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Table 2 Structural elucidation data of the selected data set (1,3-diazine derivatives)

From: Computational approaches: discovery of GTPase HRas as prospective drug target for 1,3-diazine scaffolds

Comp.

IR KBr (cm−1)

1H-NMR (DMSO-d6, ppm)

13C-NMR (DMSO-d6, ppm)

Elemental analysis (CHN); MS: m/z (M++1)

C–H

C=C str.

C–N str.

N=CH str.

C–Cl str.

Other

s1

3088.9

1596.0

1332.1

1665.8

735.7

–

7.36–7.86 (m, 18H, Ar–H), 10.0 (s, 2H, N=CH), 10.2 (s, 2H, (CH)2 of pyrimidine ring)

160.2, 145.7, 138.9, 136.2, 131.2, 130.2, 129.9, 129.9, 128.1, 128.1, 127.6

Theoretical calc: C, 60.10; H, 2.77; N, 10.51; Found: C, 60.18; H, 2.71; N, 10.56; 797

s2

2978.5

1595.2

1331.5

1665.8

736.6

1104.4 (C–O–C2H5, aralkyl ether), 3345.0 (O–H str.)

6.78–8.27 (m, 16H, Ar–H), 9.70 (s, 2H, N=CH), 10.03 (s, 2H, (CH)2 of pyrimidine ring), 3.98 (t, 4H, (CH2)2), 1.32 (d, 6H, (CH3)2)

165.6, 164.0, 153.5, 147.6, 136.6, 137.1, 132.6, 132.5, 130.4, 129.4, 129.9, 128.8, 126.4, 112.4, 107.3, 64.4, 14.8

Theoretical calc: C, 62.13; H, 3.79; N, 9.88; Found: C, 62.10; H, 3.68; N, 9.81; 849

s3

3088.0

1595.5

1337.0

1665.3

734.2

1373.8 (C–NO2, str., NO2)

7.42–8.34 (m, 18H, Ar–H), 10.04 (s, 2H, N=CH), 10.15 (s, 2H, (CH)2 of pyrimidine ring)

165.5, 164.3, 145.9, 138.9, 137.8, 137.4, 136.2, 135.3, 131.9, 130.4, 129.4, 129.8, 128.2, 127.6, 124.4

Theoretical calc: C, 58.56; H, 2.70; N, 13.66; Found: C, 58.50; H, 2.73; N, 13.70; 819

s4

3028.0

1595.4

1332.8

1664.0

735.8

3461.3 (O–H str.)

7.33–8.34 (m, 18H, Ar–H), 9.79 (s, 2H, N=CH), 10.10 (s, 2H, (CH)2 of pyrimidine ring), 6.92 (s, 2H, Ar–OH)

165.5, 164.3, 136.4, 136.4, 134.9, 130.2, 130.1, 129.9, 129.0, 128.0, 127.6, 116.3, 107.2

Theoretical calc: C, 63.01; H, 3.17; N, 11.02; Found: C, 63.05; H, 3.19; N, 11.08; 761

s5

3028.7

1595.1

1333.1

1664.5

736.4

1372.9 (C–NO2 sym. str., NO2)

7.02–8.34 (m, 18H, Ar–H), 10.0 (s, 2H, N=CH), 10.10 (s, 2H, (CH)2 of pyrimidine ring)

165.5, 164.3, 142.3, 137.8, 134.9, 132.6, 131.3, 130.2, 130.2, 129.9, 129.9, 128.1, 128.1, 127.6, 107.2

Theoretical calc: C, 58.56; H, 2.70; N, 13.66; Found: C, 58.60; H, 2.74; N, 13.69; 819

s6

3088.0

1595.4

1334.0

1664.0

735.8

1372.5 (C–NO2 sym. str., NO2)

7.02–8.34 (m, 18H, Ar–H), 10.0 (s, 2H, N=CH), 10.1 (s, 2H, (CH)2 of pyrimidine ring)

165.5, 164.3, 163.1, 145.8, 142.7, 140.0, 137.8, 136.9, 134.9, 132.7, 131.8, 130.2, 129.9, 128.1, 124.7, 107.1

Theoretical calc: C, 58.56; H, 2.70; N, 13.66; Found: C, 58.61; H, 2.76; N, 13.70; 819

s7

3028.0

1590.1

1331.9

1662.8

733.8

2826.1 (C–H str., –CH3)

6.77–8.34 (m, 18H, Ar–H), 9.67 (s, 2H, N=CH), 10.04 (s, 2H, (CH)2 of pyrimidine ring), 3.04 (s, 12H, (CH3)4)

165.5, 164.3, 145.7, 142.7, 137.8, 136.4, 134.9, 131.3, 130.2, 130.1, 129.9, 128.1, 127.6, 111.5, 107.2, 40.1

Theoretical calc: C, 64.72; H, 4.20; N, 13.72; Found: C, 64.76; H, 4.26; N, 13.74; 815

s8

3027.8

1595.3

1332.4

1664.3

736.3

3088.9 (C–O–CH3, aralkyl ether)

7.02–8.34 (m, 18H, Ar–H), 10.05 (s, 2H, N=CH), 10.10 (s, 2H, (CH)2 of pyrimidine ring), 3.84 (s, 6H, (OCH3)2)

165.5, 164.3, 163.5, 145.8, 139.9, 134.9, 132.7, 130.4, 129.8, 128.1, 128.1, 127.9, 114.9, 108.0, 52.2

Theoretical calc: C, 63.81; H, 3.57; N, 10.63; Found: C, 63.85; H, 3.61; N, 10.70; 789

s9

3025.9

1594.6

1330.9

1663.1

734.9

–

7.28–8.02 (m, 16H, Ar–H), 10.02 (s, 2H, N=CH), 10.10 (s, 2H, (CH)2 of pyrimidine ring)

165.5, 164.3, 163.5, 145.8, 137.8, 136.9, 137.7, 131.7, 130.9, 130.2, 129.8, 128.0, 128.0, 127.5, 100.0

Theoretical calc: C, 55.33; H, 2.32; N, 9.68; Found: C, 55.338; H, 2.37; N, 9.72; 865

s10

3027.4

1592.1

1332.0

1663.4

735.9

3088.5 (C–O–CH3, aralkyl ether)

6.96–7.87 (m, 18H, Ar–H), 9.20 (s, 2H, N=CH), 10.02 (s, 2H, (CH)2 of pyrimidine ring), 3.85 {s, 6H, (OCH3)2}

165.5, 164.3, 163.5, 145.8, 139.9, 135.9, 134.9, 132.7, 130.4, 129.8, 128.1, 128.1, 127.9, 115.9, 108.0, 55.2

Theoretical calc: C, 63.81; H, 3.57; N, 10.63; Found: C, 63.85; H, 3.61; N, 10.68; 789

s11

3027.2

1596.3

1331.3

1663.9

736.0

3461.4 (O–H str.), 3088.4 (C–O–CH3, aralkyl ether)

7.03–8.34 (m, 16H, Ar–H), 10.04 (s, 2H, N=CH), 10.10 (s, 2H, (CH)2 of pyrimidine ring), 3.85{s, 6H, (OCH3)2}

165.5, 164.3, 151.0, 149.0, 137.7, 136.9, 134.9, 132.7, 131.8, 130.9, 130.3, 129.8, 128.1, 128.0, 107.6, 61.3

Theoretical calc: C, 61.33; H, 3.43; N, 10.22; Found: C, 61.38; H, 3.48; N, 10.27; 821

s12

2973.4

1599.6

1329.1

1666.7

750.4

–

7.24–8.00 (m, 18H, Ar–H), 9.01 (s, 2H, N=CH), 10.10 (s, 2H, (CH)2 of pyrimidine ring)

165.6, 164.3, 162.5, 146.7, 136.2, 134.3, 131.8, 130.3, 130.2, 130.1, 129.9, 129.2, 120.0, 128.0, 127.8, 100.3

Theoretical calc: C, 60.10; H, 2.77; N, 10.51; Found: C, 60.17; H, 2.80; N, 10.55; 797

s13

2972.9

1598.7

1330.1

1698.9

750.5

3360.9 (O–H str.)

7.27–7.99 (m, 18H, Ar–H), 9.99 (s, 2H, N=CH), 10.07 (s, 2H, (CH)2 of pyrimidine ring)

165.5, 164.3, 137.7, 136.4, 130.3, 129.9, 128.9, 128.1, 117.0, 110.0

Theoretical calc: C, 63.01; H, 3.17; N, 11.02; Found: C, 63.05; H, 3.19; N, 11.07; 761

s14

2974.0

1590.9

1352.3

1695.1

750.1

–

7.26–8.00 (m, 18H, Ar–H), 9.63 (s, 2H, N=CH), 10.0 (s, 2H, (CH)2 of pyrimidine ring), 3.38–3.49 {q, 8H, (CH2)4}, 1.07–1.15 {t, 12H, (CH3)4}

167.5, 164.3, 159.3, 136.4, 131.8, 130.3, 130.1, 129.9, 128.9, 127.4, 126.6, 124.4, 111.0, 44.4, 12.7

Theoretical calc: C, 66.06; H, 4.85; N, 12.84; Found: C, 66.10; H, 4.90; N, 12.88; 871

s15

2974.4

1579.0

1328.3

1693.2

750.1

–

7.25–8.03 (m, 18H, Ar–H), 10.00 (s, 2H, N=CH), 10.04 (s, 2H, (CH)2 of pyrimidine ring)

165.5, 164.3, 136.9, 131.8, 131.7, 130.3, 130.2, 129.9, 129.2, 128.9, 128.1, 127.4, 126.6, 100.9

Theoretical calc: C, 60.10; H, 2.77; N, 10.51; Found: C, 60.15; H, 2.80; N, 10.48; 797

s16

2973.4

1597.1

1329.5

1669.7

749.8

–

7.45–8.04 (m, 20H, Ar–H), 7.55 {d, 2H, (CH)2 of N=CH}, 9.00 (s, 2H, (CH)2 of pyrimidine ring), 6.86 {t, 2H, (CH)2}, 7.34 {d, 2H, (CH)2};

167.8, 164.2, 163.9, 135.6, 134.6, 133.5, 130.2, 130.8, 129.8, 128.0, 128.3, 127.0, 127.9, 120.1, 110.1

Theoretical calc: C, 67.53; H, 3.61; N, 10.74; Found: C, 67.51; H, 3.68; N, 10.77; 787

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