The synthesis of triterpenic amides on the basis of 2,3-seco-1-cyano-19β,28-epoxy-18α-oleane-3-oic acid

  title={The synthesis of triterpenic amides on the basis of 2,3-seco-1-cyano-19$\beta$,28-epoxy-18$\alpha$-oleane-3-oic acid},
  author={Irina A. Tolmacheva and E. V. Igosheva and Victoria V. Grishko and Olga S. Zhukova and Galina Konstantinovna Gerasimova},
  journal={Russian Journal of Bioorganic Chemistry},
Novel 2,3-seco-triterpenic amides were prepared by the interaction of the chloride of 1-cyano-19β,28-epoxy-18α-oleane-3-oic acid with primary amines and synthetic and biogenic amino acids. A cytotoxic triterpenic conjugate with a residue of the ethyl ester of β-alanine was found among the synthesized nitrogen-containing derivatives. Treatment with this conjugate in a concentration of 100 μM resulted in the 45.5% survival of melanoma cells in the medium. 
Synthesis and antiviral activity of C-3(C-28)-substituted 2,3-seco-triterpenoids
Amide conjugates with four structural types of β-amino alcohols were synthesized from 2,3-seco-18αH-oleananoic and 2,3-seco-lupane C-3(C-28) mono- and dicarboxylic acids. Esters were prepared by
Synthesis of lupane and a-secolupane allylamides
Lupane C-28 monoallylamides with α-ketoxime and α-hydroxyoxime groups in ring A were prepared from betulonic acid. Formation of A-secolupane C-3(28) mono- and diallylamides was used as an example to
Synthesis and biological activity of mono- and diamides of 2,3-secotriterpene acids
Amides of four types were synthesized derived from 2,3-seco-18αH-oleanane and 2,3-secolupane mono- and dicarboxylic acids. The spectrum of diamide derivatives was expanded with C3-C3′ and C28-C28′
Allobetulin and Its Derivatives: Synthesis and Biological Activity
This review covers the chemistry of allobetulin analogs, including their formation by rearrangement from betulin derivatives, their further derivatisation, their fusion with heterocyclic rings, and


Synthesis of A-seco derivatives of betulinic acid with cytotoxic activity.
Diosphenols, as the most promising group of derivatives, were further tested on four more lines (A 549, DU 145, MCF 7, SK-Mel2, and PC-3) and confirmed activity of diosphenol 9, 10, and 11 and anhydride 22.
Lupane-type triterpenoids from Microtropis fokienensis and Perrottetia arisanensis and the apoptotic effect of 28-hydroxy-3-oxo-lup-20(29)-en-30-al.
Seven new lupane triterpenoids were isolated from bioactive methanol extracts of Microtropis fokienensis and Perrottetia arisanensis and was found to induce apoptosis of human leukemia HL60 cells and mediate cleavage of PARP and up-regulation of Bax proteins.
Development of C-20 modified betulinic acid derivatives as antitumor agents.
Pharmacological properties of the ubiquitous natural product betulin.
Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection
Because of its selective cytotoxicity against tumor cells and favorable therapeutic index, even at doses up to 500 mg/kg body weight, betulinic acid is a very promising new chemotherapeutic agent for the treatment of HIV infection and cancer.
Betulinic Acid for Cancer Treatment and Prevention
  • S. Fulda
  • Biology, Chemistry
    International journal of molecular sciences
  • 2008
Compounds that exert a direct action on mitochondria present promising experimental cancer therapeutics, since they may trigger cell death under circumstances in which standard chemotherapeutics fail.
Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay.
Since the microculture tetrazolium assay provides sensitive and reproducible indices of growth as well as drug sensitivity in individual cell lines over the course of multiple passages and several months' cultivation, it appears suitable for initial-stage in vitro drug screening.