Synthesis and Pharmacological Valorization of Derivatives of 4-Phenyl-1,5-Benzodiazepin-2-One

Table 1

Spectral data ¹H NMR, ¹³C NMR, and mass spectrometry.

Products	^1H NMR spectrum (δ in ppm)	^13C NMR spectrum (δ in ppm)	Mass spectrum MH^+ (m/z)
4-Phenyl-1,5-benzodiazepine-2-one 3	9.37 (s, NH); 8.35–7.15 (m, 9H); 3.66 (s, 2H)	167.80 (C = O); 158.64 (C = N); 139.91–137.62 (C aromatic); 130.98 (CH aromatic); 129.14–121.82 (C aromatic); 39.79 (CH2)	237
1-Octyl-4-phenyl-1,5-benzodiazepin-2-one 5a	8.15–7.24 (m, 9H, CH); 4.35 (t, 2H, N-CH2); 3.55 (q, 2H, CH2-CO); 1.86–1.10 (m, 12H, CH2); 0.78 (t, 3H, CH3)	165.62 (C = O); 128.70–122.41 (C aromatic); 47.12 (CH2-N); 40.06 (CH2-CO); 14.03 (CH3)	349
1-Nonyl-4-phenyl-1,5-benzodiazepin-2-one 5b	8.16–7.25 (m, 9H, CH); 4.30 (t, 2H, CH2-N); 3.55 (q, 2H, CH2-CO); 1.50–1.10 (m, 14H, CH2); 0.82 (t, 3H, CH3)	165.57 (C = O); 131.35–122.41 (C aromatic); 47.19 (CH2-N); 40.08 (CH2-CO); 14.09 (CH3)	363
1-Decyl-4-phenyl-1,5-benzodiazepin-2-one 5c	8.17–7.26 (m, 9H, CH); 4.20 (t, 2H, CH2-N); 3.56 (q, 2H, CH2-CO); 1.50–1.10 (m, 16H, CH2); 0.84 (t, 3H, CH3)	165.51 (C = O); 128.75–122.41 (C aromatic); 47.22 (CH2-N); 40.12 (CH2-CO); 14.11 (CH3)	377
1-Dodecyl-4-phenyl-1,5-benzodiazepin-2-one 5d	8.18–7.25 (m, 9H, CH); 4.96 (t, 2H, CH2-N); 3.58 (q, 2H, CH2-CO); 1.26–1.11 (m, 20H, CH2); 0.87 (t, 3H, CH3)	165.49 (s, CO); 162.18–122.40 (m, C aromatic); 47.26 (s, CH2-N); 40.14 (s, CH2-CO); 14.09 (s, CH3)	405

m = multiplet; q = quartet; s = singulet; t = triplet.