Synthesis and antimycobacterial activities of glycosylated amino alcohols and amines

European Journal of Medicinal Chemistry

Volumn 40, Issue 4, 2005, Pages 351-360

  Katiyar, D ^a   Tiwari, V K ^a   Tewari, N ^a   Verma, S S ^a   Sinha, S ^a   Gaikwad, A ^a   Srivastava, A ^a   Chaturvedi, V ^a   Srivastava, R ^a   Srivastava, B S ^a   Tripathi, R P ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Glycosyl amines; Glycosyl amino alcohols; MDR tuberculosis; Reductive amination; Tuberculosis

Indexed keywords

3 O BENZYL 5 CYCLOPROPYLAMINO 5,6 DIDEOXY 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE BETA IDOFURANOSE; 3 O BENZYL 5 DEOXY 1,2 O ISOPROPYLIDEN 5 OLEYLAMINO ALPHA DEXTRO XYLOFURANOSE; 3 O BENZYL 5 DEOXY 5 DODECYLAMINO 1,2 O ISOPROPYLIDENE ALPHA DEXTRO XYLOFURANOSE; 3 O BENZYL 5,6 DIDEOXY 5 DODECYLAMINO 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE ALPHA DEXTRO GLUCOFURANOSE; 3 O BENZYL 5,6 DIDEOXY 5 DODECYLAMINO 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE BETA IDOFURANOSE; 3 O BENZYL 5,6 DIDEOXY 5 HEXADECYLAMINO 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE BETA IDOFURANOSE; 3 O BENZYL 5,6 DIDEOXY 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDEN 5 OLEYLAMINO ALPHA DEXTRO GLUCOFURANOSE; 3 O BENZYL 5,6 DIDEOXY 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDEN 5 OLEYLAMINO BETA IDOFURANOSE; 5 CYCLOPROPYLAMINO 5,6 DIDEOXY 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE 3 O METHYL BETA IDOFURANOSE; 5 DEOXY 5 HEXADECYLAMINO 1,2 O ISOPROPYLIDENE 3 O METHYL ALPHA DEXTRO XYLOFURANOSE; 5,6 DIDEOXY 5 DODECYLAMINO 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE 3 O METHYL ALPHA DEXTRO GLUCOFURANOSE; 5,6 DIDEOXY 5 DODECYLAMINO 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE 3 O METHYL BETA IDOFURANOSE; 5,6 DIDEOXY 5 HEPTYLAMINO 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE 3 O METHYL BETA IDOFURANOSE; 5,6 DIDEOXY 5 HEXADECYLAMINO 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE 3 O METHYL ALPHA DEXTRO GLUCOFURANOSE; 5,6 DIDEOXY 5 HEXADECYLAMINO 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE 3 O METHYL BETA IDOFURANOSE; 5,6 DIDEOXY 6 HYDROXYMETHYL 6 HYDROXYMETHYL 1,2 O ISOPROPYLIDENE 3 O METHYL 5 OLEYLAMINO BETA IDOFURANOSE; 6 CYCLOHEXYLAMINO 6 DEOXY 1,2:3,4 DI O ISOPROPYLIDENE 7 HYDROXYMETHYL BETA GLYCERO DEXTRO GALACTOHEPTOPYRANOSE; 6 CYCLOPROPYLAMINO 6 DEOXY 1,2:3,4 DI O ISOPROPYLIDENE 7 HYDROXYMETHYL BETA GLYCERO DEXTRO GALACTOHEPTOPYRANOSE; 6 DEOXY 1,2:3,4 DI O ISOPROPYLIDENE 6 HEPTYLAMINO 7 HYDROXYMETHYL BETA GLYCERO DEXTRO GALACTOHEPTOPYRANOSE; 6 DEOXY 1,2:3,4 DI O ISOPROPYLIDENE 6 HEXADECYLAMINO 7 HYDROXYMETHYL ALPHA GLYCERO DEXTRO GALACTOHEPTOPYRANOSE; 6 DEOXY 1,2:3,4 DI O ISOPROPYLIDENE 6 HEXADECYLAMINO 7 HYDROXYMETHYL BETA GLYCERO DEXTRO GALACTOHEPTOPYRANOSE; 6 DEOXY 1,2:3,4 DI O ISOPROPYLIDENE 6 HEXADECYLAMINO ALPHA DEXTRO GALACTOPYRASONE; 6 DEOXY 1,2:3,4 DI O ISOPROPYLIDENE 7 HYDROXYMETHYL 6 OLEYLAMINO BETA GLYCERO DEXTRO GALACTOHEPTOPYRANOSE; 6 DEOXY 6 DODECYLAMINO 1,2:3,4 DI O ISOPROPYLIDENE 6 HEPTYLAMINO 7 HYDROXYMETHYL BETA GLYCERO DEXTRO GALACTOHEPTOPYRANOSE; 6 DEOXY 6 DODECYLAMINO 1,2:3,4 DI O ISOPROPYLIDENE ALPHA DEXTRO GALACTOPYRASONE; AMINE; AMINOALCOHOL; ANTIMYCOBACTERIAL AGENT; UNCLASSIFIED DRUG;

AMINATION; ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; REDUCTION; STRUCTURE ACTIVITY RELATION;

EID: 20144389749     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejmech.2004.12.002     Document Type: Article

References (26)

1. (a) E. Stokstad, Science 287 (2000), 2391. http://www.who.int/ mediacentre/factsheets/who104/en/index.html (WHO Global tuberculoasis programme-Tuberculosis Fact Sheet, 2002) World Health Organisation. Global Tuberculosis Control, WHO Report 2001.
2. (b) World Health Organisation, Geneva, Switzerland, WHO/CDS/TB/2001, 287.
3. N. Mooran World Health Organisation Nat. Med. 2 1996 377
4. C. Dye, S. Scheele, P. Dolin, V. Pathania, and M.C. Raviglione JAMA 282 1999 677 686
5. M.C. Raviglione, D.E. Snider Jr., and A. Kochi JAMA 273 1995 220 226
6. (a) P. Farmer, J. Bayona, M. Beccera, J. Henry, C. Furin, H. Hiarr, J.Y. Kim, C. Mimic, E. Nardell, S. Shin, Int. J. Tuberc. Lung Dis. 2 (1998) 869-876.
7. (b) S.W. Dooley, W.R. Jarvis, W.J. Martone, D.E. Snyder Jr., Ann. Intern. Med. 117 (1992) 257-259.
8. I. Chopra, and P. Brennan Tubercle Lung Dis. 78 2 1988 89 98
9. J.S. Blanchard Annu. Rev. Biochem. 65 1996 215 239
10. D. Mitchison, and P. Nunn Am. Rev. Respir. Dis. 133 1986 423 430
11. D.B. Young, and T.R. Garbe Res. Microbiol. 142 1991 55 65
12. N.D. Connel, and H. Nikaido Membrane permeability and transport B.R. Bloom Mycobacterium tuberculosis 1994 Pathogenesis, Protection and Control, American Society for Microbiology Washington, DC 233
13. (a) P.J. Brennan, Ann. Rev. Biochem. 64 (1995) 29-63.
14. (b) R.P. Tripathi, N. Tewari, N. Dwivedi, V. Tiwari, Med. Res. Rev. 25 (2005) 93-131.
15. N.E. Caceres, N.B. Harris, J.F. Wellehan, Z. Feng, V. Kapur, and R.G. Barletta J. Bacetriol. 179 1997 5046 5055
16. J.T. Belisle, V.D. Visaa, T. Sievert, K. Takayama, P.J. Brennan, and G.S. Besra Science 276 1997 1420 1422
17. J.A. Maddry, N. Bansal, L.E. Bermudez, R.N. Comber, I.M. Orme, and W.J. Suling Bioorg. Med. Chem. Lett. 8 1998 237 342
18. (a) R.P. Tripathi, R. Tripathi, V.K. Tiwari, L. Bala, S. Sinha, A. Srivastava, R. Srivastava, B.S. Srivastava, Eur. J. Med. Chem. 37 (2002) 773-781.
19. (b) N. Tewari, V.K. Tiwari, R.C. Mishra, R.P. Tripathi, A.K. Srivastava, R. Ahemad, R. Srivastava, B.S. Srivastava, Bioorg. Med. Chem. 11 (2003) 2911-2922.
20. (c) N. Tewari, V.K. Tiwari, R.P. Tripathi, A. Gaikwad, S. Sinha, P.K. Shukla, R. Srivastava, B.S. Srivastava, Bioorg. Med. Chem. Lett. 12 (2004) 329-332.
21. D. Katiyar, R.C. Mishra, and R.P. Tripathi J. Carbbohydr. Chem. 23 1 2004 49 70
22. J. Jurczak, S. Pikul, and T. Bauer Tetrahedron 42 1986 447 488
23. M.L. Wolform, and S.J. Hanessian Org. Chem. 27 1962 1800 1804
24. H.A. Johnson, and N.R. Thomas Bioorg. Med. Chem. Lett. 12 2002 237 241
25. L.A. Collins, and S.G. Franzblan Antimicrob. Agents Chemother. 41 1997 1004 1009
26. H. Saito, H. Tomioka, K. Sato, M. Emori, T. Yamane, and K. Yamashita Antimicrob. Agents Chemother. 35 1991 542 547