A new class of potential anti-tuberculosis agents: Synthesis and preliminary evaluation of novel acrylic acid ethyl ester derivatives

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 12, 2010, Pages 4178-4186

  Kabir, M Shahjahan ^a   Namjoshi, Ojas A ^a   Verma, Ranjit ^a   Polanowski, Rebecca ^b   Krueger, Sarah M ^b   Sherman, David ^c   Rott, Marc A ^b   Schwan, William R ^b   Monte, Aaron ^b   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

^b UNIVERSITY OF WISCONSIN LA CROSSE   (United States)

^c SEATTLE BIOMEDICAL RESEARCH INSTITUTE   (United States)

Author keywords

Anti tuberculosis; Mycobacterium smegmatis; Mycobacterium tuberculosis; Vinylamines of acrylic acid ethyl ester; Vinylether of acrylic acid ethyl ester; Vinylthioether of acrylic acid ethyl ester

Indexed keywords

2 (2 ETHOXYCARBONYL VINYLSULFANYL)BENZOIC ACID METHYL ESTER; 3 (2 ISOPROPYL PHENOXY)ACRYLIC ACID ETHYL ESTER; 3 (2 ISOPROPYL PHENYLSULFANYL)ACRYLIC ACID ETHYL ESTER; 3 (2 METHYLBENZOATE)ACRYLIC ACID ETHYL ESTER; 3 (3 FLUOROPHENOXY)ACRYLIC ACID ETHYL ESTER; 3 (3 METHYLTHIOPHENE 2 CARBOXYLATE)ACRYLIC ACID ETHYL ESTER; 3 (3 NITROPHENOXY)ACRYLIC ACID ETHYL ESTER; 3 (3,5 DIMETHOXY PHENOXY)ACRYLIC ACID ETHYL ESTER; 3 (4 CARBAMOYLPHENOXY)ACRYLIC ACID ETHYL ESTER; 3 (4 FLUORO PHENOXY)ACRYLIC ACID ETHYL ESTER; 3 (4 HYDROXY PHENYLSULFANYL)ACRYLIC ACID ETHYL ESTER; 3 (4 TERT BUTYL PHENOXY)ACRYLIC ACID ETHYL ESTER; 3 (4 TERT BUTYL PHENYLSULFANYL)ACRYLIC ACID ETHYL ESTER; 3 (BENZOTHIAZOL 2 YLOXY)ACRYLIC ACID ETHYL ESTER; 3 (BENZOTHIAZOL 2 YLSULFANYL)ACRYLIC ACID ETHYL ESTER; 3 (NAPHTALEN 1 YLOXY)ACRYLIC ACID ETHYL ESTER; 3 (NAPHTHALEN 1 YLTHIO)ACRYLIC ACID ETHYL ESTER; 3 (NAPHTHALEN 2 YLOXY)ACRYLIC ACID ETHYL ESTER; 3 (NAPHTHALEN 2 YLTHIO)ACRYLIC ACID ETHYL ESTER; 3 (O OLYLOXY)ACRYLIC ACID ETHYL ESTER; 3 (PYRIDIN 2 YLSULFANYL)ACRYLIC ACID ETHYL ESTER; 3 (PYRIDIN 3 YLOXY)ACRYLIC ACID ETHYL ESTER; 3 (PYRIMIDIN 2 YLSULFANYL)ACRYLIC ACID ETHYL ESTER; 3 (THIOPHEN 2 YLTHIO)ACRYLIC ACID ETHYL ESTER; 3 CYCLOHEXYLSULFANYL ACRYLIC ACID ETHYL ESTER; ACRYLIC ACID ETHYL ESTER; ISONIAZID; RIFAMPICIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG; 3-(4-TERT-BUTYL-PHENYLSULFANYL)ACRYLIC ACID ETHYL ESTER; 3-(BENZOTHIAZOL-2-YLSULFANYL)ACRYLIC ACID ETHYL ESTER; ACRYLIC ACID DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; COPPER; SULFIDE;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; BACILLUS CEREUS; BACTERIOSTASIS; CATALYSIS; CHEMICAL REACTION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MOUSE; MYCOBACTERIUM AVIUM; MYCOBACTERIUM CHELONEI; MYCOBACTERIUM FORTUITUM; MYCOBACTERIUM INTRACELLULARE; MYCOBACTERIUM KANSASII; MYCOBACTERIUM SMEGMATIS; NONHUMAN; STAPHYLOCOCCUS AUREUS; CHEMISTRY; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; MYCOBACTERIUM; SYNTHESIS;

ACRYLATES; ANTITUBERCULAR AGENTS; BENZOTHIAZOLES; CATALYSIS; COPPER; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM; SULFIDES;

MYCOBACTERIUM; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NEGIBACTERIA; POSIBACTERIA;

EID: 77953321477     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.05.016     Document Type: Article

References (17)

1. World Health Organization, Global Tuberculosis Report 2009, http://www.who.int/tb/publications/global_report/2009/pdf/fullreport.pdf .
2. Harper C. Nat. Med. 13 (2007) 309
3. Lew W., Pai M., Oxlade O., Martin D., and Menzies D. Ann. Intern. Med. 149 (2008) 123
4. Cox H., Kebede Y., Allamuratova S., Ismailov G., Davletmuratova G., Byrnes G., Stone C., Niemann S., Rüsch-Gerdes S., Blok L., and Doshetov D. PLoS Med. 3 (2006) e384
5. Kabir M.S., Engelbrecht K., Polanowski R., Krueger S.M., Ignasiak R., Rott M., Schwan W.R., Stemper M.E., Reed K.D., Sherman D., Cook J.M., and Monte M. Bioorg. Med. Chem. Lett. 18 (2008) 5745
6. Monte, A.; Kabir, M. S.; Cook, J. M.; Rott, M.; Schwan, W. R.; Defoe, L. U.S. Pat. Appl. Publ., 2007, 37 pp.
7. Unpublished results.
8. Neck T.V., Pannecouque C., Vanstreels E., Stevens M., Dehaen W., and Daelemans D. Bioorg. Med. Chem. 16 (2008) 9487
9. Kabir M.S., Linn M.L.V., Monte M., and Cook J.M. Org. Lett. 10 (2008) 3363
10. Kabir M.S., Lorenz M., Namjoshi O.A., and Cook J.M. Org. Lett. 12 (2010) 464
11. Kawashita Y., Ueba C., and Hayashi M. Tetrahedron Lett. 47 (2006) 4231
12. Haneda S., Zhibin G., Eda K., and Hayashi M. Organometallics 26 (2007) 6551
13. Haneda S., Adachi Y., and Hayashi M. Tetrahedron 65 (2009) 10459
14. Bourn W.R., Jansen Y., Stutz H., Warren R.M., Williamson A.-L., and van Helden P.D. Tuberculosis 87 (2007) 481
15. Hathaway W.E., Newby L.A., and Githens J.H. Blood 23 (1964) 517
16. Wayne P.A. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. 6th ed. (2005), Clinical and Laboratory Standards Institute Approved standard M7-A6
17. Mdluli K., Sherman D.R., Hickey M.J., Kreiswirth B.N., Morris S., Stover C.K., and Barry C.E. J. Infect. Dis. 174 (1996) 1085