Antimicrobial activity of new 4, 6-disubstituted pyrimidine, pyrazoline, and pyran derivatives

Archives of Pharmacal Research

Volumn 33, Issue 5, 2010, Pages 647-654

  Ramiz, Mahmoud M M ^a   El Sayed, Wael A ^b   El Tantawy, Asmaa I ^a   Abdel Rahman, Adel A H ^c  

^a MENOUFIA UNIVERSITY   (Egypt)

^b NATIONAL RESEARCH CENTRE   (Egypt)

^c Menoufia University   (Egypt)

Author keywords

Antimicrobial activity; Pyrans; Pyrazolines; Pyrimidines

Indexed keywords

2 AMINO 4 (4 BROMOPHENYL) 6 (THIOPHEN 2 YL) 4H PYRAN 3 CARBONITRILE; 2 AMINO 4 (4 CHLOROPHENYL) 6 (THIOPHEN 2 YL) 4H PYRAN 3 CARBONITRILE; 3 (4 BROMOPHENYL) 1 (THIOPHEN 2 YL)PROP 2 EN 1 ONE; 3 (4 CHLOROPHENYL) 1 (THIOPHEN 2 YL)PROP 2 EN 1 ONE; 4 (4 BROMOPHENYL) 2 (ETHYLTHIO) 6 (THIOPHEN 2 YL) 4,5 DIHYDROPYRIMIDINE; 4 (4 BROMOPHENYL) 6 (THIOPHEN 2 YL)PYRIMIDIN 2 AMINE; 4 (4 CHLOROPHENYL) 6 (THIOPHEN 2 YL)PYRIMIDIN 2 AMINE; 4 (4 CLOROPHENYL) 2 (ETHYLTHIO) 6 (THIOPHEN 2 YL) 4,5 DIHYDROPYRIMIDINE; 4 (4 CLOROPHENYL) 2 HYDRAZINYL 6 (THIOPHEN 2 YL) 4,5 DIHYDROPYRIMIDINE; 5 (4 BROMOPHENYL) 1 PHENYL 3 (THIOPHEN 2 YL) 4,5 DIHYDRO 1H PYRAZOLE; 5 (4 BROMOPHENYL) 3 (THIOPHEN 2 YL) 4,5 DIHYDROISOXAZOLE; 5 (4 CHLOROPHENYL) 1 PHENYL 3 (THIOPHEN 2 YL) 4,5 DIHYDRO 1H PYRAZOLE; 5 (4 CHLOROPHENYL) 3 (THIOPHEN 2 YL) 4,5 DIHYDROISOXAZOLE; 6 (4 BROMOPHENYL) 4 (THIOPHEN 2 YL) 5,6 DIHYDROPYRIMIDIN 2(1H) ONES; 6 (4 BROMOPHENYL) 4 (THIOPHEN 2 YL) 5,6 DIHYDROPYRIMIDIN 2(1H) THIONE; 6 (4 CHLOROPHENYL) 4 (THIOPHEN 2 YL) 5,6 DIHYDROPYRIMIDIN 2(1H) ONES; 6 (4 CHLOROPHENYL) 4 (THIOPHEN 2 YL) 5,6 DIHYDROPYRIMIDIN 2(1H) THIONE; CHALCONE DERIVATIVE; PYRAN DERIVATIVE; PYRAZOLINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PSEUDOMONAS AERUGINOSA; STREPTOMYCES;

ANTI-INFECTIVE AGENTS; CHALCONES; DOSE-RESPONSE RELATIONSHIP, DRUG; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; PYRANS; PYRAZOLES; PYRIMIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77954471425     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-010-0501-1     Document Type: Article

References (40)

1. A. A.-H. Abdel-Rahman W. A. El-Sayed H. M. Abdel-Bary A. E.-S. Abdel-Megied E. M. Morcy 2008 Amino acid derivatives. VIII. synthesis and antimicrobial evaluation of a-amino acid esters bearing an indole side chain Monatsh. Chem. 139 1095 1101 10.1007/s00706-008-0891-7 1:CAS:528: DC%2BD1cXhtVOntLbM
2. A. Agarwal K. Srivastava S. K. Puri P. M. Chauhan 2005 Synthesis of 2,4,6-trisubstituted pyrimidines as antimalarial agents Bioorg. Med. Chem. 13 4645 4650 10.1016/j.bmc.2005.04.061 1:CAS:528:DC%2BD2MXlsVCmtrc%3D 15896965 (Pubitemid 40848343)
3. Atwal, K., Preparation of 2-amino dihydropyrimidin-5-carboxylates as cardiovascular agents. U.S. Patent, 4769371, Sept. 6, 1988.
4. A. H. Bedair N. A. El-Haddy M. S. Abd El-Latif A. H. Fakery A. M. El-Agrody 2000 4-Hydroxycoumarin in heterocyclic synthesis: Part III. Synthesis of some new pyrano[2,3-d]pyrimidine, 2-substituted[1,2,4]-triazolo[1,5-c] pyrimidine and pyrimido [1,6-b][1,2,4]triazine derivatives Farmaco 55 708 714 10.1016/S0014-827X(00)00097-5 1:CAS:528:DC%2BD3MXis1Ojug%3D%3D 11204946 (Pubitemid 32037102)
5. G. Bianchi A. Tava 1987 Synthesis of (2R)(+)-2,3-dihydro-2,6-dimethyl-4H- pyran-4-one, a homologue of pheromones of a species in the hepialidae family Agric. Biol. Chem. 51 2001 2002 1:CAS:528:DyaL1cXhs1Oitrw%3D
6. Boyd, D. B., Theoretical and Physicochemical Studies on b-Lactam Antibiotics. In Morin, R. B., Gorman, M. (Eds.). b-Lactam Antibiotics, Chemistry and Biology. Academic Press, New York, Vol. 1, pp. 437-545, (1982).
7. Brown, D., In Katritzky, A. R., Rees, C. W. (Eds.). Comprehensive Heterocyclic Chemistry II. Pergamon Press, Oxford, Vol. 3, Chapter 2.13 (1996).
8. R. Capdeville E. Buchdunger J. Zimmermann A. Matter 2002 Glivec (ST1571, imatinib), a rationally developed targeted anti cancer drug Nat. Rev. Drug Discov. 1 493 502 10.1038/nrd839 1:CAS:528:DC%2BD38XkvFKlurY%3D 12120256
9. L. C. W. Chang R. F. Spanjersberg J. K. von Frijtag Drabbe Kunzel T. Mulder-Krieger G. van denHout M. W. Beukers J. Brussee A. P. Jzerman 2004 2,4,6-Trisubstituted pyrimidines as a new class of selective adenosine A1 receptor antagonists J. Med. Chem. 47 6529 6540 10.1021/jm049448r 1:CAS:528:DC%2BD2cXpslensrg%3D 15588088 (Pubitemid 39657315)
10. Dell, C. P. and Smith, C. W., Antiproliferative derivatives of 4H naphtho[1,2-b]pyran and process for their preparation. Eur. Patent, 537949, Apr. 21, 1993.
11. F. Eiden F. Denk 1991 Synthesis and CNS activity of pyran derivatives: 6,8-dioxabicyclo (3,2,1) octane Arch. Pharm. (Weinheim) 324 353 354 10.1002/ardp.19913240606 1:CAS:528:DyaK3MXkvFaisLw%3D
12. W. A. El-Sayed M. M. M. Ramiz A. A.-H. Abdel-Rahman 2008 C-Furyl glycosides. I. Synthesis and antimicrobial evaluation of C-furyl glycosides and chalcones derived therefrom Monatsh. Chem. 139 1499 1505 10.1007/s00706-008- 0941-1 1:CAS:528:DC%2BD1cXhsVSqu7rL
13. W. A. El-Sayed I. F. Nassar A. A.-H. Abdel-Rahman 2009 C-Furyl glycosides. II. Synthesis and antimicrobial evaluation of C-furyl glycosides bearing pyrazolines, isoxazolines, and 5,6-dihydropyrimidine-2(1H)-thiones Monatsh. Chem. 140 365 370 10.1007/s00706-008-0033-2 1:CAS:528: DC%2BD1MXjt1Khu7c%3D
14. A. M. El-Agrody M. S. Abd El-Latif N. A. El-Hady A. H. Fakery A. H. Bedair 2001 Heteroaromatization with 4-hydroxycoumarin. Part II. Synthesis of some new pyrano[2,3-d][1,2,4]triazolo[1,5-c]-pyrimidines and pyrimido [1,6-b][1,2,4]triazine derivatives Molecules 6 519 527 10.3390/60600519 1:CAS:528:DC%2BD3MXntleisrs%3D
15. A. M. El-Agrody M. H. El-Hakim M. S. Abd El-Latif A. H. Fakery E. M. El-Sayed K. A. El-Ghareab 2000 Synthesis of pyrano[2,3-d]pyrimidine and pyrano[3,2-e][1,2,4]triazolo[2,3-c]pyrimidine derivatives with promising antibacterial activities Acta Pharm. 50 111 120 1:CAS:528:DC%2BD3cXlsFOktLw%3D
16. V. R. Gadhachanda B. Wu Z. Wang K. L. Kuhen J. Caldwell H. Zondler H. Walter M. Havenhand Y. He 2007 4-Aminopyrimidines as novel HIV-1 inhibitors Bioorg. Med. Chem. Lett. 17 260 265 10.1016/j.bmcl.2006.09.047 1:CAS:528:DC%2BD2sXislWr 17035019 (Pubitemid 44959951)
17. A. R. Gholap K. S. Toti F. Shirazi M. V. Deshpande K. V. Srinivasan 2008 Efficient synthesis of antifungal pyrimidines via palladium catalyzed Suzuki/Sonogashira crosscoupling reaction from Biginelli 3,4-dihydropyrimidin 2(1H)-ones Tetrahedron 64 10214 10223 10.1016/j.tet.2008.08.033 1:CAS:528:DC%2BD1cXhtFelsrfJ
18. N. Grant N. Mishriky F. M. Asaad N. G. Fawzy 1998 Pyridines and pyrazolines from salicylic acid derivatives with propenone residue and their antimicrobial properties Pharmazie 53 543 547 1:CAS:528:DyaK1cXlsFGqsLc%3D 9741063
19. Greenwood, Antimicrobial Chemotherapy, 4th ed, Oxford University press, New York, pp. 114, (2000).
20. M. I. Hegab N. A. Hassan A. E. Rashad A. A. Fahmy F. M. E. Abdel-Megeid 2007 Synthesis, reactions, and antimicrobial activity of some fused thieno[2,3-d]pyrimidine derivatives Phosphorus Sulfur Silicon Relat. Elem. 182 1535 1556 10.1080/10426500701247151 1:CAS:528:DC%2BD2sXmt1antbY%3D
21. K. Hiramoto A. Nasuhara K. MichiLoshi T. Kato K. Kikugawa 1997 DNA strand-breaking activity and mutagenicity of 2,3-dihydro-3,5-dihydroxy-6-methyl- 4H-pyran-4-one (DDMP), A Maillard reaction product of glucose and glycine Mutat. Res. 395 47 56 1:CAS:528:DyaK1cXisl2htA%3D%3D 9465913
22. A. M. Janssen J. J. Scheffer A. B. Svendsen 1987 Antimicrobial activity of essential oils; a 1976-1986 literature review Planta Med. 53 395 400 10.1055/s-2006-962755 1:CAS:528:DyaL1cXhvVyktg%3D%3D 3324126 (Pubitemid 17150418)
23. Jorgensen, J. H., Jurnide, J. D., and Washington, J. A., Antimicrobial susceptibility tests. In Muarry, P. R., Baron, E. J., and Yolken, R. C. (Eds.). Manual of Clinical Microbiology, 7th ed. American Society for Microbiology, Washington, DC, pp. 1526-1543, (1999).
24. Jungheim, L. N., Holmes, R. E., Ott, J. L., Ternansky, R. J., Draheim, S. E., Neel D. A., Stepherd, T. A., and Sigmund, S. K., Abstracts of 26th Interscience Conference on Antimicrobial Agents and Chemotherapy, Sept. 28-Oct. 1, New Orleans, L.A., paper 601 (1988a).
25. Jungheim, L. N., Holmes, R. E., Ternansky, R. J., Stepherd, T. A., Neel, D. A., Draheim, S. E., Pike, A. J., and Wu, C. Y. E., Abstracts of 28th Interscience Conference on Antimicrobial Agents and Chemotherapy, Oct. 23-26, Los Angels, C.A., paper 240 (1988b).
26. L. N. Jungheim S. K. Sigmund J. W. Fisher 1987 Bicyclic pyrazolidinones, a new class of antibacterial agent based on the β-lactam model Tetrahedron Lett. 28 285 288 10.1016/S0040-4039(00)95708-3 1:CAS:528:DyaL1cXitFGlug%3D%3D
27. L. N. Jungheim S. K. Sigmund N. D. Jones J. K. Swartzendruber 1987 Bicyclic pyrazolidinones, steric and electronic effects on antibacterial activity Tetrahedron Lett. 28 289 292 10.1016/S0040-4039(00)95709-5 1:CAS:528:DyaL1cXitFGluw%3D%3D
28. A. Keutzberger X. Gillessen 1985 Antimykotische Wirkstoffe, 18. Mitt. Aromatisch substituierte 2-(4-Toluidino)pyrimidine J. Arch. Pharm. 318 370 374 10.1002/ardp.19853180414 1:CAS:528:DyaL2MXkt1amtrc%3D (Pubitemid 15148449)
29. A. G. Martinez L. J. Marco 1997 Friedlander reaction on 2-amino-3-cyano-4H-pyrans, synthesis of derivatives of 4Hpyran[ 2,3-b]quinoline, new tacrine analogues Bioorg. Med. Chem. Lett. 7 3165 3170 10.1016/S0960- 894X(97)10165-2 (Pubitemid 28009340)
30. M. Matloobi C. O. Kappe 2007 Microwave-assisted solution- and solid-phase synthesis of 2-amino-4-arylpyrimidine derivatives J. Comb. Chem. 9 275 284 10.1021/cc0601377 1:CAS:528:DC%2BD2sXlt1Ggtw%3D%3D 17348733
31. M. N. A. Nasr S. A. Said 2003 Novel 3, 3a, 4, 5, 6, 7-hexahydroindazole and arylthiazolylpyrazoline derivatives as anti-inflammatory agents Arch. Pharm. Pharm. Med. Chem. 336 551 559 10.1002/ardp.200300796 1:CAS:528: DC%2BD2cXktVKnsQ%3D%3D (Pubitemid 38076210)
32. D. Nauduri G. B. Reddy 1998 Antibacterials and antimycotics. Part 1. Synthesis and activity of 2-pyrazoline derivatives Chem. Pharm. Bull. 46 1254 1260 1:CAS:528:DyaK1cXlsFyjur4%3D 9734312
33. K. Ozeki T. Ichikawa H. Takehara K. Tanimura M. Sato H. Yaginuma 1989 Studies on antiallergy agents. III. Synthesis of 2-anilino-1,6-dihydro-6-oxo-5- pyrimidinecarboxylic acids and related compounds Chem. Pharm. Bull. 37 1780 1787 1:CAS:528:DyaK3cXlsFOltQ%3D%3D 2572333
34. C. J. Shishoo M. B. Devani G. V. Ullas S. Ananthan V. S. Bahadit 1981 Studies in the synthesis and interconversion of isomeric triazolopyrimidines J. Heterocycl. Chem. 18 43 46 10.1002/jhet.5570180109 1:CAS:528:DyaL3MXkt1Cqtb4%3D
35. N. R. Taylor A. Cleasby O. Singh T. Skarzynski A. J. Wonacott P. W. Smith S. L. Sollis P. D. Howes P. C. Cherry R. Bethell P. Colman J. Varghese 1998 Dihydropyrancarboxamides related to zanamivir: A new series of inhibitors of influenza virus sialidases. 2. Crystallographic and molecular modeling study of complexes of 4-amino-4H-pyran-6-carboxamides and sialidase from influenza virus types A and B J. Med. Chem. 41 798 807 10.1021/jm9703754 1:CAS:528: DyaK1cXhtF2murY%3D 9526556 (Pubitemid 28146237)
36. R. J. Ternansky S. E. Draheim 1990 [3.3.0] Pyrazolodinones: An efficient synthesis of a new class of synthetic antibacterial agents Tetrahedron Lett. 31 2805 2808 10.1016/0040-4039(90)80153-D 1:CAS:528:DyaK3cXlvFWhsL0%3D (Pubitemid 20179963)
37. G. Turan-Zitouni P. Chevallet F. S. Kilic K. Erol 2000 Synthesis of some thiazolyl-pyrazoline derivatives and preliminary investigation of their hypotensive activity Eur. J. Med. Chem. 35 635 641 10.1016/S0223-5234(00)00152-5 1:CAS:528:DC%2BD3cXltlGqu74%3D 10906414 (Pubitemid 30423195)
38. G. Turan-Zitouni A. Ozdemir K. Guven 2005 Synthesis of some 1-[(N,N-disubstitutedthiocarbamoylthio)acetyl]-3-(2-thienyl)-5-aryl-2 pyrazoline derivatives and investigation of their antibacterial and antifungal activities Arch. Pharm. Pharm. Med. Chem. 338 96 104 10.1002/ardp.200400935 1:CAS:528:DC%2BD2MXjvFeisL8%3D (Pubitemid 40592929)
39. G. Turan-Zitouni A. Ozdemir Z. A. Kaplanclkll P. Chevallet Y. Tunalý 2005 Synthesis and Antimicrobial Activities of Some 1-[(N,N-disubstituted-thiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines Phosphorus Sulfur Silicon Relat. Elem. 180 2717 2724 10.1080/104265090930452 1:CAS:528:DC%2BD2MXht1Smt7fE
40. M. E. A. Zaki H. A. Soliman O. A. Hiekal A. E. Rashad 2006 Pyrazolopyranopyrimidines as a class of anti inflammatory agents Z. Naturforsch. C 61c 1 5