4.2.2.12 2,2´-((6-(4-Sulfamoylphenethylamino)-1,3,5-triazine-2,4-diyl)bis(imino))di(4-methylpentanoic
acid) 21:
White solid; yield 85.8%. IR (KBr, cm-1): 3286 (w, NH), 2958 (m), 1723 (w, C=O), 1622 (s), 1557 (s),
1470 (w), 1441 (w), 1334 (m, SO2NH2), 1157 (s, SO2NH2). 1H NMR (300 MHz, DMSO-d6, 90 °C) δ: 7.75
(d, 2H, J = 8.2 Hz, 2 x Ar-H(a)), 7.41 (d, 2H, J = 8.2 Hz, 2 x Ar-H(b)), 7.02 (br s, 5H, SO2NH2, 2 x Ar-
NH, NH-CH2), 4.48 (m, 2H, NH-CH2), 3.50 (br s, 2H, 2 x H-C(2)), 2.91 (t, 2H, J = 7.4 Hz, CH2-Ar),
1.78-1.54 (m, 6H, 2 x H-C(3), 2 x H-C(4)), 0.92 (d, 6H, J = 6.4 Hz, 2 x CH3), 0.89 (d, 6H, J = 6.4 Hz, 2 x
13
CH3); C NMR (75 MHz, DMSO-d6, 90 °C) δ: 174.44, 164.08, 163.36, 144.12, 142.70, 129.42, 126.21,
52.35, 35.36, 25.00, 23.15, 22.09. HRMS (ESI/QTOF, m/z): [M + H]+ Calcd. for [C23H35N7SO6H]+
538.2442; Found: 538.2450.
4.2.2.13 2,2´-((6-(4-Sulfamoylphenylamino)-1,3,5-triazine-2,4-diyl)bis(imino))di(3-methylpentanoic acid)
22:
White solid; yield 79.9%. IR (KBr, cm-1): 3266 (w, NH), 2966 (w), 1717 (w, C=O), 1623 (m), 1590 (m),
1
1558 (s), 1497 (s), 1406 (m), 1328 (m, SO2NH2), 1154 (s, SO2NH2). H NMR (300 MHz, DMSO-d6, 90
°C) δ: 9.21 (br s, 1H, Ar-NH), 7.91 (d, 2H, J = 8.8 Hz, 2 x Ar-H(a)), 7.70 (d, 2H, J = 8.9 Hz, 2 x Ar-
H(b)), 6.93 (br s, 2H, SO2NH2), 6.68 (br s, 2H, 2 x NH-CH), 4.48 (m, 2H, 2 x H-C(2)), 1.92 (m, 2H, 2 x
H-C(3)), 1.52 (m, 2H, H-C(4)), 1.28 (m, 2H, H-C(4)), 0.95 (d, 6H, J = 6.8 Hz, 2 x C(3)-CH3), 0.90 (t, 6H,
J = 7.4 Hz, 2 x H-C(5)); 13C NMR (75 MHz, DMSO-d6, 90 °C) δ: 173.44, 165.33, 163.83, 143.57, 137.41,
126.74, 119.68, 58.26, 37.04, 25.59, 16.01, 11.64. HRMS (ESI/QTOF, m/z): [M + H]+ Calcd. for
[C21H31N7SO6H]+ 510.2129; Found: 510.2133.
4.2.2.14 2,2´-((6-(4-Sulfamoylbenzylamino)-1,3,5-triazine-2,4-diyl)bis(imino))di(3-methylpentanoic acid)
23:
White solid; yield 89.3%. IR (KBr, cm-1): 3284 (w, NH), 2966 (w), 1716 (w, C=O), 1622 (s), 1557 (s),
1463 (w), 1408 (w), 1334 (m, SO2NH2), 1157 (s, SO2NH2). 1H NMR (300 MHz, DMSO-d6, 90 °C) δ: 7.76
(d, 2H, J = 8.3 Hz, 2 x Ar-H(a)), 7.66 (br s, 1H, NH-CH2), 7.48 (d, 2H, J = 8.3 Hz, 2 x Ar-H(b)), 7.02 (s,
2H, SO2NH2), 6.84 (br s, 2H, 2 x NH-CH), 4.52 (br s, 2H, NH-CH2), 4.43 (m, 2H, 2 x H-C(2)), 1.87 (m,
2H, 2 x H-C(3)), 1.49 (m, 2H, H-C(4)), 1.47 (m, 2H, H-C(4)), 0.90 (d, 6H, J = 7.0 Hz, 2 x C(3)-CH3),
13
0.86 (t, 6H, J = 7.5 Hz, 2 x H-C(5)); C NMR (75 MHz, DMSO-d6, 90 °C) δ: 173.22, 163.68, 162.47,
144.22, 143.26, 128.16, 126.12, 58.19, 43.77, 37.03, 25.50, 15.96, 11.61. HRMS (ESI/QTOF, m/z): [M +
H]+ Calcd. for [C22H33N7SO6H]+ 524.2286; Found: 524.2290.
4.2.2.15 2,2´-((6-(4-Sulfamoylphenethylamino)-1,3,5-triazine-2,4-diyl)bis(imino))di(3-methylpentanoic
acid) 24:
White solid; yield 84.6%. IR (KBr, cm-1): 3265 (w, NH), 2965 (w), 1719 (w, C=O), 1621 (s), 1551 (s),
1459 (w), 1406 (w), 1332 (m, SO2NH2), 1157 (s, SO2NH2). 1H NMR (300 MHz, DMSO-d6, 90 °C) δ: 7.75
(d, 2H, J = 8.3 Hz, 2 x Ar-H(a)), 7.41 (d, 2H, J = 8.3 Hz, 2 x Ar-H(b)), 7.02 (br s, 3H, SO2NH2, Ar-NH),
6.72 (br s, 2H, 2 x NH-CH), 4.43 (m, 2H, 2 x H-C(2)), 3.51 (m, 2H, NH-CH2), 2.91 (m, 2H, CH2-Ar),
1.89 (m, 2H, 2 x H-C(3)), 1.49 (m, 2H, H-C(4)), 1.25 (m, 2H, H-C(4)), 0.92 (d, 6H, J = 6.9 Hz, 2 x C(3)-
CH3)), 0.88 (t, 6H, J = 7.5 Hz, 2 x H-C(5)); 13C NMR (75 MHz, DMSO-d6, 90 °C) δ: 173.31, 166.35,
163.87, 144.13, 142.68, 129.43, 126.17, 58.19, 47.18, 37.06, 35.36, 25.53, 15.99, 11.61. HRMS
(ESI/QTOF, m/z): [M + H]+ Calcd. for [C23H35N7SO6H]+ 538.2442; Found: 538.2449.
4.2.2.16
2,2´-((6-(4-Sulfamoylphenylamino)-1,3,5-triazine-2,4-diyl)bis(imino))di(4-methylthiobutanoic
acid) 25:
White solid; yield 80.4%. IR (KBr, cm-1): 3243 (w, NH), 1717 (w, C=O), 1623 (m), 1589 (m), 1558 (s),
1496 (s), 1404 (m), 1320 (m, SO2NH2), 1154 (s, SO2NH2). 1H NMR (300MHz, DMSO-d6, 90 °C) δ: 9.26
(br s, 1H, Ar-NH), 7.89 (d, 2H, J = 8.8 Hz, 2 x Ar-H(a)), 7.69 (d, 2H, J = 8.8 Hz, 2 x Ar-H(b)), 7.11 (br s,
4H, SO2NH2, 2 x NH-CH), 4.60 (br s, 2H, 2 x H-C(2)), 2.57 (m, 4H, 2 x H-C(4)), 2.15-1.97 (m, 4H, 2 x