, Chloroquinolin-4-yl)amino)octyl)-3-(1,3-dioxoisoindolin-2-yl)propanamide (7h). Yield 70%; white solid, HRMS calcd for C 26 H 27 ClN 4 O 3
20-8.30 (m, 2H, Ar-H + NH-exchangeable with D 2 O); 8.34 (d, J ¼ 5.3 Hz, 1H, Ar-H); 13 C NMR (100 MHz, DMSO-d 6 ), vol.7 ,
,
, Ar-H); 7.77 (dd, J ¼ 2.2, 9.1 Hz, vol.1
, -Chloroquinolin-4-yl)amino)butyl)-4-(1,3-dioxoisoindolin-2-yl)butanamide (7j). Yield 74%; white solid, 54 (t, J ¼ 5.9 Hz, vol.2
, Hz, vol.1, p.85
, 86 (m, 4H, Ar-H); 8.01 (d, J ¼ 2.1 Hz, 1H, Ar-H), vol.8, pp.80-87
, , vol.2
85 (t, J ¼ 5.5 Hz, 1H, NH-exchangeable with D 2 O), vol.13, p.125 ,
-Chloroquinolin-4-yl)amino)hexyl)-4-(1,3-dioxoisoindolin-2-yl)butanamide (7k). Yield 75%; white solid ,
, .67 (m, 2H, pp.61-62
, 27 (m, 2H, pp.23-26
, , vol.6
86 (m, 4H, Ar-H); 8.28 (d, J ¼ 9.0 Hz, 1H, Ar-H); 8.38 (t, J ¼ 5.5 Hz, 1H, NH-exchangeable with D 2 O); 13 C NMR (125 MHz, DMSO-d 6 ), vol.1, pp.81-88 ,
, Ar-H); 7.75 (d, J ¼ 2.3 Hz, 1H, Ar-H); 7.83-7.90 (m, 4H, Ar-H); 8.19 (d, J ¼ 5.4 Hz, 1H, Ar-H), vol.1, p.27
Ar-H); 8.13 (d, J ¼ 9.0 Hz, Ar-H); 8.37 (d, J ¼ 5.5 Hz, Ar-H); 8.45 (t, J ¼ 5.6 Hz, 1H, NH-exchangeable with D 2 O); 13 C NMR (125 MHz, DMSO-d 6 ), 167.3, 169.7. HRMS calcd for C 2 1H 16 ClFN 4 O 3, vol.1 ,
99 (m, 1H, Ar-H); 8.25 (t, J ¼ 5.7 Hz, NH-exchangeable with D 2 O); 8.29 (d, J ¼ 9.0 Hz, Ar-H); 8.39 (d, J ¼ 5.5 Hz, 1H, Ar-H); 13 C NMR (125 MHz, DMSO-d 6 ), vol.1, p.2 ,
17 (s, 2H, -CH 2 -); 6.39 (d, J ¼ 5.3 Hz, 1H, Ar-H); 7.30 (t, J ¼ 5.4 Hz, NH-exchangeable with D 2 O), vol.4 ,
,
, Ar-H); 13 C NMR (100 MHz, DMSO-d 6 ), vol.1
, , vol.121
, 127.8, 128.2 (d, J ¼ 1.9 Hz), 133.7, 135.1 (d, J ¼ 9
, Chloroquinolin-4-yl)amino)ethyl)-3-(5-?uoro-1,3-dioxoisoindolin-2-yl)propanamide (7p)
,
, m, 4H, 2Â -CH 2 -
,
, , vol.1
, Ar-H); 8.35 (d, J ¼ 5.5 Hz, 1H, Ar-H); 13 C NMR (100 MHz, DMSO-d 6 )
, + 492.1928 found 4921941. HRMS calcd for C 22 H 18 ClFN, vol.4
Chloroquinolin-4-yl)amino)butyl)-3-(5-?uoro-1,3-dioxoisoindolin-2-yl)propanamide (7q) ,
, 400 MHz): 1.38-1.45 (m, 2H, pp.177-178
98 (t, J ¼ 5.5 Hz, NHexchangeable with D 2 O); 8.21 (d, J ¼ 9.0 Hz, Ar-H); 8.33 (d, J ¼ 5.4 Hz, 1H, Ar-H); 13 C NMR (100 MHz, DMSO-d 6 ), vol.7 ,
,
NHexchangeable with D 2 O); 8.20 (d, J ¼ 9.1 Hz, Ar-H); 8.32 (d, J ¼ 5.3 Hz, 1H, Ar-H), .89 (m, 1H, Ar-H); 7.95 (t, J ¼ 5.4 Hz, vol.1, p.3 ,
, A?er sealing with a PTFE cap, the vessel was heated to 160 C for 5 min in the microwave reactor and the completion was ascertained using TLC. A?er completion, the contents were poured in water (20 mL) resulting in the precipitation of the desired product. The yellow product obtained was ?ltered and recrystallized using absolute ethanol
, DMSO-d 6 ) d 3.30-3.32 (m, 6H, 3Â -CH 2 -); 3.59-3.63 (m, 2H, -CH 2 -); 3.74-3.76 (m, 4H, 2Â -CH 2 -), vol.1
, Ar-H); 7.77 (dd, J ¼ 2.0, 9.0 Hz, 1H, Ar-H); 8.05 (d, J ¼ 2.1 Hz, 1H, Ar-H); 8.55-8.57 (m, 3H, Ar-H), vol.1, p.125
Chloroquinolin-4-yl)amino)butyl)-2-(5-morpholino-1,3-dioxoisoindolin-2-yl)acetamide (8b) ,
, , vol.6
, , vol.7
Ar-H); 7.68 (d, J ¼ 8.8 Hz, 1H, Ar-H); 7.79 (d, J ¼ 2.1 Hz, 1H, Ar-H); 8.16 (t, J ¼ 5.5 Hz, 1H, NH-exchangeable with D 2 O); 8.27 (d, J ¼ 9, Ar-H); 7.45 (dd, J ¼ 2.0, 9.0 Hz, vol.1 ,
Chloroquinolin-4-yl)amino)hexyl)-2-(5-morpholino-1,3-dioxoisoindolin-2-yl)acetamide (8c) ,
, DMSO-d 6 ) d 1.30-1.45 (m, 6H, 3Â -CH 2 -); 1.64-1.67 (m, 2H
, m, 4H, 2Â -CH 2 -
, , vol.7
Ar-H); 7.77 (d, J ¼ 2.2 Hz, 1H, Ar-H); 8.15 (t, J ¼ 5.6 Hz, 1H, NH-exchangeable with D 2 O); 8.26 (d, J ¼ 9, Hz, vol.1, issue.7 ,
, 28 (m, 8H, 4Â -CH 2 -); 3.67-3.73 (m, 6H, 3Â -CH 2 -), pp.20-23
, Ar-H); 7.06 (dd, J ¼ 2.3, 8.4 Hz, 1H, Ar-H), vol.1
50 (d, J ¼ 8.6 Hz, 1H, Ar-H), vol.7 ,
, , vol.8
-Chloroquinolin-4-yl)amino)butyl)-3-(5-morpholino-1,3-dioxoisoindolin-2-yl)propanamide (8e). Yield 82%; Yellow solid, C NMR (100 MHz, vol.1 ,
, .67 (m, 2H, vol.6, p.3
, Ar-H); 7.04 (dd, J ¼ 2.2, 8.7 Hz, 1H, Ar-H); 7.14 (d, J ¼ 2.2 Hz, 1H, Ar-H), vol.1
, -Chloroquinolin-4-yl)amino)hexyl)-3-(5-morpholino-1,3-dioxoisoindolin-2-yl)propanamide (8f). Yield 78%; yellow solid, vol.1
, 27 (m, 2H, pp.23-26
, m, 4H, 2Â -CH 2 -); 3.66-3.73 (m, 6H, 3Â -CH 2 -
, Ar-H); 7.03 (dd, J ¼ 2.1, 8.6 Hz, 1H, Ar-H); 7.15 (d, J ¼ 2.1 Hz, vol.1
, Ar-H); 8.26 (t, J ¼ 5.3 Hz, 1H, N-Hexchangeable with D 2 O); 8.34 (d, J ¼ 5.3 Hz, 1H, Ar-H), C NMR (100 MHz, vol.1
, 3-dioxoisoindolin-2-yl)acetamide (8g)
, m, 4H, 2Â -CH 2 -
m, 2H, Ar-H, NHexchangeable with D 2 O); 7.56 (d, J ¼ 8.6 Hz, 1H, Ar-H, vol.6, p.100 ,
,
, 3-dioxoisoindolin-2-yl)acetamide (8h)
, m, 2H, -CH 2 -, vol.1
, m, 2H, 2Â -CH 2 -, vol.3
, 99 (s, 1H, vol.1
18 (t, J ¼ 5.2 Hz, 1H, NH-exchangeable with D 2 O), vol.8 ,
,
, 3-dioxoisoindolin-2-yl)acetamide (8i)
, 10 (m, 2H, -CH 2 -); 3.25-3.30 (m, 2H, 2Â -CH 2 -), vol.3, pp.7-10
, Ar-H); 6.90 (dd, J ¼ 2.2, 8.8 Hz, 1H, Ar-H); 6.98 (d, vol.1
,
, , vol.8
, 3-dioxoisoindolin-2-yl)propanamide (8j)
, m, 4H, 2Â -CH 2 -
, Ar-H); 6.76 (dd, vol.1
, Ar-H); 8.23 (t, J ¼ 5.3 Hz, 1H, NH-exchangeable with D 2 O); 8.35 (d, J ¼ 5.0 Hz, 1H, Ar-H); 13 C NMR (100 MHz, DMSO-d 6 ), vol.1
, 3-dioxoisoindolin-2-yl)propanamide (8k)
m, 2H, -CH 2 -); 1.60-1.67 (m, 2H, -CH 2 -, vol.1 ,
, 25-3.30 (m, 2H
, m, 4H, 2Â -CH 2 -
,
Ar-H); 8.25 (t, J ¼ 5.3 Hz, 1H, NH-exchangeable with D 2 O); 8.36 (d, J ¼ 5.2 Hz, 1H, Ar-H); 13 C NMR (100 MHz, DMSO-d 6 ), Hz, vol.6 ,
, 3-dioxoisoindolin-2-yl)propanamide (8l)
, DMSO-d 6 ) d 1.08 (t, J ¼ 7.3 Hz, 6H, 2Â -CH 3 ); 1.35-1.45 (m, 6H, 3Â -CH 2 -), vol.1, pp.61-62
, 24-3.30 (m, 2H
, m, 4H, 2Â -CH 2 -
,
Ar-H); 8.26 (t, J ¼ 5.3 Hz, 1H, NH-exchangeable with D 2 O); 8.38 (d, J ¼ 5.2 Hz, 1H, Ar-H); 13 C NMR (100 MHz, DMSO-d 6 ), Hz, vol.6 ,
, 3-dioxoisoindolin-2-yl)acetamide (8m), vol.2
, Ar-H); 7.21 (dd, J ¼ 1.5, 8.6 Hz, 1H, Ar-H); 7.30 (d, J ¼ 1.4 Hz, 1H, Ar-H), vol.1
,
Ar-H), C NMR (125 MHz, DMSO-d 6 ), vol.1 ,
, 3-dioxoisoindolin-2-yl)acetamide (8n)
, (m, 2H, -CH 2 -); 2.44 (t, J ¼ 6.1 Hz 2H
Ar-H); 7.65 (d, J ¼ 8.5 Hz, 1H, Ar-H); 7.77 (d, J ¼ 2.0 Hz, 1H, Ar-H); 8.19 (t, J ¼ 5.7 Hz, 1H, NHexchangeable with D 2 O), vol.1 ,
, 3-dioxoisoindolin-2-yl)acetamide (8o)
,
, Ar-H), vol.1
, Ar-H); 7.75 (d, J ¼ 2.0 Hz, 1H, Ar-H); 8.16 (t, J ¼ 5.5 Hz, 1H, NH-exchangeable with D 2 O); 8.25 (d, J ¼ 9.0 Hz, 1H, Ar-H); 8.36 (d, J ¼ 5.3 Hz, 1H, Ar-H), C NMR (125 MHz, vol.1
, 3-dioxoisoindolin-2-yl)propanamide (8p), vol.1
, Ar-H), vol.1, p.49
, 28 (t, J ¼ 5.2 Hz, 1H, NHexchangeable with D 2 O); 7.40 (dd, vol.7
NH-exchangeable with D 2 O); 8.39 (d, J ¼ 5.4 Hz, 1H, Ar-H); 13 C NMR (125 MHz, DMSO-d 6 ), vol.1 ,
, 3-dioxoisoindolin-2-yl)propanamide (8q), vol.1
, 48 (s, 1H, OH); 6.47 (d, J ¼ 5.5 Hz, 1H, Ar-H), vol.2
NH-exchangeable with D 2 O); 8.40 (d, J ¼ 5.3 Hz, 1H, Ar-H); 13 C NMR (125 MHz, DMSO-d 6 ), vol.8 ,
, 3-dioxoisoindolin-2-yl)propanamide (8r), vol.1
,
, (m, 2H, -CH 2 -); 3.24-3.30 (m, 2H
16 (d, J ¼ 2.1 Hz, 1H, Ar-H), vol.7 ,
, Ar-H); 7.79 (d, J ¼ 2.1 Hz, 1H, Ar-H), J References, vol.1, p.7
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