SINTEZA 4-KINOLONOVPROTIMIKROBNIH UČINKOVIN
H3C H3C
N
N
O
O
OH
NALIDIKSNA KISLINA
Cl
N
HN N CH3
KLOROKIN
H3C
CH3
nujen del za aktivnost, vezavo na kompleks DNA/giraza ter transport
kontrola aktivnosti, doda k afiniteti na G(+)
R5
afiniteta do giraze, celična permeabilnost
F N
R
O
N
COOH x8
N R1
optimalen H, blizu vezavnemu mestu na girazi
R protibakterijski spekter in farmakokinetika
antianaerobna aktivnost in farmakokinetika
vpliv na celokupno jakost delovanja
I.
O
OH
O
O
H3C
N
N
H3C
GENE UČINK N
N
OH
O
N
N
HN
H3C
II. GENERA (SUBSTITU OH
O
O
F
O
OH
F
O
N
N
N
HN
N
HN CH3
OH
O OH
O
F O
F O
predstavnik N
N N H3C
N
N
N
O
CH3
H3C
CH3
III.
GENER (SUBST O
CH3
O
O
F
O
F
OH N
N
N
N F
N H2N
NH
OH
CH3
F
IV. GENER (TUDI 2-PI O
F
O
O
F
N
OH
N
OH
N
N
Cl
H2N
O
CH3
H2N
predstavnik
SINTEZA NALIDIKSNE KISLINE 1-etil-7-metil-4-okso-1,4-dihidro[1,8]naftiridin-3-karboksilna kislina
ENOKSACIN
Enoxacin; AT-2266; CI-919; PD-107779; Comprecin; Flumark; Penetrex; Enoxor; Almitil Chemical Name: 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid. CAS(R) Reg. No.: 74011-58-8. Phase: Launched-1986. Source: Dainippon Pharmaceutical; Almirall Prodesfarma; Pfizer; SmithKline Beecham; Recordati; Pierre Fabre; Bellon. Activity / Mechanism: Antibacterial Drugs; Quinolones.
SINTEZA ENOKSACINA 1-Etil-6-fluoro-1,4-dihidro-4-oxo-7-(1-piperazinil)-1,8-naftiridin-3-karboksilna kislina
SINTEZA ENOKSACINA- nadaljevanje
CIPROFLOKSACIN
Ciprofloxacin hydrochloride; Bay-o-9867 monohydrate; Ciproxin; Eni; Cipro; Ciflox; Ciloxan; Ciprobay; Oftacilox; Ciproxan Chemical Name: 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid hydrochloride hydrate. CAS(R) Reg. No.: 86393-32-0; 85721-33-1 (free base, anhydrous) Phase: Launched-1986. Source: Bayer; SPI Pharm.; ICN; Alcon. Activity / Mechanism: Antibacterial Ophthalmic Drugs; Antibacterial Drugs; Treatment of Cystic Fibrosis; Quinolones.
SINTEZA CIPROFLOKSACINA
1-ciklopropil-6-fluoro-1,4-dihidro-4-okso-7-(1-piperazinil)-3-kinolin karboksilna kislina
NORFLOKSACIN
Norfloxacin; AM-715; MK-0366; Lexinor; Baccidal; Barazan; Sebercim; Fulgram; Noroxin; Norflo Chemical Name: 1-Ethyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid. CAS(R) Reg. No.: 70458-96-7; 68077-27-0 (monoHCl) Phase: Launched-1984. Source: Ist. Biol. Chemioter. ABC; Merck & Co.; Merck Sharp & Dohme; ISF; AstraZeneca; Roberts. Activity / Mechanism: A
SINTEZA NORFLOKSACINA 1-etil-6-fluoro-7-(1-piperazinil)-4-okso-1,4-dihidro-3-kinolin karboksilna kislina
PEFLOKSACIN
Pefloxacin; EU 5306; RB 1589; Peflacine Chemical Name: 6-Fluoro-7-(4-methylpiperazino)-1-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid. CAS(R) Reg. No.: 70458-92-3. Phase: Launched-1985. Source: Bellon. Activity / Mechanism: Antibacterial Drugs; Quinolones.
SINTEZA PEFLOKSACINA 6-fluoro-7-(4-metilpiperazino)-1-etil-1,4-dihidro-4-oksokinolin-3-karboksilna kislina keto skupina !!
OFLOKSACIN
LEVOFLOKSACIN S-izomer
Ofloxacin; DL-8280; Hoe-280; Floxin; Ocuflox; Tarivid Chemical Name: (±)-9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido [1,2,3-de]-1,4-benzoxazine-6-carboxylic acid. CAS(R) Reg. No.: 82419-36-1. Phase: Launched-1985. Source: Daiichi Pharmaceutical; Aventis Pharma; Allergan; Ortho-McNeil. Activity / Mechanism: Antibacterial Ophthalmic Drugs; Antibiotics; Antibacterial Drugs; Quinolones.
SINTEZA OFLOKSACINA (±)-9-fluoro-3-methyl-10-(4-metil-1-piperazinil)-7-okso-2,3-dihidro-7H-pirido [1,2,3-de]-1,4benzoksazin-6-karboksilna kislina