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

Petrova, Anastasiya ; Tretyakova, Elena ; Khusnutdinova, Elmira ; Kazakova, Oxana ; Slita, Alexander ; Zarubaev, Vladimir ; Ma, Xinyuan ; Jin, Hongwei ; Xu, Huan ; Xiao, Sulong

Chemical biology & drug design, 2024-01, Vol.103 (1), p.e14370-n/a [Periódico revisado por pares]

England

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  • Título:
    Antiviral opportunities of Mannich bases derived from triterpenic N‐propargylated indoles
  • Autor: Petrova, Anastasiya ; Tretyakova, Elena ; Khusnutdinova, Elmira ; Kazakova, Oxana ; Slita, Alexander ; Zarubaev, Vladimir ; Ma, Xinyuan ; Jin, Hongwei ; Xu, Huan ; Xiao, Sulong
  • Assuntos: Animals ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Cricetinae ; Dogs ; Humans ; indole ; Indoles - pharmacology ; Influenza A Virus, H1N1 Subtype ; influenza H1N1 ; Mannich Bases ; Mannich reaction ; Molecular Docking Simulation ; Oleanolic Acid - pharmacology ; SARS-CoV-2 ; triterpenoids
  • É parte de: Chemical biology & drug design, 2024-01, Vol.103 (1), p.e14370-n/a
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: Oleanolic and glycyrrhetic acids alkyne derivatives were synthesized as a result of propargylation of the indole NH‐group condensed with the triterpene A‐ring, the following aminomethylation led to a series of Mannich bases. The synthesized compounds were tested for their potential inhibition of influenza A/PuertoRico/8/34 (H1N1) virus in Madin‐Darby canine kidney (MDCK) cell culture and SARS‐CoV‐2 pseudovirus in baby hamster kidney‐21‐human angiotensin‐converting enzyme 2 (BHK‐21‐hACE2) cells. Mannich bases of oleanolic and glycyrrhetic acids N‐propargylated indoles 7, 8, and 12 were the most efficacious against influenza virus A with IC50 7–10 μM together with a low toxicity (CC50 > 145 μM) and high selectivity index SI value 20. Indolo‐oleanolic acid morpholine amide Mannich base holding N‐methylpiperazine moiety 9 showed anti‐SARS‐CoV‐2 pseudovirus activity with EC50 value of 14.8 μM. Molecular docking and dynamics modeling investigated the binding mode of the compounds 7 and 12 into the binding pocket of influenza A virus M2 protein and compound 9 into the RBD domain of SARS‐CoV‐2 spike glycoprotein. Oleanolic and glycyrrhetic acids alkyne derivatives were synthesized as a result of propargylation of the indole NH‐group condensed with the triterpene A‐ring, the following aminomethylation led to a series of Mannich bases. The synthesized compounds were tested for their potential inhibition of influenza A/PuertoRico/8/34 (H1N1) virus and SARS‐CoV‐2 pseudovirus.
  • Editor: England
  • Idioma: Inglês
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