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6.14. Benzoic acid, 4-[[(2,5-dihydroxyphenyl)-methyl]-
amino]-, isopropyl ester (NSC 677695) (5)
6.20. Benzoic acid, 4-[[(2,5-dihydroxyphenyl)-methyl]-
amino]-, 1-adamantyl ester (NSC 680410) (11)
1
1
Gummy solid. H NMR; DMSO–d6: d 8.84 and 8.60
Mp 113–115 ꢂC. H NMR; DMSO–d6: d 8.85 and 8.60
(two s, 2H, D2O exchangeable –OH); 7.70 (d, 2H,
aromatic-H); 6.92 (t, 1H, D2O exchangeable –NH);
6.68 (d, 1H, aromatic-H); 6.63–6.16 (m, 3H, aromatic-
H); 6.50–6.48 (dd, 1H, aromatic-H); 5.07 (m, 1H,
–CH); 4.23 (d, 2H, –CH2). Anal. Calcd (C17H19NO4)
C, H, N.
(two br s, 2H, –OH); 7.64 (d, 2H); 6.87 (t, 1H, –NH);
6.67 (d, 1H); 6.60–6.58 (m, 3H); 6.48 (dd, 1H); 4.22 (d,
2H); 2.19 (s, 10H); 1.69 (s, 5H). Anal. Calcd
(C24H27NO4) C, H, N.
6.21. Benzoic acid, 4-[[(2,5-dihydroxyphenyl)-methyl]-
amino]-, 1-adamantanemethyl ester (NSC 689857) (12)
6.15. Benzoic acid, 4-[[(2,5-dimethoxyphenyl)-methyl]-
amino]-, (NSC 676622) (6)
1
Mp 183–185 ꢂC (decomposes). H NMR, DMSO–d6: d
8.85 (br s, 1H, –OH); 8.61 (br s, 1H, –OH); 7.73 (d,
2H); 6.96 (t, 1H, –NH); 6.68–6.61 (m, 4H); 6.50 (dd,
1H); 4.24 (d, 2H, –CH2N–); 3.81 (s, 2H, –OCH2–);
2.00 (s, 3H); 1.75–1.61 (m, 12H). Anal. Calcd
(C25H29NO4) C, H, N.
1
Mp 150–153 ꢂC. H NMR; DMSO–d6: d 11.98 (s, 1H,
D2O exchangeable –COOH); 7.63 (d, 2H, aromatic-H);
6.91–6.89 (m, 1H, aromatic-H); 6.85 (t, 1H, D2O
exchangeable, –NH); 6.75 (m, 2H, aromatic-H); 6.54
(d, 2H, aromatic-H); 4.23 (d, 2H, –CH2); 3.76 and
3.60 (two s, 6H, –OCH3). Anal. Calcd (C16H17NO4) C,
H, N.
6.22. Benzoic acid, 2-hydroxy-4-[[(2,5-dihydroxy-phe-
nyl)methyl]amino]-, methyl ester (NSC 687945) (13)
1
Mp 179–180 ꢂC. H NMR, DMSO–d6: d 10.84 (s, 1H,
6.16. Benzoic acid, 4-[[(2,5-dimethoxyphenyl)-methyl]-
amino]-, methyl ester (NSC 676448 (7)
–OH); 8.86 (s, 1H, –OH); 8.62 (s, 1H, –OH); 7.51 (d,
1H); 7.12 (t, 1H, –NH); 6.68 (d, 1H); 6.60 (d, 1H);
6.50 (dd, 1H); 6.26 (dd, 1H); 5.99 (d, 1H); 4.20 (d,
2H); 3.83 (s, 3H). Anal. Calcd (C15H15NO5) C, H, N.
1
Mp 111–113 ꢂC. H NMR; CDCl3: d 7.85 (d, 2H); 6.85
(d, 1H); 6.82 (d, 1H); 6.76 (dd, 1H); 6.59 (d, 2H); 4.55
(br s, 1H, D2O exchangeable, –NH); 4.36 (d, 2H);
3.83, 3.82, and 3.72 (3s, 9H). Anal. Calcd
(C17H19NO4) C, H, N.
6.23. Benzoic acid, 2-chloro-4-[[(2,5-dihydroxyphe-
nyl)methyl]amino]-, isopropyl ester (NSC 686561) (14)
1
Mp 135–137 ꢂC. H NMR, DMSO–d6: d 8.89 (s, 1H,
6.17. Benzoic acid, 4-[[(2,5-dihidroxyphenyl)-methyl]-
amino]-, benzyl ester (NSC 678634) (8)
OH); 8.62 (s, 1H, OH); 7.67 (d, 1H, ArH); 7.11 (s, 1H,
NH); 6.67 (m, 2H, ArH); 6.59 (m, 2H, ArH); 6.52 (dd,
1H, ArH); 5.07 (m, 1H, –CH); 4.22 (d, 2H, CH2); 1.31
(d, 6H, –CH3) ppm. Anal. Calcd (C17H18ClNO4) C, H,
N.
1
Gummy solid. H NMR; DMSO–d6: d 8.74 (br s, 2H,
D2O exchangeable, –OH); 7.77 (d, 2H, aromatic-H);
7.48–7.36 (m, 5H, aromatic-H); 6.99 (br s, 1H, D2O
exchangeable, –NH); 6.69–6.62 (m, 4H, aromatic-H);
6.52–6.48 (dd, 1H, aromatic-H); 5.29 (s, 2H, –CH2);
4.25 (d, 2H, CH2–N–). Anal. Calcd (C21H19NO4 Æ 0.15
EtOH, 0.3 H2O) C, H, N.
6.24. Acetophenone, 40-[[(2,5-dihydroxyphenyl)-methyl]-
amino]-(NSC 689858) (15)
1
Mp 197–199 ꢂC (decomposes). H NMR, DMSO–d6: d
8.87 (s, 1H, –OH); 8.62 (s, 1H, –OH); 7.74 (d, 2H);
7.04 (t,1H, –H); 6.68 (d, 1H); 6.62–6.60 (m, 3H); 6.49
(dd, 1H); 4.25 (d, 2H); 2.42 (s, 3H). Anal. Calcd
(C15H15NO3) C, H, N.
6.18. Benzoic acid, 4-[[(2,5-dihidroxyphenyl)-methyl]-
amino]-, 2,4-dimethyl-3-pentanyl ester (NSC 680779) (9)
Mp 78–80 ꢂC. 1H NMR; DMSO–d6: d 8.84 (s, 1H,
–OH); 8.59 (s, 1H, –OH); 7.73 (d, 2H); 6.94 (t, 1H,
–NH); 6.64 (m, 4H); 6.49 (dd, 1H); 4.68 (t, 1H);
4.24 (d, 2H); 1.99 (m 2H); 0.911, 0.909, 0.898,
and 0.895 (4s, 12H). Anal. Calcd (C21H27NO4) C, H,
N.
6.25. N,N-Diisopropylbenzamide, 4-[[(2,5-dihydroxyphe-
nyl)methyl]amino]-(NSC-689431) (16)
1
Mp 168–170 ꢂC. H NMR, DMSO–d6: d 8.79 (s, 1H,
–OH); 8.59 (s, 1H, –OH); 7.06 (d, 2H); 6.65 (m, 2H);
6.58 (d, 2H); 6.49 (dd, 1H); 6.34 (t, 1H, –NH); 4.18 (d,
2H, –CH2); 3.70 (br s, 2H, –CH); 1.29 and 1.28 (two s,
12H). Anal. Calcd (C20H26N2O3) C, H, N.
6.19. Benzoic acid, 4-[[(2,5-dihidroxyphenyl)-methyl]-
amino]-, tert-butyl ester (NSC 677696) (10)
1
Mp 158–160 ꢂC. H NMR; DMSO–d6: d 8.83 and 8.59
6.26. Benzenemethanol, 4-[[(2,5-dihydroxyphenyl)-methyl]-
amino]-.alpha.-(trifluoromethyl)- (NSC 689001) (17)
(two s, 2H, D2O exchangeable, –OH); 7.65 (d, 2H, aro-
matic H); 6.86 (t, 1H, –NH); 6.67 (d, 1H, aromatic-H);
6.60–6.59 (m, 3H, aromatic-H); 6.50–6.48 (dd, 1H, aro-
matic-H); 4.23 (d, 2H, –CH2); 1.53 (s, 9H, –(CH3)3.
Anal. Calcd (C18H21NO4) C, H, N.
1
Mp 118–120 ꢂC. H NMR, DMSO–d6: d 8.77 (s, 1H,
–OH); 8.54 (s, 1H, –OH); 7.18 (d, 2H); 6.65 (m, 2H);
6.59 (d, 2H); 6.48 (m, 2H); 6.19 (t, 1H, –NH); 4.89 (d,