Facile synthetic approach towards vasorelaxant active 4-hydroxyquinazoline-4-carboxamides

Marian N. Aziz; Siva S. Panda; Elsayed M. Shalaby; Nehmedo G. Fawzy; Adel S. Girgis

doi:10.1039/c9ra04321g

Facile synthetic approach towards vasorelaxant active 4-hydroxyquinazoline-4-carboxamides

Marian N. Aziz, Siva S. Panda, Elsayed M. Shalaby, Nehmedo G. Fawzy, Adel S. Girgis

Chemistry and Physics

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

8 Scopus citations

Abstract

A Facile synthetic approach is reported towards 4-hydroxyquinazoline-4-carboxamides 13a-i through ring expansion of 2,3-dioxoindoline-1-carboxamides 10a-c during secondary amine 11a-d nucleophilic reaction. Single crystal X-ray studies of 10c and 13d support the structures. Some of the synthesized quinazolinecarboxamides 13 show promising vasorelaxant properties with potency higher than that of Doxazosin through the pre-contracted (norepinephrine hydrochloride) rat aorta standard bioassay. Good molecular models (2D-QSAR, pharmacophore) describe the biological observations.

Original language	English (US)
Pages (from-to)	28534-28540
Number of pages	7
Journal	RSC Advances
Volume	9
Issue number	49
DOIs	https://doi.org/10.1039/c9ra04321g
State	Published - 2019

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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title = "Facile synthetic approach towards vasorelaxant active 4-hydroxyquinazoline-4-carboxamides",

abstract = "A Facile synthetic approach is reported towards 4-hydroxyquinazoline-4-carboxamides 13a-i through ring expansion of 2,3-dioxoindoline-1-carboxamides 10a-c during secondary amine 11a-d nucleophilic reaction. Single crystal X-ray studies of 10c and 13d support the structures. Some of the synthesized quinazolinecarboxamides 13 show promising vasorelaxant properties with potency higher than that of Doxazosin through the pre-contracted (norepinephrine hydrochloride) rat aorta standard bioassay. Good molecular models (2D-QSAR, pharmacophore) describe the biological observations.",

author = "Aziz, {Marian N.} and Panda, {Siva S.} and Shalaby, {Elsayed M.} and Fawzy, {Nehmedo G.} and Girgis, {Adel S.}",

note = "Funding Information: This work was supported nancially by National Research Centre, Egypt, project ID: 11010341. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2019",

doi = "10.1039/c9ra04321g",

language = "English (US)",

volume = "9",

pages = "28534--28540",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Facile synthetic approach towards vasorelaxant active 4-hydroxyquinazoline-4-carboxamides

AU - Aziz, Marian N.

AU - Panda, Siva S.

AU - Shalaby, Elsayed M.

AU - Fawzy, Nehmedo G.

AU - Girgis, Adel S.

N1 - Funding Information: This work was supported nancially by National Research Centre, Egypt, project ID: 11010341. Publisher Copyright: © The Royal Society of Chemistry.

PY - 2019

Y1 - 2019

N2 - A Facile synthetic approach is reported towards 4-hydroxyquinazoline-4-carboxamides 13a-i through ring expansion of 2,3-dioxoindoline-1-carboxamides 10a-c during secondary amine 11a-d nucleophilic reaction. Single crystal X-ray studies of 10c and 13d support the structures. Some of the synthesized quinazolinecarboxamides 13 show promising vasorelaxant properties with potency higher than that of Doxazosin through the pre-contracted (norepinephrine hydrochloride) rat aorta standard bioassay. Good molecular models (2D-QSAR, pharmacophore) describe the biological observations.

AB - A Facile synthetic approach is reported towards 4-hydroxyquinazoline-4-carboxamides 13a-i through ring expansion of 2,3-dioxoindoline-1-carboxamides 10a-c during secondary amine 11a-d nucleophilic reaction. Single crystal X-ray studies of 10c and 13d support the structures. Some of the synthesized quinazolinecarboxamides 13 show promising vasorelaxant properties with potency higher than that of Doxazosin through the pre-contracted (norepinephrine hydrochloride) rat aorta standard bioassay. Good molecular models (2D-QSAR, pharmacophore) describe the biological observations.

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DO - 10.1039/c9ra04321g

M3 - Article

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JO - RSC Advances

JF - RSC Advances

IS - 49

ER -

Facile synthetic approach towards vasorelaxant active 4-hydroxyquinazoline-4-carboxamides

Abstract

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