New 3-aminosteroid derivatives as a new family of topical antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA)

Letters in Drug Design and Discovery

Volumn 5, Issue 3, 2008, Pages 169-172

  Salmi, Chanaz ^a   Loncle, Céline ^a   Vidal, Nicolas ^a   Laget, Michèle ^a   Letourneux, Yves ^a   Brunel, Jean Michel ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Aminosteroid derivatives; Antibacterial agents; MRSA; Resistance; Squalamine

Indexed keywords

3 AMINOSTEROID; ANTIINFECTIVE AGENT; SQUALAMINE; STEROID; TRODUSQUEMINE; UNCLASSIFIED DRUG;

ANTIANGIOGENIC ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIMICROBIAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; DRUG MECHANISM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; NONHUMAN; PATHOGENESIS; PRIORITY JOURNAL;

EID: 42349098494     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018008784084018     Document Type: Article

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23. of 3β-(isopropylamino)-4-cholestene 4b: A mixture of 4-cholesten-3-one 3 (300 mg, 0.78 mmol, titanium(IV)isopropoxide (302 μL, 1.03 mmol) and isopropylamine (138 mg, 2.34 mmol) in absolute methanol (5 mL) was stirred under argon at room temperature for 12 hours. Sodium borohydride (29 mg, 0.78 mmol) was then added at -78°C and the resulting mixture was stirred for an additional 2 hours. The reaction was then quenched by adding water (1 mL) and stirring was maintained at room temperature for 20 minutes. The resulting inorganic precipitate was filtered off over a pad of Celite and washed with Et2O and ethylacetate. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to afford the expected crude amine 4b which is purified by flash chromatography on silicagel eluent: CH2Cl2/ MeOH/ NH4
24. X 808 IU (Biotek Instruments). MIC was defined for each agent from duplicate observations as the lowest concentration of compound allowing no visible growth.