Medicinal Chemistry Research
ppm, 300 MHz): 8.79 (s, 1H, NH), 8.00 (d, J = 15.8, 1H,
Hß), 7.92 (dd, J = 7.7, 1.5 Hz, 1H, ArH), 7.74 (d, J = 15.8
Hz, 1H, Hα), 7.56 (dd, J = 8.1, 1.7 Hz, 1H, ArH), 7.48–7.42
(m, 1H, ArH), 7.30 (d, J = 1.7 Hz, 1H, ArH), 7.11 (d, J =
8.2 Hz, 1H, ArH), 7.10 (d, J = 8.1 Hz, 1H, ArH), 7.01 (d, J
= 7.5 Hz, 2H, ArH), 6.91 (dd, J = 7.7, 1.2 Hz, 1H, ArH),
6.76 (td, J = 7.5, 1.1 Hz, 1H, ArH), 6.66 (dd, J = 7.9, 0.9
Hz, 1H, ArH), 3.90 (s, 3H, OCH3). 13C NMR (DMSO-d6, δ
ppm, 75 MHz): 188.5 (C=O), 158.8, 142.6, 141.6, 138.8,
137.5, 132.8, 129.0, 128.5, 126.7, 126.6, 123.9,123.4,
122.9, 122.6, 122.1, 121.2, 115.7, 115.1, 113.4, 112.3,
56.2. HRMS (ESI-MS) Calc. for C22H18NO2S [M+H]+,
359.0975; found 359.0977.
8.77 (s, 1H, NH), 7.82 (d, J = 15.7 Hz, 1H, Hß), 7.66 (d, J
= 8.8 Hz, 1H, ArH), 7.61 (d, J = 15.7 Hz, 1H, Hα), 7.50
(dd, J = 8.2, 1.8 Hz, 1H, ArH), 7.24 (s, 1H, ArH), 7.03 (d,
J = 8.0 Hz, 1H, ArH), 6.94 (td, J = 13.6, 1.6 Hz, 1H, ArH),
6.87 (d, J = 4.4 Hz, 2H, ArH), 6.73 (td, J = 7.2, 1.2 Hz, 1H,
ArH), 6.64 (d, J = 8.4 Hz, 1H, ArH), 3.82 (s, 3H, OCH3),
3.73 (s, 3H, OCH3), 3.66 (s, 3H, OCH3). 13C NMR
(DMSO-d6, δ ppm, 100 MHz): 188.8 (C=O), 156.5, 153.8,
142.8, 142.4, 141.8, 139.1, 137.8, 128.7, 127.0, 126.9,
124.2, 124.0, 123.0, 122.9, 121.6, 120.8, 115.9, 115.3,
113.5, 109.1, 62.2, 61.2, 56.7. Calc. for C24H22NO4S [M
+H]+, 420.1264; found 420.1278.
(E)-1-(10H-Phenothiazine-2-yl)-3-(2,4,5-
(E)-1-(10H-Phenothiazine-2-yl)-3-(3,4,5-
trimethoxyphenyl)-prop-2-en-1-one (FS6)
trimethoxyphenyl)-prop-2-en-1-one (FS3)
Red solid. Yield: 55.3 %. Melting point (m.p.): 212.2–
214.2 °C. H NMR (DMSO-d6, δ ppm, 300 MHz): 8.79 (s,
1
Violet solid. Yield: 21.4 %. Melting point (m.p.): 226.3–
1
226.7 °C. H NMR (DMSO-d6, δ ppm, 400 MHz): 8.78 (s,
1H, NH), 8.02 (d, J = 15.6 Hz, 1H, Hß), 7.63 (d, J = 15.5
Hz, 1H, Hα), 7.58 (d, J = 1.7 Hz, 1H, ArH), 7.48 (s, 1H,
ArH), 7.29 (d, J = 1.7 Hz, 1H, ArH), 7.06 (d, J = 8.0 Hz,
1H, ArH), 7.00 (td, J = 7.7, 1.4 Hz, 1H, ArH), 6.91 (dd, J
= 7.7, 1.3 Hz, 1H, ArH), 6.79–6.73 (m, 2H, ArH), 6.67 (dd,
J = 7.9, 1.0 Hz, 1H, ArH), 3.88 (d, J = 8.6 Hz, 6H, OCH3),
3.81 (s, 3H, OCH3). 13C NMR (DMSO-d6, δ ppm, 75
MHz): 188.4 (C=O), 154.8, 153.3, 143.5, 142.6, 141.7,
138.9, 137.9, 128.4, 126.7, 126.5, 123.5, 122.8, 122.5,
119.0, 115.8, 115.1, 114.7, 113.4, 111.5, 98.0, 56.9, 56.3.
Calc. for C24H22NO4S [M+H]+, 419.1186; found
419.1187.
1H, NH), 7.75–7.60 (m, 3H, ArH), 7.27 (s, 1H, ArH), 7.18
(s, 2H, ArH), 7.06 (d, J = 8.1 Hz, 1H, ArH), 7.00–6.96 (m,
1H, ArH), 6.89 (d, J = 7.7 Hz, 1H, ArH), 6.74 (t, J = 7.5
Hz, 1H, ArH), 6.64 (d, J = 8.1 Hz, 1H, ArH), 3.69 (s, 3H,
OCH3), 3.32 (s, 6H, OCH3). 13C NMR (DMSO-d6, δ ppm,
100 MHz): 188.7 (C=O), 153.8, 145.0, 142.8, 141.8, 137.7,
130.9, 128.7, 127.0, 126.7, 124.2, 123.3, 122.8, 121.7,
115.9, 115.3, 113.6, 107.2, 60.8, 56.8. HRMS (ESI-MS)
Calc. for C24H22NO4S [M+H]+, 420.1264; found
420.1251.
(E)-1-(10H-Phenothiazine-2-yl)-3-(4-
methoxyphenyl)-prop-2-en-1-one (FS4)
(E)-1-(10H-Phenothiazine-2-yl)-3-(2,4-
dimethoxyphenyl)-prop-2-en-1-one (FS7)
Red solid. Yield: 21.4 % (66 %, Saranya and Ravi 2013).
1
Melting point (m.p.): 226.3–226.7 °C. H NMR (DMSO-
(Do et al. 2016) Red solid. Yield: 28.3 % (49 %, Do et al.
2016). Melting point (m.p.): 189.2–190.4 °C. 1H NMR
(DMSO-d6, δ ppm, 400 MHz): 8.76 (s, 1H, NH), 7.92 (d, J
= 15.7 Hz, 1H, Hß), 7.84 (d, J = 8.8 Hz, 1H, ArH), 7.59 (d,
J = 15.7 Hz, 1H, Hα), 7.51 (dd, J = 8.1, 1.8 Hz, 1H, ArH),
7.26 (s, 1H, ArH), 7.03 (d, J = 8.1 Hz, 1H, ArH), 7.00–6.96
(m, 1H, ArH), 6.89 (d, J = 7.7 Hz, 1H, ArH), 6.74 (t, 7.5 Hz,
1H, ArH), 6.65–6.59 (m, 3H, ArH), 3.88 (s, 3H, OCH3),
3.81 (s, 3H, OCH3). 13C NMR (DMSO-d6, δ ppm, 100
MHz): 188.6 (C=O), 163.8, 160.7, 142.8, 141.9, 139.3,
138.0, 130.8, 128.7, 127.0, 126.8, 123.7, 122.9, 122.8,
119.5, 116.6, 116.0, 115.9, 113.6, 107.1, 99.0, 56.5, 56.2.
Calc. for C23H20NO3S [M+H]+, 390.1158; found 390.1154.
d6, δ ppm, 300 MHz): 8.78 (s, 1H, NH), 7.82 (d, J = 8.9
Hz, 2H, ArH), 7.66 (d, J = 4.9 Hz, 2H, ArH), 7.60 (dd, J
= 8.1, 1.7 Hz, 1H, ArH), 7.30 (d, J = 1.8 Hz, 1H, ArH),
7.04 (d, J = 15.5 Hz, 1H), 6.99 (dd, J = 7.2, 1.2 Hz, 3H,
ArH), 6.91 (dd, J = 7.7, 1.4 Hz, 1H, ArH), 6.75 (td, J =
7.5, 1.2 Hz, 1H, ArH), 6.66 (dd, J = 7.9, 1.4 Hz, 1H,
ArH), 3.82 (s, 3H, OCH3). 13C NMR (DMSO-d6, δ ppm,
75 MHz): 188.3 (C=O), 161.9, 144.2, 142.6, 141.7,
137.6, 131.2, 128.4, 127.8, 126.7, 126.6, 123.7, 122.9,
122.5, 119.8, 115.7, 115.1, 114.9, 113.4, 55.9. HRMS
(ESI-MS) Calc. for C22H18NO2S [M+H]+, 359.0975;
found 359.0975.
(E)-1-(10H-Phenothiazine-2-yl)-3-(2,3,4-
trimethoxyphenyl)-prop-2-en-1-one (FS5)
(E)-1-(10H-Phenothiazine-2-yl)-3-(2,3-
dimethoxyphenyl)-prop-2-en-1-one (FS9)
Dark violet solid. Yield: 26.5 %. Melting point (m.p.):
174.6–175.4 °C. H NMR (DMSO-d6, δ ppm, 400 MHz):
Claret red solid. Yield: 62.4 %. Melting point (m.p.): 180.1–
181.3 °C. H NMR (DMSO-d6, δ ppm, 400 MHz): 8.77 (s,
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