Synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis

European Journal of Pharmaceutical Sciences

Volumn 30, Issue 1, 2007, Pages 26-35

  Gundersen, Lise Lotte ^a   Charnock, Colin ^b   Negussie, Ayele Hailu ^a   Rise, Frode ^a   Teklu, Solomon ^a  

^a UNIVERSITY OF OSLO   (Norway)

^b OSLO METROPOLITAN UNIVERSITY   (Norway)

Author keywords

Antimicrobial; Indolizine; Tuberculosis

Indexed keywords

(2 METHYLINDOLIZIN 1 YL)(PHENYL)METHANONE; 1 (1 HEXEN 1 YL) 2,3 DIPHENYLINDOLIZINE 7 CARBONITRILE; 1 (1 HYDROXY 2,2 DIMETHYLPROPYL) 2,3 DIPHENYLINDOLIZINE 7 CARBONITRILE; 1 (1 HYDROXY 3 METHYLBUTYL) 2,3 DIPHENYLINDOLIZINE 7 CARBONITRILE; 1 (1 HYDROXYBUTYL) 2,3 DIPHENYLINDOLIZINE 7 CARBONITRILE; 1 (1 HYDROXYDECYL) 2,3 DIPHENYLINDOLIZINE 7 CARBONITRILE; 1 (1 HYDROXYHEXYL) 2,3 DIPHENYLINDOLIZINE 7 CARBONITRILE; 1 (1 HYDROXYOCTYL) 2,3 DIPHENYLINDOLIZINE 7 CARBONITRILE; 1 (1 HYDROXYPENTYL) 2,3 DIPHENYLINDOLIZINE 7 CARBONITRILE; 1 (1 HYDROXYPROPYL) 2,3 DIPHENYLINDOLIZINE 7 CARBONITRILE; 1 [2 (TRIMETHYLSILYL)ETHOXYMETHOXY] PHENYLMETHYL 2,3 DIPHENYLINDOLIZINE 7 CARBONITRILE; 1 BENZOYL 2 PHENYLINDOLIZINE 7 CARBONITRILE; 2 METHYLINDOLIZINE 1 CARBONITRILE; 2 PHENYLINDOLIZINE 1 CARBONITRILE; 3 (1 BENZOYL 2 PHENYLINDOLIZIN 3 YL) 1,3 DIPHENYLPROPAN 1 ONE; 4 CYANO 1 (METHOXYCARBONYLMETHYL)PYRIDINIUM BROMIDE; 4 CYANO N METHYLPYRIDINIUM CHLORIDE; [1 ( ETHOXYPHENYLMETHYL) 2,3 DIPHENYLINDOLIZIN 1 YL]ETHANONE; [1 (2 NITRO 1 PHENYLETHYL) 2,3 DIPHENYLINDOLIZIN 1 YL]PENTANONE; [1 (HYDROXYPHENYLMETHYL) 2,3 DIPHENYLINDOLIZIN 1 YL]ETHANONE; [1 (HYDROXYPHENYLMETHYL) 2,3 DIPHENYLINDOLIZIN 1 YL]PENTANONE; [1 (METHOXYPHENYLMETHYL) 2,3 DIPHENYLINDOLIZIN 1 YL]ETHANONE; [1 [2 (TRIMETHYLSILYL)ETHOXYMETHOXY]PHENYLMETHYL 2,3 DIPHENYLINDOLIZIN 1 YL]ETHANONE; [1 [2 (TRIMETHYLSILYL)ETHOXYMETHOXY]PHENYLMETHYL 2,3 DIPHENYLINDOLIZIN 1 YL]PENTANONE; INDOLIZIN 1 YL(PHENYL)METHANONE; INDOLIZINE 1 CARBONITRILE; INDOLIZINE DERIVATIVE; N (CARBOXYMETHYL)PYRIDINIUM CHLORIDE; PHENYL(2 PHENYLINDOLIZIN 1 YL)METHANONE; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA KRUSEI; DRUG SYNTHESIS; MYCOBACTERIUM TUBERCULOSIS; PRIORITY JOURNAL;

ANIMALS; ANTIFUNGAL AGENTS; ANTIPROTOZOAL AGENTS; ANTITUBERCULAR AGENTS; CELL SURVIVAL; CERCOPITHECUS AETHIOPS; INDOLIZINES; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; VERO CELLS;

EID: 33845380273     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2006.09.006     Document Type: Article

References (33)

1. Brown E.D., and Wright G.D. New targets and screening approaches in antimicrobial drug discovery. Chem. Rev. 105 (2005) 759-774
2. Ceder O., and Sharif M.R. The reaction of indolizines with esters of orthoformic acid: synthesis of tris-indolizine molecular propellers. Chem. Ber. 120 (1987) 239-242
3. Collins L., and Franzblau S.G. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother. 41 (1997) 1004-1009
4. Dainis I. Indolizines. I. Direct synthesis of acylindolizines from substituted pyridinium salts. Aust. J. Chem. 25 (1972) 1003-1024
5. Global Alliance for TB Drug Development, 2005. The Need for New TB Drugs, http://www.tballiance.org/.
6. Gundersen L.-L., Malterud K.E., Negussie A.H., Rise F., Teklu S., and Østby O.B. Indolizines as novel potent inhibitors of 15-lipoxygenase. Bioorg. Med. Chem. 11 (2003) 5409-5419
7. Gundersen L.-L., Negussie A.H., Rise F., and Østby O.B. Antimycobacterial activity of 1-substituted indolizines. Arch. Pharm. Pharm. Med. Chem. 336 (2003) 191-195
8. Hurst J., Melton T., and Wibberley D.G. Indolizines. III. J. Chem. Soc. (1965) 2948-2955
9. Krapcho A.P. Synthetic applications of dealkoxycarbonylations of malonate esters, β-keto esters, α-cyano esters and related compounds in dipolar aprotic media-part I. Synthesis (1982) 805-822
10. Lemke T.L. Antiparasitic agents. In: Williams D.A., and Lemke T.L. (Eds). Foye's Principles of Medicinal Chemistry. 5th ed. (2002), Lipincott Williams and Wilkins, Philadelphia 867
11. Lipinski C.A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Meth. 44 (2000) 235-249
12. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug. Deliv. Rev. 46 (2001) 3-26
13. Lipshutz B.H., and Pegram J.J. β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group. Tetrahedron Lett. 21 (1980) 3343-3346
14. Lipshutz B.H., and Miller T.A. Deprotection of β-(trimethylsilyl)ethoxymethyl (SEM) ethers: a convenient general procedure. Tetrahedron Lett. 30 (1989) 7149-7152
15. Mahon J., Mehta L.K., Middleton R.W., Parrick J., and Rami H.K. Studies of some indolizine derivatives useful as fluorophores. J. Chem. Res. (S) (1992) 362-363
16. Nasir A.I., Gundersen L.-L., Rise F., Antonsen Ø., Kristensen T., Langhelle B., Bast A., Custers I., Haenen G.R.M.M., and Wikström H. Inhibition of lipid peroxidation mediated by indolizines. Bioorg. Med. Chem. Lett. 8 (1998) 1829-1832
17. National Committee for Clinical Laboratory Standards. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. Approved Standard M27-A (1997), National Committee for Clinical Laboratory Standards, Wayne, PA
18. Orme I., Secrist J., Anathan S., Kwong C., Maddry J., Reynolds R., Poffenberger A., Michael M., Miller L., Krahenbuh J., Adams L., Biswas A., Franzblau S.G., Rouse D., Winfield D., and Brooks J. Search for new drugs for treatment of tuberculosis. Antimicrob. Agents Chemother. 45 (2001) 1943-1946
19. Østby O.B., Dalhus B., Gundersen L.-L., Rise F., Bast A., and Haenen G.R.M.M. Synthesis of 1-substituted 7-cyano-2,3-diphenylindolizines and evaluation of antioxidant properties. Eur. J. Org. Chem. 9 (2000) 3763-3770
20. Østby O.B., Gundersen L.-L., Rise F., Antonsen Ø., Fosnes K., Larsen V., Bast A., Custers I., and Haenen G.R.M.M. Synthesis of 5-substituted pyrrolo[1,2-b]pyridazines with antioxidant properties. Arch. Pharm. Pharm. Med. Chem. 334 (2001) 21-24
21. Pauls H., and Kroehnke F. Investigations on 2-chloropyridinium salts. III. Reactions with CH-acidic compounds and cyclization to indolizines. Chem. Ber. 110 (1977) 1294-1303
22. Pratt E.F., and McGovern T.P. Oxidation by solids. III. Benzalanilines from N-benzylanilines and related oxidations by manganese dioxide. J. Org. Chem. 29 (1964) 1540-1543
23. Sashida H., Kato M., and Tsuchiya T. Thermal rearrangements of cyclic amine ylides. VIII. Intramolecular cyclization of 2-ethynylpyridine N-ylides into indolizines and cycl[3.2.2]azines. Chem. Pharm. Bull. 36 (1988) 3826-3832
24. Shipman M. Product class 16: indolizines. Sci. Synth. 10 (2001) 745-787
25. Tamura Y., Tsuimoto N., Sumida Y., and Ikeda M. Intramolecular 1,5-cyclization of ylides. Synthesis of pyrazolo[1,5-a]pyridines and indolizines. Tetrahedron 28 (1972) 21-27
26. Teklu S., Gundersen L.-L., Malterud K.E., Larsen T., and Rise F. Indolizine 1-sulfonates as potent inhibitors of 15-lipoxygenase from soybeans. Bioorg. Med. Chem. 13 (2005) 3127-3139
27. Teklu S., Gundersen L.-L., Rise F., and Tilset M. Electrochemical studies of biologically active indolizines. Tetrahedron 61 (2005) 4643-4656
28. Vakalopoulos A., and Hoffmann H.M.R. Novel deprotection of SEM ethers: a very mild and selective method using magnesium bromide. Org. Lett. 2 (2000) 1447-1450
29. Vorland L.H., Ulvatne H.M., Andersen J., Haukland H., Rekdal Ø., Svendsen J.S., and Gutteberg T. Lactoferricin of bovine origin is more active than lactoferricins of human, murine and caprine origin. Scand. J. Infect. Dis. 30 (1998) 513-517
30. Wadsworth D.H., Bender S.L., Smith D.L., Luss H.R., and Weidner C.H. Indolizines. 2. Preparation of 1- and 3-indolizinols and their esters. J. Org. Chem. 51 (1986) 4639-4644
31. Wadsworth D.H., Weidner C.H., Bender S.L., Nuttall R.H., Luss H.R., and Henry R. Indolizines. 3. Oxidation products of indolizinols: radicals, ions, and oxidized dimers. J. Org. Chem. 54 (1989) 3652-3660
32. World Health Organization, 2004. Workplan: Genomics and Discovery Research Committee, http://www.who.int/tdr/grants/workplans/gdr3.htm.
33. Zhang L., Liang F., Sun L., Hu Y., and Hu H. A novel and practical synthesis of 3-unsubstituted indolizines. Synthesis (2000) 1733-1737