Title: Synthesis and pharmacological evaluation of some novel 4-isopropyl thiazole based sulfonyl derivatives as potent antimicrobial and anti tubercular agents”
Article Type: Orginal article
Order of Authors: Suresh Kumar GV 1*, Rajendra Prasad Y2, Chandrashekar SM3,
General structure for 3a-e
Structure / R1 / R2 / M.p (oC)a/crystallization
solvent / Yield
(%) / H1 NMR / C13 NMR / Mass data
3a / / - / 162-164 (Ethanol) / 79 / 7.1–7.6 (8H, phenyl), 7.22 (s, 1H, thiazole-C5),
3.04 (m, 1H, isopropyl),
1.52(d, J = 8.5 Hz, 6H, 2CH3)
4.16(s, 2H, CH2) / - / 491.02 (M+2), 489.02
3b / / - / 188-191 (Ethanol) / 79 / 7.2–7.7 (9H, phenyl), 7.25 (s, 1H, thiazole-C5),
3.12 (m, 1H, isopropyl), 1.55(d, J = 8.5 Hz, 6H, 2CH3)
4.08(s, 2H, CH2) / 161.24 (thiazole C4),
164.26 (thiazole C2),
141.11 (triazole-C5),
120– 152 (Ar),
11.89 (thiazole-C5),
23.98 (tertiary-1C- isopropyl),
23.65 (terminal 2CH3-isopropyl)
27.24(CH2) / 461.10 (M+1), 460.09
3c / / - / 169-171 (Ethanol) / 83 / 7.2–7.4 (9H, phenyl),
7.33 (s, 1H, thiazole-C5),
3.06 (m, 1H, isopropyl),
1.52(d, J = 8.5 Hz, 6H, 2CH3)
4.12(s, 2H, CH2) / - / -
3d / / 165-168 (Ethanol) / 81 / 7.2–7.8 (8H, phenyl),
7.54 (s, 1H, thiazole-C5),
3.02 (m, 1H, isopropyl),
1.54(d, J = 8.5 Hz, 6H, 2CH3)
4.04(s, 2H, CH2) / - / -
3e / / - / 171-178 (Ethanol) / 91 / 7.1–7.6 (9H, phenyl), 7.54 (s, 1H, thiazole-C5),
3.08 (m, 1H, isopropyl),
1.54(d, J = 8.5 Hz, 6H, 2CH3)
4.14(s, 2H, CH2) / - / 477.09 (M+1) 476.09
General Structure 7a-q
Structure / Ring1 / Ring-2 / H1 NMR / C13 NMR7a / / / 168-172 (Ethanol) / 71 / 9.62 (s, 1H, N=CH),
7.2–7.5 (6H, phenyl & ), 7.52 (s, 1H, thiazole-C5),
2.92 (m, 1H, isopropyl), 1.25(d, J = 8.5 Hz, 6H, 2CH3)
4.19(s, 2H, CH2) / - / 553.0(M+2) and
551.02 (in the ratio of 1:1)
7b / / / 182-184 (Ethanol) / 66 / 9.25 (s, 1H, N=CH),
7.2–7.7 (7H, phenyl & ), 7.45 (s, 1H, thiazole-C5),
2.97(m, 1H, isopropyl), 1.22(d, J = 8.5 Hz, 6H, 2CH3)
4.08(s, 2H, CH2) / - / -
7c / / / 179-181 (Ethanol) / 74 / 9.33 (s, 1H, N=CH),
7.1–7.6 (7H, phenyl & ), 7.32 (s, 1H, thiazole-C5),
2.92(m, 1H, isopropyl), 1.27(d, J = 8.5 Hz, 6H, 2CH3)
4.12(s, 2H, CH2) / - / -
7d / / / 166-169 (Ethanol) / 62 / 9.36 (s, 1H, N=CH),
7.1–7.8 (7H, phenyl & ), 7.46 (s, 1H, thiazole-C5),
2.85(m, 1H, isopropyl), 1.27(d, J = 8.5 Hz, 6H, 2CH3)
4.13(s, 2H, CH2) / - / 534.24, 536.11 (M+2),
7e / / / 174-178 (Ethanol) / 65 / 9.31 (s, 1H, N=CH),
7.1–7.6 (7H, phenyl ), 7.42 (s, 1H, thiazole-C5),
2.84(m, 1H, isopropyl), 1.22(d, J = 8.5 Hz, 6H, 2CH3)
4.17(s, 2H, CH2) / 162.25(HC=N),
160.69 (thiazole C4),
152.68 (thiazole C2),
140.51 (triazole-C5),
124– 156 (Ar),
115.61 (thiazole-C5),
27.68 (tertiary-1C- isopropyl),
22.65 (terminal 2CH3-isopropyl)
26.25 (CH2) / -
7f / / / 165-167 (Ethanol) / 78 / 9.25 (s, 1H, N=CH),
7.1–7.7 (8H, phenyl ), 7.38 (s, 1H, thiazole-C5),
2.88(m, 1H, isopropyl), 1.29(d, J = 8.5 Hz, 6H, 2CH3)
4.21(s, 2H, CH2) / - / -
7g / / / 173-175
(Ethanol) / 73 / 9.22 (s, 1H, N=CH),
7.1–7.8 (8H, phenyl ), 7.43 (s, 1H, thiazole-C5),
2.82(m, 1H, isopropyl), 1.26(d, J = 8.5 Hz, 6H, 2CH3)
4.12(s, 2H, CH2) / - / 472.0, 474.08 (M+2),
7h / / / 166-164 (Ethanol) / 69 / 9.36 (s, 1H, N=CH),
7.1–7.5 (8H, phenyl ), 7.48 (s, 1H, thiazole-C5),
2.86(m, 1H, isopropyl), 1.24(d, J = 8.5 Hz, 6H, 2CH3)
4.12(s, 2H, CH2) / 161.26(HC=N),
162.8 (thiazole C4),
151.25(thiazole C2),
141.29 (triazole-C5),
123– 158 (Ar),
114.44 (thiazole-C5),
26.44 (tertiary-1C- isopropyl),
22.66 (terminal 2CH3-isopropyl)
24.44 (CH2)
7i / / / 173-176 (Ethanol) / 74 / 9.38 (s, 1H, N=CH),
7.1–7.8 (7H, phenyl ), 7.48 (s, 1H, thiazole-C5),
2.84(m, 1H, isopropyl), 1.18(d, J = 8.5 Hz, 6H, 2CH3)
4.06(s, 2H, CH2) / - / -
7j / / / 154-158 (Ethanol) / 61 / 9.43 (s, 1H, N=CH),
7.1–7.6 (8H, phenyl ), 7.52 (s, 1H, thiazole-C5),
2.39(m, 1H, isopropyl), 1.24(d, J = 8.5 Hz, 6H, 2CH3)
4.11(s, 2H, CH2) / - / -
7k / / / 161-163 (Ethanol) / 78 / 9.65 (s, 1H, N=CH),
7.1–7.6 (8H, phenyl ), 7.56 (s, 1H, thiazole-C5),
2.65(m, 1H, isopropyl), 1.16(d, J = 8.5 Hz, 6H, 2CH3)
4.12(s, 2H, CH2) / - / -
7l / / / 167-169 (Ethanol) / 73 / 9.67 (s, 1H, N=CH),
7.1–7.7 (8H, phenyl ), 7.59 (s, 1H, thiazole-C5),
2.44(m, 1H, isopropyl), 1.18(d, J = 8.5 Hz, 6H, 2CH3)
4.09(s, 2H, CH2) / - / 532.00, 533.00 (M+1), 534.00 (M+2),
7m / / / 152-154 (Ethanol) / 54 / 9.32 (s, 1H, N=CH),
7.1–7.8 (9H, phenyl ), 7.52 (s, 1H, thiazole-C5),
2.19(m, 1H, isopropyl), 1.28(d, J = 8.5 Hz, 6H, 2CH3)
4.09(s, 2H, CH2)
7n / / / 167-169 (Ethanol) / 72 / - / - / 437.12 (100.0%), 438.13 (M+1)
439.12 (M+2
7o / / / 168-171 (Ethanol) / 75 / 9.32 (s, 1H, N=CH),
7.1–7.8 (8H, phenyl ), 7.55 (s, 1H, thiazole-C5),
2.49(m, 1H, isopropyl), 1.28(d, J = 8.5 Hz, 6H, 2CH3)
4.02(s, 2H, CH2) / 159.69(HC=N),
161.41 (thiazole C4),
152.64(thiazole C2),
139.18 (triazole-C5),
123– 158 (Ar),
114.44 (thiazole-C5),
26.68 (tertiary-1C- isopropyl),
22.41 (terminal 2CH3-isopropyl)
24.92 (CH2) / -
7p / / / 169-173 (Ethanol) / 83 / 9.69 (s, 1H, N=CH),
7.1–7.7 (8H, phenyl ), 7.41 (s, 1H, thiazole-C5),
2.41(m, 1H, isopropyl), 1.51(d, J = 8.5 Hz, 6H, 2CH3)
4.12(s, 2H, CH2)
10a-h
10a / / - / 142-146 (Ethanol) / 69 / 7.2–7.8 (4H, phenyl), 7.43 (s, 1H, thiazole-C5),3.03 (m, 1H, isopropyl), 1.52(d, J = 8.5 Hz, 6H, 2CH3)
4.19(s, 2H, CH2) / 164.69 (oxadiazole-C2),
164.11(thiazole C4),
153.32 (oxadiazole-C5),
151.62(thiazole-C2),
122– 165 (Ar),
114.69 (thiazole-C5),
31.43 (tertiary-1C-isopropyl),
21.69 (terminal 2CH3-isopropyl)
19.85(CH2)
10b / / - / 152-154 (Ethanol) / 81 / 7.2–7.6 (4H, phenyl), 7.26 (s, 1H, thiazole-C5),
3.09 (m, 1H, isopropyl), 1.57(d, J = 8.5 Hz, 6H, 2CH3)
4.18(s, 2H, CH2) / - / -
10c / / - / 163-165 (Ethanol) / 77 / 7.2–7.7 (4H, phenyl), 7.31 (s, 1H, thiazole-C5),
3.04 (m, 1H, isopropyl), 1.45(d, J = 8.5 Hz, 6H, 2CH3)
4.02(s, 2H, CH2) / - / -
10d / / - / 127-129 (Ethanol) / 71 / 7.2–7.6 (5H, phenyl), 7.24 (s, 1H, thiazole-C5),
3.12 (m, 1H, isopropyl), 1.51(d, J = 8.5 Hz, 6H, 2CH3)
4.19(s, 2H, CH2) / 163.22 (oxadiazole-C2),
162.32 (thiazole C4),
150.36 (oxadiazole-C5),
157.54(thiazole-C2),
122– 175 (Ar),
113.25 (thiazole-C5),
32.55 (tertiary-1C-isopropyl),
22.25 (terminal 2CH3-isopropyl)
28.12(CH2) / -
10e / / 129-131 (Ethanol) / 83 / 7.2–7.8(4H, phenyl), 7.16 (s, 1H, thiazole-C5),
3.09 (m, 1H, isopropyl), 1.57(d, J = 8.5 Hz, 6H, 2CH3)
4.06(s, 2H, CH2)
10f / / 116-119 (Ethanol) / 71 / 7.2–7.7(4H, phenyl), 7.06 (s, 1H, thiazole-C5),
3.11 (m, 1H, isopropyl), 1.57(d, J = 8.5 Hz, 6H, 2CH3)
4.15(s, 2H, CH2)
10g / / 119-121 (Ethanol) / 78 / 7.2–7.7(3H, phenyl), 7.16 (s, 1H, thiazole-C5),
3.18 (m, 1H, isopropyl), 1.57(d, J = 8.5 Hz, 6H, 2CH3)
4.11(s, 2H, CH2)
10h / / 125-127 (Ethanol) / 78 / 7.2–7.6(3H, phenyl),
7.14 (s, 1H, thiazole-C5),
3.12(m, 1H, isopropyl), 1.52(d, J = 8.5 Hz, 6H, 2CH3)
4.13(s, 2H, CH2)
2