38736-77-5Relevant articles and documents
Synthesis and Antiviral Activity of Hydrazides and Substituted Benzalhydrazides of Betulinic Acid and Its Derivatives
Flekhter,Boreko,Nigmatullina,Pavlova,Nikolaeva,Savinova,Eremin,Baltina,Galin,Tolstikov
, p. 296 - 301 (2003)
New nitrogen-containing derivatives of betulinic and betulonic acids, hydrazides and N′-benzalhydrazides, were synthesized. Their antiviral activities toward viruses of influenza A virus, herpes simplex type I virus, enterovirus ECHO6, and HIV-1 were studied in vitro. Betulinic acid 3-oxime was found to have the highest activity against the influenza virus. Betulonic acid, betulinic acid 4-chlorobenzalhydrazide, betulonic acid 3-oxime benzalhydrazide, and betulinic acid hydrazide inhibited the replication of herpes simplex type I virus. Betulinic acid hydrazide also showed antiviral activity toward HIV-1. All the derivatives of betulinic acid under study displayed a low antiviral activity toward enterovirus ECHO6.
Epimerization of Hydroxyl Group in Lupan Series Triterpenoids
Symon,Kaplun,Vlasenkova,Gerasimova,Shon, Le Bang,Litvin,Kozlova,Surkova,Shvets
, p. 185 - 189 (2007/10/03)
Two methods of obtaining 3α-betulinic acid and related compounds from their 3β-epimers were studied: the reaction of bimolecular substitution and the stereoselective reduction of 3-ketoderivatives. The substitution of acyloxy by formyloxy group in 3-O-tosyllupeol or of the belulin hydroxyl by benzoyloxy group resulted only in Δ2, 3-elimination products, with none of the expected products of bimolecular substitution being found. The catalytic hydrogenation of betulonic acid over Raney nickel resulted only in reduction of the isopropenyl double bond, whereas the use of 5% Ru/C gave a 60:40 mixture of epimers of dihydrobetulinic acid. Practically the same mixture of betulinic acid epimers was obtained when reducing betulonic acid with L-Selectride. The cytotoxic activity of 3α-betulinic acid increased toward the Bro melanoma cells and decreased toward the MS melanoma cells.
Synthesis of betulinic acid derivatives with activity against human melanoma
Kim, Darrick S. H. L.,Pezzuto, John M.,Pisha, Emily
, p. 1707 - 1712 (2007/10/03)
Betulinic acid has been modified at C-3, C-20, and C-28 positions and the toxicity of the derivatives has been evaluated against cultured human melanoma (MEL-2) and human epidermoid carcinoma of the mouth (KB) cell lines. This preliminary investigation demonstrates that simple modifications of the parent structure of betulinic acid can produce potentially important derivatives, which may be developed as antitumor drugs.
