A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives

A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives

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4-Anilinoquinazolines have been widely studied as anticancer agents. Despite the widespread utility of this class of compounds, the reported syntheses of 4-anilinoquinazolines require multistep and low-yielding pathways. A novel strategy to prepare 4-anilinoquinazoline derivatives based on the cycli...

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Main Authors: Zahra Haghighijoo, Zahra Rezaei, Samaneh Taheri, Meysam Jani, Soghra Khabnadideh
Format: Article
Language:English
Published: Shiraz University of Medical Sciences 2015-09-01
Series:Trends in Pharmaceutical Sciences
Online Access:https://tips.sums.ac.ir/article_42168_b8b3e3595f6f5983a1538abfd978a581.pdf
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spelling doaj-2f9a7ec61f44497d9eeb6e6b170efdb22021-07-14T06:10:37ZengShiraz University of Medical SciencesTrends in Pharmaceutical Sciences2423-56522015-09-011317317842168A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivativesZahra Haghighijoo0Zahra RezaeiSamaneh Taheri1Meysam Jani2Soghra Khabnadideh3Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, I.R.Iran. Department of Medicinal Chemistry, Faculty of Pharmacy Mazandaran University of Medical Sciences, Sari, I.R.IranDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, I.R.Iran.Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, I.R.Iran.Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, I.R.Iran.4-Anilinoquinazolines have been widely studied as anticancer agents. Despite the widespread utility of this class of compounds, the reported syntheses of 4-anilinoquinazolines require multistep and low-yielding pathways. A novel strategy to prepare 4-anilinoquinazoline derivatives based on the cyclization of anthranilic acid is described. By using of dichloro anthranilic acid we could etherified the quinazoline ring in order to mimic the erlotinib structure as a tyrosine kinase inhibitor. Our new compounds contain different substitutions at the meta-positions of the quinazoline ring instead of the ortho-positions of erlotinib. We synthesized ten new 4-anilinoquinazoline derivatives (17-26) in only 4 steps with desirable yields. Key words: Synthesis, Erlotinib, Anilinoquinazolines, EGFR.https://tips.sums.ac.ir/article_42168_b8b3e3595f6f5983a1538abfd978a581.pdf
collection DOAJ
language English
format Article
sources DOAJ
author Zahra Haghighijoo
Zahra Rezaei
Samaneh Taheri
Meysam Jani
Soghra Khabnadideh
spellingShingle Zahra Haghighijoo
Zahra Rezaei
Samaneh Taheri
Meysam Jani
Soghra Khabnadideh
A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives
Trends in Pharmaceutical Sciences
author_facet Zahra Haghighijoo
Zahra Rezaei
Samaneh Taheri
Meysam Jani
Soghra Khabnadideh
author_sort Zahra Haghighijoo
title A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives
title_short A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives
title_full A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives
title_fullStr A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives
title_full_unstemmed A rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives
title_sort rapid and convenient method for synthesis of anilinoquinazoline: an improved synthesis of erlotinib derivatives
publisher Shiraz University of Medical Sciences
series Trends in Pharmaceutical Sciences
issn 2423-5652
publishDate 2015-09-01
description 4-Anilinoquinazolines have been widely studied as anticancer agents. Despite the widespread utility of this class of compounds, the reported syntheses of 4-anilinoquinazolines require multistep and low-yielding pathways. A novel strategy to prepare 4-anilinoquinazoline derivatives based on the cyclization of anthranilic acid is described. By using of dichloro anthranilic acid we could etherified the quinazoline ring in order to mimic the erlotinib structure as a tyrosine kinase inhibitor. Our new compounds contain different substitutions at the meta-positions of the quinazoline ring instead of the ortho-positions of erlotinib. We synthesized ten new 4-anilinoquinazoline derivatives (17-26) in only 4 steps with desirable yields. Key words: Synthesis, Erlotinib, Anilinoquinazolines, EGFR.
url https://tips.sums.ac.ir/article_42168_b8b3e3595f6f5983a1538abfd978a581.pdf
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