O., Kumar A., Gautam D. C., J. Fluor. Chem., 132, 420–426 (2011). 4) Bonsignore L., Cottiglia F., Elkhaili H., Jehl F., Lavagna S. M., Loy G., Manna F., Monteil H., Pompei D., Secci D., Farmaco, 53, 425–430 (1998). 5) Usera A. R., Dolan P., Kensler T. W., Posner G. H., Bioorg. Med. Chem., 17, 5627–5631 (2009). 6) Pal T. K., Dey T., Chakrabarty A., Dey D., Ghosh S. K., Pathak T., Bioorg. Med. Chem. Lett., 20, 3777–3780 (2010). 7) Silvestri R., Artico M., La Regina G., De Martino G., La Colla M., Loddo R., La Colla P., Farmaco, 59, 201–210 (2004). 8) Zhang C., Lovering F., Behnke M., Zask A., Sandanayaka V., Sun L., Zhu Y., Xu W., Zhang Y., Levin J. I., Bioorg. Med. Chem. Lett., 19, 3445–3448 (2009). 9) Santelli-Rouvier C., Barret J. M., Farrell C. M., Sharples D., Hill B. T., Barbe J., Eur. J. Med. Chem., 39, 1029–1038 (2004). 10) Murafuji T., Fujiwara Y., Yoshimatsu D., Miyakawa I., Migita K., Mikata Y., Eur. J. Med. Chem., 46, 519–525 (2011). 11) El-Sayed Ali T., Eur. J. Med. Chem., 44, 4385–4392 (2009). 12) Onnis V., Cocco M. T., Fadda R., Congiu C., Bioorg. Med. Chem., 17, 6158–6165 (2009). 13) Karki R., Thapa P., Kang M. J., Jeong T. C., Nam J. M., Kim H. L., Na Y., Cho W. J., Kwon Y., Lee E. S., Bioorg. Med. Chem., 18, 14) Gomez-Monterrey I., Campiglia P., Grieco P., Diurno M. V., Bolognese A., La Colla P., Novellino E., Bioorg. Med. Chem., 11, 3769–3775 (2003). 15) Valderrama J. A., González M. F., Pessoa-Mahana D., Tapia R. A., Fillion H., Pautet F., Rodriguez J. A., Theoduloz C., Schmeda- Hirschmann G., Bioorg. Med. Chem., 14, 5003–5011 (2006). 16) Kast R., Scheuerle A., Wirtz C., Karpel-Massler G., Halatsch M., Anticancer Agents Med. Chem. 11, 756–761 (2011). 17) Bissinger E. M., Heinke R., Spannhoff A., Eberlin A., Metzger E., Cura V., Hassenboehler P., Cavarelli J., Schüle R., Bedford M. T., Sippl W., Jung M., Bioorg. Med. Chem., 19, 3717–3731 (2011). 18) Dinsmore C. J., Williams T. M., O’Neill T. J., Liu D., Rands E., Culberson J. C., Lobell R. B., Koblan K. S., Kohl N. E., Gibbs J. B., Oliff A. I., Graham S. L., Hartman G. D., Bioorg. Med. Chem. Lett., 9, 3301–3306 (1999). 19) Vedula M.S., Pulipaka A. B., Venna C., Chintakunta V. K., Jinnapally S., Kattuboina V. A., Vallakati R. K., Basetti V., Akella V., Rajgopal S., Reka A. K., Teepireddy S. K., Mamnoor P. K., Rajagopalan R., Bulusu G., Khandelwal A., Upreti V. V., RaoMamidi S., Eur. J. Med. Chem., 38, 811–824 (2003). 20) Wadher S. J., Puranik M. P., Karande N. A., Yeole P. G., International Journal of Pharmtech. Research, 1, 22–23 (2009). 21) Ghorab M. M., Radwan M. A. A., Taha N. M. H., Amin N. E., Shehab M. A., Faker I. M. I., Phosphorus Sulfur Silicon Relat. Elem., 183, 2906–2917 (2008). 22) Ghorab M. M., Amin N. E., El Gaby M. S. A., Taha N. M. H., Shehab M. A., Faker I. M. I., Phosphorus Sulfur Silicon Relat. Elem., 183, 2918–2928 (2008). 23) Ghorab M. M., Amin N. E., El Gaby M. S. A., Taha N. M. H., Shehab M. A., Faker I. M. I., Phosphorus Sulfur Silicon Relat. Elem., 183, 2929–2942 (2008). 24) Ghorab M. M., Radwan M. A. A., Taha N. M. H., Amin N. E., Shehab M. A., Faker I. M. I., Phosphorus Sulfur Silicon Relat. Elem., 183, 2891–2905 (2008). 25) Al-Said M. S., Bashandy M. S., Al-Qasoumi S. I., Ghorab M. M., Eur. J. Med. Chem., 46, 137–141 (2011). 26) Leonard D. M., J. Med. Chem., 40, 2971–2990 (1997). 27) Rowinsky E. K., Windle J. J., Von Hoff D. D., J. Clin. Oncol., 17, 3631–3652 (1999). 28) Liu M., Bryant M. S., Chen J., Lee S., Yaremko B., Lipari P., Malkowski M., Ferrari E., Nielsen L., Prioli N., Dell J., Sinha D., Syed J., Korfmacher W. A., Nomeir A. A., Lin C. C., Wang L., Taveras A. G., Doll R. J., Njoroge F. G., Mallams A. K., Remiszewski S., Catino J. J., Girijavallabhan V. M., Bishop W. R., Cancer Res., 58, 4947–4956 (1998). 29) Prendergast G. C., Davide J. P., deSolms S. J., Giuliani E. A., Graham S. L., Gibbs J. B., Oliff A., Kohl N. E., Mol. Cell. Biol., 14, 4193–4202 (1994). 30) Lerner E. C., Qian Y., Blaskovich M. A., Fossum R. D., Vogt A., Sun J., Cox A. D., Der C. J., Hamilton A. D., Sebti S. M., J. Biol. Chem., 270, 26802–26806 (1995). 31) Cox A. D., Der C. J., Biochim. Biophys. Acta, 1333, 51–71 (1997). 32) Lund A. H., van Lohuizen M., Genes Dev., 18, 2315–2335 (2004). 33) Schneider R., Bannister A. J., Kouzarides T., Trends Biochem. Sci., 27, 396–402 (2002). 34) Bedford M. T., Richard S., Mol. Cell, 18, 263–272 (2005). 35) Tang J., Frankel A., Cook R. J., Kim S., Paik W. K., Williams K. R., Clarke S., Herschman H. R., J. Biol. Chem., 275, 7723–7730 (2000). 36) Pawlak M. R., Scherer C. A., Chen J., Roshon M. J., Ruley H. E., Mol. Cell. Biol., 20, 4859–4869 (2000). 37) Herrmann F., Lee J., Bedford M. T., Fackelmayer F. O., J. Biol. Chem., 280, 38005–38010 (2005). 38) Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J. T., Bokesch H., Kenney S., Boyd M. R., J. Natl. Cancer Inst., 82, 1107–1112 (1990)en_US
dc.identifier.doihttps://doi.org/
dc.identifier.otherhttps://doi.org/
dc.identifier.urihttps://cutt.ly/brX7i5c
dc.language.isoenen_US
dc.publisherChemical and Pharmaceutical Bulletinen_US
dc.relation.ispartofseriesChem. Pharm. Bull.;60 (8) 1019–1028
dc.subjectsulfoneen_US
dc.subjectpyridineen_US
dc.subjectpyrazolopyrimidineen_US
dc.subjectbenzochromeneen_US
dc.subjectanticancer activityen_US
dc.titleDapson in Heterocyclic Chemistry, Part V: Synthesis, Molecular Docking and Anticancer Activity of Some Novel Sulfonylbiscompounds Carrying Biologically Active Dihydropyridine, Dihydroisoquinoline, 1,3-Dithiolan, 1,3-Dithian, Acrylamide, Pyrazole, Pyrazolopyrimidine and Benzochromenemoietiesen_US
dc.typeArticleen_US

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