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Quinolines
Quinoline alkaloids are found in a wide variety of compounds including dyes, organic materials, biologically active compounds and natural products. BioBlocks currently offers a diverse assortment of over 1,100 substituted quinoline scaffolds. Substitutents include halogen atoms, hydrazines, aryl groups, tri-fluoromethyl groups, esters, nitriles, hydroxyl groups and carboxylic acids. Substitution patterns off the quinoline core vary in position, quantity and combination. All analogs are available in 100 mg to multi-gram quantities.
Quinoline containing drugs have been employed for treatment of parasitic infections such as malaria1 and leishmaniasis.2 The tumorcidal agents streptonigrin,3 luotonin A,4 dynemicin A,5 and camptothecin6 are also built around quinoline cores. Further pharmacological properties have been exhibited by quinoline containing compounds such as HIV-1 replication inhibition7 and inhibition of VEGF receptors for the treatment of West Nile Virus.8 In additional to their pharmaceutical uses, quinoline derivatives have been used as ligands for the preparation of OLED phosphorescent complexes9 and as conjugated polymers used as selective chemosensors of the fluoride and metal ions.10
The schemes below illustrate the versatility of the chemistry possible with 4-halo substituted quinolines. Aromatic substitution with a variety of nucleophiles proceeds at to afford products in good yields (scheme 1).11 Treatment of the 4-halo substituted quinolines with alkenes under standard Heck and Suzuki conditions have also been described (scheme 2).12 The resulting vinyl quinolines act as Michael acceptors and may be further functionalized with strong nucleophiles.
scheme 1
scheme 2
Triazolo-quinoline derivatives have been synthesized by treatment of 2-hydrazino-quinolines with aldehydes (scheme 3). Such products have been employed as novel Neurokinin (NK1) receptor ligands.13
scheme 3
(1) Foley, M.; Tilley, L. Pharmacol. Ther. 1998, 79, 55-87.
(2) Croft, S. L.; Coombs, G. H. Trends Parasitol. 2003, 19, 502-508.
(3) Bringmann, G.; Reichert, Y.; Kane, V. V. Tetrahedron 2004, 60, 3539-3574.
(4) Wang, H.; Ganesan, A. Tetrahedron Lett. 1998, 39, 9097-9098.
(5) Myers, A. G.; Tom, N. J.; Fraley, M. E.; Cohen, S. B.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 6072-6094.
(6) Comins,
D. L.; Hong, H.; Saha, J. K.; Jianhua, G. J. Org. Chem. 1994, 59,
5120-5121.
(7) Normand-Bayle, M.; Bérnard, C.; Zouhiri, F.; Mouscadet, J. F.; Leh, H.; Thomas, C. M.; Mbemba, G.; Desmaële, D.; d’Angelo, J. Bioorg. Med. Chem. Lett. 2005, 15, 4019.
(8) Goodell, J. R.; Puig-Basagoiti, F.; Forshey, B. M.; Shi, P. Y.; Ferguson, D. M. J. Med. Chem. 2006, 49, 2127.
(9) Kim, J. L.; Shin,
(10) (a) Tong, H.; Wang, L.; Jing, X.; Wang, F. Macromolecules 2003, 36, 2584. (b) Tumambac, G. E.; Rosencrance, C. M.; Wolf, C. Tetrahedron 2004, 60, 11293.
(11) (a) Madrid, Peter B.; Sherrill,
John; Liou, Ally P.; Weisman, Jennifer L.; DeRisi, Joseph L.; Guy, R. Kiplin. Bioorganic
& Medicinal Chemistry Letters 2005,
15(4), 1015-1018.
(b) Kawashima, Tadashi; Nagayama, Satoshi; Nakao, Kazunari; Tanaka,
Hirotaka., WO 2008007211.
(12) Miller, William Henry; Pearson, Neil David; Pendrak, Israil; Seefeld, Mark Andrew.. WO 2003064421.
(13) Cappellia, A.; Giuliania, G.; Anzinia, M.; Riitanob, D.; Giorgic, G.; Vomeroa, S. Bioorganic & Medicinal Chemistry Letters 2008, 16, 6850-6859.