New stereoselective titanium reductive amination synthesis of 3-amino and polyaminosterol derivatives possessing antimicrobial activities.
A series of 3-amino and polyaminosterol analogues of squalamine and trodusquemine were synthesized involving a new stereoselective titanium reductive amination reaction in high chemical yields of up to 95% in numerous cases. These derivatives were evaluated for their in vitro antimicrobial properties against human pathogens. Activity was highly dependent on the different compounds' structures involved and best results have been obtained with aminosterol derivatives 4b, 4e and 6i exhibiting activities against yeasts, Gram positive and Gram negative bacteria at average concentrations of 6.25-12.5 microg/mL.
Salmi
Chanaz
C
Laboratoire SESNAB, Biosciences, UMR-MD-1, case 342, Faculté de St Jérôme, Université Paul Cézanne, Av. Escadrille Normandie Niemen, 13397 Marseille, Cedex 20, France.
Loncle
Celine
C
Vidal
Nicolas
N
Letourneux
Yves
Y
Brunel
Jean Michel
JM
D000586:Amination; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002776:Cholestanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002777:Cholestanols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015195:Drug Design; D008826:Microbial Sensitivity Tests; D010084:Oxidation-Reduction; D011073:Polyamines / Q000737:chemistry*; D012680:Sensitivity and Specificity; D013096:Spermine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013261:Sterols / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry*
C441128:3-N-1(spermine)-7, 24-dihydroxy-5-cholestane 24-sulfate; D000890:Anti-Infective Agents; D002776:Cholestanes; D002777:Cholestanols; D011073:Polyamines; D013261:Sterols; D013096:Spermine; D014025:Titanium; C079655:squalamine