Abstract
The quinolones, similar to the sulfonamides and nitrofurans, are totally synthetic chemical compounds used to combat infections (Albrecht 1977). They are derived by substitution of 1,4-dihydro-4-oxo-quinoline-3-carboxylic acids (structural formula 1) at the nitrogen atom of position 1.
Keywords
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Abdalla GM, Sowell JW Sr (1987) Synthesis of 8-cyano-l,4-dihydro-4-oxopyrrolo[l,2- a]pyrimidine-3-carboxylic acids as potential antimicrobial agents. J Heterocycl Chem 24:297
Abdalla GM, Sowell JW (1990) Synthesis of 3-benzoyl-4,7-dihydro-7-oxopyrrolo[3,2- b]pyridine-6-carboxylic acid derivatives as potential antimicrobial agents. J Heterocycl Chem 27:1201
Abdulla RF, Emmrick TL, Taylor HM (1977a) A new synthetic approach to 4(lh)- pyridone derivatives. I. l-Alkyl-3,5-diaryl-4(lh)-pyridones. Synth Commun 7:305
Abdulla RF, Fuhr KH, Taylor HM (1977b) New synthetic approaches to 4(lh)- pyridones. II. Derivatives having nonaromatic substituents. Synth Commun 7:313
Agui H, Mitani T, Nakashita M, Nakagome T (1971) Studies on quinoline derivatives and related compounds. I. A new synthesis of l-alkyl-l,4-dihydro-4-oxo-3-quinolinecarboxylic acids. J Heterocycl Chem 8:357
Agui H, Komatsu T, Nakagome T (1975a) Studies on quinoline derivatives and related compounds. II. Synthesis of 5-substituted l-ethyl-l,4-dihydro-4-oxo-3-quinolinecarboxylic acid (1). J Heterocycl Chem 12:557
Agui H, Tobiki H, Nakagome T (1975b) Studies on quinoline derivatives and related compounds. III. A novel pyridine synthesis to give substituted l,4-dihydro-4-oxonicotinic acids (1). J Heterocycl Chem 12:1245
Albrecht R (1977) Development of antibacterial agents of the nalidixic acid type. Prog Drug Res 21:9
Altreuther P (1987) Data on chemistry and toxicology of Baytril. Vet Med Rev 2:87
Ames DE, Chapman RF, Kucharska HZ (1964) Cinnolines. V.l. Methylation of some substituted cinnolines. J Chem Soc 5659
Ames DE, Leung OT, Singh AG (1983) Synthesis of l-aryl-4-oxo-lH,4H-cinnoline-3- carboxylic acid esters. Synthesis 52
Aoki M, Kamata M, Otsuka T, Shimma N, Yokose K (1988) European patent 259 804 (12.09.1986), Hoffmann-La Roche. Chem Abstr 109:73478r
Atarashi S, Yokohama S, Yamazaki K, Sakano K, Imamura M, Hayakawa I (1987) Synthesis and antibacterial activities of optically active ofloxacin and its fluoromethyl derivative. Chem Pharm Bull (Tokyo) 35:1896
Atarashi S, Tsurumi H, Fujiwara T, Hayakawa I (1991) Asymmetric reduction of 7,8- difluoro-3-methyl-2H-l,4-benzoxazine. Synthesis of a key intermediate of (S)-(-)- Ofloxacin (DR-3355). J Heterocycl Chem 28:329
Atarashi S, Imamura M, Kimura Y, Yoshida A, Hayakawa I (1993) Fluorocyclopropyl quinolones. 1. Synthesis and structure-activity relationships of l-(2- fluorocyclopropyl)-3-pyridonecarboxylic acid antibacterial agents. J Med Chem 36:3444
Augeri DJ, Fray AH, Kleinman EF (1990) Synthesis and antibacterial activity of 2,3- dehydroofloxacin. J Heterocycl Chem 27:1509
Bacon ER, Daum SJ (1991) Synthesis of 7-ethyl-4,7-dihydro-4-oxo-2-(4- pyridinyl)thieno[2,3-b]pyridine-5-carboxylic acid. J Heterocycl Chem 28:1953
Balogh M, Hermecz I, Meszaros Z, Simon K, Pusztay L, Horvath G, Dvortsak P (1980) Studies on chemotherapeutics. I. Synthesis of 5-substituted-4-oxo-l,4-dihydro-3-pyridinecarboxylic acid derivatives. J Heterocycl Chem 17:359
Barber HJ, Washbourn K, Wragg WR (1961) A new cinnoline synthesis. I. Cyclisation of mesoxalyl chloride phenylhydrazones to give substituted 4-hydroxycinnoline-3-carboxylic acids. J Chem Soc 2828
Barker JM, Huddleston PR, Jones AW (1978) Thienyl analogues of the alkaloids. 3. Analogues of echinorine and echinopsine; a convenient synthesis of thieno [3,2-b] pyridines. J Chem Res 393
Bassini C, Bismara C, Carlesso R, Feriano A, Gaviraghi G, Marchioro C, Perboni A, Shaw RE, Tamburini B, Tarzia G, Xerri L (1993) Synthesis and antimicrobial activity of DNA-gyrase inhibiting derivatives of 4-oxo-l,4-dihydro-3- pyridinecarboxylic acid. Farmaco [Sci] 48:159
Bauditz R (1987) Results of clinical studies with Baytril in calves and pigs. Vet Med Rev 2:122
Bayomi SM, Price KE, Sowell JW (1985) Synthesis of 7-oxopyrrolo[3,2-b] pyridine-6- carboxylic acid derivatives as potential antimicrobial agents. J Heterocycl Chem 22:83
Bell MR, Zalay AW, Oesterlin R, Schane P, Potts GO (1970) Basic ethers of l-(p- hydroxyphenyl)-2-phenyl-l,2,3,4-tetrahydroquinoline and l-(p-hydroxyphenyl)-2- phenylindole. Antifertility agents. J Med Chem 13:664
Biere H, Seelen W (1976) Verfahren zur Darstellung von 4-oxo-l,4- dihydropyridincarbonsäurederivaten. Liebigs Ann Chem 1972
Boamah PY, Haider N, Heinisch G (1990) Pyrido [2,3-c]pyridazines structurally related to nalidixic acid. Arch Pharm (Weinheim) 323:207
Borsche W, Herbert A (1941) Synthesen mit 5-Nitro-2-brom-acetophenon. Liebigs Ann Chem 546:293
Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Remuzon P, Weber A, Oki T, Masuyoshi M (1989) Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationships of new 1-substituted derivatives. J Med Chem 32:537
Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Kiechel JR, Remuzon P, Weber A, Oki T, Masuyoshi M, Kessler RE, Fung-Tome J, Desiderio J (1990) Fluoronaphthyridines and quinolones as antibacterial agents. 2. Synthesis and structure-activity relationships of new 1-tert-butyl 7-substituted derivatives. J Med Chem 33:1344
Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Ledonssal B, Remuzon P, Kessler RE, Fung-Tome J (1992) Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted-6-fluoro-7- (cycloalkylamino)-l,4-dihydro-4-oxo-l,8-naphthyridine-3-carboxylic acids. J Med Chem 35:518
Braish TF, Fox DE (1990) Synthesis of (S,S)- and (R,R)-2-alkyl-2,5- diazabicyclo[2.2.1]heptanes. J Org Chem 55:1684
Bridges AJ, Sanchez JP (1990) Synthesis of 7-amino-l,4-dihydro-4-oxo-6- (trifluoromethyl)-l,8-naphthyridines. The use of methylidenemalonate as an activating group and a sulfur assisted cyclization. J Heterocycl Chem 27:1527
Brundage RP, Lesher GY (1976) US patent 3 928 366 (10.03.1974), Sterling Drug. Chem Abstr 84:74253
Camps R (1901) Von der Amidophenylpropiolsäure zur Kynurensäure und deren Verwandten. Chem Ber 34:2703
Cecchetti V, Fravolini A, Fringuelli R, Mascellani G, Pagella PG, Palmioli M, Segre G, Terni P (1987) Synthesis of 7,12-dihydropyrido[3,4-b:5,4-b]diindoles. A novel class of rigid, planar benzodiazepine receptor ligands. J Med Chem 30:456
Cecchetti V, Fravolini A, Schiafella F (1991) One-pot synthesis of rufloxacin. Synth Commun 21:2301
Cecchetti V, Fravolini A, Pagella PG, Savino A, Tabarrini O (1993) Quinoline- carboxylic acids. 3. Synthesis and antibacterial evaluation of 2-substituted-7-oxo- 2,3-dihydro-7H-pyrido[l,2,3-de] [l,4]benzothiazine-6-carboxylic acids related to rufloxacin. J Med Chem 36:3449
Chiarino D, Napoletano M, Sala A (1988) Synthesis of 4,7-dihydro-4-oxoisoxazolo[5,4- b]pyridine-5-carboxylic acid derivatives as potential antimicrobial agents. J Heterocycl Chem 25:231
Chu DTW (1985a) South African patent 852 802 (27.11.1985), Abbott Lab. Chem Abstr 106:213930x
Chu DTW (1985b) A regiospecific synthesis of l-methylamino-6-fluoro-7-(4- methylpiperazin-l-yl)-l,4-dihydro-4-oxoquinoline-3-carboxylic acid. J Heterocycl Chem 22:1033
Chu DTW (1990) Syntheses of 6-fluoro-7-piperazin-l-yl-9-cyclopropyl-2,3,4,9- tetrahydroisothiazolo[5,4-b]quinoline-3,4-dione and 6-fluoro-7-piperazin-l-yl-9- p-fluorophenyl-2,3,4,9-tetrahydroisothiazolo[5,4-b] quinoline-3,4-dione. J Heterocycl Chem 27:839
Chu DTW, Claiborne AK (1987) Short syntheses of l,2,3,5-tetrahydrp-5- oxopyrrolo[l,2-a]quinoline-4-carboxylic acid and l,2,3,4-tetrahydro-6H-6- oxopyrido[l,2-a]quinoline-5-carboxylic acid derivatives. J Heterocycl Chem 24:1537
Chu DTW, Claiborne AK (1990) Practical synthesis of iminochlorothioformates: application of iminochlorothioformates in the synthesis of novel 2,3,4,9- tetrahydroisothiazolo[5,4b][l,8]naphthyridine-3,4-diones and 2,3,4,9-tetrahy- droisothiazolo[5,4-b]quinoline-3,4-dione derivatives. J Heterocycl Chem 27: 1191
Chu DTW, Fernandes PB, Claiborne AK, Pihuleac E, Nordeen CW, Maleczka RE Jr, Pernet AG (1985) Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents. J Med Chem 28:1558
Chu DTW, Fernandes PB, Pernet AG (1986) Synthesis and biological activity of benzothiazolo [3,2-a] quinolone antibacterial agents. J Med Chem 29:1531
Chu DTW, Lee CM, Li Q, Cooper CS, Plattner JJ (1992) WO 9 116 894 (02.05.1990), Abbott Lab. Chem Abstr 117:26583b
Coburn RA, Gala D (1982) Synthesis of 8-amino-6-methoxycinnoline. A precursor for 2-azaprimaquine. J Heterocycl Chem 19:757
Culbertson TP (1991) Synthesis of 4H-l,4-benzothiazine 1-oxide and 1,1-dioxide. Analogs of quinolone antibacterial agents. J Heterocycl Chem 28:1701
Dalhoff A, Petersen U, Endermann R (1996) In vitro activity of BAY 12–8039, a new methoxyquinolone. Chemotherapy (Basel) 42:410–425
Di Cesare P, Bouzard D, Essiz M, Jacquet JP, Ledonssal B, Kiechel JR, Remuzon P, Kessler RE, Fung-Tome J, Desiderio J (1992) Fluoronaphthyridines and quinolones as antibacterial agents. 5. Synthesis and antimicrobial activity of chiral l-tert-butyl-6-fluoro-7-substituted-naphthyridones. J Med Chem 35:4205
Dohmori R, Kadoya S, Takamura I, Suzuki N (1976) Synthetic chemotherapeutic agents. I. Synthesis of 2-substituted thiazolo [5,4-f] quinoline derivatives. Chem Pharm Bull (Tokyo) 24:130
Domagala JM, Heifetz CL, Hutt MP, Mich TF, Nichols JB, Solomon M, Worth DF (1988) 1-substituted 7-[3-[(ethylamino)methyl]-l-pyrrolidinyl]-6,8-difluoro-l,4- dihydro-4-oxo-3-quinolinecarboxylic acids. New quantitative structure-activity relationships at N2 for the quinolone antibacterials. J Med Chem 31:991
Dowlatshahi HA (1985) Synthesis of ethyl 7-methoxy-4-oxocinnoline-3-carboxylate. Synth Commun 15:1095
Egawa H, Miyamoto T, Minamida A, Nishimura Y, Okada H, Uno H, Matsumoto J (1984) Pyridonecarboxylic acids as antibacterial agents. 4. Synthesis and antibacterial activity of 7-(3-amino-l-pyrrolidinyl)-l-ethyl-6-fluoro-l,4-dihydro-4-oxo-l,8- naphthyridine-3-carboxylic acid and its analogues. J Med Chem 27:1543
Egawa H, Miyamoto T, Matsumoto J (1986) A new synthesis of 7H-pyrido[l,2,3- de][l,4]benzoxazine derivatives including an antibacterial agent, ofloxacin. Chem Pharm Bull (Tokyo) 34:4038
Fengler G, Grohe K (1984) DOS 3 229 126 (04.08.1982) Bayer AG. Chem Abstr 100:209385g
Fengler G, Arlt D, Grohe K (1984a) DOS 3 229 124 (04.08.1982) Bayer AG. Chem Abstr 101:90953u
Fengler G, Arlt D, Grohe K, Zeiler H-J, Metzger K (1984b) DOS 3 229 125 (04.02.1982) Bayer AG, Chem Abstr 101:7176z
Frigola J, Colombo A, Más J, Parés J (1987) Synthesis, structure elucidation and chemotherapeutic activity of 6-substituted l-ethyl-l,4-dihydro-7-[(l- imidazoly)phenyhnethyl]-4-oxo-3-quinolinecarboxylic acids. J Heterocycl Chem 24:399
Fromtling RA, Castañer J (1996) Trovafloxacin-Mesylate. Drugs Fut 21:496–505
Georgopapadakou NH, Dix BA, Angehrn P, Wick A, Olson GL (1987) Monocyclic and tricyclic analogs of quinolones: mechanism of action. Antimicrob Agents Chemother 31:614
Gerster JF (1973) DOS 2 264 163 (12.07.1973) Riker Laboratories Inc. Chem Abstr 79:92029y
Goueffon Y, Montay G, Roquet F, Pesson M (1981) New synthetic antimicrobial agent: l,4-di-hydro-l-ethyl-6-fluoro-7-(4-methyl-l-piperazinyl)-4-oxo-quinoline-3-car- boxylic acid (1589 RB). C R Acad Sci Biol (Paris) 292:37
Gould RG, Jacobs WA (1939) The synthesis of certain substituted quinolines and 5,6- benzoquinolines. J Am Chem Soc 61:2890
Grohe K (1986) DOS 3 502 935 (29.09.1984) Bayer AG. Chem Abstr 105:226051r
Grohe K (1992) DOS 4 015 299 (14.11.1991) Bayer AG. Chem Abstr 117:4811y
Grohe K (1993) The importance of the cycloaracylation process for the synthesis of modern fluoroquinolones. J Prakt Chem 335:397
Grohe K, Heitzer H (1987a) Synthese von 4-Chinolon-3-carbonsäuren. Liebigs Ann Chem 29
Grohe K, Heitzer H (1987b) Synthese von l-Amino-4-chinolon-3-carbonsäuren. Liebigs Ann Chem 871
Grohe K, Schriewer M (1987) DOS 3 522 406 (22.06.1985) Bayer AG. Chem Abstr 107:23351g
Grohe K, Zeiler H-J, Metzger K (1980) DOS 2 808 070 (24.02.1978) Bayer AG. Chem Abstr 92:41916w
Grohe K, Zeiler H-J, Metzger K (1981) DOS 2 903 850 (01.02.1979) Bayer AG. Chem Abstr 95:43152e
Grohe K, Zeiler H-J, Metzger K (1983) DOS 3 142 854 (29.10.1981) Bayer AG. Chem Abstr 99:53790h
Grohe K, Petersen U, Zeiler H-J, Metzger K (1985) DOS 3 318 145 (18.05.1983) Bayer AG. Chem Abstr 102:78744q
Grohe K, Zeiler H-J, Metzger K (1986) DOS 3 409 922 (17.03.1984) Bayer AG. Chem Abstr 104:88589y
Hägen SE, Domagala JM, Heifetz CL, Johnson J (1991) Synthesis and biological activity of 5-alkyl-l,7,8-trisubstituted-6-fluoroquinoline-3-carboxylic acids. J Med Chem 34:1155
Harris ND (1991) Cyclization of diethyl 3,4-diisobutoxyanilino-methylenemalonate. Synthesis 256
Hayakawa I, Kimura Y (1990) European patent 341 493 (27.04.1988), Daiichi Seiyaku. Chem Abstr 113:40473f
Hayakawa I, Tanaka Y (1984) Facile synthesis of thiazolo[4,5-b]- and thieno[3,2- b]pyridine derivatives by a novel pyridine cyclization reaction via enamine intermediates. Heterocycles 22:1697
Hayakawa I, Hiramitsu T, Tanaka Y (1984) Synthesis and antibacterial activities of substituted 7-oxo-2,3-dihydro-7H-pyrido[l,2,3-de] [1,4]benzoxazine-6-carboxylic acids. Chem Pharm Bull (Tokyo) 32:4907
Hayakawa I, Atarashi S, Yokohama S, Imamura M, Sakano M, Furukawa M (1986) Synthesis and antibacterial activities of optically active ofloxacin. Antimicrob Agents Chemother 29:163
Heindl J, Keim HW, Dogs E, Seeger A, Herrmann C (1977) Untersuchungen über die antibakterielle Aktivität von Chinoloncarbonsäuren. IX (1). Azaanaloga. Di- und trisubstituierte l,4-Dihydro-4-oxo-l,5-naphthyridin-3-carbonsäuren und 1-Äthyl- 4-pyridon-3-carbonsäure. Eur J Med Chem 12:549
Hirose T, Mishio S, Matsumoto J, Minami S (1982) Pyridone-carboxylic acids as antibacterial agents. I. Synthesis and antibacterial activity of l-alkyl-l,4-dihydro-4- oxo-1,8- and l,6-naphthyridine-3-carboxylic acids. Chem Pharm Bull (Tokyo) 30:2399
Högberg T, Khannal I, Drake SD, Mitscher LA, Shen LL (1984) Structure-activity relationships among DNA gyrase inhibitors. Synthesis and biological evaluation of 1,2-dihydro-4,4-dimethyl-1-oxo-2-naphthalenecarboxylic acids as 1-carba bioisosteres of oxolinic acid. J Med Chem 27:306
Huffman KR, Schaefer FC, Peters GA (1962) Reaction of s-triazine with acidic a-methylene compounds. J Org Chem 27:551
Irikura T, Koga H, Murayama S (1981) Belgian patent 887 574 (19.08.1980), Kyorin Pharm Co. Chem Abstr 95:187096n
Irikura T, Suzue S, Murayama S, Hirai K, Ishizaki T (1987) European patent 195 316 (08.03.1985), Kyorin Pharm. Chem Abstr 106:50068f
Ishikawa H, Tabusa F, Miyamoto H, Kano M, Ueda H, Tamaoka H, Nakagawa K (1989)Studies on antibacterial agents. I. Synthesis of substituted 6,7-dihydro-l- oxo-lH,5H-benzo[i,j]-quinolizine-2-carboxylic acids. Chem Pharm Bull (Tokyo) 37:2103
Ishikawa H, Uno T, Miyamoto H, Ueda H, Tamaoka H, Tominage M, Nakagawa K (1990)Studies on antibacterial agents. II. Synthesis and antibacterial activities of substituted l,2-dihydro-6-oxo-6H-pyrrolo[3,2,1-ij]quinoline-5-carboxylic acids. Chem Pharm Bull (Tokyo) 38:2459
Ishizaki T, Suzue S, Irikura T (1985) New synthesis of fluoroquinolonecarboxylic acid. J Chem Soc Jpn 10:2054
Itoh Y, Kato H, Ogawa N, Koshinaka E, Suzuki T, Yagi N (1985) DOS 3 433 924 (19.09.1983), Horikuri Pharm Co. Chem Abstr 103:123517b
Jefson MR, McGuirk (1988) European patent 215 650 (18.05.1985), Pfizer Inc. Chem Abstr 108:94417q
Jefson MR, McGuirk PR (1989) US patent 4 775 668 (19.08.1986), Pfizer Inc. Chem Abstr 110:57534w
Jinbo Y, Kondo H, Inoue Y, Taguchi M, Tsujishita H, Kotera Y, Sakamoto F, Tsukamoto G (1993a) J Med Chem 36:2621
Itoh Y, Kato H, Ogawa N, Koshinaka E, Suzuki T, Yagi N (1985) DOS 3 433 924 (19.09.1983), Hokuriku Pharm Co. Chem Abstr 103:123517b
Jefson MR, McGuirk PR (1988) European patent 215 650 (18.05.1985), Pfizer Inc. Chem Abstr 108:94417q
Jefson MR, McGuirk PR (1989) US patent 4 775 668 (19.08.1986), Pfizer Inc. Chem Abstr 110:57534w
Jinbo Y, Kondo H, Inoue Y, Taguchi M, Tsujishita H, Kotera Y, Sakamoto F, Tsukamoto G (1993a) Synthesis and antibacterial activity of a new series of tetracyclic pyridone carboxylic acids. J Med Chem 36:2621
Jinbo Y, Taguchi M, Inoue Y, Kondo H, Miyasake T, Tsujishida H, Sakamoto F, Tsukamoto G (1993b) Synthesis and antibacterial activity of a new series of tetracyclic pyridone carboxylic acids. J Med Chem 36:3148
Jinbo Y, Kondo H, Inoue Y, Taguchi M, Tsujishita H, Kotera Y, Sakamoto F, Tsukamoto G (1994) Synthesis and antibacterial activity of thiazolopyrazine- incorporated tetracyclic quinolone antibacterials. J Med Chem 37:586
Jordis U, Sauter F, Rudolf M, Gan C (1988) Synthesen neuer Chinolon- Chemotherapeutika, 1. Mitt. Pyridochinoline und Pyridophenanthroline als “lin- benzo-Nalidixinsäure”-Derivate. Monatsschr Chem 119:761
Kametani T, Kigasawa K, Hiiragi M, Wakisaka K, Kusama O, Sugi H, Kawasaki K (1977) Synthetic studies on chemotherapeutics. II. (1) Synthesis of phenyl- substituted l,4-dihydro-4-oxonicotinic acid derivatives. [Studies on the syntheses of heterocyclic compounds. Part 704 (2)]. J Heterocycl Chem 14:477
Kaminsky D, Meltzer RJ (1968) Quinolone antibacterial agents. Oxolinic acid and related compounds. J Med Chem 11:160
Kilbourn EE, Seidel MS (1972) Synthesis of n-alkyl-3-carboxy-4-pyridones. J Org Chem 37:1145
Kimura Y, Miyamoto T, Matsumoto T, Minami S (1976) Syntheses of pyrimido[4,5- c]pyridazine derivatives. I. A novel reaction of a-diazo-j3-oxo-5-(4-chloropyri- midine)propionate with hydrazine leading to l,2-dihydro-4-hydroxypyrimido[4,5- c]pyridazine-3-carboxamide. Chem Pharm Bull (Tokyo) 24:2637
Koga H, Itoh A, Murayama S, Suzue S, Irikura T (1980) Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted l-alkyl-l,4-dihydro-4- oxoquinoline-3-carboxylic acids. J Med Chem 23:1358
Kondo H, Taguchi M, Inoue Y, Sakamoto F, Tsukamoto G (1990) Synthesis and antibacterial activity of thiazolo-, oxazolo-, and imidazolo[3,2-a][l,8]naphthyri- dinecarboxylic acids. J Med Chem 33:2012
Laborde E, Kiely JS, Culbertson TP, Lesheski LE (1993) Quinolone antibacterials: synthesis and biological activity of carbon isosteres of the 1-piperazinyl and 3- amino-l-pyrrolidinyl side chains. J Med Chem 36:1964
Le Hao Dong P, Coquelet C, Bastide JM, Lebecq JC (1981) Nouveaux agents antibactériens II. Dérivés pyrazolo-azaquinoléiniques. Eur J Med Chem Chim Ther 16:39
Lesher GY, Carabateas PM (1973) DOS 2 224 090 (30.11.1972), Sterling Drug Inc. Chem Abstr 78:84280n
Lesher GY, Froelich EJ, Gruett MD, Bailey JH, Brundage RP (1962) 1,8- naphthyridine derivatives. A new class of chemotherapeutic agents. J Med Pharm Chem 5:1063
Leysen DC, Haemers A, Bollaert W (1984) Thiazolopyridine analogs of nalidixic acid. 2. Thiazolo[4,5-b]pyridines. J Heterocycl Chem 21:1361
Liu J, Guo H (1992) Synthesis and antibacterial activity of 1-(substituted pyrrolyl)- 7-(substituted amino)-6-fluoro-l,4-dihydro-4-oxo-3-quinolinecarboxylic acids. J Med Chem 35:3469
Markees DG, Schwab LS, Vegotsky A (1974) Synthesis and antibacterial activity of some substituted 4-quinolone-3-carboxylic acids. J Med Chem 17:137
Matsumoto J, Minami S (1975) Pyrido [2,3-d] pyrimidine antibacterial agents. 3.8-alkyl- and 8-vinyl-5,8-dihydro-5-oxo-2-(l-piperazinyl)pyrido[2,3-d]pyrimidine-6-car- boxylic acids and their derivatives. J Med Chem 18:74
Matsumoto J, Miyamoto T, Minamida A, Nishimura Y, Egawa H, Nishimura H (1984a) Synthesis of fluorinated pyridines by the Balz-Schiemann Reaction. An alternative route to enoxacin, a new antibacterial pyridonecarboxylic acid. J Heterocycl Chem 21:673
Matsumoto J, Miyamoto T, Minamida A, Nishimura Y, Egawa H, Nishimura H (1984b) Pyridonecarboxylic acids as antibacterial agents. 2. Synthesis and structure-activity relationships of 1,6,7-trisubstituted 1,4-dihydro-4-oxo-l,8- naphthyridine-3-carboxylic acids, including enoxacin, a new antibacterial agent. J Heterocycl Chem 27:292
Matsumoto J, Miyamoto T, Egawa H, Nakamura S (1988) European patent 242 789 (25.04.1986), Dainippon Pharm. Chem Abstr 108:150325x
Meth-Cohn O (1986) The synthesis of quinolines from N-alkylformanilides and activated acetic acids. Synthesis 76
Minami S, Shono T, Matsumoto J (1971) Pyrido [2,3-d] pyrimidine antibacterial agents. II. Piromidic acid and related compounds. Chem Pharm Bull (Tokyo) 19:1426
Mitscher LA, Flynn DL, Gracey HE, Drake SD (1979) Quinolone antimicrobial agents. 2. Methylenedioxy positional isomers of oxolinic acid. J Med Chem 22:1354
Mitscher LA, Sharma PN, Chu DTW, Shen LL, Pernet AG (1987) Chiral DNA Gyrase inhibitors. 2. Asymmetric synthesis and biological activity of the enantiomers of 9- fluoro-3-methyl-10-(4-methyl-l-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[l,2,3- de]-l,4-benzoxazine-6-carboxylic acid (ofloxacin). J Med Chem 30:2283
Miyamoto H, Ueda H, Otsuka T, Aki S, Tamaoka H, Tominaga M, Nakagawa K (1990) Studies on antibacterial agents. III. Synthesis and antibacterial activities of substituted l,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acids. Chem Pharm Bull (Tokyo) 38:2472
Miyamoto T, Matsumoto T (1988) A new cinnoline ring construction by the reaction of 2-diazo-3-(2-fluorophenyl)-3-oxopropionates with tri-n-butylphosphine. Chem Pharm Bull (Tokyo) 36:1321
Miyamoto T, Matsumoto J (1990a) Fluorinated pyrido[2,3-c]pyridazines. II. Synthesis and antibacterial activity of 1,7-disubstituted 6-fluoro-4-(lH)-oxopyrido[2,3- c]pyridazine-3-carboxylic acids. Chem Pharm Bull (Tokyo) 38:3359
Miyamoto T, Matsumoto T (1990b) Fluorinated pyrido[2,3-c]pyridazines. I. Reductive cyclization of ethyl 2-diazo-2-(5-fluoro-2-halonicotinoyl)acetate with trialkylphos- phine. Chem Pharm Bull (Tokyo) 38:3211
Miyamoto T, Egawa H, Matsumoto J (1987a) Pyridonecarboxylic acids as antibacterial agents. VIII. An alternative synthesis of enoxacin via fluoronicotinic acid derivatives. Chem Pharm Bull (Tokyo) 35:2280
Miyamoto T, Egawa H, Shibamori K, Matsumoto J (1987b) Synthesis and reactions of 7-substituted l-cyclopropyl-6-fluoro-l,4-dihydro-4-oxo-l,8-naphthyridine-3- carboxylic acids as an antibacterial agent. J Heterocycl Chem 24:1333
Miyamoto T, Matsumoto J, Chiba K, Egawa H, Shibamori K, Minamida A, Nishimura Y, Okada H, Kataoka M, Fujita M, Hirose T, Nakano J (1990) Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including Sparfloxacin, a new quinolone antibacterial agent with improved potency. J Med Chem 33:1645
Miyamoto T, Kimura Y, Matsumoto J, Minami S (1978) Syntheses of pyrimido[4,5- c]pyridazine derivatives. II. A novel reaction of a-diazo-j8-oxo-5-(4-chloropyrimi- dine)propionate with triphenyl phosphine leading to l,4-dihydro-4-oxopyrimido- [4,5-c] pyridazine-3-carboxylate. Chem Pharm Bull (Tokyo) 26:14
Moran DB, Ziegler CB Jr, Dunne TS, Kuck NA, Lin Y (1989) Synthesis of novel 5- fluoro analogues of norfloxacin and ciprofloxacin. J Med Chem 32:1313
Nagano H, Yokota T, Katok Y (1990) European patent 342 675 (19.05.1988), Chugai Pharm. Chem Abstr 113:6175j
Narita H, Konishi Y, Nitta J, Nagaki H, Kitayama I, Watanabe Y, Saikawa I (1986a) Pyridonecarboxylic acids as antibacterial agents. I. Synthesis and structure-activity relationship of l-aryl-6-(4-dimethylaminophenyl)-4-pyridone-3-carboxylic acids. Yakugaku Zasshi 106:775
Narita H, Konishi Y, Nitta J, Kobayashi Y, Watanabe Y, Minami S, Saikawa I (1986b) Pyridonecarboxylic acids as antibacterial agents. II. Synthesis and structure- activity relationship of l-(4-hydroxyphenyl)-6-substituted-4-pyridone-3- carboxylic acids. Yakugaku Zasshi 106:782
Narita H, Konishi Y, Nitta J, Miyazima M, Watanabe Y, Yotsuji A, Saikawa I (1986c) Pyridonecarboxylic acids as antibacterial agents. III. Synthesis and structure-activity relationship of l-(4-fluorophenyl)- and l-(2,4-difluorophenyl)-6-substituted-4- pyridone-3-carboxylic acids. Yakugaku Zasshi 106:788
Narita H, Konishi Y, Nitta J, Kittayama I, Miyazima M, Watanabe Y, Yotsuji A (1986d) Pyridonecarboxylic acids as antibacterial agents. V. Synthesis and structure-activity relationship of 7-amino-6-fluoro-l-(fluorophenyl)-4-oxo-l,8- naphthyridine-3-carboxylic acids. Yakugaku Zasshi 106:802
Narita H, Todo J, Nitta J, Nakagi H, Lino F, Miyajima M, Fukuoka Y, Saikawa I (1990) DOS 3 913 245 (23.04.1988), Toyama Chem. Chem Abstr 113:78417n
Nishimura Y, Matsumoto J (1987) Pyridonecarboxylic acids as antibacterial agents. 9. Synthesis and antibacterial activity of 1-substituted 6-fluoro-l,4,-dihydro-4-oxo-7- (4-pyridyl)-l,8-naphthyridine-3-carboxylic acids. J Med Chem 30:1622
O’Neill BT (1990) European patent 370 686 (23.11.1988), Pfizer Inc. Chem Abstr 113:191182v
Ockenden DW, Schofield K (1953) Cinnolines. Part XXXIII. Some 3-aryl-4- hydroxycinnolines. J Chem Soc 3706
Okada T, Tsuji T, Tsushima T, Ezumi K, Yoshida T, Matsuura S (1991a) Synthesis and antibacterial activities of novel oxazine and thiazine ring-fused tricyclic quinolonecarboxylic acids: 10-(alicyclic amino)-9-fluoro-7-oxo-7H-pyrido[l,2,3- de][l,4]benzoxazine-6-carboxylic acids and the corresponding 1-Thia congeners. J Heterocycl Chem 28:1067
Okada T, Tsuji T, Tsushima T, Yoshida T, Matsuura S (1991b) Synthesis and antibacterial activities of novel dihydrooxazine and dihydrothiazine ring-fused tricyclic quinolonecarboxylic acids: 9-fluoro-3-methylene-10-(4-methylpiperazin-l-yl)-7- oxo-2,3-dihydro-7H-pyrido[l,2,3-de][l,4]benzoxazine-6-carboxylic acid and its 1- Thia congeners. J Heterocycl Chem 28:1061
Okumura K, Inoue K, Tomie M, Adachi T, Kondo K (1974a) Japanese patent 7 410 519 (19.02.1969), Tanabe Seiyaku. Chem Abstr 81:120503k
Okumura K, Inoue K, Tomie M, Adachi T, Kondo K (1974b) Japanese patent 7 410 520 (19.02.1969), Tanabe Seiyaku. Chem Abstr 81:120504m
Otsubo J, Manabe Y, Kazuyuki K (1982) Belgian patent 891 537 (18.12.1980), Otsuka Pharm Co. Chem Abstr 97:92321j
Parikh VD, Fray AH, Kleinman EF (1988) Synthesis of 8,9-difluoro-2-methyl-6-oxo- l,2-dihydropyrrolo[3,2,1-ij]quinoline-5-carboxylic acid. J Heterocycl Chem 25:1567
Pesson M, Chabassier S (1974) Chimie organique — nitriles et amide-oximes d’acides alkyl-8 oxo-5 dihydro-5.8 pyrido [2,3-d] pyrimidine-6 carboxyliques. C R Acad Sci [C] 279:413
Pesson M, Antoine M, Chabassier S, Geiger S, Girard P, Richer D, de Lajudie P, Horvath E, Leriche B, Patte S (1974a) Antibactériens dérivés des acides alkyl-8- oxo-5-dihydro-5,8 pyrido [2,3-d] pyrimidine-6 carboxyliques. I. Nouveau procédé de préparation. Eur J Med Chem Chim Ther 9:585
Pesson M, Antoine M, Chabassier S, Girard MP, Richer D (1974b) Chimie organique. Synthèse d’acides alkyl-8 oxo-5 dihydro-5.8 pyrido-[2.3-d] pyrimidine-6 carboxyliques. C R Acad Sci [C] 278:717
Pesson M, Antoine M, Chabassier S, Geiger S, Girard P, Richer D, de Lajudie P, Horvath E, Leriche B, Patte S (1974c) Antibactériens dérivés des acides alkyl-8 oxo-5 dihydro-5,8 pyrido [2,3-d] pyrimidine-6 carboxyliques. II. Dérivés pipérazinyl-2 et (alkyl-4 pipérazinyl)-2. Eur J Med Chem Chim Ther 9:591
Pesson M, de Lajudie P, Antoine M, Girard P, Chabassier S (1975) Synthèse d’acides alkyl-1 oxo-4 dihydro-1,4 benzo [h] naphtyridine-1.6 carboxyliques-3 à action antibactérienne. C R Acad Sci [C] 280:1385
Pesson M, de Lajudie P, Antoine M, Chabassier S, Girard P (1976) Acides alkyl-1 oxo- 4 dihydro-1,4 pyrido [2.3-b]quinoxaline-3 carboxyliques à action antibactérienne. C R Acad Sci [C] 282:861
Pesson M, Antoine M, Benichon J-L, de Lajudie P, Horvath E, Leriche B, Patte S (1980) Antibactériens de synthèse — dérivés des acides pyrido (2,3-e) as.triazine-7 carboxyliques. Eur J Med Chem 15:269
Petersen U, Grohe K, Zeiler H-J, Metzger K (1986) European patent 167 763 (04.06.1984), Bayer AG. Chem Abstr 104:186447v
Petersen U, Grohe K, Schriewer M, Schenke T, Haller I, Metzger K, Endermann R, Zeiler H-J (1989) DOS 3 711 193 (02.04.1987), Bayer AG. Chem Abstr 110:114697c
Petersen U, Schenke T, Krebs A, Grohe K, Schriewer M, Haller I, Metzger KG, Endermann R, Zeiler HJ (1988) Bayer AG, EP 350 733
Petersen U, Krebs A, Schenke T, Grohe K, Schriewer M, Haller I, Metzger K, Endermann R, Zeiler H-J (1991) European patent 401 623 (07.06.1989),Bayer AG. Chem Abstr 114:207234x
Petersen U, Krebs A, Schenke T, Philipps T, Grohe K, Bremm KD, Endermann R, Metzger KG, Haller I (1992) Bayer AG, EP 550 903; Chem Abstr 120:8616x
Price CC, Roberts RM (1946) The synthesis of 4-hydroxyquinolines. I. Through ethoxymethylenemalonic ester. J Am Chem Soc 68:1204
Prudchenko AT, Shchegoleva GS, Barkhash VA, Vorozhtsov NN Jr (1967) Some reactions of pentafluorobenzoylacetic ester. Zh Obshch Khim 37:2366
Prudchenko AT, Shchegoleva GS, Barkhash VA, Vorozhtsov NN Jr (1968) Reactions of ethyl pentafluorobenzoylacetate. Chem Abstr 69:36059q
Radi S, Hradil P (1991) Synthesis of some l-alkyl-l,4-dihydro-4-oxo-l,7- naphthyridine-3-carboxylic acids. Collect Czech Chem Commun 56:2420
Radi S, Zikan V (1989) Synthesis and antimicrobial activity of some 3-oxo-3H- pyrido[3,2,1-kl]phenoxazine-2-carboxylic acids. Collect Czech Chem Commun 54:506
Radi S, Zikan V (1989) Synthesis of some l-aryl-l,4-dihydro-4-oxoquinoline-3- carboxylic acids and their antibacterial activity. Collect Czech Chem Commun 54:2181
Radi S, Houskova V, Zikan V (1988) Priprava nekterych nekondenzovanych derivatu l,4-dihydro-4-oxo-3-pyridin-A 3-pyridazinkarboxylove kyseliny jako potencialnich antimikrobialne ucinnych latek. Cesk Farm 37:71
Radi S, Houskova V, Zikan V (1989) Priprava substituovanych l,6-difenyl-l,4-dihydro- 4-oxo-3-pyridazinkarboxylovych kyselin. Cesk Farm 38:114
Radi S, Moural J, Bendova R (1990) Synthesis and antibacterial activity of some l-aryl-l,4-dihydro-4-oxocinnoline-3-carboxylic acids. Collect Czech Commun 55:1311
Radi S, Kovarova L, Moural J, Bendova R (1991) Structural modification and new methods for preparation of ofloxacin analogs. Collect Czech Commun 56:1937
Remuzon P, Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Kiechel JR, Ledonssal B, Kessler RE, Fung-Tome J (1991) Fluoronaphthyridines and quinolones as antibacterial agents. 3. Synthesis and structure-activity relationships of new 1-(1,1- dimethyl-2-fluoroethyl), l-[l-methyl-l-(fiuoromethyl)-2-fiuoroethyl], and 1-[1,1- (difluoromethyl)-2-fluoroethyl] substituted derivatives. J Med Chem 54:29
Remuzon P, Bouzard D, Di Cesare P, Dussy C, Jacquet J-P, Jaegly A (1992) Synthesis and antibacterial activity of new 5-substituted l-cyclopropyl-6-fluoro-7- piperazinyl-l,4-dihydro-4-oxo-l,8-naphthyridine-3-carboxylic acids. J Heterocycl Chem 29:985
Rohlfing SR, Gerster JF, Kvam DC (1976) Bioevaluation of the antibacterial flumequine for urinary tract use. Antimicrob Agents Chemother 10:20
Rufer C, Schwarz K (1977) Untersuchungen über die antibakterielle Aktivität von Chinoloncarbonsäuren. VII (1). Azaanaloga. In 2-Position durch Pyrazole substituierte 8-Äthyl-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidin-6-carbonsäuren. Eur J Med Chem Chim Ther 12:236
Sanchez JP, Ashok K, Trehan K, Nichols JB (1987) The synthesis of a pyrido[2,3- c]pyridazine: a cinnoline related to 6-fluoronalidixic acid. J Heterocycl Chem 24:55
Sanchez JP, Bridges AJ, Busch R, Domagala JM, Gogliotti RD, Hagen SE, Heifetz CL, Joannides ET, Sesnie JC, Shapiro MA, Szotek DL (1992) New 8- (trifluoromethyl)-substituted quinolones. The benefits of the 8-fiuoro group with reduced phototoxic risk. J Med Chem 35:361
Sandison AA, Tennant G (1974) A new heterocyclisation reaction leading to cinnolin- 4(lH)-one derivatives. J Chem Soc Chem Commun 752
Santilli AA, Wanser SV, Kim DH, Scotese AC (1975) Synthesis of 5,6,7,8-tetrahydro- 5-oxopyrido[2,3-d]pyrimidine-6-carbonitriles and -6-carboxylic acid esters. J Heterocycl Chem 12:311
Sato K, Matsuura Y, Inoue M, Une T, Osada Y, Ogawa Y, Ogawa H, Mitsuhashi S (1982) In vitro and in vivo activity of DL-8280, a new oxazine derivative. Antimicrob Agents Chemother 22:548
Sauter F, Jordis U, Tanyolac S, Martinek P (1988a) Thieno[3,2-g]chinolin- und [1] Benzothieno-[5,6,7-ij]chinolizincarbonsäurederivate. Arch Pharm (Weinheim) 321:241
Sauter F, Jordis U, Tanyolac S (1988b) Synthesen neuer Chinolon-Chemothera- peutika, 3. Mitt. Sci Pharm 56:73
Sauter F, Jordis U, Martinek P (1989) Synthesis of novel quinolone-type drugs. Part 4. Pyrido[3,2,1-gh][l,7]phenanthroline- and benzo[i,j]quinolizine-carboxylic acids. Sci Pharm 57:7
Sawa Y, Kato T, Masuda T, Hori M, Fujimora H (1975) Studies on the syntheses of analgesics. IV. Syntheses of l,2,3,4-tetrahydro-5H-benzazepine derivatives. Chem Pharm Bull (Tokyo) 23:1917
Scheer M (1987a) Studies on the antibacterial activity of Baytril. Vet Med Rev 2:90
Scheer M (1987b) Concentrations of active ingredient in the serum and in tissues after oral and parenteral administration of Baytril. Vet Med Rev 2:104
Schofield K, Simpson JCE (1945) Cinnolines. III. The Richter reaction. J Chem Soc 512
Schriewer M, Grohe K (1988) DOS 3 615 767 (10.05.1986), Bayer AG. Chem Abstr 108:94416p
Schriewer M, Grohe K, Zeiler H-J, Metzger K (1987a) DOS 3 543 513 (10.12.1985), Bayer AG. Chem Abstr 107:154342c
Schriewer M, Grohe K, Zeiler H-J, Metzger K (1987b) DOS 3 600 891 (15.01.1986), Bayer AG. Chem Abstr 107:198345k
Schriewer M, Grohe K, Zeiler H-J, Metzger K (1987c) DOS 3 509 546 (16.03.1985), Bayer AG. Chem Abstr 106:4900y
Schriewer M, Grohe K, Hagemann H, Zeiler H-J, Metzger K (1988a) DOS 3 623 757 (15.07.1986), Bayer AG. Chem Abstr 109:86326q
Schriewer M, Grohe K, Petersen U, Haller I, Metzger K, Endermann R, Zeiler H-J (1988b) DOS 3 702 393 (28.01.1987), Bayer AG. Chem Abstr 109:230824v
Schroeder MC, Kiely JS (1988) Synthesis of a novel tricyclic 4-quinolone. Incorporation of a spirb-cyclopropyl group at N1 by bridging to C2. J Heterocycl Chem 25:1796
Schwan TJ, Freedman R, Pollack JR (1983) Synthesis, structure elucidation and antibacterial activity of 6-ethyl-6,9-dihydro-9-oxopyrazolo[3,4-f]quinoline-8- carboxylic acid. J Heterocycl Chem 20:1351
Segawa J, Kitano M, Kazuno K, Tsuda M, Shirahase I, Ozaki M, Matsuda M, Kise M (1992a) Studies on pyridonecarboxylic acids [1]. 2. Synthesis and antibacterial activity of 8-substituted 7-fluoro-5-oxo-5H-thiazolo[3,2-a] quinoline-4-carboxylic acids. J Heterocycl Chem 29:1117
Segawa J, Kitano M, Kazuno K, Matsuoka M, Shirahase I, Ozaki M, Matsuda M, Tomii Y, Kise M (1992b) Studies on pyridonecarboxylic acids. 1. Synthesis and antibacterial evaluation of 7-substituted-6-halo-4-oxo-4H-[l,3] thiazeto[3,2-a] quinoline- 3-carboxylic acids. J Med Chem 35:4727
Shoup RR, Castle RN (1965) Cinnoline chemistry. XI. The ultraviolet spectra of halogen substituted 4-hydroxy- and 4-mercaptocinnolines. J Heterocycl Chem 2:63
Singh B (1991) Synthesis of 2-aza analog of rosoxacin. J Heterocycl Chem 28:881
Staiger RP, Miller EB (1959) Isatoic anhydride. IV. Reactions with various nucleo- philes. J Org Chem 24:1214
Stanovnik B, Tisler M (1974) Convenient cyclization of o-difunctional heterocycles with N,N-dimethylformamide dimethyl acetal. Synthesis 120
Stefancich G, Artico M, Corelli F, Massa S, Panico S, Simonetti N (1985) l-ethyl-6- fluoro-l,4-dihydro-4-oxo-7-(lH-pyrrol-l-yl)-quinoline-3-carboxylic acid, a new fluorinated compound of oxacin family with high broad-spectrum antibacterial activities. Farmaco [Sci] 40:237
Strehlke P (1977) Untersuchungen über die antibakterielle Aktivität von Chinoloncarbonsäuren. VIII (1) Azaanaloga. Eine neue Synthese antibak- teriell wirksamer 1,7-disubstituierter l,4-Dihydro-4-oxo-l,6-naphthyridin-3- carbonsäuren. Eur J Med Chem Chim Ther 12:541
Suzuki N, Tanaka Y, Dohmori R (1979) Synthesis of antimicrobial agents. I. Synthesis and antimicrobial activities of thiazoloquinoline derivatives. Chem Pharm Bull (Tokyo) 27:1
Taguchi M, Kondo H, Inoue Y, Kawahata Y, Jinbo Y, Sakamoto F, Tsukamoto G (1992) Synthesis and antibacterial activity of new tetracyclic quinolone antibacte- rials. J Med Chem 35:94
Taylor EC, Heindel ND (1967) Cyclizations of anthranilate-acetylenedicarboxylate adducts. A facile route to 2,8-dicarboalkoxy-4(lH)-quinolinones. J Org Chem 32:3339
Terni P, Rugarli PL, Maiorana S, Pagella PG, Fusco R (1988) European patent 252,352 (01.07.1986), Mediolanum Farm. Chem Abstr 109:129034n
Todo Y, Yamafuji T, Nagumo K, Kitayama I, Nagaki H, Miyajima M, Konishi Y, Narita H, Takano S, Seikawa I (1987) DOS 3 601 517 (20.01.1986). Toyama Chem. Chem Abstr 107:77777u
Toja E, Kettenring J, Goldstein B, Tarzia G (1986a) Pyrrolopyridine analogs of nalidixic acid. 2. Pyrrolo[3,4-b]pyridines. J Heterocycl Chem 23:1561
Toja E, Tarzia G, Ferrari P, Tuan G (1986b) Pyrrolopyridine analogs of nalidixic acid. 1. Pyrrolo [2,3-b] pyridines. J Heterocycl Chem 23:1555
Von Liebig J (1853) Ueber Kynurensäure. Ann Chem 86:125
Von Liebig J (1858) Ueber Kreatin und Kynurensäure im Hundeharn. Ann Chem 108:354
Von Richter V (1883) Ueber Cinnolinderivate. Chem Ber 16:677
Wentland MP, Lesher GY, Reumann M, Gruett MD, Singh B, Aldous SC, Dorff PH, Rake JB, Coughlin SA (1993) Mammalian topoisomerase II inhibitory activity of l-cyclopropyl-6,8-difluoro-l,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3- quinolinecarboxylic acid and related derivatives. J Med Chem 36:2801
White WA (1970) DOS 2 005 104 (06.08.1970), Eli Lilly & Co. Chem Abstr 73:77269j
Wick AE (1979) DOS 2 901 868 (18.01.1978), Hoffmann-La Roche. Chem Abstr 91:211273h
Xiao W, Krishnan R, Lin Y-I, Delos Santos EF, Kuck NA, Babine RE, Lang SA Jr (1989) Synthesis and in vitro antibacterial activity of some 1- (difluoromethoxyphenyl)quinolone-3-carboxylic acids. J Pharm Sci 78:585
Zeiler H-J, Grohe K (1984) The in vitro and in vivo activity of ciprofloxacin. Eur J Clin Microbiol 3:339
Zhang MQ, Haemers A, Vanden Berghe D, Pattyn SR, Bollaert W (1991) Quinolone antibacterials. 2. 6-substituted-7-(2-thiazolyl and thiazolidinyl)quinolones. J Heterocycl Chem 28:685
Ziegler CB Jr, Moran DB, Fenton TJ, Lin Y-I (1990) The Synthesis and biological activity of 8-fluoro-9-(4-methyl-l-piperazinyl)-6-oxo-6H-benzo[c]quinolizine-5- carboxylic acid. J Heterocycl Chem 27:587
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1998 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Grohe, K. (1998). The Chemistry of the Quinolones: Methods of Synthesizing the Quinolone Ring System. In: Kuhlmann, J., Dalhoff, A., Zeiler, HJ. (eds) Quinolone Antibacterials. Handbook of Experimental Pharmacology, vol 127. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-80364-2_2
Download citation
DOI: https://doi.org/10.1007/978-3-642-80364-2_2
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-80366-6
Online ISBN: 978-3-642-80364-2
eBook Packages: Springer Book Archive