X. Dang et al.
Bioorganic Chemistry 114 (2021) 105015
446.1336
1H), 7.19 – 7.13 (m, 1H), 5.43 (d, J = 14.6 Hz, 2H), 5.34 (s, 2H), 2.40 (s,
3H), 2.27 (s, 3H). 13C NMR (101 MHz, dmso) δ 166.94, 164.91, 153.90,
139.12, 137.78, 135.50, 135.47, 134.15, 134.04, 133.73, 133.62,
133.09, 131.65, 130.60, 130.55, 130.47, 130.42, 129.66, 129.33,
128.63, 126.73, 125.74, 124.64, 123.67, 118.89, 118.01, 96.81, 59.49,
40.62, 40.41, 40.20, 40.00, 39.78, 39.58, 39.37, 30.03, 21.34, 15.28.
4.1.4. (2-((4-methyl-2-phenylthiazol-5-yl)methoxy)-2-oxoethyl)
triphenylphosphonium bromide (D3)
White solid, yield 40%. 1H NMR (400 MHz, DMSO‑d6) δ 7.87 – 7.82
(m, 5H), 7.78 – 7.70 (m, 12H), 7.54 – 7.51 (m, 3H), 5.37 (d, J = 14.7 Hz,
2H), 5.34 (s, 2H), 2.27 (s, 3H), 1.24 (s, 1H). 13C NMR (101 MHz,
DMSO‑d6) δ 166.81, 164.90, 153.99, 135.50, 135.47, 134.15, 134.04,
133.12, 130.97, 130.55, 130.42, 129.76, 126.40, 124.80, 118.89,
118.00, 59.48, 30.01, 29.46, 15.29. HRMS(ESI) m/z C31H27NO2PS calcd
for [M]+ 508.1496, found: 508.1434.
HRMS(ESI) m/z
C
32H29NO2PS, calcd for [M]+ 522.1651, found:
522.1641
4.1.11. (2-((4-methyl-2-(p-tolyl)thiazol-5-yl)methoxy)-2-oxoethyl)
triphenylphosphonium bromide (D10)
White solid, yield 85%. 1H NMR (400 MHz, DMSO‑d6) δ 7.86 – 7.70
(m, 17H), 7.33 (d, J = 8.0 Hz, 2H), 5.43 (d, J = 14.6 Hz, 2H), 5.33 (s,
2H), 2.36 (s, 3H), 2.26 (s, 3H). 13C NMR (101 MHz, DMSO‑d6) δ 166.94,
153.84, 140.86, 135.49, 135.46, 134.15, 134.04, 130.54, 130.41,
130.29, 126.34, 124.23, 118.89, 118.00, 59.49, 29.45, 21.41, 15.28.
4.1.5. (2-((4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)methoxy)-
2-oxoethyl)triphenylphosphonium bromide (D4)
White solid, yield 82%. 1H NMR (400 MHz, DMSO‑d6) δ 8.07 (d, J =
8.2 Hz, 2H), 7.90 (d, J = 8.3 Hz, 2H), 7.86 – 7.69 (m, 15H), 5.43 (d, J =
14.7 Hz, 2H), 5.37 (s, 2H), 2.31 (s, 3H). 13C NMR (101 MHz, CDCl3) δ
164.36, 164.34, 135.09, 133.97, 133.86, 133.35, 133.25, 131.30,
130.47, 130.34, 130.23, 130.10, 126.56, 126.49, 126.02, 125.98,
117.34, 77.32, 77.00, 76.69, 59.07, 29.64, 15.12. HRMS(ESI) m/z
HRMS(ESI) m/z
C
32H29NO2PS, calcd for [M]+ 522.1651, found:
522.1641
4.1.12. (2-((4-methyl-2-(4-nitrophenyl)thiazol-5-yl)methoxy)-2-oxoethyl)
triphenylphosphonium bromide (D11)
C
32H26F3NO2PS, calcd for [M]+ 576.1368 , found: 576.1301.
Yellow solid, yield 67%.1H NMR (400 MHz, DMSO‑d6) δ 8.40 – 8.34
(m, 2H), 8.13 – 8.09 (m, 2H), 7.86 – 7.69 (m, 15H), 5.42 (d, J = 14.7 Hz,
2H), 5.39 (s, 2H), 2.32 (s, 3H). 13C NMR (101 MHz, DMSO‑d6) δ 164.04,
154.87, 148.62, 138.46, 135.52, 135.49, 134.15, 134.04, 130.56,
130.43, 127.47, 127.39, 125.11, 118.86, 117.98, 59.34, 15.29. HRMS
(ESI) m/z C31H26N2O4PS, calcd for [M]+ 553.1345, found: 553.1319
4.1.6. (2-((2-(4-fluorophenyl)-4-methylthiazol-5-yl)methoxy)-2-oxoethyl)
triphenylphosphonium bromide (D5)
White solid, yield 48%. 1H NMR (400 MHz, DMSO‑d6) δ 7.91 – 7.72
(m, 15H), 7.71 – 7.68 (m, 2H), 7.40 – 7.35 (m, 2H), 5.41 (d, J = 14.7 Hz,
2H), 5.34 (s, 2H), 2.27 (s, 3H). 13C NMR (101 MHz, dmso) δ 165.63,
164.92, 164.88, 154.01, 135.50, 135.47, 134.14, 134.04, 130.55,
130.42, 130.42, 129.78, 128.77, 128.68, 126.71, 126.69, 124.91,
118.87, 117.99, 116.94, 116.72, 59.43, 29.97, 15.26. HRMS(ESI) m/z
4.1.13. (2-((2-(4-methoxyphenyl)-4-methylthiazol-5-yl)methoxy)-2-
oxoethyl)triphenylphosphonium bromide (D12)
C
31H26FNO2PS, calcd for [M + H]+ 527.1479, found: 527.1466
White solid, yield 80%. 1H NMR (400 MHz, DMSO‑d6) δ 7.88 – 7.70
(m, 17H), 7.09 – 7.05 (m, 2H), 5.44 – 5.39 (m, 2H), 5.33 – 5.30 (m, 2H),
3.83 (s, 3H), 2.24 (s, 3H).13C NMR (101 MHz, DMSO‑d6) δ 166.78,
161.51, 153.71, 135.50, 135.47, 134.15, 134.04, 130.55, 130.42,
128.01, 125.92, 123.62, 118.89, 118.00, 115.10, 59.53, 55.87, 29.97,
15.27. HRMS(ESI) m/z C32H29NO3PS, calcd for [M + H]+ 539.1679,
found: 539.1688
4.1.7. (2-((2-(4-chlorophenyl)-4-methylthiazol-5-yl)methoxy)-2-
oxoethyl)triphenylphosphonium bromide (D6)
White solid, yield 88%. 1H NMR (400 MHz, DMSO‑d6) δ 7.87 – 7.68
(m, 17H), 7.59 (d, J = 8.7 Hz, 2H), 5.43 (d, J = 14.7 Hz, 2H), 5.35 (s,
2H), 2.28 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 164.37, 164.34, 135.08,
133.97, 133.86, 133.36, 133.25, 131.29, 130.47, 130.34, 130.23,
130.10, 129.23, 127.47, 120.52, 118.21, 77.32, 77.00, 76.69, 59.11,
32.93, 15.09. HRMS(ESI) m/z C31H26ClNO2PS, calcd for [M + H]+
543.1183 , found: 543.1109
4.1.14. (2-((2-(4-isopropoxyphenyl)-4-methylthiazol-5-yl)methoxy)-2-
oxoethyl)triphenylphosphonium bromide (D13)
White solid, yield 67%. 1H NMR (400 MHz, Chloroform-d) δ 7.88 –
7.50 (m, 18H), 6.91 (s, 2H), 5.14 (s, 2H), 4.61 (p, J = 6.1 Hz, 1H), 2.25
(s, 2H), 1.97 (s, 3H), 1.36 (s, 6H). 13C NMR (101 MHz, cdcl3) δ 164.25,
135.09, 135.06, 134.36, 134.03, 133.33, 133.22, 131.33, 130.49,
130.36, 127.82, 115.92, 115.77, 77.34, 77.02, 76.70, 70.09, 21.98,
21.95, 15.04, 14.56. HRMS(ESI) m/z C34H33NO3PS, calcd for [M]+
566.1913, found: 566.1982
4.1.8. (2-((2-(4-bromophenyl)-4-methylthiazol-5-yl)methoxy)-2-
oxoethyl)triphenylphosphonium bromide (D7)
White solid, yield 63%. 1H NMR (400 MHz, DMSO‑d6) δ 7.86 – 7.69
(m, 18H), 7.52 (dd, J = 5.0, 2.0 Hz, 1H), 5.41 (d, J = 14.7 Hz, 2H), 5.34
(s, 2H), 2.28 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 166.24, 164.42,
154.06, 135.12, 135.09, 133.95, 133.85, 133.34, 133.23, 132.18,
130.48, 130.35, 130.24, 130.11, 129.00, 127.68, 126.29, 120.57,
118.16, 117.28, 77.35, 77.03, 76.71, 59.12, 32.87, 15.09, HRMS(ESI)
m/z C31H26BrNO2PS, calcd for [M]+ 586.06, found: 586.0609
4.1.15. (2-((2-(4-(benzyloxy)phenyl)-4-methylthiazol-5-yl)methoxy)-2-
oxoethyl)triphenylphosphonium bromide (D14)
White solid, yield 61%. 1H NMR (400 MHz, DMSO‑d6) δ 7.88 – 7.67
(m, 17H), 7.50 – 7.33 (m, 5H), 7.16 (dd, J = 8.0, 5.9 Hz, 2H), 5.41 (d, J
= 14.7 Hz, 2H), 5.32 (s, 2H), 5.19 (s, 2H), 2.25 (s, 3H). 13C NMR (101
MHz, dmso) δ 166.72, 164.90, 160.61, 153.73, 137.11, 135.50, 135.47,
134.15, 134.04, 130.55, 130.42, 129.33, 128.93, 128.63, 128.42,
128.21, 128.02, 126.14, 125.74, 123.69, 118.89, 118.01, 115.94, 69.92,
59.54, 40.62, 40.42, 40.21, 40.00, 39.79, 39.58, 39.37, 30.00, 15.27.
4.1.9. (2-((4-methyl-2-(o-tolyl)thiazol-5-yl)methoxy)-2-oxoethyl)
triphenylphosphonium bromide (D8)
White solid, yield 89%. 1H NMR (400 MHz, DMSO‑d6) δ 7.88 – 7.68
(m, 16H), 7.42 – 7.33 (m, 3H), 5.43 (d, J = 14.6 Hz, 2H), 5.36 (s, 2H),
2.29 (s, 3H).13C NMR (101 MHz, dmso) δ 166.50, 164.87, 153.25,
136.13, 135.52, 135.49, 134.15, 134.05, 132.41, 132.10, 130.55,
130.42, 130.21, 129.71, 126.90, 125.14, 118.90, 118.01, 59.39, 40.58,
40.37, 40.16, 39.95, 39.74, 39.53, 39.32, 29.95, 21.61, 15.31. HRMS
(ESI) m/z C32H29NO2PS, calcd for [M + H]+ 523.1729, found: 523.1793
HRMS(ESI) m/z
C
38H33NO3PS, calcd for [M]+ 614.1913, found:
614.1903
4.1.16. (2-((4-methyl-2-(4-((4-(trifluoromethyl)benzyl)oxy)phenyl)
thiazol-5-yl)methoxy)-2-oxoethyl)triphenylphosphonium bromide (D15)
White solid, yield 71%.1H NMR (400 MHz, DMSO‑d6) δ 7.86 – 7.69
(m, 23H), 5.40 (d, J = 14.7 Hz, 2H), 5.32 (d, J = 3.9 Hz, 4H), 2.25 (s,
3H). 13C NMR (101 MHz, dmso) δ 166.63, 164.90, 160.29, 153.75,
142.04, 135.57, 135.50, 135.47, 134.15, 134.04, 130.55, 130.42,
4.1.10. (2-((4-methyl-2-(m-tolyl)thiazol-5-yl)methoxy)-2-oxoethyl)
triphenylphosphonium bromide (D9)
White solid, yield 70%. 1H NMR (400 MHz, DMSO‑d6) δ 7.85 – 7.71
(m, 15H), 7.42 (d, J = 7.6 Hz, 1H), 7.35 – 7.32 (m, 1H), 7.27 – 7.22 (m,
8