3',4'-dihydrospiro[piperidine-4,2'-(1'H)quinoline] derivatives as new antioxidant agents with acetylcholinesterase inhibitory property

Letters in Drug Design and Discovery

Volumn 7, Issue 10, 2010, Pages 710-715

  Kouznetsov, Vladimir V ^a   Méndez, Leonor Y Vargas ^b   Acevedo, Amner Muñoz ^a  

^a UNIVERSIDAD INDUSTRIAL DE SANTANDER   (Colombia)

^b UNIVERSIDAD SANTO TOMÁS   (Colombia)

Author keywords

2'(17f)quinoline derivatives; AChE inhibitory activity; Antioxidant capacity; Dihydrospiro piperidine 4; Intramolecular Friedel Crafts cyclization; Multifunctional drug discovery

Indexed keywords

3',4' DIHYDROSPIRO[PIPERIDINE 4,2' (1'H)QUINOLINE] DERIVATIVE; 4 ALLYL 4 ARYLAMINOPIPERIDINES DERIVATIVE; 6 METHYL 3',4' DIHYDROSPIRO[PIPERIDINE 4,2' (1'H)QUINOLINE] DERIVATIVE; ANTIOXIDANT; CHOLINESTERASE INHIBITOR; UNCLASSIFIED DRUG; [2,2' AZINOBIS (3 ETHYLBENZOTHIAZOLINE 6 SULPHONIC ACID)];

ANTIOXIDANT ACTIVITY; ARTICLE; BIOASSAY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; IC 50; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 78650637204     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570180811007010710     Document Type: Article

References (37)

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28. Selected spectral data: Compound 18, white solid, mp 129-130 °C, IR (KBr, cm-1): 3360 (vNH), 1629 (vN-C=O).-1H NMR (CDCl3, 400 MHz): 1.35 (3H, d, J = 6.7 Hz, 4'-CH3), 1.45 (1H, t, J = 12.7 Hz, 3'-Ha), 1.58-1.80 (4H, m, 3(5)-H), 1.89-1.96 (1H, ddd, J = 13.0, 10.6, 5.5 Hz, 3'-He), 2.92 (1H, st, J = 6.1 Hz, 4'-H), 3.45-3.66 (3H, m, 2-Ha y 6-H), 3.86 (1H, dt, J = 13.9, 5.2 Hz, 2-He), 3.93 (1H, bs, N-H), 4.08 (2H, d, J = 4.7 Hz, CH2-Cl), 6.52 (1H, d, J = 7.9 Hz, 8'-H), 6.70 (1H, t, J = 7.4 Hz, 6'-H), 7.00 (1H, t, J = 7.6 Hz, 7'-H), 7.16 (1H, d, J = 7.7 Hz, 5'-H). 13C NMR (CDCl3, 400 MHz): 20.2/20.2, 26.6/26.6, 34.8/35.6, 38.2/38.3, 38.4/39.2, 41.0, 41.6/41.9, 42.4/42.5, 49.2/49.2, 114.5, 117.5/117.6, 125.4/125.5, 126.9 (2C), 142.5, 164.9/165.0. GC-MS, m/z (relative intensity): tR 25.25 min., 292 (M+, 44), 277 (14), 257 (34), 241 (35), 215 (35), 172 (100), 156 (90), 144 (86), 130 (24), 120 (58), 77 (29), 70 (24), 56 (22). Anal. Calcd for C16H21ClN2O: C, 65.63; H, 7.23; N, 9.57. Found: C, 65.44; H, 7.51; N, 9.35. Compound 19, white solid, mp 116-117 °C, IR (KBr, cm-1 ): 3298 (VNH), 1629 (VN-C=O). 1H NMR (CDCl3, 400 MHz): 1.35 (3H, d, J-6.7 Hz, 4'-CH3), 1.39-1.47 (3H, m, 3'-Ha, 4''-Ha), 1.54-1.71 (8H, m, 3(5)-H, 3''(5'')-H), 1.92 (1H, dd, J-13.1, 5.5 Hz, 3'-He), 2.41 (4H, s, 2''(6'')-H), 2.94 (1H, st, J-6.1 Hz, 4'-H), 3.13 (2H, s, CH2-CO), 3.38-4.02 (5H, m, 2(6)-H y N-H), 6.52 (1H, d, J-7.9 Hz, 8'-H), 6.68 (1H, t, J-7.1 Hz, 6'-H), 6.99 (1H, t, J-7.6 Hz, 7'-H), 7.15 (1H, d, J-7.7 Hz, 5'-H). 13C NMR (CDCl3, 400 MHz): 20.3, 24.0, 26.0 (2C), 26.6/26.7, 35.2/36.0, 37.8/38.0, 38.8/39.7, 41.7/41.8, 42.0, 49.4, 54.4 (2C), 62.6/62.7), 114.5, 117.3/117.4, 125.6/125.6, 126.9 (2C), 142.8, 168.5/168.6. GC-MS, m/z (relative intensity): tR 30.33 min., 341 (M+, 3), 243 (0.2) 215 (1), 172 (2), 156 (2), 144 (5), 130 (2), 117 (1), 98 (100), 84 (3), 69 (2), 55 (3). Anal. Calcd for C21H31N3O: C, 73.86; H, 9.15; N, 12.30. Found: C, 73.68; H, 9.04; N, 12.45.
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