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

Abstract

A series of sixteen A-ring modified (2,3-indolo-, 2-benzylidene) oleanonic acid derivatives, holding some cyclic amines, linear polyamines and benzylaminocarboxamides at C28, has been synthesized and screened for antiviral activity against influenza A/PuertoRico/8/34 (H1N1) and Dengue virus serotypes of DENV-1, -2, -3, -4. It was found that 28-homopiperazine 2 and 3-N-phthalyl 22 amides of oleanonic acid demonstrated high potency with selectivity index SI 27 (IC50 21 μM) and 42 (IC50 12 μM). Oleanonic acid aminoethylpiperazine amide 6 and C-azepano-erythrodiol 23 appeared to be the most effective compounds against DENV-1 (IC50′s 67 and 107 μM) and -2 (IC50′s 86 and 68 μM correspondingly) serotypes.

Synthesis and Cholinesterase Inhibitory Potency of 2,3-Indolo-oleanolic Acid and Some Related Derivatives

“…At first, a library of 3-oxo-oleanolic acid 1 and its homopiperazine amides 2-7 (Figure 1), obtained as described previously [17][18][19], were screened against AChE and BChE inhibitory activity. [17] and its homopiperazine amides 2 and 3 [18], 4-7 [19].…”

“…At first, a library of 3-oxo-oleanolic acid 1 and its homopiperazine amides 2-7 (Figure 1), obtained as described previously [17][18][19], were screened against AChE and BChE inhibitory activity. The series of C28-modified derivatives were synthesized based on 2,3-indolooleanolic acid 9 (Scheme 2).…”

“…Acylation of 2,3-indolo- The series of C28-modified derivatives were synthesized based on 2,3-indolo-oleanolic acid 9 (Scheme 2). Homopiperazinamide 11 was synthesized according to [19]. Treatment of 11 with chloroacetonitrile led to 12 with a 77% yield.…”

Phytochemical study of Euphorbia cyathophora collected in Dan Phuong, Hanoi and its antidengue activity against DENV1‐4 virus serotypes

“…The procedure of this method was described in Refs. [9][10][11]. Denge virus serotypes DENV-1, DENV-2, DENV-3 and DENV-4 were bred in BHK-21 cell line.…”

Antiviral opportunities of Mannich bases derived from triterpenic N‐propargylated indoles

“…Amides, semi‐ and thiosemicarbazones, and 1,2,3‐thiadiazoles of glycyrrhetic acid were effective as inhibitors of ZIKV‐induced cytopathic effect, viral NS1 production, and infectivity of ZIKV with IC 50 < 1 μM (Baltina et al., 2021). Recently, oleanonic acid aminoethylpiperazine amide and C‐azepano‐erythrodiol were found as effective compounds against DENV‐1 and DENV‐2 serotypes (Smirnova et al., 2022). Given the above, further research in the field of optimizing the use of derivatives of oleanolic and glycyrrhetic acids could led to the development of new antiviral drugs and effective schemes for their combined use.…”