An expeditious entry to rare tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones: A single-step gateway synthesis of glochidine congeners

Jeong Moo Seo; Ahmed H.E. Hassan; Yong Sup Lee

doi:10.1016/j.tet.2019.130760

An expeditious entry to rare tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones: A single-step gateway synthesis of glochidine congeners

Jeong Moo Seo
, Ahmed H.E. Hassan
, Yong Sup Lee

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

15 Citations (Scopus)

Abstract

A single-step gateway synthesis of glochidine and its congeners that possess the rare uncommon tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidine core was developed employing histamine and readily available γ-ketoesters. Key features of the developed reaction involve tandem three C–N bonds formation and concomitant annulation of two rings in one pot to access this unique and complex tricyclic structure. Exploration of the unknown bioactivity of these compounds revealed that they elicit antiproliferative activity comparable to the anticancer drug imatinib against 6 cancer cell lines.

Original language	English
Article number	130760
Journal	Tetrahedron
Volume	75
Issue number	51
DOIs	https://doi.org/10.1016/j.tet.2019.130760
Publication status	Published - 20 Dec 2019

Bibliographical note

Publisher Copyright:
© 2019 Elsevier Ltd

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Anticancers
Cyclization reactions
Imidazo[1,5-c]pyrrolo[1,2-a]pyrimidines
N-Acyliminium ions
Natural products analogs
Tandem reaction
Tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones

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10.1016/j.tet.2019.130760

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title = "An expeditious entry to rare tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones: A single-step gateway synthesis of glochidine congeners",

abstract = "A single-step gateway synthesis of glochidine and its congeners that possess the rare uncommon tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidine core was developed employing histamine and readily available γ-ketoesters. Key features of the developed reaction involve tandem three C{\textendash}N bonds formation and concomitant annulation of two rings in one pot to access this unique and complex tricyclic structure. Exploration of the unknown bioactivity of these compounds revealed that they elicit antiproliferative activity comparable to the anticancer drug imatinib against 6 cancer cell lines.",

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author = "Seo, \{Jeong Moo\} and Hassan, \{Ahmed H.E.\} and Lee, \{Yong Sup\}",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2019",

month = dec,

day = "20",

doi = "10.1016/j.tet.2019.130760",

language = "English",

volume = "75",

journal = "Tetrahedron",

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T2 - A single-step gateway synthesis of glochidine congeners

AU - Seo, Jeong Moo

AU - Hassan, Ahmed H.E.

AU - Lee, Yong Sup

PY - 2019/12/20

Y1 - 2019/12/20

N2 - A single-step gateway synthesis of glochidine and its congeners that possess the rare uncommon tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidine core was developed employing histamine and readily available γ-ketoesters. Key features of the developed reaction involve tandem three C–N bonds formation and concomitant annulation of two rings in one pot to access this unique and complex tricyclic structure. Exploration of the unknown bioactivity of these compounds revealed that they elicit antiproliferative activity comparable to the anticancer drug imatinib against 6 cancer cell lines.

AB - A single-step gateway synthesis of glochidine and its congeners that possess the rare uncommon tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidine core was developed employing histamine and readily available γ-ketoesters. Key features of the developed reaction involve tandem three C–N bonds formation and concomitant annulation of two rings in one pot to access this unique and complex tricyclic structure. Exploration of the unknown bioactivity of these compounds revealed that they elicit antiproliferative activity comparable to the anticancer drug imatinib against 6 cancer cell lines.

KW - Anticancers

KW - Cyclization reactions

KW - Imidazo[1,5-c]pyrrolo[1,2-a]pyrimidines

KW - N-Acyliminium ions

KW - Natural products analogs

KW - Tandem reaction

KW - Tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones

UR - https://www.scopus.com/pages/publications/85075399408

U2 - 10.1016/j.tet.2019.130760

DO - 10.1016/j.tet.2019.130760

M3 - Article

AN - SCOPUS:85075399408

SN - 0040-4020

VL - 75

JO - Tetrahedron

JF - Tetrahedron

IS - 51

M1 - 130760

ER -

An expeditious entry to rare tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones: A single-step gateway synthesis of glochidine congeners

Abstract

Bibliographical note

UN SDGs

Keywords

Access to Document

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