Y. Zuo et al. / Bioorg. Med. Chem. 20 (2012) 296–304
299
(M+H)+.Anal. Calcd for C16H14FN3OS3: C, 50.64; H, 3.72; N, 11.07.
Found: C, 50.45; H, 3.50; N, 10.89.
3H, –CH(CH3)), 4.22 (q, J = 7.2 Hz, 2H, –OCH2), 4.68 (q, J = 7.2 Hz,
1H, –SCH), 7.94 (s, 1H, Ar-H), 8.11 (s, 1H, Ar-H). ESI-MS: 501.9
(M+H)+. Anal. Calcd for C18H20BrN3O3S3: C, 43.03; H, 4.01; N,
8.36. Found: C, 43.04; H, 3.85; N, 8.21.
2.5.11. Data for 1k
Yield: 65%; mp: 137–138 °C. 1H NMR (600 MHz, CDCl3): d 1.37
(s, 9H, –C(CH3)3), 1.40 (t, J = 7.2 Hz, 3H, –CH3), 4.45 (q, J = 7.2 Hz,
2H, –OCH2), 8.04 (s, 1H, Ar-H), 8.08 (s, 1H, Ar-H). ESI-MS: 429.9
(M+H)+. Anal. Calcd for C16H16ClN3O3S3: C, 44.69; H, 3.75; N,
9.77. Found: C, 44.80; H, 4.00; N, 9.60.
2.5.20. Data for 1t
Yield: 75%; mp: 94–95 °C. 1H NMR (400 MHz, CDCl3): d 1.21 (t,
J = 7.2 Hz, 3H, –CH3), 1.38 (s, 9H, –C(CH3)3), 1.76 (s, 6H, –SC(CH3)2),
4.17 (q, J = 7.2 Hz, 2H, –OCH2), 7.98 (s, 1H, Ar-H), 8.10 (s, 1H, Ar-H).
ESI-MS: 515.9 (M+H)+. Anal. Calcd for C19H22BrN3O3S3: C, 44.18; H,
4.29; N, 8.14. Found: C, 44.11; H, 4.50; N, 8.15.
2.5.12. Data for 1l
Yield: 58%; mp: 103–105 °C. 1H NMR (400 MHz, CDCl3): d 1.25
(t, J = 7.2 Hz, 3H, –CH3), 1.37 (s, 9H, –C(CH3)3), 4.17 (s, 2H, –
SCH2), 4.22 (q, J = 7.2 Hz, 2H, –OCH2), 7.91 (s, 1H, Ar-H), 7.95 (s,
1H, Ar-H). ESI-MS: 443.0 (M)+. Anal. Calcd for C17H18ClN3O3S3: C,
45.99; H, 4.09; N, 9.46. Found: C, 46.11; H, 4.42; N, 9.54.
2.5.21. Data for 1u
Yield: 63%; oil. 1H NMR (400 MHz, CDCl3): d 1.26 (t, J = 7.2 Hz,
3H, –CH3), 1.38 (s, 9H, –C(CH3)3), 2.90 (t, J = 6.8 Hz, 2H, –CH2CO),
3.59 (t, J = 6.8 Hz, 2H, –SCH2), 4.16 (q, J = 7.2 Hz, 2H, –OCH2), 7.96
(s, 1H, Ar-H), 8.07 (s, 1H, Ar-H). ESI-MS: 501.8 (M+H)+. Anal. Calcd
for C18H20BrN3O3S3: C, 43.03; H, 4.01; N, 8.36. Found: C, 42.80; H,
4.30; N, 8.23.
2.5.13. Data for 1m
Yield: 65%; oil. 1H NMR (400 MHz, CDCl3): d 1.26 (t, J = 7.2 Hz,
3H, –CH3), 1.38 (s, 9H, –C(CH3)3), 1.71 (d, J = 7.2 Hz, 3H, –CH(CH3)),
4.22 (q, J = 7.2 Hz, 2H, –OCH2), 4.67 (q, J = 7.2 Hz, 1H, –SCH), 7.91 (s,
1H, Ar-H), 7.95 (s, 1H, Ar-H). ESI-MS: 458.0 (M + H)+. Anal. Calcd for
C18H20ClN3O3S3: C, 47.20; H, 4.40; N, 9.17. Found: C, 47.42; H, 4.69;
N, 9.03.
2.5.22. Data for 1v
Yield: 62%; oil. 1H NMR (400 MHz, CDCl3): d 1.25 (t, J = 7.2 Hz,
3H, –CH3), 1.38 (s, 9H, –C(CH3)3), 2.13–2.20 (m, 2H, –CH2–), 2.49
(t, J = 7.2 Hz, 2H, –CH2CO), 3.41 (t, J = 7.2 Hz, 2H, –SCH2), 4.12 (q,
J = 7.2 Hz, 2H, –OCH2), 7.94 (s, 1H, Ar-H), 8.07 (s, 1H, Ar-H). ESI-
MS: 537.8 (M+Na)+. Anal. Calcd for C19H22BrN3O3S3: C, 44.18; H,
4.29; N, 8.14. Found: C, 44.44; H, 4.50; N, 8.19.
2.5.14. Data for 1n
Yield: 54%; mp: 98–99 °C. 1H NMR (400 MHz, CDCl3): d 1.21 (t,
J = 7.2 Hz, 3H, –CH3), 1.38 (s, 9H, –C(CH3)3), 1.76 (s, 6H, –SC(CH3)2),
4.17 (q, J = 7.2 Hz, 2H, –OCH2), 7.92 (s, 1H, Ar-H), 7.98 (s, 1H, Ar-H).
ESI-MS: 472.0 (M+H)+. Anal. Calcd for C19H22ClN3O3S3: C, 48.34; H,
4.70; N, 8.90. Found: C, 48.50; H, 4.90; N, 8.61.
2.5.23. Data for 1w
Yield: 70%; mp: 131–133 °C. 1H NMR (600 MHz, CDCl3): d 1.38
(s, 9H, –C(CH3)3), 2.30 (t, J = 2.4 Hz, 1H, –CH), 4.13 (d, J = 2.4 Hz,
2H, –SCH2), 8.00 (s, 1H, Ar-H), 8.10 (s, 1H, Ar-H). ESI-MS: 440.4
(M)+. Anal. Calcd for C16H14BrN3OS3: C, 43.64; H, 3.20; N, 9.54.
Found: C, 43.83; H, 3.53; N, 9.74.
2.5.15. Data for 1o
Yield: 42%; oil. 1H NMR (400 MHz, CDCl3): d 1.26 (t, J = 7.2 Hz,
3H, –CH3), 1.38 (s, 9H, –C(CH3)3), 2.90 (t, J = 7.2 Hz, 2H, –CH2CO),
3.59 (t, J = 7.2 Hz, 2H, –SCH2), 4.16 (q, J = 7.2 Hz, 2H, –OCH2), 7.90
(s, 1H, Ar-H), 7.96 (s, 1H, Ar-H). ESI-MS: 457.4 (M)+. Anal. Calcd
for C18H20ClN3O3S3: C, 47.20; H, 4.40; N, 9.17. Found: C, 47.43; H,
4.51; N, 9.22.
2.6. X-ray diffraction
A colorless block shaped crystal of 1n (0.16 ꢁ 0.12 ꢁ 0.10 mm)
was selected and mounted on a Bruker SMART APEX CCD Single
Crystal Diffraction System with graphite-monochromated MoK
a
2.5.16. Data for 1p
radiation (k = 0.71073 Å) and x-ray provided by a fine-focus sealed
tube operated at 50 kV and 30 mA.40 The crystal determined at
298(2) K was crystallized in the monoclinic, C2/c space group with
a = 21.842(2) Å, b = 9.3205(8) Å, c = 24.884(2) Å, b = 115.026(3)°,
Yield: 52%; oil. 1H NMR (400 MHz, CDCl3): d 1.25 (t, J = 7.2 Hz,
3H, –CH3), 1.37 (s, 9H, –C(CH3)3), 2.15–2.19 (m, 2H, –CH2–), 2.49
(t, J = 6.8 Hz, 2H, –CH2CO), 3.41 (t, J = 6.8 Hz, 2H, –SCH2), 4.12 (q,
J = 7.2 Hz, 2H, –OCH2), 7.90 (s, 1H, Ar-H), 7.95 (s, 1H, Ar-H). ESI-
MS: 471.6 (M+H)+. Anal. Calcd for C19H22ClN3O3S3: C, 48.34; H,
4.70; N, 8.90. Found: C, 48.63; H, 4.91; N, 8.93.
V = 4590.1(8) Å3, Z = 4, dcalcd = 1.366 g/cm3 and la(MoK ) =
a
0.464 mmꢀ1. Lattice constants were determined with the Bruker
SAINT software package using peak centers for 6195 reflections.41
Then a full hemisphere of diffracted intensities with an
x scan
2.5.17. Data for 1q
width of 0.30° was measured. A total of 14627 integrated reflection
intensities having 2.06° < h < 26.0° were produced using the Bruker
program SAINT and 4517 of these reflections were unique. The
Bruker software package SHELXTL42 was used to solve the structure
using ‘direct methods’ techniques. All stages of weighted full-
matrix least-squares refinement were conducted using F2O data
with the SHELXTL Version 6.10 software package. All the non-
hydrogen atoms were found from the difference maps and refined
anisotropically. All the hydrogen atoms were located their ideal
positions with C–H@0.98 Å (methyl) and 0.93 Å (aromatic) and
their isotropic thermal parameters of were fixed at values 1.5
(methyl) or 1.2 (aromatic) times of the equivalent isotropic ther-
mal parameter of their parent carbon atoms. A total of 268 param-
eters were refined in the refinement. Final agreement factors at
convergence are: R1 = 0.0535, wR2 = 0.1410 and Gof = 1.068 for
Yield: 79%; mp: 111–112 °C. 1H NMR (400 MHz, CDCl3): d 1.38
(s, 9H, –C(CH3)3), 2.30 (t, J = 2.4 Hz, 1H, –CH), 4.13 (d, J = 2.4 Hz,
2H, –SCH2), 7.93 (s, 1H, Ar-H), 8.00 (s, 1H, Ar-H). ESI-MS: 395.5
(M)+. Anal. Calcd for C16H14ClN3OS3: C, 48.53; H, 3.56; N, 10.61.
Found: C, 48.60; H, 3.80; N, 10.65.
2.5.18. Data for 1r
Yield: 44%; mp: 104–105 °C. 1H NMR (400 MHz, CDCl3): d 1.27
(t, J = 7.2 Hz, 3H. –CH3), 1.37 (s, 9H, –C(CH3)3), 4.16 (s, 2H, –
SCH2), 4.22 (q, J = 7.2 Hz, 2H, –OCH2), 7.94 (s, 1H, Ar-H), 8.08 (s,
1H, Ar-H). ESI-MS: 487 (MꢀH)+, 489.0 (M+H)+. Anal. Calcd for
C17H18BrN3O3S3: C, 41.80; H, 3.71; N, 8.60. Found: C, 41.62; H,
3.90; N, 8.52.
2.5.19. Data for 1s
3892 independent reflections with I >2r(I); R1 = 0.0606, wR2 =
0.1463 and Gof = 1.068 for all the 4517 independent reflections.
The largest shift/s.u. was 0.000 in the final refinement cycle. The
Yield: 60%; mp: 88–90 °C. 1H NMR (600 MHz, CDCl3): d 1.26 (t,
J = 7.2 Hz, 3H, –CH3), 1.40 (s, 9H, –C(CH3)3), 1.71 (d, J = 7.2 Hz,