Synthesis and antiviral activity of C-3(C-28)-substituted 2,3-seco-triterpenoids

Azepanodipterocarpol is potential candidate for inhibits influenza H1N1 type among other lupane, oleanane, and dammarane A-ring amino-triterpenoids

“…A lupane 2,3-seco aldehydoacid, diacid, 3-aldoxime derivatives can suppress the reproduction of HSV-1 and Flu A (EC 50 from 0.06 to 21.3 μM) [35,36]. Ethyl β-alaninate diamide 2,3 seco-lupane was shown to combine antiherpetic (EC 50 4.1 μM) and anti-HIV activity (EC 50 5.1 μM) [37] and C-28 amide conjugate with a 2aminpropane-1,3-diol was the most active compound against herpes simplex virus type I (5.7 μM, MTC/EC 50 32.2) [38]. Inhibition of the serotype A viruses with a protection index of 60% by 2,3-and 3,4-seco-dammarane acids was reported in [39].…”

“…Earlier, examples of the high antiviral activity of triterpenoid seco derivatives are presented [34][35][36][37][38][39]. Unfortunately, in contrast to the above data, 3,4-seco-3-aminoderivatives 16-19 were practically inactive against Flu A with SI values from 1 to 3.…”

Synthesis, Anti-Influenza H1N1 and Anti-Dengue Activity of A-Ring Modified Oleanonic Acid Polyamine Derivatives

“…Lupane 3,4-seco-3,28-bis-methylpiperazine-amide showed IC 50 27 µM and SI 7.1 against the Flu A H1N1 strain [ 43 ]. The Lupane-type conjugate with 2-aminopropane-1,3-diol was active against herpes simplex virus type I (5.7 μM, MTC/EC 50 32.2) [ 44 ].…”

Recent Achievements in Medicinal and Supramolecular Chemistry of Betulinic Acid and Its Derivatives ‡

“…Amide conjugates with four structural types of β-amino alcohols were synthesized from 2,3-seco-18α H -oleananoic and 2,3-seco-lupane C-3(C-28) mono- and dicarboxylic acids, in order to prepare novel agent for treating herpes simplex virus, types 1 and 2 (Scheme 10) [68]. Esters were prepared by a reaction of C(3)-hydroxy derivatives of A-seco-triterpenoids with dicarboxylic acid anhydrides.…”