Development of bivalent oleanane-type triterpenes as potent HCV entry inhibitors

New seco-limonoids from Cipadessa baccifera: Isolation, structure determination, synthesis and their antiproliferative activities

“…All the reactions proceeded smoothly and yielded the target compounds (10-13) in moderate to good yields (65 to 90%) which were shown in experimental section (Supporting information & table -2). All the compounds were well characterized by 1 H NMR, 13 C NMR and ESI HRMS spectral data.…”

“…the chemistry and pharmacology of these compounds have attracted great interest in medicinal chemistry. Unlike the structural modification/simplification studies on triterpenoids[12][13][14][15], modification of limonoids has had little attention and, therefore, very little is known with respect to their analogue synthesis and their biological properties. To the best of our knowledge, there are no reports in the literature with regard to the cipaferen G analogues and their activities.…”

Recent progress in the antiviral activity and mechanism study of pentacyclic triterpenoids and their derivatives

“…[116][117][118][119] Compound 41, a 3-O--chacotriosyl substituted methyl ursolate derivative, showed potent anti-influenza A (H5N1) virus entry activity with IC 50 at 6.00-8.54 M. 119 In another work, both the chacotriosyl and the aglycone moiety have been reported to have an important effect on the activity against influenza virus and the anti-influenza activity could be improved when the disubstituted amide was introduced to the C17-COOH position. 120 The introduction of dimethylamine at the C17-COOH provides the compound 42, which showed the most potent anti-influenza activity (IC 50 In view of the broad antiviral spectrum of PTs, [85][86][87]89 our group established an anti-influenza virus drug screening model and screened a mini-library of PT-glycoconjugates. Based on a plaque formation inhibition assay, the acetylated galactose-OA conjugate Y3 (43) and the acetylated galactose-UA conjugate Y5 (44), were found to have the best anti-WSN activity (IC 50 : 5 M).…”

“…It was found that compound 29 exhibited dramatically enhanced activity with an IC 50 value in the subnanomolar ranges. 86 It is well known that the low solubility in biological matrixes and the high hydrophobicity of PTs hinder their applications, particularly in the development of therapeutic agents. Given the limited solubility of PTs, a series of triterpenecyclodextrin (CD) conjugates were synthesized to improve the solubility and maintain the activity of triterpenes.…”

Synthesis andin vitropharmacological evaluation ofN-[(1-benzyl-1,2,3-triazol-4-yl)methyl]-carboxamides ond-secoestrone scaffolds

“…Introduction of a terminal alkyne function onto the carboxyl group was planned by using propargylamine and peptide coupling reagents, followed by the formation of triazoles from the alkynes by using differently substituted benzyl azides as dipoles. The resulting N-[(1-benzyl-1,2,3-triazol-4-yl)methyl]carboxamide structural moiety is completely or partially present in a number of literature drug candidate examples: in small molecules and in triterpenoids with diverse biological activities, such as antitumour or antiviral [22][23][24] . Certain carboxamido-or triazolylderivatives of estrone (C15 or C16 substituted) are able to inhibit the 17b-hydroxysteroid dehydrogenase type 1 (17b-HSD1) isozyme 5,25,26 and to block the estrone to 17b-estradiol conversion.…”