TY - JOUR

T1 - The Reaction of Fenchone and Camphor Hydrazones with 5-Acyl-4-Pyrones as a Method for the Synthesis of New Polycarbonyl Conjugates

T2 - Tautomeric Equilibrium and Antiviral Activity

AU - Viktorova, Viktoria V

AU - Obydennov, Dmitrii L

AU - Kovaleva, Kseniya S

AU - Yarovaya, Olga I

AU - Khasanov, Shokhrukh A

AU - Bormotov, Nikolay I

AU - Esaulkova, Iana L

AU - Serova, Olga A

AU - Zarubaev, Vladimir V

AU - Shishkina, Larisa N

AU - Salakhutdinov, Nariman F

AU - Sosnovskikh, Vyacheslav Y

N1 - © 2024 Wiley-VHCA AG, Zurich, Switzerland.

PY - 2025/1

Y1 - 2025/1

N2 - Selective synthesis of polycarbonyl conjugates of (+)-fenchone and (+)-camphor was carried out (44-91 % yields) via the ring-opening transformation of 5-acyl-4-pyrones with hydrazones of the corresponding monoterpenoids. A strong influence of the hydrazone fragment on the observed tautomeric equilibrium of the tricarbonyl system was shown. Although the major tautomer of the conjugates is the acyclic polycarbonyl form, the camphor-based conjugates undergo new type of ring-chain tautomerism, diketoenaminone-dihydropyridone equilibrium, and predominantly exist in the cyclic dihydropyridone form in DMSO-d6. The polyketones can undergo intramolecular cyclization to form N-amino-4-pyridones in high selectivity. In vitro screening for activity against the influenza virus H1 N1 and vaccinia virus was estimated for the obtained conjugates. The (+)-fenchone derivatives demonstrated the higher activity against vaccinia virus than camphor derivatives. The conjugate, which was prepared from diethyl isochelidonate and hydrazone (+)-fenchone, showed the highest activity against vaccinia virus (SI=17).

AB - Selective synthesis of polycarbonyl conjugates of (+)-fenchone and (+)-camphor was carried out (44-91 % yields) via the ring-opening transformation of 5-acyl-4-pyrones with hydrazones of the corresponding monoterpenoids. A strong influence of the hydrazone fragment on the observed tautomeric equilibrium of the tricarbonyl system was shown. Although the major tautomer of the conjugates is the acyclic polycarbonyl form, the camphor-based conjugates undergo new type of ring-chain tautomerism, diketoenaminone-dihydropyridone equilibrium, and predominantly exist in the cyclic dihydropyridone form in DMSO-d6. The polyketones can undergo intramolecular cyclization to form N-amino-4-pyridones in high selectivity. In vitro screening for activity against the influenza virus H1 N1 and vaccinia virus was estimated for the obtained conjugates. The (+)-fenchone derivatives demonstrated the higher activity against vaccinia virus than camphor derivatives. The conjugate, which was prepared from diethyl isochelidonate and hydrazone (+)-fenchone, showed the highest activity against vaccinia virus (SI=17).

KW - Camphor/chemistry

KW - Antiviral Agents/chemical synthesis

KW - Hydrazones/chemistry

KW - Pyrones/chemistry

KW - Vaccinia virus/drug effects

KW - Influenza A Virus, H1N1 Subtype/drug effects

KW - Microbial Sensitivity Tests

KW - Structure-Activity Relationship

KW - Molecular Structure

KW - Stereoisomerism

KW - Camphanes

KW - Norbornanes

UR - https://www.mendeley.com/catalogue/1b820a9d-2e97-3ba7-99ec-3e6b1a3cd158/

U2 - 10.1002/cbdv.202401461

DO - 10.1002/cbdv.202401461

M3 - Article

C2 - 39233581

VL - 22

JO - Chemistry and Biodiversity

JF - Chemistry and Biodiversity

SN - 1612-1872

IS - 1

M1 - e202401461

ER -