Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis

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Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis. / Novikova, Daria; Grigoreva, Tatyana; Gurzhiy, Vladislav; Tribulovich, Vyacheslav.

In: International Journal of Molecular Sciences, Vol. 24, No. 14, 11339, 12.07.2023.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{706caa560da048b8bbb50b158a28d1c1,

title = "Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis",

abstract = "The biological activity of compounds directly depends on the three-dimensional arrangement of affinity fragments since a high degree of pharmacophore compliance with the binding site is required. 3-Benzylidene oxindoles are privileged structures due to their wide spectrum of biological activity, synthetic availability, and ease of modification. In particular, both kinase inhibitors and kinase activators can be found among 3-benzylidene oxindoles. In this work, we studied model compounds obtained via oxindole condensation with aldehydes and alkylphenones. These condensation products can exist in the form of E- and Z-isomers and also undergo isomerization in solutions. The factors causing isomeric transformation of these compounds were established. Comparative kinetic studies to obtain quantitative characteristics of UV-driven isomerization were first performed. The results obtained indicate dramatic differences in two subclasses, which should be considered when developing biologically active molecules. ",

keywords = "Isomerism, Kinetics, Oxindoles, benzylidene oxindole, E-Z isomerism, photoinduced isomerization, isomerization kinetics, photostationary state",

author = "Daria Novikova and Tatyana Grigoreva and Vladislav Gurzhiy and Vyacheslav Tribulovich",

year = "2023",

month = jul,

day = "12",

doi = "10.3390/ijms241411339",

language = "English",

volume = "24",

journal = "International Journal of Molecular Sciences",

issn = "1422-0067",

publisher = "MDPI AG",

number = "14",

}

RIS

TY - JOUR

T1 - Is It Possible to Obtain a Product of the Desired Configuration from a Single Knoevenagel Condensation? Isomerization vs. Stereodefined Synthesis

AU - Novikova, Daria

AU - Grigoreva, Tatyana

AU - Gurzhiy, Vladislav

AU - Tribulovich, Vyacheslav

PY - 2023/7/12

Y1 - 2023/7/12

N2 - The biological activity of compounds directly depends on the three-dimensional arrangement of affinity fragments since a high degree of pharmacophore compliance with the binding site is required. 3-Benzylidene oxindoles are privileged structures due to their wide spectrum of biological activity, synthetic availability, and ease of modification. In particular, both kinase inhibitors and kinase activators can be found among 3-benzylidene oxindoles. In this work, we studied model compounds obtained via oxindole condensation with aldehydes and alkylphenones. These condensation products can exist in the form of E- and Z-isomers and also undergo isomerization in solutions. The factors causing isomeric transformation of these compounds were established. Comparative kinetic studies to obtain quantitative characteristics of UV-driven isomerization were first performed. The results obtained indicate dramatic differences in two subclasses, which should be considered when developing biologically active molecules.

AB - The biological activity of compounds directly depends on the three-dimensional arrangement of affinity fragments since a high degree of pharmacophore compliance with the binding site is required. 3-Benzylidene oxindoles are privileged structures due to their wide spectrum of biological activity, synthetic availability, and ease of modification. In particular, both kinase inhibitors and kinase activators can be found among 3-benzylidene oxindoles. In this work, we studied model compounds obtained via oxindole condensation with aldehydes and alkylphenones. These condensation products can exist in the form of E- and Z-isomers and also undergo isomerization in solutions. The factors causing isomeric transformation of these compounds were established. Comparative kinetic studies to obtain quantitative characteristics of UV-driven isomerization were first performed. The results obtained indicate dramatic differences in two subclasses, which should be considered when developing biologically active molecules.

KW - Isomerism

KW - Kinetics

KW - Oxindoles

KW - benzylidene oxindole

KW - E-Z isomerism

KW - photoinduced isomerization

KW - isomerization kinetics

KW - photostationary state

UR - https://www.mendeley.com/catalogue/12364e39-fcaf-303a-a3ac-b7e445bf22a3/

U2 - 10.3390/ijms241411339

DO - 10.3390/ijms241411339

M3 - Article

C2 - 37511099

VL - 24

JO - International Journal of Molecular Sciences

JF - International Journal of Molecular Sciences

SN - 1422-0067

IS - 14

M1 - 11339

ER -

ID: 108185667