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(2H, d, J=8.1 Hz), 7.953(2H, d, J=8.1 Hz). 19F NMR
(300 MHz) À76.214. HRMS calcd for C22H21F3O4: 406.14311;
Found: 406.13919. 6c MS (EI, 70 ev) m/z: 448; IR umax (cmÀ1
,
1
KBr): 1699 (C¼O); H NMR (300 MHz, CDCl3): 0.941–1.951
(15H, m), 2.637 (2H, m), 4.062 (2H, m), 4.381 (2H, m), 6.507
(1H, s), 6.720 (1H, s), 7.686 (2H, d, J=7.8 Hz), 7.971 (2H, d,
J=7.8 Hz). 19F NMR (300 MHz) À63.107. HRMS calcd for
C25H27F3O4: 448.18953; Found: 448.19087. 8 MS (EI, 70 ev)
1
m/z: 306; IR umax (cmÀ1, KBr): 1683(C ¼O), 3072 (OH); H
NMR (300 MHz, CD3COCD3): 6.818 (1H, s), 6.857 (1H, dd,
J=2.1, 8.4), 6.899 (1H, d, J=2.1 Hz), 7.692 (1H, d, J=8.4
Hz), 7.774 (2H, d, J=6.8 Hz), 8.220 (2H, d, J=6.8 Hz),
10.138 (1H, s). 19F NMR (300 MHz) À68.627. Anal. calcd for
C16H9F3O3: C, 62.75, H, 2.96; Found C, 62.90, H, 3.44. 9a MS
(EI, 70ev) m/z: 320; IR umax (cmÀ1, KBr): 1702 (C¼O); 1H
NMR (300 MHz, CDCl3): 3.972 (3H, s), 6.806 (1H, dd, J=2.1,
9.3Hz), 6.821 (1H, s), 7.709 (2H, d, J=8.4 Hz), 7.726 (1H, d,
J=2.1 Hz), 7.745 (1H, d, J=9.3Hz), 8.009 (2H, d, J=8.4
Hz). 19F NMR (300 MHz) À71.206. 9b MS (EI, 70 ev) m/z:
16. All the new compounds were characterized by detailed
spectroscopic analysis. 4 MS (EI, 70 ev) m/z: 322; IR umax
(cmÀ1, KBr): 1682 (C¼O), 3096, 3312 (OH); 1H NMR
(300 MHz, DMSO-d6): 6.100 (1H, d, J=1.5 Hz), 6.230 (1H,
d, J=1.5 Hz), 6.688 (1H, s), 7.801 (2H, d, J=8.1 Hz), 8.076
(2H, d, J=8.1 Hz), 11.006 (1H, s), 11.082 (1H, s). 19F NMR
(300 MHz) À70.95. Anal. calcd for C16H9F3O4: C, 59.64, H,
2.82; Found C, 59.44, H, 2.85. 5a MS (EI, 70 ev) m/z: 350; IR
umax (cmÀ1, KBr): 1705 (C¼O); 1H NMR (300 MHz, CDCl3):
3.952 (3H, s), 3.972 (3H, s), 6.156 (1H, d, J=1.8 Hz), 6.412
(1H, d, J=1.8 Hz), 6.755 (1H, s), 7.671 (2H, d, J=8.4 Hz),
7.958 (2H, d, J=8.4 Hz). 19F NMR (300 MHz) À62.686. 5b
MS (EI, 70 ev) m/z: 378; IR umax (cmÀ1, KBr): 1699 (C¼O);
1H NMR (300 MHz, CDCl3): 1.447–1.596 (6H, m), 4.162–
4.293(4H, m), 6.184 ( 1H, d, J=1.5 Hz), 6.412 (1H, d, J=1.5
Hz), 6.765 (1H, s), 7.717 (2H, d, J=8.1 Hz), 8.004 (2H, d,
J=8.1 Hz). 19F NMR (300 MHz) À76.240. 5c MS (EI, 70 ev)
m/z: 406; IR umax (cmÀ1, KBr): 1699 (C¼O); 1H NMR
(300 MHz, CDCl3): 1.066–1.114 (6H, m), 1.839–1.970 (4H, m),
4.014–4.111 (4H, m), 6.147 (1H, s), 6.373 (1H, s), 6.708 (1H,
s), 7.670 (2H, d, J=8.1 Hz), 7.958 (2H, d, J=8.1 Hz). 19F
NMR (300 MHz) À63.108. Anal. calcd for C22H21F3O4: C,
65.02, H, 5.21; Found C, 64.57, H, 5.19. 5d MS (EI, 70 ev) m/
z: 502; IR umax (cmÀ1, KBr): 1702 (C¼O); 1H NMR
(300 MHz, CDCl3): 5.137 (2H, s), 5.298 (2H, s), 6.277 (1H, d,
J=1.8), 6.480 (1H, d, J=1.8), 6.757 (1H, s), 7.333–7.507
(10H, m), 7.685 (2H, d, J=8.1 Hz), 7.968 (2H, d, J=8.1 Hz).
19F NMR (300 MHz) À62.768. Anal. calcd for C30H21F3O4:
C, 71.71, H, 4.21; Found C, 71.69, H, 4.17. 5e MS (EI, 70 ev)
m/z: 518; IR umax (cmÀ1, KBr): 1707 (C¼O); 1H NMR
(300 MHz, CDCl3): 0.683–1.896 (26H, m), 4.038–4.108 (4H,
m), 6.132 (1H, d, J=1.2 Hz), 6.363 (1H, d, J=1.2 Hz), 6.704
(1H, s), 7.661 (2H, d, J=8.4 Hz), 7.950 (2H, d, J=8.4). 19F
NMR (300 MHz) À62.709. HRMS calcd for C30H37F3O4:
518.26158; Found: 518.26439. 5f MS (EI, 70 ev) m/z: 546; IR
1
334; IR umax (cmÀ1, KBr): 1693(C ¼O); H NMR (300 MHz,
CDCl3): 1.492 (3H, t, J=6.9 Hz), 4.163(2H, q, J=6.9 Hz),
6.759 (1H, dd, J=2.1 Hz, 6.6), 6.780 (1H, s), 7.680 (2H, d,
J=8.4 Hz), 7.697 (1H, d, J=2.1 Hz), 7.705 (1H, d, J=6.6
Hz), 7.975 (2H, d, J=8.4 Hz). 19F NMR (300 MHz) À71.206.
Anal. calcd for C18H13F3O3: C, 64.67, H, 3.92; Found C,
65.23, H, 4.21. 9c MS (EI, 70 ev) m/z: 348; IR umax (cmÀ1
,
KBr): 1706 (C¼O); 1H NMR (300 MHz, CDCl3): 1.086 (3H, t,
J=7.5), 1.856–1.925 (2H, m), 4.059 (2H, t, J=6.6 Hz), 6.763
(1H, dd, J=2.4, 6.6 Hz), 6.781 (1H, d, J=6.6 Hz), 6.794 (1H,
s), 7.690 (2H, d, J=8.1 Hz), 7.704 (1H, d, J=2.4 Hz), 7.988
(2H, d, J=8.1 Hz). 19F NMR (300 MHz) À71.203. Anal. calcd
for C19H15F3O3: C, 65.52, H, 4.34; Found C, 65.32, H, 4.32.
9d MS (EI, 70 ev) m/z: 346; IR umax (cmÀ1, KBr): 1707 (C¼O);
1H NMR (300 MHz, CDCl3): 4.681–4.652 (2H, m), 5.505–
5.363 (2H, m), 6.028–6.120 (1H, m), 6.770 (1H, s), 6.786 (1H,
dd, J=2.1, 7.5 Hz), 6.798 (1H, d, J=7.5 Hz), 7.670 (2H, d,
J=7.8 Hz), 7.709 (1H, d, J=2.1 Hz), 7.960 (2H, d, J=7.8
Hz). 19F NMR (300 MHz) À67.021. Anal. calcd for
C19H13F3O3: C, 65.90, H, 3.70; Found C, 65.89, H, 3.89. 9e
MS (EI, 70 ev) m/z: 418; IR umax (cmÀ1, KBr): 1701 (C¼O);
1H NMR (300 MHz, CDCl3): 0.909 (3H, t, J=6.6 Hz), 1.313–
1.880 (12H, m), 4.088 (2H, t, J=6.6 Hz), 6.764 (1H, dd,
J=2.1, 6.6 Hz), 6.779 (1H, d, J=2.1 Hz), 6.789 (1H, s), 7.688
(2H, d, J=6.8 Hz), 7.712 (1H, d, J=6.6 Hz), 7.985 (2H, d,
J=6.8 Hz). 19F NMR (300 MHz) À68.437. Anal. calcd for
C24H25F3O3: C, 68.89, H, 6.02; Found C, 69.10, H, 6.13. 11
MS (EI, 70 ev) m/z: 306; IR umax (cmÀ1, KBr): 1778 (C¼O);
1H NMR (300 MHz, CD3COCD3): 6.781 (1H, s), 6.822 (1H,
dd, J=2.1, 7.8 Hz), 6.864 (1H, d, J=2.1 Hz), 7.656 (2H, d,
J=8.4 Hz), 7.821 (1H, d, J=7.8), 8.174 (2H, d, J=8.4 Hz),
10.118 (1H, s). 19F NMR (300 MHz) À70.772. Anal. calcd for
C16H9F3O3: C, 62.75, H, 2.96; Found C, 62.69, H, 2.97. 12a
MS (EI, 70 ev) m/z: 320; IR umax (cmÀ1, KBr): 1702 (C¼O);
1H NMR (300 MHz, CDCl3): 3.974 (3H, s), 6.798 (1H, s),
6.818 (1H, dd, J=2.1, 7.8 Hz), 7.710 (1H, d, J=2.1), 7.715
(2H, d, J=8.4), 7.747 (1H, d, J=7.8 Hz), 8.004 (2H, d, J=8.4
Hz). 19F NMR (300 MHz) À70.493. 12b MS (EI, 70 ev) m/z:
1
umax (cmÀ1, KBr): 1699 (C¼O); H NMR (300 MHz, CDCl3):
0.884–0.920 (6H, m), 1.501–1.274 (20H, m), 1.826–1.941 (4H,
m), 4.057–4.150 (4H, m), 6.151 (1H, d, J=1.2), 6.382 (1H, d,
J=1.2 Hz), 6.722 (1H, s), 7.682 (2H, d, J=8.4 Hz), 7.972 (2H,
d, J=8.4 Hz). 19F NMR (300 MHz) À76.194. HRMS calcd
for C32H41F3O4: 546.29234; Found: 546.29570. 5g MS (EI, 70
ev) m/z: 602; IR umax (cmÀ1, KBr): 1703(C ¼O); 1H NMR
(300 MHz, CDCl3): 0.884–0.920 (6H, m), 1.298–1.496 (28H,
m), 1.822–1.938 (4H, m), 4.053–4.145 (4H, m), 6.146 (1H, d,
J=1.2 Hz), 6.378 (1H, d, J=1.2), 6.717 (1H, s), 7.679 (2H, d,
J=8.1 Hz), 7.967 (2H, d, J=8.1 Hz). 19F NMR (300 MHz)
À76.194. HRMS calcd for C36H49F3O4: 602.35545; Found:
602.35829. 6a MS (EI, 70 ev) m/z: 364; IR umax (cmÀ1, KBr):
1696 (C¼O); 1H NMR (300 MHz, CDCl3): 2.079 (3H, s),
3.965 (3H, s), 4.185 (3H, s), 6.530 (1H, s), 6.730 (1H, s), 7.675
(2H, d, J=8.1 Hz), 7.947 (2H, d, J=8.1 Hz). 19F NMR
(300 MHz) À76.261. HRMS. calcd for C19H15F3O4:
364.08929; Found: 364.09225. 6b MS (EI, 70 ev) m/z: 406; IR
1
334; IR umax (cmÀ1, KBr): 1700 (C¼O); H NMR (300 MHz,
CDCl3): 1.499 (3H, t, J=6.9 Hz), 4.175 (2H, q, J=6.9 Hz),
6.760 (1H, dd, J=2.1, 7.8 Hz), 6.784 (1H, d, J=2.1 Hz), 6.799
(1H, s), 7.690 (2H, d, J=8.4 Hz), 7.715 (1H, d, J=7.8 Hz),
7.990 (2H, d, J=8.4 Hz). 19F NMR (300 MHz) À73.059. Anal.
calcd for C18H13F3O3: C, 64.67, H, 3.92; Found C, 65.45, H,
4.22. 12c MS (EI, 70 ev) m/z: 346; IR umax (cmÀ1, KBr): 1707
(C¼O); 1H NMR (300 MHz, CDCl3): 4.664–4.691 (2H, m),
5.369–5.515 (2H, m), 6.033–6.126 (1H, m), 6.787 (1H, s), 6.814
(1H, d, J=2.1), 7.671 (2H, d, J=7.8 Hz), 7.675 (1H, d, J=7.5
Hz), 7.719 (1H, dd, J=2.1, 7.5 Hz), 7.978 (2H, d, J=7.8 Hz).
19F NMR (300 MHz) À56.761. Anal. calcd for C19H13F3O3:
1
umax (cmÀ1, KBr): 1699 (C¼O); H NMR (300 MHz, CDCl3):
1.081 (3H, t, J=7.2), 1.433 (3H, t, J=6.9), 1.501 (3H, t,
J=6.9), 2.655 (2H, q, J=7.2 Hz), 4.163(2H, q, J=6.9 Hz),
4.456 (2H, q, J=6.9 Hz), 6.491 (1H, s), 6.703(1H, s), 7.665