Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE): Rapid access to the diarene-fused 1,4,7-triazecine ring system

Результат исследований: Научные публикации в периодических изданияхстатьянаучнаярецензирование

1 цитирование (Scopus)

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The tricyclic ring system of the antiviral drug nevirapine has been employed to test the workability of the hydrated imidazoline ring expansion (HIRE) reaction which was previously exemplified for [1.4]oxazepine and [1.4]thiazepine counterparts. The imidazoline nucleus was grafted onto the lactam moiety of nevirapine in two high-yielding steps. Subsequent N-alkylation and the HIRE reaction proceeded as envisioned and delivered rare ring-expanded diarene-fused 1,4,7-triazecines with a diversity of alkyl substituents at the lactam nitrogen atom. These findings extend the scope of the HIRE reaction to the medicinally prominent [1.4]diazepine chemical space.

Язык оригиналаанглийский
Страницы (с-по)20-22
ЖурналTetrahedron Letters
Том60
Номер выпуска1
DOI
СостояниеОпубликовано - 2019

Ключевые слова

    Предметные области Scopus

    • Биохимия
    • Поиск новых лекарств
    • Органическая химия

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    @article{98f84b315694441780632f3370911bfe,
    title = "Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE): Rapid access to the diarene-fused 1,4,7-triazecine ring system",
    abstract = "The tricyclic ring system of the antiviral drug nevirapine has been employed to test the workability of the hydrated imidazoline ring expansion (HIRE) reaction which was previously exemplified for [1.4]oxazepine and [1.4]thiazepine counterparts. The imidazoline nucleus was grafted onto the lactam moiety of nevirapine in two high-yielding steps. Subsequent N-alkylation and the HIRE reaction proceeded as envisioned and delivered rare ring-expanded diarene-fused 1,4,7-triazecines with a diversity of alkyl substituents at the lactam nitrogen atom. These findings extend the scope of the HIRE reaction to the medicinally prominent [1.4]diazepine chemical space.",
    keywords = "1,4,7-triazecines, Hydrated imidazoline ring expansion, Medium-sized rings, Nevirapine, [1.4]diazepines",
    author = "Sergey Grintsevich and Alexander Sapegin and Elena Reutskaya and Mikhail Krasavin",
    year = "2019",
    doi = "10.1016/j.tetlet.2018.11.044",
    language = "English",
    volume = "60",
    pages = "20--22",
    journal = "Tetrahedron Letters",
    issn = "0040-4039",
    publisher = "Elsevier",
    number = "1",

    }

    Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE) : Rapid access to the diarene-fused 1,4,7-triazecine ring system. / Grintsevich, Sergey; Sapegin, Alexander; Reutskaya, Elena; Krasavin, Mikhail.

    В: Tetrahedron Letters, Том 60, № 1, 2019, стр. 20-22.

    Результат исследований: Научные публикации в периодических изданияхстатьянаучнаярецензирование

    TY - JOUR

    T1 - Antiviral drug nevirapine as a template for hydrated imidazoline ring expansion (HIRE)

    T2 - Rapid access to the diarene-fused 1,4,7-triazecine ring system

    AU - Grintsevich, Sergey

    AU - Sapegin, Alexander

    AU - Reutskaya, Elena

    AU - Krasavin, Mikhail

    PY - 2019

    Y1 - 2019

    N2 - The tricyclic ring system of the antiviral drug nevirapine has been employed to test the workability of the hydrated imidazoline ring expansion (HIRE) reaction which was previously exemplified for [1.4]oxazepine and [1.4]thiazepine counterparts. The imidazoline nucleus was grafted onto the lactam moiety of nevirapine in two high-yielding steps. Subsequent N-alkylation and the HIRE reaction proceeded as envisioned and delivered rare ring-expanded diarene-fused 1,4,7-triazecines with a diversity of alkyl substituents at the lactam nitrogen atom. These findings extend the scope of the HIRE reaction to the medicinally prominent [1.4]diazepine chemical space.

    AB - The tricyclic ring system of the antiviral drug nevirapine has been employed to test the workability of the hydrated imidazoline ring expansion (HIRE) reaction which was previously exemplified for [1.4]oxazepine and [1.4]thiazepine counterparts. The imidazoline nucleus was grafted onto the lactam moiety of nevirapine in two high-yielding steps. Subsequent N-alkylation and the HIRE reaction proceeded as envisioned and delivered rare ring-expanded diarene-fused 1,4,7-triazecines with a diversity of alkyl substituents at the lactam nitrogen atom. These findings extend the scope of the HIRE reaction to the medicinally prominent [1.4]diazepine chemical space.

    KW - 1,4,7-triazecines

    KW - Hydrated imidazoline ring expansion

    KW - Medium-sized rings

    KW - Nevirapine

    KW - [1.4]diazepines

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    U2 - 10.1016/j.tetlet.2018.11.044

    DO - 10.1016/j.tetlet.2018.11.044

    M3 - Article

    VL - 60

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    JO - Tetrahedron Letters

    JF - Tetrahedron Letters

    SN - 0040-4039

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