Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.
A simple and highly efficient synthetic route has been developed for synthesis of (R)-rugulactone (1a), (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one (1b) and its 4S epimer 1c by employing proline-catalyzed alpha-aminooxylation, Sharpless epoxidation, Mitsunobu reaction as chirality introuducing steps. The antibacterial and antifungal activity of the compounds 1a, 1b and 1c were evaluated. 1a and 1b showed better antibacterial activity against Pseudomonas aeroginosa (MIC=12.5 microg/ml for 1a, 25 microg/ml for 1b) Klebsiella pneumonia (MIC=25 microg/ml for 1a). Compounds (1a, 1b, 1c) exhibited good to moderate antifungal activity.
Reddy
D Kumar
DK
Natural Products Laboratory, Organic Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India.
Shekhar
V
V
Prabhakar
P
P
Chinna Babu
B
B
Siddhardha
B
B
Murthy
U S N
US
Venkateswarlu
Y
Y
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D031369:Cryptocarya / Q000737:chemistry; D005658:Fungi / Q000187:drug effects; D006801:Humans; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D009181:Mycoses / Q000188:drug therapy; D016328:NF-kappa B / Q000037:antagonists & inhibitors; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C554437:6-(4-hydroxy-6-phenylhex-2-enyl)-5,6-dihydropyran-2-one; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D007783:Lactones; D016328:NF-kappa B; D011753:Pyrones; C548571:rugulactone