Synthesis and antibacterial activity of aromatic and heteroaromatic amino alcohols

Chemical Biology and Drug Design

Volumn 78, Issue 5, 2011, Pages 876-880

  de Almeida, Camila G ^a   Reis, Samira G ^a   de Almeida, Angelina M ^a   Diniz, Claudio G ^a   da Silva, Vânia L ^a   Le Hyaric, Mireille ^a  

^a FEDERAL UNIVERSITY OF JUIZ DE FORA   (Brazil)

Author keywords

Amino alcohols; Antibacterial; Aromatic; E. coli; Lipophilicity

Indexed keywords

ALCOHOL; ALDEHYDE; AMINOALCOHOL; ANTIBIOTIC AGENT; AROMATIC COMPOUND; NITROFURAL;

AGAR DIFFUSION; AMINATION; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERICIDAL ACTIVITY; BACTERIOSTASIS; BROTH DILUTION; CONTROLLED STUDY; ESCHERICHIA COLI; INHIBITION KINETICS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; RING OPENING; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; SYNTHESIS;

AMINO ALCOHOLS; ANTI-BACTERIAL AGENTS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE-ACTIVITY RELATIONSHIP;

STAPHYLOCOCCUS EPIDERMIDIS;

EID: 80054111051     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2011.01231.x     Document Type: Article

References (25)

1. Tally F.P., DeBruin M.F. (2000) Development of daptomycin for gram-positive infections. J Antimicrob Chemother;46:523-526.
2. Sader H.S., Gales A.C., Pfaller M.A., Mendes R.E., Zoccoli C., Barth A., Jones R.N. (2001) Pathogen frequency and resistance patterns in Brazilian hospitals: summary of results from three years of the SENTRY Antimicrobial Surveillance Program. Braz J Infect Dis;5:200-214.
3. Obritsch M.D., Fish D.N., MacLaren R., Jung R. (2005) Nosocomial infections due to multidrug-resistant Pseudomonas aeruginosa: epidemiology and treatment options. Pharmacotherapy;25:1353-1364.
4. Demain A.L., Sanchez S. (2009) Microbial drug discovery: 80years of progress. J Antibiot;62:5-16.
5. Katiyar D., Tiwari K.V., Tewari N., Verma S.S., Sinha S., Gaikwad A., Srivastava A., Chaturvedi V., Srivastava R., Srivastava B.S., Tripathi R.P. (2005) Synthesis and antimycobacterial activities of glycosylated amino alcohols and amines. Eur J Med Chem;40:351-360.
6. Salmi C., Loncle C., Letourneux Y., Brune J.M. (2008) Efficient preparation of secondary aminoalcohols through a Ti(IV) reductive amination procedure. Application to the synthesis and antibacterial evaluation of new 3β-N-[hydroxyalkyl]aminosteroid derivatives. Tetrahedron;64:4453-4459.
7. Almeida M.V., Le Hyaric M., Amarante G.W., Lourenço M.C.S., Brandão M.L.L. (2007) Synthesis of amphiphilic galactopyranosyl diamines and amino alcohols as antitubercular agents. Eur J Med Chem;42:1076-1083.
8. Almeida C.G., Garbois G.D., Amaral L.M., Diniz C.G., Le Hyaric M. (2010) Relationship between structure and antibacterial activity of lipophilic N-acyldiamines. Biomed Pharmacother;64:287-290.
9. Correa T.A., Reis E.F.C., Alves L.L., Alves C.S., Castro S.B.R., Dias A.T., Taveira A.F., Le Hyaric M., Couri M.R.C., Ferreira A.P., Almeida M.V. (2010) Preparation of amino alcohols condensed with carbohydrates: evaluation of cytotoxicity and inhibitory effect on NO production. Chem Biol Drug Des;76:451-456.
10. Collins C.H., Lynes P.M., Grange J.M. (1995) Microbiological Methods, 7th edn. Britain: Butterwort-Heinemann Ltd.; p. 175-190.
11. Sun F., Xu G., Wu J., Yang L. (2006) Efficient lipase-catalyzed kinetic resolution of 4-arylmethoxy-3-hydroxybutanenitriles: application to an expedient synthesis of a statin intermediate. Tetrahedron Asymmetry;17:2907-2913.
12. Sabitha G., Subba Reddy B.V., Abraham S., Yadav J.S. (1999) Microwave promoted synthesis of β-aminoalcohols in dry media. Green Chem;1:251-252.
13. National Committee for Clinical Laboratory Standards (2001) Methods for Dilution and Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, 5th edn, Vol. 20, no. 2. Approved Standard M 7.A5. Wayne, PA: NCCLS.
14. CLSI (2007) Performance Standards for Antimicrobial Susceptibility Testing, 17th Informational Supplement. CLSI Document M100-S16, 26. Wayne, PA: CLSI.
15. Alviano W.S., Alviano D.S., Diniz C.G., Antoniolli A.R., Alviano C.S., Farias L.M., Carvalho M.A.R., Souza M.M.G., Bolognese A.M. (2008) In vitro antioxidant potential of medicinal plant extracts and their activities against oral bacteria based on Brazilian folk medicine. Arch Oral Biol;53:545-552.
16. Gokel G.W., Dishong D.M., Diamond C.J.J. (1980) Lariat ethers. Synthesis and cation binding properties of macrocyclic polyethers possessing axially disposed secondary donor groups. J Chem Soc Chem Commun;5:1053-1054.
17. Hu Y., Qiao L., Qin Y., Zhao X., Chen X., Wang X., Wang F. (2009) Synthesis and Stabilization of Novel Aliphatic Polycarbonate from Renewable Resource. Macromolecules;42:9251-9254.
18. Hasegawa J., Hamada M., Miyamoto T., Nishide K., Kajimoto T., Uenishi J., Node M. (2005) The application of phenylmethanethiol and benzenethiol derivatives as odorless organo-sulfur reagents in the synthesis of thio-sugars and thio-glycosides. Carbohydr Res;340:2360-2368.
19. Chong H., Ma X., Lee H., Bui P., Song H.A., Birch N. (2008) Synthesis and evaluation of novel polyaminocarboxylate-based antitumor agent. J Med Chem;51:2208-2215.
20. Fujieda H., Usui S., Suzuki T., Nakagawa H., Ogura M., Makishima M., Miyata N. (2007) Phenylpropanoic acid derivatives bearing a benzothiazole ring as PPARδ-selective agonists. Bioorg Med Chem Lett;17:4351-4357.
21. Meyers A.I., Himmelsbach R.J., Reuman M. (1983) Reductive cleavage of aryl oxazolines to benzaldehydes and substituted toluenes. J Org Chem;48:4053-4058.
22. Cho T.K., Kang S.K. (2005) Direct and indirect reductive amination of aldehydes and ketones with solid acid-activated sodium borohydride under solvent-free conditions. Tetrahedron;61:5725-5734.
23. Schirok H., Li-Sommer Y., Brands M., Lobell M., Tersteegen A., Himmel H., Schlemmer K., Lang D., Petersen K., Renz M., Mumberg D., Hoffmann J., Siemeister G., Boemer U. (2009) Preparation of tricyclic nitrogen heterocyclic compounds and related heteroanalogs for the prevention or treatment of cancer. PCT Int. Appl. WO 2009033581.
24. Alonso F., Riente P., Yus M. (2008) Hydrogen-transfer reductive amination of aldehydes catalysed by nickel nanoparticles. Synlett;9:1289-1292.
25. Leskovsek V., Urleb U. (1994) A new approach to the synthesis of N-arylalkyl amino alcohols. Synth Com;24:1415-1424.