20066-05-1

Upstream product

• 186581-53-3 diazomethane 
• 25576-27-6 3-oxolupan-28-ic acid 
• 77-78-1 dimethyl sulfate 
• 4356-31-4 methyl betulonate 
• 145803-56-1 2α-bromo methyl dihydro betulonate 
• 145803-55-0 2,2-dibromo methyl dihydro betulonate 
• 107-15-3 ethylenediamine 
• 2259-06-5 methyl betulinate 
• 4550-88-3 dihydromethylbetulinate 
• 4481-62-3 betulonic acid 
• 55029-05-5 lupane-3β,28-diol 
• 472-15-1 Betulinic acid 
• 38736-78-6 dihydrobetulinic acid 

Relevant academic research and scientific papers

triterpenoid pyrazines and benzopyrazines with cytotoxic activity

Twelve lupane, 18α-oleanane, and des-E-lupane derivatives (1a-5b) were either extracted from natural sources or synthesized from betulinic acid (1a) and betulin (2). Compounds 1b, 1c, 3b, 3c, 4b, 4c, 5a, and 5b were then used as starting materials for further synthesis of a series of pyrazines and benzopyrazines (6a-18); 20 of them are new (6a-6c, 7a-7d, and 10a-18). Activity of pyrazine 6a against the T-lymphoblastic leukemia cell line CEM encouraged us to synthesize several new esters (6b-6d) to study structure-activity relationships with respect to substitution of the carboxyl group at position 28. The synthesized compounds were tested for cytotoxicity against a variety of cancer cell lines of different histogenetic origin, and the results were compared with cytotoxicity of the known starting compounds. Significant cytotoxic activity against A 549, K 562, and multidrug-resistant K 562-tax cell lines was found in pyrazines 6a, 6d, and 6e.

First examples of hydroxycyclopropanation in the series of lupane triterpenoids

Hydroxycyclopropanation at the ester group in the series of lupane triterpenoids was performed for the first time using 3,3-ethylenedioxybetulonic acid methyl ester and its 20,29-dihydro analog as substrates.

Synthesis of lupane triterpenoids with triphenylphosphonium substituents and studies of their antitumor activity

New derivatives of lupane triterpenoids, viz., 20,29-dihydrobetulinic and 3-epi-20,29-dihydrobetulinic acid derivatives containing triphenylphosphonium fragments as substituents were synthesized. These compound considerably exceed betulinic acid in antitu

Synthesis of oxadiazole derivative of pentacyclic triterpenoid and its biological activity

Triterpenoid betunilic acid is extracted from outer bark of Biscofia javanica blume from Darjeeling hilly region and carried out transformative reaction to introduce oxadiazole moiety to ring A of the triterpenoid which was identified as 28-carbomethoxy lupan (2,3-c)-1′,2′,5′-oxadiazole. The derivative obtained has been selected for its antibacterial and fungicidal activity at different concentrations with respect to the parent compound. The structures of these compounds were established based on spectroscopic (UV, IR, NMR) analysis.

Denomination of 2-bromo-3-keto triterpenoids using N,N-dimethylaniline

Reflux of 2α-bromo/2,2-dibromolupanone (1/1a), methyl 2α-bromo/2,2-dibromodihydrobetulonate (2/2a) and 2/4α-bromofriedelin (3/3a) with N,N-dimethylaniline (DMA) resulted in the formation of lupanone, methyl dihydrobetulonate and friedelin, respectively in very good yields. The products have been characterized by spectroscopic analysis [IR, NMR ( 1H and 13C) and MS] and optical rotation as well as by comparison with the data reported in literature.

Studies on the reactions of 2-bromo-3-ketotriterpenoids: Part III--Reaction of Li/EDA on 2α-bromo and 2,2-dibromo derivatives of lupanone and methyl dihydrobetulonate

The reaction of lithium in ethylenediamine with 2,2-dibromo (1/1') and 2α-bromo (2/2') derivatives of lupanone (3) and methyl dihydrobetulonate (3') furnishes lupanone/methyl dihydrobetulonate (3/3') and the pyrazine derivative (4/4').

HOMOGENEOUS HYDROGENATION AND DEUTERATION OF PENTACYCLIC TRITERPENOIDS: DOUBLE BONDS IN SIDE-CHAINS

The reduction of terminal double bonds in the side chains on the rings A and E of pentacyclic triterpenoids by means of tris(triphenylphosphine)rhodium chloride permits selective reduction of dienes and labelling with deuterium with a low scattering.The effect of the amount of the catalyst and the solvent used on the rate of reduction was studied in the case of 3β,28-diacetylbetulin.