Synthesis, characterization, biocide and toxicological activities of di-n-butyl- and diphenyl-tin(IV)-salicyliden-beta-amino alcohol derivatives.
The one pot reaction of salicylaldehyde 1, beta-amino alcohols 2a-2c, and di-n-butyltin(IV) oxide 3a or diphenyltin(IV) oxide 3b produced five diorganotin(IV) compounds, 4a-4c, 5a, and 5c, in good yields. All compounds were characterized by IR, (1)H, (13)C, and (119)Sn NMR spectroscopy, and elemental analysis; furthermore, compounds 4b, 4c, 5a, and 5c were characterized by X-ray diffraction analysis. After the structural characterization, all of the compounds were tested in vitro against Bacillus subtilis (Gram-positive, strain ATCC 6633), Escherichia coli (Gram-negative, strain DH5alpha), Pseudomonas aeruginosa (Gram-negative, strain BH3), Desulfovibrio longus (strain DSM 6739), and Desulfomicrobium aspheronum (strain DSM 5918) to assess their antimicrobial activity. Compounds 4 and 5 demonstrated a wide range of bactericidal activities against the tested aerobic (one Gram-positive and two Gram-negative subtypes) and anaerobic bacteria (two sulfate-reducing bacteria, SRB). Compound 5 had better bactericidal performances than compound 4. For all of the compounds, the acute toxicity was measured using luminescent bacteria toxicity (LBT-Microtox) tests to track their further environmental impact. According to these results and in order to fulfill environmental regulations, the toxicity of the compounds studied herein can be modulated through the proper selection of the disubstituted tin(IV) moiety.
Zamudio-Rivera
Luis S
LS
Programa de Ingeniería Molecular, Instituto Mexicano del Petróleo, Eje Central Lázaro Cárdenas No.152, Apartado Postal 14-805, 07730 México, D.F.
George-Tellez
Rocio
R
López-Mendoza
Gerson
G
Morales-Pacheco
Adela
A
Flores
Eugenio
E
Höpfl
Herbert
H
Barba
Victor
V
Fernández
Francisco J
FJ
Cabirol
Nathalie
N
Beltrán
Hiram I
HI
D000605:Amino Alcohols / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D010776:Photobacterium / Q000187:drug effects; D013329:Structure-Activity Relationship; D014001:Tin / Q000737:chemistry*
D000605:Amino Alcohols; D009942:Organometallic Compounds; D014001:Tin