Abstract
Quinolone derivatives have attracted considerable attention due to their medicinal properties. This review covers many synthetic routes of quinolones preparation with their antibacterial properties. Detailed study with structure-activity relationship among quinolone derivatives will be helpful in designing new drugs in this field.
Keywords: Quinolones, fluoroquinolones, antibacterial, biological activity, naphthyridine, synthesis.
Graphical Abstract
[PMID: 11858629]
[http://dx.doi.org/10.2165/00003495-198733040-00003] [PMID: 3297617]
[http://dx.doi.org/10.1128/AAC.38.12.2877] [PMID: 7695276]
[http://dx.doi.org/10.1071/PH490272]
[http://dx.doi.org/10.1016/S0040-4039(00)85103-5]
[http://dx.doi.org/10.1071/PH490272]
[http://dx.doi.org/10.1021/jm01240a021] [PMID: 14056431]
[http://dx.doi.org/10.1002/(SICI)1098-1128(199609)16:5<433:AID-MED3>3.0.CO;2-W] [PMID: 8865150]
[http://dx.doi.org/10.1021/jm00186a014] [PMID: 7452690]
[http://dx.doi.org/10.1021/jm990438d] [PMID: 10841806]
(b)Krishnan, R.; Lang, S.A. Antibacterial activity of 6,8-disubstituted-quinolone-3-carboxylic acids. J. Pharm. Sci., 1986, 75(12), 1185-1187.
[http://dx.doi.org/10.1002/jps.2600751214] [PMID: 3104580]
(c)Sanna, P.; Sequi, P.A.; Piras, S.; Paglietti, G. Reaction of 5-aminobenzotriazoles with methyl propiolate. formation of triazolo[4,5-f]quinolines and related compounds. Unusual products in the Michael addition reaction of 2-methyl-2h-5-aminobenzotriazole. Heterocycles, 1995, 45, 2459-2474.
[http://dx.doi.org/10.3987/COM-95-7145]
[http://dx.doi.org/10.1016/S0065-2725(08)60667-4]
[http://dx.doi.org/10.1021/ja01265a088]
[http://dx.doi.org/10.1128/aac.43.5.1077] [PMID: 10223917]
[http://dx.doi.org/10.1248/cpb.19.1426]
[http://dx.doi.org/10.1021/jm00235a017] [PMID: 803246]
[http://dx.doi.org/10.1002/jhet.5570220421]
[http://dx.doi.org/10.1021/jm00400a016] [PMID: 3361584]
[http://dx.doi.org/10.1093/jac/31.1.73] [PMID: 8383104]
[http://dx.doi.org/10.1093/jac/31.4.505] [PMID: 7605398]
[http://dx.doi.org/10.1128/AAC.43.5.1077] [PMID: 10223917]
[http://dx.doi.org/10.1128/AAC.23.4.559]
[http://dx.doi.org/10.1128/AAC.25.4.518] [PMID: 6732221]
[http://dx.doi.org/10.1128/aac.24.1.54] [PMID: 6226241]
[http://dx.doi.org/10.1248/cpb.30.2399] [PMID: 7139814]
[http://dx.doi.org/10.1021/jm00369a011] [PMID: 6422043]
[http://dx.doi.org/10.1002/0471264180.or005.04]
[PMID: 5596176]
[http://dx.doi.org/10.1086/321846]
[http://dx.doi.org/10.1128/AAC.23.5.641] [PMID: 6575721]
[http://dx.doi.org/10.1007/978-3-0348-7098-6_1] [PMID: 339272]
[http://dx.doi.org/10.1021/jm00149a003] [PMID: 3934382]
[http://dx.doi.org/10.1021/jm00216a010] [PMID: 406396]
[http://dx.doi.org/10.1021/jm00158a037] [PMID: 3090265]
[http://dx.doi.org/10.1002/jhet.5570210309]
[http://dx.doi.org/10.1021/jo01316a039]
[http://dx.doi.org/10.1021/jm00161a036] [PMID: 3783594]
[http://dx.doi.org/10.1016/S0040-4020(01)92570-0]
[http://dx.doi.org/10.1021/jo01031a067]
[http://dx.doi.org/10.1055/s-1979-28830]
[http://dx.doi.org/10.1021/jm00400a017] [PMID: 2834557]
[http://dx.doi.org/10. 1021/jm00158a037]
[http://dx.doi.org/10.1002/cber.19320650722]
[http://dx.doi.org/10.1021/jm00086a007] [PMID: 1573632]
[http://dx.doi.org/10.1128/AAC.33.1.1] [PMID: 2540705]
[http://dx.doi.org/10.1093/jac/26.3.381] [PMID: 2228828]
[http://dx.doi.org/10.1093/jac/19.5.611] [PMID: 3112094]
[PMID: 7751043]
[http://dx.doi.org/10.1093/jac/19.5.605]
[http://dx.doi.org/10.1055/s-1975-23685]
[http://dx.doi.org/10.1002/jps.2600571210] [PMID: 5708346]
[http://dx.doi.org/10.1016/0022-328X(91)83143-R]
[http://dx.doi.org/10.1248/cpb.41.148] [PMID: 8448815]
[http://dx.doi.org/10.1021/jm9507082] [PMID: 8576916]
[http://dx.doi.org/10.1021/jm990015b]
(b)Simon, H.; Kraus, A. Mechanistische Untersuchungen über Glykosylamine, Zuckerhydrazone, Amadori-Umlagerungsprodukte und Osazone. Fortschr. Chem. Forsch., 1970, 14, 430-471.
[http://dx.doi.org/10.1007/BFb0050813]
[http://dx.doi.org/10.1021/jm990015b] [PMID: 10508438]
[http://dx.doi.org/10.1016/S0008-6215(96)00321-7]
(b)Gervay, J.; Hadd, M.J. Anionic additions to glycosyl iodides: highly stereoselective syntheses of β C-, N-, and O-glycosides. J. Org. Chem., 1997, 62, 6961-6967.
[http://dx.doi.org/10.1021/jo970922t]
[http://dx.doi.org/10.1016/S0096-5332(08)60392-6] [PMID: 13292324]
[http://dx.doi.org/10.1021/jm0100335] [PMID: 11428933]
[http://dx.doi.org/10.1021/jm000153x] [PMID: 11020298]
[http://dx.doi.org/10.1002/jhet.5570350429]
[http://dx.doi.org/10.1021/jm970202e] [PMID: 9357525]
[http://dx.doi.org/10.1021/jm990191k] [PMID: 10514290]
[http://dx.doi.org/10.1135/cccc19892181]
[http://dx.doi.org/10.1002/ardp.19963290403] [PMID: 8669982]
[http://dx.doi.org/10.1248/cpb.44.1074] [PMID: 8689718]
[http://dx.doi.org/10.1021/jm020328y] [PMID: 12620077]
[http://dx.doi.org/10.1093/jac/33.4.685] [PMID: 8056688]
[http://dx.doi.org/10.1021/jm00074a027] [PMID: 8230135]
[http://dx.doi.org/10.1021/jm00046a019] [PMID: 7932562]
[http://dx.doi.org/10.1248/cpb.44.1376] [PMID: 8706143]
[http://dx.doi.org/10.1248/cpb.48.1667] [PMID: 11086894]
[http://dx.doi.org/10.1128/AAC.23.4.559] [PMID: 6222695]
[http://dx.doi.org/10.1016/S0040-4039(97)01334-8]
[http://dx.doi.org/10.1016/S0040-4039(96)02390-8]
[http://dx.doi.org/10.1002/chin.200027259]
[http://dx.doi.org/10.1021/jm030272n] [PMID: 12904069]
[http://dx.doi.org/10.1021/jm00398a003] [PMID: 3346869]
[http://dx.doi.org/10.1021/jm00006a017] [PMID: 7699714]
[http://dx.doi.org/10.1021/jm950558v] [PMID: 8558512]
[http://dx.doi.org/10.1128/AAC.35.2.345] [PMID: 1827242]
[http://dx.doi.org/10.1128/AAC.38.2.163]
[http://dx.doi.org/10.1128/AAC.35.8.1679] [PMID: 1656873]
[http://dx.doi.org/10.1002/qsar.19910100405]
[http://dx.doi.org/10.1021/ja00997a067]
[http://dx.doi.org/10.1021/jm960414w] [PMID: 8960555]
[http://dx.doi.org/10.2165/00003495-199500492-00009] [PMID: 8549407]
[http://dx.doi.org/10.1128/AAC.41.6.1250] [PMID: 9174179]
[PMID: 9614214]
[http://dx.doi.org/10.1021/jm9903390] [PMID: 11020296]
[http://dx.doi.org/10.1021/jm049721p]
[http://dx.doi.org/10.3109/03602537708993766]
[http://dx.doi.org/10.1021/jm00105a013] [PMID: 1992156]
[http://dx.doi.org/10.1016/0223-5234(96)88301-2]
[http://dx.doi.org/10.1021/bi00435a039]
[http://dx.doi.org/10.1016/0960-894X(96)00430-1]
[http://dx.doi.org/10.1016/S0223-5234(98)80028-7]
[http://dx.doi.org/10.3109/07853899708998743] [PMID: 9073324]
[http://dx.doi.org/10.1021/acs.jmedchem.6b01615]
[http://dx.doi.org/10.2165/00003495-199500492-00016] [PMID: 8549277]
[http://dx.doi.org/10.1021/jo00368a017]
[http://dx.doi.org/10.1021/jm0105326] [PMID: 12014972]
[http://dx.doi.org/10.1021/jm00079a028]
[http://dx.doi.org/10.1016/S0960-894X(03)00399-8] [PMID: 12824037]
[http://dx.doi.org/10.1016/j.ejmech.2008.01.042]
[http://dx.doi.org/10.1128/AAC.49.9.3977-3979.2005] [PMID: 16127087]
[http://dx.doi.org/10.13005/ojc/290216]
[http://dx.doi.org/10.1016/j.ejmech.2013.06.056] [PMID: 23933534]