Synthesis and pharmacophore modeling of novel quinazolines bearing a biologically active sulfonamide moiety

1. M.M. Ghorab, S. E. Barakat, H. M. Saker andM. M. Abd Rabo, Synthesis and antitumor activity of some novel quinazoline derivatives bearing the biologically active thione moiety, Arzneim. Forsch./Drug Res. 56 (2006) 665-670; DOI: 10.1002/chin.200703141.10.1002/chin.200703141Search in Google Scholar

2. S. E. Barakat, M. M. Ghorab, H. M. Saker and M. M. Abd Rabo, Novel quinazolinone derivatives as possible antitumor agents, Phosphorus Sulfur Silicon 182 (2007) 65-77; DOI: 10.1080/ 10426500600867042.10.1080/10426500600867042Search in Google Scholar

3. M. M. Ghorab, S. M. Abdel-Gawad and M. S. A. El-Gaby, Synthesis and evaluation of some new fluorinated hydroquinazoline derivatives as antifungal agents, Farmaco 55 (2000) 249-255; DOI: 10.1016/S0014-827X(00)00029-X.10.1016/S0014-827X(00)00029-XSearch in Google Scholar

4. S. M. Abdel-Gawad, M. S. A. El-Gaby and M. M. Ghorab, Synthesis and antifungal activity of novel pyrano[2’,3’:4,5]thiazolo[2,3-b]quinazolines, pyrido[2’,3’:4,5]thiazolo[2,3-b]quinazolines and pyrazolo[2’,3’:4,5]thiazolo[2,3-b]quinazolines, Farmaco 55 (2000) 287-292; DOI: 10.1016/S0014- -827X(00)00042-2.Search in Google Scholar

5. M.M. Ghorab, S. G. Abdel-Hamide, M. S. A. El-gaby and S. M. El-Sayed, Synthesis and effect of some new [1,2,4]triazolo [4,3-a]quinazolin-5(4H)-ones and related compounds on Ehrlich ascites carcinoma cells, Acta Pharm. 49 (1999) 1-10.Search in Google Scholar

6. M.M. Ghorab, S. G. Abdel-Hamide and S. M. El-Sayed, Novel quinazolone derivatives as antitumor agents, Phosphorus Sulfur Silicon 142 (1998) 57-68; DOI: 10.1080/10426509808029666.10.1080/10426509808029666Search in Google Scholar

7. S. Jantova, D. Hudecova, S. Stankova and L. Ruzekova, Antibacterial effect of substituted 4-quinazolylhydrazines and their arylhydrazones determined by a modified microdilution method, Folia Microbiol. 40 (1995) 611-614; DOI: 10.1007/BF02818517.10.1007/BF02818517Search in Google Scholar

8. N. B. Patel, J. C. Patel and G. G. Barat, Synthesis and antimicrobial activity of 2-[2-(2,6-dichlorophenyl) amino]benzyl-3-(5-substituted phenyl-4,5-dihydro-1H-pyrazol-3-yl-amino)-6,8-dibromoquinazolin-4(3H)ones, J. Young Pharm. 2 (2010) 173-182; DOI: 10.4103/0975-1483.63165.10.4103/0975-1483.63165Search in Google Scholar

9. V. Gupta, S. K. Kashaw, V. Jatav and P. Mishra, Synthesis and antimicrobial activity of some new 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2-styrylquinazoline-4(3H)-ones, Med. Chem. Res. 17 (2008) 205-211; DOI: 10.1007/s00044-007-9054-3.10.1007/s00044-007-9054-3Search in Google Scholar

10. P. Kumar, C. Nath, K. P. Bhargava and K. Shanker, Synthesis and antiparkinsonian activity of styryl quinazolones, Pharmazie 37 (1982) 802-804.Search in Google Scholar

11. F. Roubinek, J. Vavrina and Z. Budesinsky, 3-Aminoalkyl- and 3-benzyl-4(3H)-quinazolinones, Collect. Czech. Chem. Commun. 47 (1982) 630-635; DOI: 10.1135/cccc19820630.10.1135/cccc19820630Search in Google Scholar

12. G. Y. Zhixiong, R. K. Bakshi,M. Chen, S. P. Rohrer, S. D. Feighner, S. S. Pong, A. D. Howard, A. Blake, E. T. Birzin, L. Locco, R. M. Parmar, W. W. S. Chan, J. M. Schaeffer, R. G. Smith, A. A. Patchett and R. P. Nargaund, Modeling directed design and biological evaluation of quinazolinones as non-peptidic growth hormone secretagogues, Bioorg. Med. Chem. Lett. 10 (2000) 5-8; DOI: 10.1016/S0960-894X(99)00584-3.10.1016/S0960-894X(99)00584-3Search in Google Scholar

13. V. Alagarsamy, S. Murugesan, K. Dhanabal, M. Murugan and E. De Clercq, Anti-HIV, antibacterial and antifungal activities of some novel 2-methyl-3-(substituted methylamino)-(3H)-quinazolin-4-ones, Indian J. Pharm. Sci. 69 (2007) 304-307; DOI: 10.4103/0250-474X.33167.10.4103/0250-474X.33167Search in Google Scholar

14. S. K. Pandey, A. Singh, A. Singh and A. Nizamuddin, Antimicrobial studies of some novel quinazolinones fused with [1,2,4]-triazole, [1,2,4]-triazine and [1,2,4,5]-tetrazine rings, Eur. J. Med. Chem. 44 (2009) 1188-1197; DOI: 10.1016/j.ejmech.2008.05.033.10.1016/j.ejmech.2008.05.03318614258Search in Google Scholar

15. S. Jantova, R. Ovadekova, S. Letasiova, K. Spirkova and S. Stankovsky, Antimicrobial activity of some substituted triazoloquinazolines, Folia Microbiol. 50 (2005) 90-94; DOI: 10.1007/BF02931453.10.1007/BF0293145316110909Search in Google Scholar

16. M. S. Al-Said, M. M. Ghorab, M. S. Al-Dosari and M. M. Hamed, Synthesis and in vitro anticancer evaluation of some novel hexahydroquinoline derivatives having a benzenesulfonamide moiety, Eur. J. Med. Chem. 46 (2011) 201-207; DOI: org/10.1016/j.ejmech.2010.11.002.10.1016/j.ejmech.2010.11.00221112675Search in Google Scholar

17. M. M. Ghorab, E. Noaman, M. M. F. Ismail, Y. A. Ammar, H. I. Heiba and M. Y. Sayed, Novel antitumor and radioprotective sulfonamides containing pyrrolo[2,3-d]pyrimidines, Arzneim. Forsch/Drug Res. 56 (2006) 405-413; DOI: 10.1002/chin.200643177.10.1002/chin.200643177Search in Google Scholar

18. M. M. Ghorab, Z. H. Ismail, S. M. Abdel-Gawad and A. Abdel Aziem, Antimicrobial activity of amino acid, imidazole, and sulfonamide derivatives of pyrazolo[3,4-d]pyrimidine, Heteroatom. Chem. 15 (2004) 57-62; DOI: 10.1002/hc.10212.10.1002/hc.10212Search in Google Scholar

19. Y. Genç, R. Özkanca and Y. Bekdemir, Antimicrobial activity of some sulfonamide derivatives on clinical isolates of Staphylococcus aureus, Ann. Clin. Microbiol. Antimicrob. 7 (2008) 17-23; DOI: 10.1186/1476-0711-7-17.10.1186/1476-0711-7-17254643318715512Search in Google Scholar

20. M. S. Al-Said, M. S. Bashandy, S. I. Al-Qasoumi and M. M. Ghorab, Anti-breast cancer activity of some novel 1,2-dihydropyridine, thiophene and thiazole derivatives, Eur. J. Med. Chem. 46 (2011) 137-141; DOI: 10.1016/j.ejmech.2010.10.024.10.1016/j.ejmech.2010.10.02421093116Search in Google Scholar

21. S. Guccion, A. Raffaelli, G. V. Barretta, L. M. Scolaro, S. Pucci and F. Russo, Potential of alkyl orthoformates as alkylating agents of non-electron rich nitrogen heterocycles, J. HeterocyclicChem. 32 (1995) 1149-1158; DOI: 10.1002/jhet.5570320409.10.1002/jhet.5570320409Search in Google Scholar

22. Y. Murti, A. K. Singh and D. Pathak, New 6-bromo-2-methyl-3-(substituted phenyl)-(3H)-quinazolin-4-ones with antimicrobial and antiinflammatory activities, Indian J. Pharm. Sci. 73 (2011) 333-337; DOI: 10.4103/0250-474X.93512.Search in Google Scholar

23. Z. H. Chohan, M. H. Youssoufi, A. Jarranpour and T. B. Hadda, Identification of antibacterial and antifungal pharmacophore sites for potent bacteria and fungi inhibition: indolenyl sulfonamide derivatives, Eur. J. Med. Chem. 45 (2010) 1189-1199; DOI: 10.1016/j.ejmech.2009.11.029.10.1016/j.ejmech.2009.11.02920005022Search in Google Scholar

24. G. Wolber and T. Langer, LigandScout: 3-D pharmacophores derived from protein-bound ligands and their use as virtual screening filters, J. Chem. Inf. Model. 45 (2005) 160-169; DOI: 10.1021/ ci049885e.Search in Google Scholar

25. S. Friederike, L. Sven, H. Thomas, S. Karsten, L. F. Philip and H. Hans-Dieter, Pharmacophore definition and three-dimensional quantitative structure-activity relationship study on structurally diverse prostacyclin receptor agonists, Mol. Pharmacol. 62 (2002) 1103-1111; DOI: 10.1124/ mol.62.5.1103.10.1124/mol.62.5.110312391273Search in Google Scholar

26. S. John, S. Thangapandian, S. Sakkiah and K. W. Lee, Potent bace-1 inhibitor design using pharmacophore modeling, in silico screening and molecular docking studies, BMC Bioinform. 12 (2011) S1-S28; DOI: 10.1186/1471-2105-12-S1-S28.10.1186/1471-2105-12-S1-S28304428321342558Search in Google Scholar

27. J. Garín, E. Meléndez, F. L. Merchán, P. Merino, J. Orduna, T. Tejero, Synthesis of unsymmetrical diheteroarylbenzenes: Benzoazole and quinazoline derivatives, J. Heterocycl. Chem. 28 (1991) 359-363; DOI: 10.1002/jhet.5570280229.10.1002/jhet.5570280229Search in Google Scholar

28. I. Graefe, K. Kottke, H. Kuehmstedt and D. Knoke, Synthesis of 3-hetaryl-4-oxo-2-thioxo- and 3-heterotaryl-2,4-dioxo-1,2,3,4-tetrahydroquinazolines, Pharmazie 45 (1990) 530-531; ChemInform22 (1991); DOI: 10.1002/chin.199148179.10.1002/chin.199148179Search in Google Scholar

29. A. A. Fahmi, S. C. Mekki, H. A. Alber, A. S. Shawlai, H. N. Hassaneen and H. Abdelhamid, A Facile synthesis of some pyrazolo analogues of tricyclic purine derivative via hydrazonoyl halides, J. Chem. Res. 12 (1994) 140-149.Search in Google Scholar

30. J. Fathi, V. Masand, R. Jawarkar, R. Mouhoub and T. Ben Hadda, POM as efficient tools to predict and improve both antibacterial and antifungal activity of aryl aldazines, J. Comput. Meth. Mol. Des. 1 (2011) 57-68.Search in Google Scholar