Effects of skeletal modifications of ciprofloxacin on ... - ResearchGate

190 JOURNAL <strong>of</strong> CHINESE CLINICAL MEDICINE VOLUME 2|NUMBER 4|April 2007
2 H,H -12);EIMS m /z (% rel.abund.) :441 ( M +
,
44) ,397 (12) ,329 (2) ,231 (12畅4),203 (23).
1 -Cyclopropyl唱7唱[ 4 唱( 2, 2唱dimethylpropanoyl )唱1唱
piperazinyl ]唱6唱fluoro唱4 唱oxo唱1 , 4唱dihydro唱3唱quino唱
line carboxylic acid (5 )
Yield:0畅80 g (80%);M.P.= 28 0 ℃ ~28 2 ℃ ; IR nmax
cm -1
: 3520 , 3467, 3093, 2960, 1722, 1669, 1441,
1385,1256,1013; 1
H -NMR (300 MHz -DMSO唱d 6 ):
d 8畅6 (s,1 H,H -2 ) , 7畅9 (d,1H, J =2畅6 Hz, H -
5),7畅5(d,1 H,J =5畅3 Hz,H -8),4畅3(s,1H,H -
11) ,3畅7 (s,4H,H -16,20),2畅4(s,4H, H -1 7 , H
-19) ,1畅2 (d,2H,J =3畅7 Hz,H -13) ,1畅0 (s,2H,
H -12) ,1畅04 (s,9H,H -3 ′,4′,5′);EIMS m /z (%
rel.abund.):414 (M +
,14),370 (32),335 (85),
330 (2畅8),314 (32),288 (33),270 (11),256
(13),148 (8),56 (100).
1唱Cyclopropyl唱6唱fluoro唱(4唱octanoyl唱1唱pipera唱zinyl)唱
4唱oxo唱1,4唱dihydro唱3唱quinoline carboxylic acid (6)
Yield:0畅48 g (43%);M.P.= 229℃ ~231 ℃;IR nmax
cm -1
: 3461 , 3094, 2957, 1726, 1629, 1468, 1264,
1124; 1
H唱NMR (300 MHz唱DMSO唱d 6 ):d 8畅6 (s,1H,
H -2),7畅9(d,1H,J =7畅8 Hz,H -5),7畅5(d,1H,J
=2畅9 Hz,H -8),4畅1(t,1H, J =7 畅4 Hz,H -2 ′),
3畅8 (s,1H, H -11),3畅4 (s,4H, H -16,20),2畅4
( s,4H,H -17,19),1畅29 -1畅21 ( m,10H, H -3 ′,
4′,5 ′,6′,7′) ,0畅87 ( s,2H, H -13 ) .0畅86 ( s,2H,H
-12),0畅84 (d,2H,J =7 畅3 Hz,H -8 ′);EIMS m /z
(% rel.abund.):457 ( M +
,10),437 (2畅5),413
(2畅4) ,370 (2) ,342 ( 13) ,286 (12) ,231 (100 ) ,56
(90畅5).
1唱Cyclopropyl唱6唱fluoro唱7唱( 4唱nonanoyl唱1唱piperazinyl )唱
4唱oxo唱1,4唱dihydro唱3唱quinoline carboxylic acid (7)
Yield:0畅73 g (73%);M.P.= 151℃ ~153℃;
IR nm ax cm -1
: 3467,3358, 3093,2923, 1722,1628,
1469,1384,1340,1257,1023; 1
H唱NMR (300 MHz唱
DMSO唱d 6 ):d 8畅6 (s,1H, H -2),7畅9 (d,1H, J =
7畅8 Hz,H -5),7畅5 (d,1H , J =2 畅9 Hz, H -8),
4畅1 (t,1H, J =7 畅4 Hz, H -2 ′) ,3畅8 (s,1H, H -
11),3畅4(s,4H ,H -16,20),2畅4 (s,4 H, H -1 7 ,
19),1畅31 -1畅71 ( m,12H , H -3 ′,4′,5′,6′,7′,
8′),0畅87 (s,2 H,H -13 ) , 0畅86 ( s,2H, H -12),
0畅84 ( d,2H, J =7 畅3 Hz, H -8 ′);EIMS m /z (%
rel.abund.): 471 ( M +
, 2 ), 384 ( 1畅6), 345
(11畅7),231 (35),71 (12),56 (100) .
1 唱Cyclopropyl唱7 唱(4唱decanoyl唱1唱piperazinyl) 7唱6 唱flu唱
oro唱4唱oxo唱1, 4 唱dihydro唱3唱quinoline carboxylic acid
(8 )
Yield:0畅68 g (68%);M.P.= 10 7 ℃ ~10 9 ℃ ; IR nmax
cm -1
: 3466 , 3093, 3011, 2923, 1723, 1628, 1469,
1385,1340,1257; 1
H -NMR (300 MHz -DMSO -
d 6 ):d 8畅6 (s,1H,H -2),7畅9(d,1H,J =7畅8 Hz,H
-5 ) ,7 畅5(d,1H,J =2畅9 Hz,H -8) ,4畅1 (t,1H,J =
7畅4 Hz,H -2 ′),3畅8(s,1H,H -11),3畅4(s,4H,H
-16,20) ,2畅4 (s,4H,H -17,19),1畅29 -1畅21 ( m,
10H, H -3 ′,4′,5′,6′,7′),0畅87 (s,2H, H -13).
0畅86 (s,2H,H -1 2 ) , 0畅85 ( t,3H,J =7 畅3 Hz,H -
10′);EIMS m /z (% rel.abund.) :485 (M +
,16 ),384
(11) ,330 (10) ,311 ( 29) ,301 (34) ,289 (44) ,275
(46) ,257 (36) ,245 ( 52) ,231 (83) ,56 (100) .
7 唱( 4唱Benzoyl唱1唱piperazinyl )唱1唱cyclopropyl唱6唱fluo唱
ro唱4唱oxo唱1, 4唱dihydro唱3唱quinoline carboxylic acid
(9 )
Yield:0畅53 g (53%);M.P.= 273℃ ~275 ℃;IR nmax
cm -1
: 3408 , 3056, 2919, 1720, 1622, 1529, 1486,
1387,1330,1251,1008; 1
H -NMR (300 MHz -DM唱
SO -d6 ):d 8畅6 (s,1 H,H -2 ) , 7畅9 (d,1H, J =7 畅8
Hz,H -5),7畅5(d,1H,J =2畅9 Hz, H -8),7畅5-
7畅4 (m,1H, H -3 ′,4′,5 ′,6′,7′),3畅8(s,1 H,H -
11),3畅3 (s,4H, H -16,20),3畅2 (s,4H, H -1 7 ,
19),2畅1 (s,2H,H -13) ,1畅3 (s,2 H,H -12 ) ; EIMS
m /z (% rel.abund.) : 391 ( M +
,44畅3),286 (1),
257 (11),231 (5),177 (3),159 (1),56 (70).
7 唱[4唱(2唱Chlorobenzoyl)唱1 唱piperazinyl]唱1唱cyclopro唱
pyl唱6 唱fluoro唱4 唱oxo唱1,4唱dihydro唱3唱quinoline carbox唱
ylic acid (10 )
Yield:0畅80 g (80%);M.P.=191℃ ~193℃;IR nmax
cm -1
: 3468 , 3058, 2959, 1717, 1627, 1464, 1399,
1340,1292; 1
H -NMR (300 MHz -DMSO -d 6 ):d
15畅0 (s,1H,H -14 ),8畅6 (s,1H,H -20 ) ,7畅9 (d,
1 H,J =7畅8 Hz,H -5 ) ,7 畅5(d,1 H,J =5 畅5 Hz, H -
8),7畅6(dd,J =8畅5 Hz,H -3 ′),7畅4(ddd, J =8 畅5
Hz,H -4 ′),7畅3 (dd, J =8畅5 Hz, H -6 ′), 7畅22
( ddd,J =8畅5 Hz,H -5 ′),3畅8(d,1H,J =1畅2 Hz,H
-11) ,3畅4 (s,4 H,H -16,20 ) ,2畅4 (s,4H,H -1 7 ,
19),1畅1 (d,2H,J =2畅3 Hz,H -13),0畅9(s,2H,H
-12);EIMS m /z (% rel.abund.):560 (M +
,17),
516 (49),432 (2),390 (4),314 (10),288 (12),
257 (16),7 (22),230 (61),2 (19),148 (20),4