Allylic hydroxylation through acid catalysed epoxy ring opening of betulinic acid derivatives

Synthetic Communications

Volumn 35, Issue 16, 2005, Pages 2143-2148

  Pramanick, Swapan ^a   Mandal, Suparna ^a   Mukhopadhyay, Sibabrata ^a   Jha, Sailen ^b  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b JADAVPUR UNIVERSITY   (India)

Author keywords

Allylic hydroxylation; Betulinic acid derivatives

Indexed keywords

3 CHLOROPERBENZOIC ACID; ACID; ALLYL ALCOHOL; BETULIC ACID; EPOXIDE; HYDROXYL GROUP; INORGANIC ACID; LUPANE; TRITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; HYDROXYLATION; RING OPENING;

EID: 23844523419     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910500180568     Document Type: Article

References (7)

1. Hasimoto, F.; Kashiwada, Y.; Cosentino, L. M.; Chen, C. H.; Garrett, P. E.; Lee, K. H. Anti-Aids agents-XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Biorg. Med. Chem. 1997, 5, 2133-2143.
2. Steele, J. C.; Warhurst, D. C.; Kirby, G. C.; Simmonds, M. S. In vitro and in vivo evaluation of betulinic acid as antimalarial. Phytother. Res. 1999, 13, 367-368.
3. Mukherjee, P. K.; Saha, K.; Das, J.; Pal, M.; Saha, B. P. Studies on the antiinflammatory activity of Nelumbo nucifera. Planta Med. 1997, 63, 367-368.
4. Pisha, E.; Chai, H.; Lee, I. S.; Chagwedera, T. E.; Farnsworth, N. R.; Cordell, G. A.; Beecher, C. W. W.; Fong, H. H. S.; Kinghorn, A. D.; Brown, D. M.; Wani, M. C.; Wall, M. E.; Hieken, T. J.; DasGupta, T. K.; Pezzuto, J. M. Discovery of betulinic acid as a selective inhibitor of human malanoma that functions by induction of apoptosis. Nature Medicine 1995, 1, 1046-1051.
5. Roy Chowdhury, A.; Mandal, S.; Mitra, B.; Sharma, S.; Mukhopadhyay, S.; Majumder, H. K. Betulinic acid, a potent inhibitor of eukaryotic topoisomerase I: Identification of the inhibitory step, the major functional group responsible and development of more potent derivatives. Med. Sci. Monit. 2002, 8, BR254-260.
6. Roy Chowdhury, A.; Mandal, S.; Goswami, A.; Ghosh, M.; Mandal, L.; Chakraborty, D.; Ganguly, A.; Tripathi, G.; Mukhopadhyay, S.; Bandyopadhyay, S.; Majumder, H. K. Dihydrobetulinic acid induces apoptosis in Leishmania donovani by targeting DNA topoisomerase I and II: Implications in antileishmanial therapy. Molecular Medicine 2003, 9, 26-36.
7. Chakravarty, A. K.; Das, B.; Mukhopadhyay, S. Peracid oxidation products of swertanone, the novel triterpene of swertia chirata. Tetrahedron 1991, 47, 2337-2350.