Nucleosides 8 [18]: Ribosylation of fused quinazolines-synthesis of new [1,2,4]triazolo[5,1-b]- and [1,2,4]triazino[3,2-b]quinazoline nucleosides of fluorescence interest

Journal of Chemistry

Volumn , Issue , 2013, Pages

  Break, Laila Mohamed ^a   Abdelnabi Mosselhi, Mosselhi ^a,b   Elshafai, Nagi Mohamed ^c  

^a TAIF UNIVERSITY   (Saudi Arabia)

^b CAIRO UNIVERSITY   (Egypt)

^c Kafrelsheikh University   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84876591548     PISSN: 20909063     EISSN: 20909071     Source Type: Journal    
DOI: 10.1155/2013/612756     Document Type: Article

References (53)

1. Li Y., Soni P. B., Liu L., Zhang X., Liotta D. C., Lutz S., Synthesis of fluorescent nucleoside analogs as probes for 2′-deoxyribonucleoside kinases. Bioorganic and Medicinal Chemistry Letters 2010 20 3 841 843 2-s2.0-74049152991 10.1016/j.bmcl.2009.12.097
2. Katritzky A. R., Ozcan S., Todadze E., Labeling of nucleosides with fluorescent 6-chloro-2,3-napthalimide. Bioorganic and Medicinal Chemistry Letters 2010 20 17 5326 5328 2-s2.0-77955659777 10.1016/j.bmcl.2010.06.100
3. Zhao X. J., Huang C. Z., Huang C. Z., Small organic molecules as fluorescent probes for nucleotides and their derivatives. Trends in Analytical Chemistry 2010 29 4 354 367 2-s2.0-77950519617 10.1016/j.trac.2009.12.011
4. Tor Y., Fluorescent nucleoside analogs: synthesis, properties, and applications. Tetrahedron 2007 63 17 3425 3426 2-s2.0-33947241841 10.1016/j.tet.2007.01.070 (Pubitemid 46428339)
5. Medza G., Wierzchowski J., Kierdaszuk B., Shugar D., Fluorescence emission properties of 8-aza analogues of caffeine, theophylline, and related N -alkyl xanthines. Bioorganic and Medicinal Chemistry 2009 17 6 2585 2591 2-s2.0-62149135932 10.1016/j.bmc.2009.01.007
6. Nasr T., Li Z., Nakagawa O., Taniguchi Y., Ono S., Sasaki S., Selective fluorescence quenching of the 8-oxoG-clamp by 8-oxodeoxyguanosine in ODN. Bioorganic and Medicinal Chemistry Letters 2009 19 3 727 730 2-s2.0-58549104316 10.1016/j.bmcl.2008.12.036
7. Pertenbreiter F., Meier C., Synthesis and properties of cyclosal-phosphatetriesters of fluorescent bicyclic nucleoside analogues (BCNAS). Antiviral Research 2009 82 A62
8. Nowak J., Skalski B., Gdaniec Z., Milecki J., Synthesis of an acyclic nucleoside analog of highly fluorescent luminarosine. Tetrahedron Letters 2009 50 15 1671 1673 2-s2.0-60649088492 10.1016/j.tetlet.2008.10.045
9. El-Hashash M. A., Rizk S. A., El-Bassiouny F. A., Darwish K. M., Uses of 2-ethoxy-4(3H) quinazolinone in synthesis of quinazoline and quinazolinone derivatives of antimicrobial activity: the solvent effect. Global Journal of Health Science 2012 4 162 173
10. Stout M. G., Robins R. K., The synthesis of some quinazoline nucleosides. Journal of Organic Chemistry 1968 33 3 1219 1225 2-s2.0-0014266658
11. Dunkel M., Pfleiderer W., Nucleosides. XLVIII. Syntheses and properties of quinazoline N-1-ribofuranosides. Nucleosides and Nucleotides 1991 10 4 799 817 2-s2.0-0025780619
12. Dunkel M., Pfleiderer W., Nucleosides. IL synthesis and properties of 2,4-quinazolinedione N-1- 2'deoxy-, 3'-deoxy- and 2',3'-dideoxynucleosides. Nucleosides and Nucleotides 1992 11 2-4 787 819 2-s2.0-0026596155
13. Dunkel M., Pfleiderer W., Nucleosides. LII. Synthesis and properties of quinazoline-3'- azidonucleosides. Nucleosides and Nucleotides 1993 12 2 125 137 2-s2.0-0027466359 (Pubitemid 23091140)
14. Chien T.-C., Chen C.-S., Chern J.-W., Nucleosides XIII. Facile synthesis of 4-amino-1-(2-deoxy- β -D- ribofuranosyl)quinazolin-2-one as a 2′-deoxycytidine analog for oligonucleotide synthesis. Journal of the Chinese Chemical Society 2005 52 6 1237 1244 2-s2.0-33745811236 (Pubitemid 44028896)
15. El-Baih F. E. M., Bakari S. B. A., Hijazi A. A., Synthesis and spectroscopic properties of quinazolinedione derivatives. Journal of King Abdelaziz University 2004 16 41 53 10.4197/Sci.16-1.5
16. Rajappan V. P., Schneller S. W., An 8-aminoimidazo[4,5- g ]quinazoline carbocyclic nucleoside: a ring-extended analog of 5′-noraristeromycin. Tetrahedron 2001 57 44 9049 9053 2-s2.0-0035968873 10.1016/S0040-4020(01)00909-7 (Pubitemid 32973908)
17. El-Hashash M. A., Rizk S. A., El-Bassiouny F. A., Darwish K. M., Reactivity of 2-ethoxyquinazolin- 4-yl hydrazine and its use in synthesis of novel quinazoline derivatives of antimicrobial activity. Global Journal of Health Science 2012 4 174 183
18. Mosselhi M. A. N., Break L. M., NUCLEOSIDES 7: synthesis, structure and biological activity of new 6-arylidenamino-2-thio- and 2-benzylthiopyrimidine N -Nucleosides. Nucleosides Nucleotides and Nucleic Acids 2011 30 9 681 695 10.1080/15257770.2011.597628
19. Break L. M., Shmiss N. A. M. M., Mosselhi M. A. N., Synthesis of some new s-nucleoside derivatives of 2-thioxo and (2,4-Dithioxo)-5,6,7,8- Tetrahydrobenzo-Thieno[2,3- d ]Pyrimidin-4-(3H)Ones. Phosphorus, Sulfur and Silicon and the Related Elements 2010 185 8 1615 1622 2-s2.0-77955337330 10.1080/10426500903147159
20. Metwally N. H., Abdalla M. A., Mosselhi M. A. N., El-Desoky E. A., Synthesis and antimicrobial activity of some new N-glycosides of 2-thioxo-4-thiazolidinone derivatives. Carbohydrate Research 2010 345 9 1135 1141 2-s2.0-77953133584 10.1016/j.carres.2010.04.011
21. Mosselhi M. A. N., Neidlein R., Nucleosides 515: synthesis of novel 1,2,4-triazolo[3,4- c ]-1,2,4-triazole nucleosides. Nucleosides, Nucleotides and Nucleic Acids 2009 28 11-12 1095 1103 2-s2.0-77949626743 10.1080/ 15257770903368377
22. Mosselhi M. A. N., Seliger H., Nucleosides 31: synthesis of novel 1,3,4-oxadiazole nucleosides. Journal of Chemical Research S 2001 9 359 361 2-s2.0-0034761913
23. Mosselhi M. A. N., Nucleosides. I. Ribosylation of 8-substituted theophylline derivatives. Nucleosides and Nucleotides 1993 12 5 431 439 2-s2.0-0027199537 (Pubitemid 23216172)
24. Mosselhi M. A. N., Nucleosides 2: synthesis and properties of 3,4-diaryl-4,5-dihydro-1-(β-D-ribofuranosyl)-1,2,4-triazole-5-thiones. Nucleosides and Nucleotides 1999 18 9 2043 2049 2-s2.0-0032833767 (Pubitemid 29455570)
25. Bowie R. A., Edwards P. N., Nicholson S., Taylor P. J., Thomson D. A., Covalent hydrates as intermediates in heterocyclic rearrangements. Part 3. The alkali-catalysed transformations of 1,5-diamino-1 H-s -triazolo[1,5- c ]quinazolinium bromide. Journal of the Chemical Society, Perkin Transactions 2 1979 12 1708 1714 2-s2.0-37049109116
26. Freri M., Synthesis of novel derivatives of α β diketo esters. Gazzetta Chimica Italiana 1939 68 612 618
27. Abdelaziz N., Barghash A.-E., Alkerdawy M. A., Abudahab E. A. S., Synthesis and antiviral testing of certain derivatives of thiazolo[4, 3-b]-benzothiazoles, thiazolo[3', 4':2, 3][1, 2, 4]-triazolo[5, 1-b]-, {triazino-[3, 2-b]-and triazepino[3, 2-b]}- quinazolines. Alexandria Journal of Pharmaceutical Science 2004 18 109 113
28. Break L. M., Mosselhi A. N., Synthesis, Structure and antimicrobial activity of new 3- & 2-arylmethyl and arylacyl-3H-[1, 2, 4]triazino[3, 2-b]-quinazoline-2, 6(1H)diones as expected as DNA Fluorphores. Research Journal of Chemcal Science 2012 2 5 23 28
29. Vorbruggen H., Krolikiewicz K., Bennua B., Nucleoside syntheses, XXII: nucleoside synthesis with trimethylsilyl triflate and perchlorate as Catalysts. Chemische Berichte 1981 114 4 1234 1255 10.1002/cber.19811140404
30. Shawali A. S., Ali N. A. H., Ali A. S., Osman D. A., Synthesis and biological activity of new functionalised cyclohepta[4,5]thieno[2,3- d ][1,2,4] triazolo[4,3- a ]pyrimidin-5-ones. Journal of Chemical Research 2006 5 327 332 2-s2.0-33745744201 (Pubitemid 44014516)
31. 13C NMR Spectroscopy 1984 Stuttgart, Germany Georg Thieme Publisher
32. Larsen J. S., Abdel Aal M. T., Pedersen E. B., Nielsen C., Synthesis and anti-HIV activity of HEPT and S-DABO-analogues with 5-benzyl and 5-phenyl substituents. Journal of Heterocyclic Chemistry 2001 38 3 679 683 2-s2.0-0034937387 (Pubitemid 32624706)
33. Hassan N. A., Novel synthesis of S-glycosides derived from 5,6-di-substituted thieno[2,3- d ]pyrimidin-4-one-2-thiones. Journal of Sulfur Chemistry 2005 26 4-5 343 352 2-s2.0-31344443103 10.1080/17415990500456723
34. Sinkeldam R. W., Greco N. J., Tor Y., Fluorescent analogs of biomolecular building blocks: design, properties, and applications. Chemical Reviews 2010 110 5 2579 2619 2-s2.0-77952531703 10.1021/cr900301e
35. Godde F., Toulme J. J., Moreau S., 4-amino-1 H-benzo[ g ]quinazoline-2-one: a fluorescent analog of cytosine to probe protonation sites in triplex forming oligonucleotides. Nucleic Acids Research 2000 28 15 2977 2985 2-s2.0-0034238088 (Pubitemid 30601341)
36. Hawkins M. E., Pfleiderer W., Jungmann O., Balis F. M., Synthesis and fluorescence characterization of pteridine adenosine nucleoside analogs for DNA incorporation. Analytical Biochemistry 2001 298 2 231 240 2-s2.0-0035892607 10.1006/abio.2001.5399 (Pubitemid 33105237)
37. Seaman S., Fluorescent nucleosides as probes for DNA structure and recognition [Ph.D. thesis] 2004 San Diego, Calif, USA University of California San Diego
38. Gardarsson H., Sigurdsson S. Th., Large flanking sequence effects in single nucleotide mismatch detection using fluorescent nucleoside Çf. Bioorganic and Medicinal Chemistry 2010 18 16 6121 6126 2-s2.0-77955467027 10.1016/j.bmc.2010.06.060
39. Xie Y., Maxson T., Tor Y., Fluorescent ribonucleoside as a FRET Acceptor for tryptophan in native proteins. Journal of the American Chemical Society 2010 132 34 11896 11897 2-s2.0-77956072696 10.1021/ja105244t
40. Tanpure A. A., Srivatsan S. G., Synthesis and photophysical characterisation of a fluorescent nucleoside analogue that signals the presence of an abasic Site in RNA. Chemical Biology Journal 2012 13 16 2392 2399
41. Dziuba D., Postupalenko V. Y., Spadafora M., Klymchenko A. S., Guerineau V., Mely Y., Benhida R., Burger A., A universal nucleoside with strong two-band switchable fluorescence and sensitivity to the environment for investigating DNA interactions. Journal of American Chemical Society 2012 134 24 10209 10213
42. Chemla D. S., Zyss J., Non Linear Optical Properties of Organic Molecules and Crystals 1987 1-2 Orlando, Fla, USA Academic Press
43. Altaf M., Chaudhry M. A., Zahid M., Study of optical band gap of zinc-borate glasses. Journal of Research 2003 14 2 253 259
44. + Journal of Physics and Chemistry of Solids 2003 64 4 641 650 2-s2.0-0037388604 10.1016/S0022-3697(02)00365-7
45. 2 (SLP) glass system. Optical Material 2000 15 3 181 186 10.1016/S0925-3467(00)00033-1 (Pubitemid 32032323)
46. Hagfeldt A., Gratzel M., Light-induced redox reactions in nanocrystalline systems. Chemical Review 1995 95 1 49 68 10.1021/cr00033a003
47. Salavati-Niasari M., Mir N., Davar F., A novel precursor in preparation and characterization of nickel oxide nanoparticles via thermal decomposition approach. Journal of Alloys and Compounds 2010 493 1-2 163 168 2-s2.0-77249120521 10.1016/j.jallcom.2009.11.153
48. El-Shehawy A. A., Abdo N. I., El-Barbary A. A., Lee J. -S., Alternating copolymers based on 2,1,3-benzothiadiazole and hexylthiophene: positioning effect of hexyl chains on the photophysical and electrochemical properties. European Journal of Organic Chemistry 2011 25 4841 4852
49. Gáplovsky A., Donovalová J., Magdolen P., Toma S., Zahradnik P., Spectroscopic study of 2-[2-(4-cyclaminophenyl)ethen-1-yl] benzothiazoles and their N -allylbenzothiazolium bromides. Solvent and substituent effects on their ultraviolet-visible and fluorescence spectra. Spectrochimica Acta A 2002 58 2 363 371 2-s2.0-0037079560 10.1016/S1386-1425(01) 00545-5 (Pubitemid 33110433)
50. Ezzat N. S., Synthesis of some quinazolines and imidazolo-[1, 5- a ]-3, 1-benzoxazine-4-one derivatives. Royal Air Force Journal of Science 2008 19 37 44
51. Abdul Jabar Kh., Atia A. J. K., Al-Mufrgeiy S. S., Synyhesis and antibacterial activities of new 3-nmino-2-methyl-quinazolin-4 (3h)-one derivatives. American Journal of Chemistry 2012 2 3 150 156
52. Breitung E. M., Shu C. F., McMahon R. J., Thiazole and thiophene analogues of donor-acceptor stilbenes: molecular hyperpolarizabilities and structure-property relationships. Journal of the American Chemical Society 2000 122 6 1154 1160 2-s2.0-0034673355 10.1021/ja9930364 (Pubitemid 30117451)
53. Zhang X. H., Wong O. Y., Gao Z. Q., Lee C. S., Kwong H. L., Lee S. T., Wu S. K., A new blue-emitting benzothiazole derivative for organic electroluminescent devices. Materials Science and Engineering B 2001 85 2-3 182 185 2-s2.0-0035934397 10.1016/S0921-5107(01)00607-9 (Pubitemid 32673993)