Click chemistry: Studies on the synthesis of novel fluorous tagged triazol-4-yl substituted quinazoline derivatives and their biological evaluation - Theoretical and experimental validation

European Journal of Medicinal Chemistry

Volumn 45, Issue 1, 2010, Pages 78-84

  Mani Chandrika, P ^a   Yakaiah, T ^b   Gayatri, G ^b   Pranay Kumar, K ^b   Narsaiah, B ^b   Murthy, U S N ^b   Raghu Ram Rao, A ^c  

^a KAKATIYA UNIVERSITY   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^c PANJAB UNIVERSITY   (India)

Author keywords

Click reaction; Perfluoroalkyl azides; Propargylation; Quinazolines; Selective cyclisation; Sharpless conditions

Indexed keywords

2 (2,6 DIFLUOROPHENYL) 3 [[1 (3,3,4, 4,5,5,6,6,7,7,8,8,8 TRIDECAFLUOROOCTYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL]QUINAZOLIN 4(3H) ONE; 2 (2,6 DIFLUOROPHENYL) 3 [[1 (3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10 HEPTADECAFLUORODECYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL]QUINAZOLIN 4(3H) ONE; 2 PHENYL 3 (PROP 2 YNYL)QUINAZOLIN 4(3H) ONE; 2 PHENYL 3 [[1 (3,3,4, 4,5,5,6,6,7,7,8,8,8 TRIDECAFLUOROOCTYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL]QUINAZOLIN 4(3H) ONE; 2 PHENYL 3 [[1 (3,3,4, 4,5,5,6,6,7,7,8,8,9,9,10,10,10 HEPTADECAFLUORODECYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL]QUINAZOLIN 4(3H) ONE; 2 PHENYL 4 (PROP 2 YNYLOXY)QUINAZOLINE; 2 PHENYL 4 [[1 (3,3,4, 4,5,5,6,6,7,7,8,8,9,9,10,10,10 HEPTADECAFLUORODECYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]QUINAZOLINE; 2 PHENYL 4 [[1 (3,3,4,4,5,5,6,6,7,7,8,8,8 TRIDECAFLUOROOCTYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]QUINAZOLINE; 2 PHENYL 4 [[3 (3,3,4, 4,5,5,6,6,7,7,8,8,9,9,10,10,10 HEPTADECAFLUORODECYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]QUINAZOLINE; 3 [[1 (3,3,4, 4,5,5,6,6,7,7,8,8, 9,9,10,10,10 HEPTADECAFLUORODECYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 2 (TRIFLUOROMETHYL)QUINAZOLIN 4(3H) ONE; 3 [[1 (3,3,4, 4,5,5,6,6,7,7,8,8,8 TRIDECAFLUOROOCTYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 2 (TRIFLUOROMETHYL)QUINAZOLIN 4(3H) ONE; 4 [[1 (3,3,4, 4,5,5,6,6,7,7,8,8,8 TRIDECAFLUOROOCTYL) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]QUINAZOLINE; 4 [[1 (3,3,4, 4,5,5,6,6,7,7,8,8,9,9,10,10,10 HEPTADECAFLUORODE) 1H 1,2,3 TRIAZOL 4 YL]METHOXY]QUINAZOLINE; AMPHOTERICIN B; ANTIINFECTIVE AGENT; PENICILLIN G; QUINAZOLINE DERIVATIVE; STREPTOMYCIN; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CLICK REACTION; CONTROLLED STUDY; CYCLOADDITION; DRUG SCREENING; DRUG SYNTHESIS; FUNGAL STRAIN; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; REACTION OPTIMIZATION; THEORETICAL STUDY;

ANTI-INFECTIVE AGENTS; BACTERIA; FUNGI; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUINAZOLINES; REPRODUCIBILITY OF RESULTS; THERMODYNAMICS; TRIAZOLES;

EID: 72049093193     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.09.027     Document Type: Article

References (46)

1. In: Coffey S. (Ed). Rodd's Chemistry of Carbon Compounds. second ed. vol. 4 (1978), Elsevier, Amsterdam (Chapter 46)
2. Jhone S. In: Juker E. (Ed). Progress in Drug Research vol. 26 (1982), Birkhauser Verlag AG, Basel, Switzerland 259
3. Brown D.J. The Chemistry of Heterocyclic Compounds (1996), J. Wiley & Sons, New York
4. Hynes B.J., Tomazic A., Kumar A., and Kumar V. J. Heterocycl. Chem. 28 (1991) 1981-1986
5. Jiang J.B., Hesson D.P., Dusak B.A., Dexter D.L., and Kang G.T. J. Med. Chem. 33 (1990) 1721-1728
6. Tani J., Yamada Y., Oine T., Ochiai T., Ishida R., and Inoue I. J. Med. Chem. 22 (1979) 95-99
7. Ochiai T., and Ishida R. Jpn J. Pharmacol. 32 (1982) 427-438
8. Raffa D., Daidone G., Schillaci D., Maggio B., and Plescia F. Pharmazie 54 (1999) 251-254
9. Rosowsky A., Andrew T.P., Ronald A.F., and Sherry F.Q. J. Med. Chem. 42 (1999) 1007-1017
10. Shah B.R., Bhatt J.J., Patel H.H., Undavia N.H., Trivedi P.B., and Desai N.C. Indian J. Chem. 34B (1995) 201
11. Robert J.A., and Russell H.E. J. Med. Chem. 15 (1972) 335-336
12. Jantova S., Greif G., Spirkova K., Stankovsky S., and Oravcova M. Folia Microbiol. (Praha) 45 (2000) 133
13. Guersoy A., and Illhan N. Farmaco 50 (1995) 559-563
14. Pandeya S.N., Sriram D., Nath G., and DeClereq E. Pharm. Acta Helv. 74 (1999) 11-17
15. Caroll S.S., Stahlhut M., Greb J., and Olsen D.B. J. Biol. Chem. 269 (1994) 32351-32357
16. Lopez S.E., Rosales M.E., Canelon C.E., Valverode E.A., Narvaez R.C., Charris J.E., Giannini F.A., Enriz R.D., Carrasco M., and Zacchino S. Hetrocycl. Commun. 7 (2000) 473-480
17. Farghaly A.O., and Moharram A.M. Boll. Chim. Farm. 138 (1999) 280-289
18. Jantova S., Hudecova D., Stankovsty S., and Ruzotoval H. Folia Microbiol. (1995) 611-614
19. Chan J.H., Hong J.S., Kuyper L.F., Baccanari D.P., Joyner S.S., Tansik R.L., Boytos C.M., and Rudolph S.K. J. Med. Chem. 38 (1995) 3608-3616
20. Castaldo R., Gump D., and McCormack J. Antimicrob. Agents Chemother. 15 (1979) 81
21. Bartroli J., Turmo E., Algueró M., Boncompte E., Vericat M., Conte L., Ramis J., Merlos M., and García-Rafanell J. J. Forn. J. Med. Chem. 41 (1998) 1869-1882
22. Hertel L.W., Kroin J.S., Misner J.W., and Tustin J.M. J. Org. Chem. 53 (1988) 2406-2409
23. In: Filler R., et al. (Ed). Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications. Studies in Organic Chemistry vol. 48 (1993) p362
24. Chae J., Konno T., Ishihara T., and Yamanaka H. Chem. Lett. 33 (2004) 314-315
25. Lermontov S.A., Shkavrov S.V., and Pushin A.N. J. Fluor. Chem. 105 (2000) 141-147
26. Wu Y.-M., Deng J., Fang S., and Chen Q.-Y. J. Fluor. Chem. 125 (2004) 1415-1423
27. Mekni N., and Baklouti A. J. Fluor. Chem. 129 (2008) 1073-1075
28. Soloshonok V.A. Enantio Controlled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets (1999), Wiley, New York
29. Kukhar V.P., and Soloshonok V.A. Fluorine-Containing Amino Acids: Synthesis and Applications (1995), Wiley, New York
30. Zandt M.C.V., Jones M.L., Gunn D.E., Geraci L.S., Jones J.H., Sawicki D.R., Sredy J., Jacot J.L., Dicioccio A.T., Petrova T., Mitschler A., and Podjarny A.D. J. Med. Chem. 48 (2005) 3141-3152
31. Mani Chandrika P., Yakaiah T., Raghu Ram Rao A., Narsaiah B., Chakra Reddy N., Sridhar V., and Venkateshwara Rao J. Eur. J. Med. Chem. 43 (2008) 846-852
32. Rao A.R.R., and Bahekar R.H. Indian J. Chem. 38 (1999) 434-439
33. Rao A.R.R., and Bahekar R.H. Arzneim. Forsch. Drug Res. 51 (2001) 284-292
34. Maitraie D., Reddy G.V., Rao V.V.V.N.S.R., Kanth S.R., Rao P.S., and Narsaiah B. J. Fluor. Chem. 118 (2002) 73-79
35. Kanth S.R., Reddy G.V., Kishore K.H., Rao P.S., Narsaiah B., and Murthy U.S.N. Eur. J. Med. Chem. 41 (2006) 1011-1016
36. Yakaiah T., Lingaiah B.P.V., Narsaiah B., Shireesha B., Ashok Kumar B., Gururaj S., Parthasarathy T., and Sridhar B. BioOrg. Med. Chem. Lett. 17 (2007) 3445-3453
37. Yakaiah T., Lingaiah B.P.V., Narsaiah B., Pranay Kumar K., and Murthy U.S.N. Eur. J. Med. Chem. 43 (2008) 341-347
38. Kolb H.C., and Sharpless K.B. Drug Discov. Today 8 (2003) 1128-1137
39. Rakesh V., Perumal S., Srinivasan C., and Rao C.N.R. Chem. Phys. Lett. 27 (2007) 118-121
40. Bogentoft C., Krongberg L., and Danielsson B. Acta Pharm. Suec. 6 (1969) 489-500
41. Hori M., and Ohtaka H. Chem. Pharm. Bull. 41 (1993) 1114-1117
42. Usifoh C.O., and Scriba G.K.E. Arch. Pharm. Med. Chem. 333 (2000) 261-266
43. Tornoe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
44. Himo F., Lovell T., Hilgraf R., Rostovtsev V.V., Noodleman L., Sharpless K.B., and Fokin V.V. J. Am. Chem. Soc. 127 (2005) 210-216
45. NCCLS. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria, Which Grows Aerobically. fifth ed. (2000), NCCLS, Villanova, PA Approved Standard M 7-A 5
46. Margery Linday E. Practical Introduction to Microbiology (1962), E & F.N. Spon, UK p. 177