Synthesis of new betulonic and oleanonic acid amides

Abstract

and oleanonic acids with diethylenetriamine, triethylenetetramine, and spermidine were synthesized. Antitumor activity in vitro was not found for the conjugate of betulonic acid with diethylenetriamine.

A-Ring-Modified Triterpenoids and Their Spermidine–Aldimines with Strong Antibacterial Activity

“…Substances were detected by 10% H 2 SO 4 with subsequent heating to 100-120 • C for 2-3 min. Betulonic aldehyde [24], compounds 1 [20], 3 [21], ursonic acid and 4 [22], 11 [23] were obtained according to the methods described previously.…”

“…The reaction of ursonic or oleanonic acid chlorides with diethylenetriamine led to amides 10 and 11 in yields of 85 and 73%, respectively. The data for the latter amide have been previously presented [23].…”

Evaluation of Cytotoxicity and α-Glucosidase Inhibitory Activity of Amide and Polyamino-Derivatives of Lupane Triterpenoids

“…The target derivatives were purified by column chromatography in good yields and their structure was confirmed by the NMR spectra, in which the signals of amide bond were found at δ 4.00 and 5.55 ppm in 1 Н NMR spectra, and δ 174.51 and 177.56 ppm in 13 С NMR spectra, respectively. As mentioned above, a series of branched extra-amino-triterpenoids 5–26 were synthesized according to already described methods [ 6 , 9 , 18 , 20 , 23 , 24 , 26 , 27 , 28 ] ( Figure 1 ). These compounds are presented by C2, C3, or C28-derivatives of betulin, betulinic, and betulonic acids, methyl betulonate, or azepanobetulin.…”

“… Compound 5 [ 26 ] ; compounds 6 , 7 , 11 , 12 , 14 , 15 , 16 , 19 [ 23 ] ; compounds 8 , 9 , 13 [ 18 ] ; 10 [ 27 ] ; 17 [ 28 ] ; 18, 25 , 26 [ 6 ] ; 20 , 21 [ 20 ] ; 22, 24 [ 24 ] ; 23 [ 9 ] . …”

“…The main chemical modifications of triterpenic acids with polyamines are based on direct coupling with commercially available di- and tri-amines [ 4 , 8 , 11 ], as well as 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) oligo-methylene amines [ 8 ]. On the other hand, we have successfully introduced a polyamine chain into the triterpene core by the reactions of cyanoethylation followed by a reduction of the nitrile group based on triterpenic alcohols, oximes, amines, and amides, and this approach allowed us to obtain a broad library of branched extra-amino-triterpenoids [ 6 , 9 , 17 , 18 , 20 , 23 , 24 ]. In this paper, we focused on the evaluation of their cytotoxicity toward the NCI-60 cancer cell line panel, α-glucosidase inhibitory, and antimicrobial activities, as well as synthesis of two new lupane carboxamides.…”