JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
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123.42, 121.96, 118.89, 116.47, 116.25, 113.09, 108.23, 88.29, 38.53, 86%; mp 263–267 ꢂC; 1H NMR (400 MHz, DMSO-d6): d 8.73 (d,
34.13. ESI-MS: [M ꢃ I]þ (C27H22FN2Sþ): m/z 425.0; HPLC retention J ¼ 8.4 Hz, 1H), 8.08 (dd, J ¼ 14.8, 8.3 Hz, 2H), 7.99–7.89 (m, 3H),
time was 3.63 min.
7.73 (t, J ¼ 7.6 Hz, 1H), 7.66 (d, J ¼ 8.3 Hz, 1H), 7.63–7.56 (m, 3H),
7.51 (s, 1H), 7.40 (t, J ¼ 7.5 Hz, 1H), 7.09 (d, J ¼ 8.5 Hz, 2H), 6.82 (s,
2-((E)-4-bromostyryl)-1-methyl-4-((E)-(3-methylbenzo[d]thiazol-
2(3H)-ylidene) methyl)quinolin-1-ium iodide (A3). Rufous solid, yield 1H), 4.11 (s, 3H), 3.96 (s, 3H), 3.91 (s, 3H). 13C NMR (100 MHz,
87%; Mp 307–309 ꢂC; 1HNMR (400 MHz, DMSO-d6): d 8.76 (d, DMSO-d6): d 160.41, 158.29, 151.39, 146.68, 140.01, 139.75, 138.21,
J ¼ 8.2 Hz, 1H), 8.18 (d, J ¼ 8.2 Hz, 1H), 8.05 (d, J ¼ 7.6 Hz, 1H), 8.00 132.41, 129.64, 127.29, 127.12, 125.65, 124.43, 123.36, 123.04,
(d, J ¼ 7.3 Hz, 1H), 7.90 (d, J ¼ 7.8 Hz, 2H), 7.86 – 7.70 (m, 5H), 7.63 122.70, 122.25, 118.06, 117.75, 113.67, 111.81, 106.95, 86.87, 54.80,
(d, J ¼ 19.0 Hz, 3H), 7.44–7.37 (m, 1H), 6.92 (s, 1H), 4.12 (d, 37.30, 32.91. ESI-MS: [M ꢃ I]þ (C28H25N2OSþ): m/z 437.0; HPLC
J ¼ 30.4 Hz, 3H), 4.01 (s, 3H). 13C NMR (100 MHz, DMSO-d6): d retention time was 2.95 min.
159.57, 154.63, 148.40, 140.95, 139.64, 139.49, 133.58, 130.62,
2-((E)-3-methoxystyryl)-1-methyl-4-((E)-(3-methylbenzo[d]thiazol-
129.43, 128.50, 126.83, 125.82, 124.67, 124.14, 123.91, 123.48, 2(3H)-ylidene) methyl)quinolin-1-ium iodide (A9). Rufous solid, yield
123.17, 118.73, 113.10, 111.03, 87.33, 37.56, 34.09. ESI-MS: [M ꢃ I]þ 87%; mp 252–256 ꢂC; 1H NMR (400 MHz, DMSO-d6): d 8.50 (d,
(C27H22BrN2Sþ): m/z 486.9; HPLC retention time was 3.52 min.
J ¼ 8.5 Hz, 1H), 7.83–7.73 (m, 3H), 7.70 (d, J ¼ 7.7 Hz, 1H), 7.56 (dd,
J ¼ 15.5, 11.8 Hz, 2H), 7.39 (dd, J ¼ 16.2, 9.3 Hz, 3H), 7.31 (d,
2-((E)-2,4-dichlorostyryl)-1-methyl-4-((E)-(3-methylbenzo[d]thiazol-
2(3H)-ylidene)methyl)quinolin-1-ium iodide (A4). Purple solid, yield J ¼ 8.2 Hz, 1H), 7.24 (t, J ¼ 7.5 Hz, 1H), 7.09 (s, 1H), 6.99 (t,
87%; Mp 271–275 ꢂC; 1H NMR (400 MHz, DMSO-d6): d 8.74 (d, J ¼ 7.4 Hz, 1H), 6.92 (d, J ¼ 8.3 Hz, 1H), 6.52 (s, 1H), 3.81 (d,
J ¼ 7.8 Hz, 1H), 8.18 (d, J ¼ 8.7 Hz, 1H), 8.10 (d, J ¼ 8.5 Hz, 1H), 7.96 J ¼ 12.7 Hz, 3H), 3.74 (s, 3H), 3.65 (s, 3H). 13C NMR (100 MHz,
(d, J ¼ 7.0 Hz, 2H), 7.85 (d, J ¼ 15.8 Hz, 1H), 7.73 (t, J ¼ 17.6 Hz, 4H), DMSO-d6): d 158.57, 157.74, 152.11, 147.18, 140.32, 138.85, 135.87,
7.59 (t, J ¼ 10.7 Hz, 2H), 7.52 (s, 1H), 7.39 (d, J ¼ 7.2 Hz, 1H), 6.91 (s, 133.43, 132.33, 128.64, 128.40, 126.69, 125.29, 124.49, 123.62,
1H), 4.11 (s, 3H), 3.98 (s, 3H). 13C NMR (100 MHz, DMSO-d6): d 123.54, 123.47, 122.65, 121.28, 121.09, 118.61, 112.79, 111.99,
159.90, 151.68, 148.25, 140.85, 139.37, 135.67, 134.83, 134.75, 107.86, 87.84, 56.28, 38.22, 34.02. ESI-MS: [M ꢃ I]þ (C28H25N2OSþ):
133.87, 132.23, 130.11, 129.89, 128.67, 128.48, 127.11, 125.98, m/z 437.0; HPLC retention time was 3.14 min.
125.67, 124.94, 123.97, 123.19, 118.98, 113.33, 108.68, 88.78, 38.68,
2-((E)-3,4-dimethoxystyryl)-1-methyl-4-((E)-(3-methylbenzo[d]thia-
34.31. ESI-MS: [M ꢃ I]þ (C27H21Cl2N2Sþ): m/z 475.0; HPLC retention zol-2(3H)-ylidene)methyl)quinolin-1-ium iodide (A10). Brown solid,
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time was 4.29 min.
yield 89%; mp 266–270 ꢂC; H NMR (400 MHz, DMSO-d6): d 8.73 (d,
J ¼ 8.2 Hz, 1H), 8.14 (s, 1H), 8.05 (d, J ¼ 7.8 Hz, 1H), 7.99–7.95 (m,
1-methyl-4-((E)-(3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)-2-
((E)-4-methyl styryl)quinolin-1-ium iodide (A5). Red solid, yield 85%; 1H), 7.91 (d, J ¼ 7.3 Hz, 1H), 7.69 (s, 1H), 7.62 (d, J ¼ 6.7 Hz, 2H),
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mp 275–278 ꢂC; H NMR (400 MHz, DMSO-d6): d 8.77 (d, J ¼ 8.3 Hz, 7.58 (s, 3H), 7.47 (d, J ¼ 8.1 Hz, 1H), 7.39 (d, J ¼ 7.6 Hz, 2H), 7.07 (d,
1H), 8.19 (d, J¼ 8.8 Hz, 1H), 8.07 (d, J¼ 7.8 Hz, 1H), 8.00 (t, J¼ 7.9 Hz, J ¼ 8.2 Hz, 1H), 6.85 (s, 1H), 6.65 (s, 1H), 4.16 (s, 3H), 3.97 (s, 3H),
1H), 7.85 (d, J ¼ 7.9 Hz, 2H), 7.75 (dd, J ¼ 9.7, 5.6 Hz, 3H), 7.63 (dt, 3.91 (s, 3H), 3.85 (s, 3H). 13C NMR (100 MHz, DMSO-d6): d 158.57,
J ¼ 15.6, 9.9 Hz, 3H), 7.43–7.34 (m, 3H), 6.92 (s, 1H), 4.17 (s, 3H), 157.74, 152.11, 147.13, 140.32, 138.85, 135.87, 133.43, 132.33,
4.00 (d, J ¼ 8.1 Hz, 3H), 2.41 (s, 3H). 13C NMR (100 MHz, DMSO-d6): 128.64, 128.40, 126.69, 125.29, 124.49, 123.62, 123.54, 123.47,
d 159.92, 152.60, 148.26, 141.32, 141.05, 140.79, 139.52, 133.74, 122.65, 122.41, 87.70, 56.28, 37.96, 33.94. ESI-MS: [M ꢃ I]þ
132.99, 130.03, 128.95, 128.55, 126.97, 125.69, 124.69, 124.27, (C29H27N2O2Sþ): m/z 467.0; HPLC retention time was 5.72 min.
124.01, 123.48, 121.10, 119.03, 113.14, 108.44, 88.27, 38.53, 34.12,
1-methyl-4-((E)-(3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)-2-
21.57. ESI-MS: [M ꢃ I]þ (C28H25N2Sþ): m/z 421.2; HPLC retention ((E)-2-(pyridine-3-yl)vinyl)quinolin-1-ium iodide (A11). Rufous solid,
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time was 3.38 min.
yield 88%; mp 288–291 ꢂC; H NMR (400 MHz, DMSO-d6): d 9.10 (s,
1H), 8.77 (s, 1H), 8.66 (d, J ¼ 3.7 Hz, 1H), 8.39 (d, J ¼ 7.3 Hz, 1H),
2-((E)-4-(dimethylamino)styryl)-1-methyl-4-((E)-(3-methylbenzo[d]-
thiazol-2(3H)-y lidene)methyl)quinolin-1-ium iodide (A6). Purple solid, 8.17 (s, 1H), 8.06 (d, J ¼ 7.5 Hz, 1H), 7.99 (s, 1H), 7.91 (d, J ¼ 15.9 Hz,
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yield 89%; mp 301–304 ꢂC; H NMR (400 MHz, DMSO-d6): d 8.70 (d, 1H), 7.74 (s, 2H), 7.67 (d, J ¼ 18.3 Hz, 1H), 7.65–7.52 (m, 3H), 7.41 (s,
J ¼ 8.3 Hz, 1H), 8.13 (d, J ¼ 8.8 Hz, 1H), 8.03 (d, J ¼ 7.7 Hz, 1H), 1H), 6.91 (s, 1H), 4.16 (s, 3H), 4.00 (s, 3H). 13C NMR (100 MHz,
7.97–7.92 (m, 1H), 7.79 (d, J ¼ 8.9 Hz, 2H), 7.71 (d, J ¼ 7.8 Hz, 1H), DMSO-d6): d 160.23, 151.88, 151.12, 150.40, 148.29, 140.98, 139.45,
7.69–7.64 (m, 2H), 7.63 (s, 1H), 7.56 (t, J ¼ 7.8 Hz, 1H), 7.43 (d, 137.63, 135.15, 133.81, 131.47, 128.59, 127.05, 125.70, 124.83,
J ¼ 15.7 Hz, 1H), 7.36 (t, J ¼ 7.6 Hz, 1H), 6.79 (d, J ¼ 9.1 Hz, 3H), 4.13 (s, 124.41, 124.37, 124.29, 123.98, 123.45, 119.01, 113.27, 108.47,
3H), 3.94 (s, 3H), 3.05 (s, 6H). 13C NMR (100 MHz, DMSO-d6): d 158.77, 88.58, 38.62, 34.22. ESI-MS: [M ꢃ I]þ (C26H22N3Sþ): m/z 408.0; HPLC
153.24, 152.30, 147.53, 142.83, 141.10, 139.57, 133.43, 130.97, 128.40, retention time was 1.97 min.
126.63, 125.57, 124.30, 124.05, 123.92, 123.38, 123.11, 118.93, 115.10,
2-((E)-2–(1H-indol-3-yl)vinyl)-1-methyl-4-((E)-(3-methylbenzo[d]thia-
112.74, 112.16, 108.03, 87.58, 38.28, 33.91. ESI-MS: [M ꢃ I]þ zol-2(3H)-ylidene)methyl)quinolin-1-ium iodide (A12). Rufous solid,
(C29H28N3Sþ): m/z 450.1; HPLC retention time was 5.44 min.
yield 85%; mp 298–303 ꢂC; 1H NMR (400 MHz, DMSO-d6): d 11.97
(s, 1H), 8.62 (d, J ¼ 8.4 Hz, 1H), 8.20 (s, 1H), 8.09 (d, J ¼ 7.3 Hz, 1H),
1-methyl-4-((E)-(3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)-2-
((E)-4-(methyl thio)styryl)quinolin-1-ium iodide (A7). Rufous solid, 8.03 (d, J ¼ 8.8 Hz, 1H), 7.98 (d, J ¼ 7.8 Hz, 1H), 7.88 (dd, J ¼ 15.5,
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yield 90%; mp 293–295 ꢂC; H NMR (400 MHz, DMSO-d6): d 8.73 (d, 5.5 Hz, 2H), 7.63 (t, J ¼ 7.6 Hz, 1H), 7.51 (q, J ¼ 8.4 Hz, 4H), 7.33–7.23
J ¼ 7.8 Hz, 1H), 8.14 (d, J ¼ 8.4 Hz, 1H), 8.06–8.02 (m, 1H), 8.00–7.95 (m, 4H), 6.70 (d, J ¼ 8.5 Hz, 1H), 4.07 (s, 3H), 3.83 (s, 3H). 13C NMR
(m, 1H), 7.87 (d, J ¼ 8.5 Hz, 2H), 7.76–7.68 (m, 3H), 7.64 (s, 1H), (100 MHz, DMSO-d6): d 158.34, 153.65, 147.23, 140.96, 139.40,
7.61–7.55 (m, 2H), 7.42–7.35 (m, 3H), 6.87(s, 1H), 4.13(s, 3H), 3.97 136.84, 133.30, 128.29, 126.47, 125.49, 125.13, 124.14, 123.92,
(d, J ¼ 3.7 Hz, 3H), 2.56 (s, 3H). 13C NMR (100 MHz, DMSO-d6): d 123.80, 123.38, 123.26, 121.71, 120.70, 118.78, 114.21, 113.98,
159.81, 152.50, 148.16, 142.08, 141.04, 140.86, 139.51, 133.71, 113.05, 112.54, 107.63, 87.39, 38.20, 33.84. ESI-MS: [M ꢃ I]þ
132.08, 129.41, 128.54, 126.94, 126.07, 125.67, 124.68, 124.26, (C29H24N3Sþ): m/z 446.1; HPLC retention time was 2.81 min.
123.98, 123.44, 120.95, 119.01, 113.11, 108.42, 38.53, 34.11, 14.77.
1-methyl-4-((E)-(3-methylbenzo[d]thiazol-2(3H)-ylidene)methyl)-2-
ESI-MS: [M ꢃ I]þ (C28H25N2S2þ): m/z 453.0; HPLC retention time ((E)-2-(naphth alen-2-yl)vinyl)quinolin-1-ium iodide (A13). Black solid,
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was 3.45 min.
yield 85%; mp 299–304 ꢂC; H NMR (400 MHz, DMSO-d6): d 8.78 (d,
J ¼ 8.3 Hz, 1H), 8.41 (s, 1H), 8.18 (t, J ¼ 8.1 Hz, 2H), 8.11–8.04 (m,
2-((E)-4-methoxystyryl)-1-methyl-4-((E)-(3-methylbenzo[d]thiazol-
2(3H)-ylidene) methyl)quinolin-1-ium iodide (A8). Brown solid, yield 2H), 8.01 (d, J ¼ 4.9 Hz, 3H), 7.91 (s, 1H), 7.85 (s, 1H), 7.75