LIPOPHILIC HEXADENTATE ALUMINUM COMPLEXES OF NEW PHENOLATE-DERIVATIZED CYCLOHEXANETRIAMINE LIGANDS AND THEIR EFFECT ON THE PEPTIDE-TRANSPORT SYSTEM (PTS-1)

The compounds (RsalH(2))(3)tachH(3) (R = H, NO2, OMe) have been synthesized by Schiff base condensation between cis-1,3,5-triaminocyclohexane and a substituted salicylaldehyde, followed by reduction with KBH4. Reaction of these compounds with aluminum(III) salts gives uncharged hexacoordinate N3O3 complexes of type Al(RsalH(2))(3)-tach. The complexes have been characterized by a combination of infrared, H-1 and C-13{H-1} NMR, and mass spectroscopy. Structures of Al(salH(2))(3)tach and Al(NO2)(3)tach have been determined by X-ray crystallography. Al(salH(2))(3)tach: monoclinic, P2(1)/n, a = 15.047(2) Angstrom b = 11.355(1) Angstrom, c = 15.201(2) Angstrom, beta = 93.59(6)degrees, V = 2592(1) Angstrom(3), Z = 4, R = 0.038, R(w) = 0.052. Al(NO(2)salH(2))(3)tach: monoclinic, P2(1)/n, a = 12.305(1) Angstrom, b = 12.072(2) Angstrom, c = 20.229(3) Angstrom, beta = 90.26(1)degrees, V = 3005(1) Angstrom(3), Z = 4, R = 0.040, R(w) = 0.047. The partition coefficients between 1-octanol and water for the complexes Al(RsalH(2))(3)tach have the values 33.0, 9.0, and 4.4 for the derivatives with R = H, NO2,and OMe, respectively. We show that (NO(2)salH(2))(3)tachH(3) affects the action of aluminum on the peptide transport system (PTS-1).