Substituted 3-((Z)-2-(4-nitrophenyl)-2-(1H-tetrazol-5-yl) vinyl)-4H-chromen-4-ones as novel anti-MRSA agents: Synthesis, SAR, and in-vitro assessment

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 16, 2008, Pages 4678-4681

  Diwakar, Santosh D ^a,b   Bhagwat, Sachin S ^a   Shingare, Murlidhar S ^b   Gill, Charansing H ^b  

^a Wockhardt Research Centre   (India)

^b DR BABASAHEB AMBEDKAR MARATHWADA UNIVERSITY   (India)

Author keywords

Anti MRSA; Chromones; Convergent; E. faecalis; Tetrazole

Indexed keywords

ANTIINFECTIVE AGENT; CHROMENE DERIVATIVE; TETRAZOLE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENTEROCOCCUS FAECALIS; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; STREPTOCOCCUS PNEUMONIAE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANTI-BACTERIAL AGENTS; CARBOXYLIC ACIDS; CHEMISTRY, PHARMACEUTICAL; CHROMONES; DRUG DESIGN; ESCHERICHIA COLI; HUMANS; METHICILLIN RESISTANCE; MICROBIAL SENSITIVITY TESTS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAZOLES;

METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NEGIBACTERIA; POSIBACTERIA;

EID: 49049098838     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.07.007     Document Type: Article

References (39)

1. Dean F.M. Naturally Occurring Oxygen Ring Compounds (1963), Butterworth's, London 281
2. Havsteen B. Biochem. Pharmacol. 23 (1983) 1141
3. Nohara A., Kuriki H., Saijo T., Sugihara H., Kanno M., and Sanno Y. J. Med. Chem. 20 (1977) 141
4. El-Shaaer H.M., Foltinova P., Lacova M., Chovancova J., and Stankovicova H. IL Farmaco 53 (1998) 224
5. Hou Y., Higashiya S., and Fuchigami T. J. Org. Chem. 64 (1999) 3346
6. Sanno Y., Nohara A., Kuriki H., and Koda A. J. Takeda Res. Lab. 33 (1974) 225
7. Butler R.N. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry vol. 4 (1996), Pergamon, Oxford, U.K.
8. Singh H., Chawla A.S., Kapoor V.K., Paul D., and Malhotra R.K. Prog. Med. Chem. 17 (1980) 151
9. Ellis G.P., and Shaw D. J. Med. Chem. 15 (1972) 865
10. Ellis G.P., and Shaw D. J. Chem. Soc., Perkin Trans. 1 (1972) 779
11. Nohara A., Kuriki H., Saijo T., Sugihara H., Kanno M., and Sanno Y. J. Med. Chem. 20 (1977) 141
12. Thayer A.M. Chem. Eng. News. 84 23 (2006) 15
13. Price W.A., Silva A.M.S., and Cavaleiro J.A.S. Heterocycles 36 (1993) 2601
14. Pinto D.C.G.A., Silva A.M.S., and Cavaleiro J.A.S. J. Heterocycl. Chem. 33 (1996) 1887
15. Silva A.M.S., Pinto D.C.G.A., Tavares H.R., Cavaleiro J.A.S., Jimeno M.L., and Elguero J. Eur. J. Org. Chem. (1998) 2031
16. Pinto D.C.G.A., Silva A.M.S., and Cavaleiro J.A.S. New J. Chem. 24 (2000) 85
17. Ellis G.P. Chem. Heterocycl. Compd. 35 (1977) 929
18. Prousek J. Collect. Czech. Chem. Commun. 58 (1993) 3014
19. Chem. Abstr. 1994, 120, 217542j.
20. Vogel's Textbook of Practical Organic Chemistry, Vth edition, 2004, 857.
21. 2), 7.50 (d, 2H, ArH, J = 8.0 Hz), 8.16 (d, 2H, ArH, J = 8.0 Hz); ESI(-ve): 204.5.
22. Demko Z.P., and Sharpless K.B. J. Org. Chem. 66 (2001) 7945
23. Amantini D., Beleggia R., Fringuelli F., Pizzo F., and Vaccaro L. J. Org. Chem. 69 (2004) 2896
24. Demko Z.P., and Sharpless K.B. Org. Lett. 4 (2002) 2525
25. Margita Lacova., Dusan Loos., Mikulas Furdik., Maria Matulova., and Hafez M. Molecules 3 (1998) 149
26. Ghosh C.K. J. Heterocycl. Chem. 20 (1983) 1437
27. 3)
28. NOE experiment is performed on 7b. Irradiation of the methylene proton at C-2 of the chromone ring (δ = 9.75) showed no effect on other protons, whereas irradiation of the vinyl proton (δ = 8.46) showed an increase of aromatic protons (δ = 8.43-8.84). Thus, structure as well as regiochemistry (Z) of the double bond is confirmed.
29. Gill C.H., Karale B.K., and Dalvi N.R. Indian J. Chem. B 44B (2005) 1522
30. Duncia J.V., Pierce M.E., and Santella J.B. J. Org. Chem. 56 (1991) 2395
31. Ditrich M. J. Heterocycl. Chem. 14 (1977) 757
32. Jie C., Diana A., and Shcherbakova I.V. J. Heterocycl. Chem. 33 (1996) 1107
33. Branko S.J., and Blaise W.L. J. Heterocycl. Chem. 35 (1998) 405
34. David A., Romia B., Francesco F., Ferdinado P., and Luigi V. J. Org. Chem. 69 (2004) 2896
35. De Souza N.J., Gupte S.V., Deshpande P.K., Desai V.N., Bhawsar S.B., Yeole R.D., Shukla M.C., Strahilevitz J., Hooper D.C., Bozdogan B., Appelbaum P.C., Jacobs M.R., Shetty N., Patel M.V., Jha R., and Khorakiwala H.F. J. Med. Chem. 48 (2005) 5232
36. Clinical and Laboratory Standard Institute (Formerly NCCLS). Methods for dilution for antimicrobial susceptibility tests for bacteria that grow aerobically: Approved Standard M7-A6. NCCLS, Villanova, PA, USA, 2003.
37. Domagala J.M., Hanna L.D., Heifetz C.L., Hutt M.P., Mich T.F., Sanchez J.P., and Solomon M. J. Med. Chem. 29 (1986) 394
38. Leclercq R. Antimicro. Res. 34 (2002) 482
39. Sander P., Belova L., Kidan Y.G., Pfister P., Mankin A.S., and Bottger E.C. Mol. Micro. 46 (2002) 1295